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A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

5 Beds ⋅ 7 Baths ⋅ 24190774 MLS

A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

28 Walden Hill Rd, Guilford

Welcome to lakefront living at its finest on Candlewood Lake. Set on a private, level waterfront lot with over 450' of shoreline, this exceptional 3-bedroom home, rebuilt in 2006, offers breathtaking panoramic views and more than 6,000 SF of living space in one of the lake's most coveted settings. Designed for comfortable living and entertaining, the spacious main level flows seamlessly from inviting living and family rooms into an open kitchen and dining area. Generously sized rooms throughout provide comfort and flexibility, while every room enjoys stunning water views, creating an extraordinary connection to the lake. The lower level offers additional living space ideal for guests, fitness, hobbies, or entertaining, with direct access to the outdoor living areas and waterfront. Outside, professionally landscaped gardens frame the property and create a beautiful backdrop for lakeside living. Relax on the patios, enjoy the private dock, or simply take in the ever-changing scenery. The level shoreline provides effortless access to the water, a rare and highly sought-after feature on Candlewood Lake. Just 75 miles from Manhattan, this remarkable property offers the perfect balance of peaceful waterfront living and convenient access to New York City. A detached garage with bonus space above provides added flexibility. Located in the sought-after Hollywyle community, this is more than a home-it's a rare opportunity to experience the very best of Candlewood Lake.

3 Beds ⋅ 4 Baths ⋅ 24184415 MLS

Welcome to lakefront living at its finest on Candlewood Lake. Set on a private, level waterfront lot with over 450' of shoreline, this exceptional 3-bedroom home, rebuilt in 2006, offers breathtaking panoramic views and more than 6,000 SF of living space in one of the lake's most coveted settings. Designed for comfortable living and entertaining, the spacious main level flows seamlessly from inviting living and family rooms into an open kitchen and dining area. Generously sized rooms throughout provide comfort and flexibility, while every room enjoys stunning water views, creating an extraordinary connection to the lake. The lower level offers additional living space ideal for guests, fitness, hobbies, or entertaining, with direct access to the outdoor living areas and waterfront. Outside, professionally landscaped gardens frame the property and create a beautiful backdrop for lakeside living. Relax on the patios, enjoy the private dock, or simply take in the ever-changing scenery. The level shoreline provides effortless access to the water, a rare and highly sought-after feature on Candlewood Lake. Just 75 miles from Manhattan, this remarkable property offers the perfect balance of peaceful waterfront living and convenient access to New York City. A detached garage with bonus space above provides added flexibility. Located in the sought-after Hollywyle community, this is more than a home-it's a rare opportunity to experience the very best of Candlewood Lake.

1 Oak Dr, New Fairfield

On Top of the World. Unparalleled Estate with complete privacy and breathtaking panoramic views overlooking Lake Lillinonah and distant hills in premier Bridgewater location. Newly constructed state-of-the-art 5-bedroom Main House, 2-bedroom Guest House, Pool & Pool Cabana. Long paved driveway winds through magnificent grounds with extraordinary mature landscaping curated with pristine specimen trees & bushes and beautifully designed gardens. Sunlit from dawn until dusk, this Georgian colonial was masterfully crafted with the highest quality materials featuring high ceilings, expansive walls of windows and exquisite architectural symmetry. A captivating Living Room with central fireplace, a formal Dining Room and a Sunroom are oriented due west with floor-to ceiling windows capturing exquisite sunset views. Chef's Kitchen with spacious Butler's Pantry. Inviting entrance gallery designed to showcase works of art. Two first-floor primary-bedroom suites with 3 exquisite full baths, custom walk-in dressing closets, and a handsome home office. Three additional bedrooms are located on the 2nd floor with adjacent upstairs Family Room. Indoor exercise pool. Gym/Wellness Spa with full bath. 3-car attached garage. Seamless indoor/outdoor living. Irrigation system. Cutting-edge mechanical systems. Gated entrance. 26+/- acres surrounded by land trust. Must See. Not replicable.

5 Beds ⋅ 7 Baths ⋅ 24178176 MLS

On Top of the World. Unparalleled Estate with complete privacy and breathtaking panoramic views overlooking Lake Lillinonah and distant hills in premier Bridgewater location. Newly constructed state-of-the-art 5-bedroom Main House, 2-bedroom Guest House, Pool & Pool Cabana. Long paved driveway winds through magnificent grounds with extraordinary mature landscaping curated with pristine specimen trees & bushes and beautifully designed gardens. Sunlit from dawn until dusk, this Georgian colonial was masterfully crafted with the highest quality materials featuring high ceilings, expansive walls of windows and exquisite architectural symmetry. A captivating Living Room with central fireplace, a formal Dining Room and a Sunroom are oriented due west with floor-to ceiling windows capturing exquisite sunset views. Chef's Kitchen with spacious Butler's Pantry. Inviting entrance gallery designed to showcase works of art. Two first-floor primary-bedroom suites with 3 exquisite full baths, custom walk-in dressing closets, and a handsome home office. Three additional bedrooms are located on the 2nd floor with adjacent upstairs Family Room. Indoor exercise pool. Gym/Wellness Spa with full bath. 3-car attached garage. Seamless indoor/outdoor living. Irrigation system. Cutting-edge mechanical systems. Gated entrance. 26+/- acres surrounded by land trust. Must See. Not replicable.

289 Northrop St, Bridgewater

Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty-three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for modern living. A spacious chef's kitchen anchors the home, flowing seamlessly into elegant dining and living rooms, a relaxed family room, and expansive outdoor entertaining spaces. Details such as a wood-burning fireplace, rich hardwood floors, bluestone terraces, and a gracious screened porch elevate the experience. An in-ground pool and tranquil wildlife pond complete the idyllic setting. A stately circular drive leads to the 1860s carriage house, offering a beautifully appointed two-bedroom guest residence. Further along, the 1929 Barn House provides yet another charming haven for hosting family and friends. Winding paths traverse a landscape of remarkable diversity-open meadows, mature woodlands, and picturesque waterways-while multiple elevated sites offer breathtaking panoramic views and future possibilities. Surrounded by over 1,000 acres of protected farmland along the Ten Mile River watershed, the estate ensures privacy without isolation.

7 Beds ⋅ 7 Baths ⋅ 24170697 MLS

Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty-three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for modern living. A spacious chef's kitchen anchors the home, flowing seamlessly into elegant dining and living rooms, a relaxed family room, and expansive outdoor entertaining spaces. Details such as a wood-burning fireplace, rich hardwood floors, bluestone terraces, and a gracious screened porch elevate the experience. An in-ground pool and tranquil wildlife pond complete the idyllic setting. A stately circular drive leads to the 1860s carriage house, offering a beautifully appointed two-bedroom guest residence. Further along, the 1929 Barn House provides yet another charming haven for hosting family and friends. Winding paths traverse a landscape of remarkable diversity-open meadows, mature woodlands, and picturesque waterways-while multiple elevated sites offer breathtaking panoramic views and future possibilities. Surrounded by over 1,000 acres of protected farmland along the Ten Mile River watershed, the estate ensures privacy without isolation.

151 Benson Hill Rd, Dover

Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among notable estate properties and near Brett Woods Conservation Area (186 acres) and the Roy and Margot Larsen Wildlife Sanctuary (155 acres), with convenient access to the centers of Fairfield, Southport, and Westport and approximately 55 miles to Manhattan. Construction will begin after purchase and execution of the build contract. The site is approved for a pool, and a pool house can be added at additional cost. Also offered as land only, MLS #24114632, asking $1,300,000. Concept drawings, renderings, and photos are for design intent and aesthetic review. A rare opportunity to build in bucolic Greenfield Hill.

5 Beds ⋅ 6 Baths ⋅ 24132064 MLS

Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among notable estate properties and near Brett Woods Conservation Area (186 acres) and the Roy and Margot Larsen Wildlife Sanctuary (155 acres), with convenient access to the centers of Fairfield, Southport, and Westport and approximately 55 miles to Manhattan. Construction will begin after purchase and execution of the build contract. The site is approved for a pool, and a pool house can be added at additional cost. Also offered as land only, MLS #24114632, asking $1,300,000. Concept drawings, renderings, and photos are for design intent and aesthetic review. A rare opportunity to build in bucolic Greenfield Hill.

22 Brett Rd, Fairfield

$3,700,000

Nestled between the Lower Connecticut River and Long Island Sound, encircled by conservancy, this enchanting compound offers five distinct living environments blending the timeless character of early New England architecture with modern spaces for today's style of living. At the heart of the estate is a beautifully preserved 1787 Cape, with original fireplaces, rich with warmth and history. It is surrounded by formal English boxwood gardens, an intimate outdoor environment for restorative moments. The soaring post-and-beam barn with grand interiors, and a dramatic glass facade overlooking the quad creates an unforgettable setting for romantic and elegant entertaining on both a small and large scale. Two thoughtfully designed cottages provide private, charming and fully independent guest retreats. Reimagined in 2017, the Pool House introduces a modern contrast to the estate's historic soul. It features a full kitchen with double height ceilings, a book-lined great room, and a fully equipped gym, and seamless indoor-outdoor living besides the private Gunite pool, firepit, and alfresco dining areas. "The Greenhouse" offers a magical, foliage-filled glass ambience with softly glowing lights, a pavilion that transforms effortlessly from a refined clubroom into the most romantic of reception spaces. The expansive grounds feature gently cascading streams, a private pond, and generously landscaped gardens that create a truly one-of-a-kind.

7 Beds ⋅ 7 Baths ⋅ 24173300 MLS

Nestled between the Lower Connecticut River and Long Island Sound, encircled by conservancy, this enchanting compound offers five distinct living environments blending the timeless character of early New England architecture with modern spaces for today's style of living. At the heart of the estate is a beautifully preserved 1787 Cape, with original fireplaces, rich with warmth and history. It is surrounded by formal English boxwood gardens, an intimate outdoor environment for restorative moments. The soaring post-and-beam barn with grand interiors, and a dramatic glass facade overlooking the quad creates an unforgettable setting for romantic and elegant entertaining on both a small and large scale. Two thoughtfully designed cottages provide private, charming and fully independent guest retreats. Reimagined in 2017, the Pool House introduces a modern contrast to the estate's historic soul. It features a full kitchen with double height ceilings, a book-lined great room, and a fully equipped gym, and seamless indoor-outdoor living besides the private Gunite pool, firepit, and alfresco dining areas. "The Greenhouse" offers a magical, foliage-filled glass ambience with softly glowing lights, a pavilion that transforms effortlessly from a refined clubroom into the most romantic of reception spaces. The expansive grounds feature gently cascading streams, a private pond, and generously landscaped gardens that create a truly one-of-a-kind.

155 Joshuatown Rd, Lyme

$3,695,000

Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a higher elevation, the home enjoys FEMA compliance with fewer stairs to the main living level than many neighboring properties. Sunlight pours through oversized windows, illuminating beautifully proportioned living spaces designed for both everyday comfort and effortless entertaining. The stunning chef's kitchen opens seamlessly to inviting gathering spaces and out to a private backyard featuring a spacious patio, outdoor fireplace, mature landscaping, and room for a pool. The flexible floor plan lives as four bedrooms, with a private third-floor suite and adjacent full bath offering an ideal extra bedroom, guest retreat, office or bonus space. Thoughtful features, including a full-house generator, provide an added layer of comfort and confidence, allowing the home to perform as beautifully as it lives. Adjacent to the coveted Sunnieholme neighborhood, this is a rare opportunity to own a beautifully crafted home in one of Fairfield's most desirable beachside locations, where coastal living, convenience, and enduring quality come together.

4 Beds ⋅ 5 Baths ⋅ 24193922 MLS

Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a higher elevation, the home enjoys FEMA compliance with fewer stairs to the main living level than many neighboring properties. Sunlight pours through oversized windows, illuminating beautifully proportioned living spaces designed for both everyday comfort and effortless entertaining. The stunning chef's kitchen opens seamlessly to inviting gathering spaces and out to a private backyard featuring a spacious patio, outdoor fireplace, mature landscaping, and room for a pool. The flexible floor plan lives as four bedrooms, with a private third-floor suite and adjacent full bath offering an ideal extra bedroom, guest retreat, office or bonus space. Thoughtful features, including a full-house generator, provide an added layer of comfort and confidence, allowing the home to perform as beautifully as it lives. Adjacent to the coveted Sunnieholme neighborhood, this is a rare opportunity to own a beautifully crafted home in one of Fairfield's most desirable beachside locations, where coastal living, convenience, and enduring quality come together.

110 Judson Rd, Fairfield

$3,690,000

Situated on approximately twenty acres and surrounded by Litchfield Land Trust's Prospect Mountain Preserve and the private holdings of the Marshepaug Club, Arcadia stands as one of Litchfield County's premier properties. The current owners are exceptional stewards and have made significant investments in the dwellings, infrastructure, and surrounding landscape. Rarely does a property come to market that includes a fully renovated home, a meticulously restored barn, pastures, meadows, and gardens. The perfect blend of classic Colonial architecture and tasteful, high-quality modern amenities. Highlights include five en-suite bedrooms, a Vermont slate roof, wide-plank oak flooring, a professional chef's kitchen with a Lacanche range, antique beams, and a wellness center with a sauna and gym space. The property features a comprehensive technology package with integrated smart-home systems, advanced connectivity, security, climate, lighting, and irrigation controls. The current owners thoughtfully reimagined the barn complex for entertaining, incorporating a guest suite, party room, wine cellar, catering scullery, workroom, loft, bar, and hot tub within a screened-in porch. Outdoor entertaining spaces abound, with stone patios, gardens, mahogany decking, pergolas and views. The property is minutes from skiing at Mohawk Mt. and Litchfield Land Trust trails. Arcadia represents an exceptional and rare opportunity to enjoy a country lifestyle within two hours of New York City.

5 Beds ⋅ 6 Baths ⋅ 24204600 MLS

Situated on approximately twenty acres and surrounded by Litchfield Land Trust's Prospect Mountain Preserve and the private holdings of the Marshepaug Club, Arcadia stands as one of Litchfield County's premier properties. The current owners are exceptional stewards and have made significant investments in the dwellings, infrastructure, and surrounding landscape. Rarely does a property come to market that includes a fully renovated home, a meticulously restored barn, pastures, meadows, and gardens. The perfect blend of classic Colonial architecture and tasteful, high-quality modern amenities. Highlights include five en-suite bedrooms, a Vermont slate roof, wide-plank oak flooring, a professional chef's kitchen with a Lacanche range, antique beams, and a wellness center with a sauna and gym space. The property features a comprehensive technology package with integrated smart-home systems, advanced connectivity, security, climate, lighting, and irrigation controls. The current owners thoughtfully reimagined the barn complex for entertaining, incorporating a guest suite, party room, wine cellar, catering scullery, workroom, loft, bar, and hot tub within a screened-in porch. Outdoor entertaining spaces abound, with stone patios, gardens, mahogany decking, pergolas and views. The property is minutes from skiing at Mohawk Mt. and Litchfield Land Trust trails. Arcadia represents an exceptional and rare opportunity to enjoy a country lifestyle within two hours of New York City.

287 Prospect Mountain Rd, Litchfield

$3,625,000

Tucked away from the road and set above the CT river on over three acres, this amazing waterfront home is also a secluded personal resort, complete with a pool, spa, and private beach. Designed to showcase river views from every vantage point, the home features high ceilings, floor to ceiling windows, and an expansive open-concept floor plan that brings in an abundance of natural light. A living room with a fireplace, formal dining area, and family room all lead out to a large deck, which offers plenty of room for outdoor entertaining or just admiring the scenic waterfront setting. A well-appointed chef's kitchen with a center island and plenty of storage space faces the family room. A first- floor primary bedroom offers an office/sitting area with another fireplace, a generous ensuite bathroom with both a soaking tub and walk-in shower. A spacious laundry/mud room leads from the kitchen to the three-car garage. A sunroom overlooks the pool deck, which includes a gunite in-ground pool, a large patio area, and a fantastic outdoor kitchen with a built-in grill and bar area perfect for al fresco dining. The second-floor landing is open to the first floor below, and has two bedrooms both with ensuite bathrooms, and sitting area. The finished walk-out lower level leads to another patio area overlooking the private beach. A large family room, a full kitchen, two more bedrooms and a full bathroom complete the lower floor, offering plenty of room for visitors.

5 Beds ⋅ 5 Baths ⋅ 24191233 MLS

Tucked away from the road and set above the CT river on over three acres, this amazing waterfront home is also a secluded personal resort, complete with a pool, spa, and private beach. Designed to showcase river views from every vantage point, the home features high ceilings, floor to ceiling windows, and an expansive open-concept floor plan that brings in an abundance of natural light. A living room with a fireplace, formal dining area, and family room all lead out to a large deck, which offers plenty of room for outdoor entertaining or just admiring the scenic waterfront setting. A well-appointed chef's kitchen with a center island and plenty of storage space faces the family room. A first- floor primary bedroom offers an office/sitting area with another fireplace, a generous ensuite bathroom with both a soaking tub and walk-in shower. A spacious laundry/mud room leads from the kitchen to the three-car garage. A sunroom overlooks the pool deck, which includes a gunite in-ground pool, a large patio area, and a fantastic outdoor kitchen with a built-in grill and bar area perfect for al fresco dining. The second-floor landing is open to the first floor below, and has two bedrooms both with ensuite bathrooms, and sitting area. The finished walk-out lower level leads to another patio area overlooking the private beach. A large family room, a full kitchen, two more bedrooms and a full bathroom complete the lower floor, offering plenty of room for visitors.

409 River Rd, Deep River

$3,600,000

Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

5 Beds ⋅ 5 Baths ⋅ 24183686 MLS

Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

268 South St, Roxbury

$3,600,000

Potential for residential conversion in the heart of downtown Greenwich. Located just two doors from Greenwich Avenue and moments from the Metro-North train station, 37 Arch Street presents an exceptionally rare opportunity to create a one-of-a-kind in-town residence, mixed-use property, or continue as boutique commercial space. Situated within the Central Greenwich Business District zone, the property offers potential for residential, mixed-use, office, retail, or medical use (buyer to conduct all due diligence with the Town of Greenwich). This charming circa-1815 Federal-style building offers approximately 3,090 SF on an oversized 8,158 SF lot with the rare convenience of 8 on-site outdoor parking spaces plus 2 garage spaces - an extraordinary amenity for downtown Greenwich. The property is currently configured as executive office space and is in excellent condition, providing flexibility for investors, developers, or owner-users seeking immediate income while planning a future conversion or redevelopment. Prime walk-to-town location near Greenwich Avenue's luxury shopping, restaurants, parks, and transportation in one of Fairfield County's most sought-after downtown locations.

8 Beds ⋅ 3 Baths ⋅ 24174202 MLS

Potential for residential conversion in the heart of downtown Greenwich. Located just two doors from Greenwich Avenue and moments from the Metro-North train station, 37 Arch Street presents an exceptionally rare opportunity to create a one-of-a-kind in-town residence, mixed-use property, or continue as boutique commercial space. Situated within the Central Greenwich Business District zone, the property offers potential for residential, mixed-use, office, retail, or medical use (buyer to conduct all due diligence with the Town of Greenwich). This charming circa-1815 Federal-style building offers approximately 3,090 SF on an oversized 8,158 SF lot with the rare convenience of 8 on-site outdoor parking spaces plus 2 garage spaces - an extraordinary amenity for downtown Greenwich. The property is currently configured as executive office space and is in excellent condition, providing flexibility for investors, developers, or owner-users seeking immediate income while planning a future conversion or redevelopment. Prime walk-to-town location near Greenwich Avenue's luxury shopping, restaurants, parks, and transportation in one of Fairfield County's most sought-after downtown locations.

37 Arch St, Greenwich

$3,600,000

Create your Ridgefield legacy with this proposed luxury residence. With four or five en-suite bedrooms and an open floor plan, our elevated property with sweeping views is a once in a lifetime opportunity on an impeccable homesite. Opportunities like this are nearly extinct. This spectacular 3-acre parcel, one of the last remaining premiere building sites in Ridgefield, offers a rare opportunity to create a home as remarkable as its address. In Fairfield County's crown jewel address boasting award winning schools, a vibrant downtown, the Aldrich Contemporary Art Museum, Ridgefield Playhouse, Ridgefield Golf Course, hiking trails all within an easy commute to Manhattan. This is a rare chance to build our designs or your own vision with top local builder. Must contact listing broker for information. Please only serious inquiries. Builder will discuss lot sale only if you insist on your own contractor.

5 Beds ⋅ 6 Baths ⋅ 24118657 MLS

Create your Ridgefield legacy with this proposed luxury residence. With four or five en-suite bedrooms and an open floor plan, our elevated property with sweeping views is a once in a lifetime opportunity on an impeccable homesite. Opportunities like this are nearly extinct. This spectacular 3-acre parcel, one of the last remaining premiere building sites in Ridgefield, offers a rare opportunity to create a home as remarkable as its address. In Fairfield County's crown jewel address boasting award winning schools, a vibrant downtown, the Aldrich Contemporary Art Museum, Ridgefield Playhouse, Ridgefield Golf Course, hiking trails all within an easy commute to Manhattan. This is a rare chance to build our designs or your own vision with top local builder. Must contact listing broker for information. Please only serious inquiries. Builder will discuss lot sale only if you insist on your own contractor.

399 Ridgebury Rd, Ridgefield

$3,595,000

Exquisite Stonington Estate. Set amidst 10.19 manicured acres of breathtaking privacy and natural beauty, the extraordinary Crossover Estate offers the very best of refined coastal living just moments from the charming Stonington Borough and Historic Downtown Mystic. The best of One-Level Living. This exceptional family compound is bordered by a tranquil pond and brook on one side, with a picturesque estuary leading to Long Island Sound on the other. Ideally positioned between Boston and New York City, and only minutes to Mystic, Watch Hill and the Mystic Amtrak station, this remarkable estate offers effortless access for both weekend escapes and year-round enjoyment. The best of one-level living with an expansive and luxurious primary suite. The stunning main residence features 4 spacious bedrooms, 3 Full 2 Half beautifully appointed baths, designed with elegant comfort and seamless entertaining in mind. Exceptional interior finishes include a gourmet chef's kitchen with premium Wolf appliances, steam oven, microwave drawer, custom cabinetry, and sophisticated designer details throughout. Complimenting the main residence is a charming 3 Bedroom 1,276 Sq Ft Guest House, along with a spectacular pool and pool house complete with full kitchen, bath, and sauna, and Sports Court. Also - Main House with 3 Br Guest House, Pool with Pool House and Sports Court situated on 10.19 manicured acres and including 11.07 acre building lot are available for $4,459,000. Continued:

7 Beds ⋅ 6 Baths ⋅ 24189710 MLS

Exquisite Stonington Estate. Set amidst 10.19 manicured acres of breathtaking privacy and natural beauty, the extraordinary Crossover Estate offers the very best of refined coastal living just moments from the charming Stonington Borough and Historic Downtown Mystic. The best of One-Level Living. This exceptional family compound is bordered by a tranquil pond and brook on one side, with a picturesque estuary leading to Long Island Sound on the other. Ideally positioned between Boston and New York City, and only minutes to Mystic, Watch Hill and the Mystic Amtrak station, this remarkable estate offers effortless access for both weekend escapes and year-round enjoyment. The best of one-level living with an expansive and luxurious primary suite. The stunning main residence features 4 spacious bedrooms, 3 Full 2 Half beautifully appointed baths, designed with elegant comfort and seamless entertaining in mind. Exceptional interior finishes include a gourmet chef's kitchen with premium Wolf appliances, steam oven, microwave drawer, custom cabinetry, and sophisticated designer details throughout. Complimenting the main residence is a charming 3 Bedroom 1,276 Sq Ft Guest House, along with a spectacular pool and pool house complete with full kitchen, bath, and sauna, and Sports Court. Also - Main House with 3 Br Guest House, Pool with Pool House and Sports Court situated on 10.19 manicured acres and including 11.07 acre building lot are available for $4,459,000. Continued:

455 Stonington Rd, Stonington

$3,595,000

Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined living. Set on a .45 private lot, this meticulously maintained antique residence spans approximately 3,769 square feet and captures serene water views from its beautifully landscaped grounds. Despite its central village location, just moments to shops, dining, and marinas, the home offers an exceptional sense of privacy and tranquility. Rich in architectural charm, the home features soaring ceilings, expansive windows, and elegant, light-filled interiors that reflect generations of thoughtful stewardship. Once known as one of the village's grand homes, its legacy continues today as a warm and inviting retreat with sophisticated style and historic integrity. Designed for both everyday living and entertaining, the property includes a spacious three-car garage and generous living areas that honor its past while accommodating modern lifestyles. The grounds unfold toward the water, offering a peaceful backdrop and a true connection to Essex's coastal beauty. This Historic Essex Village waterfront home is a rare offering where heritage, location, and lifestyle converge.

5 Beds ⋅ 4 Baths ⋅ 24190330 MLS

Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined living. Set on a .45 private lot, this meticulously maintained antique residence spans approximately 3,769 square feet and captures serene water views from its beautifully landscaped grounds. Despite its central village location, just moments to shops, dining, and marinas, the home offers an exceptional sense of privacy and tranquility. Rich in architectural charm, the home features soaring ceilings, expansive windows, and elegant, light-filled interiors that reflect generations of thoughtful stewardship. Once known as one of the village's grand homes, its legacy continues today as a warm and inviting retreat with sophisticated style and historic integrity. Designed for both everyday living and entertaining, the property includes a spacious three-car garage and generous living areas that honor its past while accommodating modern lifestyles. The grounds unfold toward the water, offering a peaceful backdrop and a true connection to Essex's coastal beauty. This Historic Essex Village waterfront home is a rare offering where heritage, location, and lifestyle converge.

10 Scholes Ln, Essex

$3,595,000

Welcome home to the Gold Coast of Norwalk. Location, space and timeless design come together in this stunning turn-key colonial with waterviews of Long Island Sound. Set on one acre in Norwalk's coveted Shorehaven neighborhood, it's just a short walk to Sandy Beach and the Sprite Island Yacht Club boat launch. Custom features and 10-foot ceilings elevate the main level and make it ideal for both everyday living and entertaining. The family room flows seamlessly into the eat-in kitchen. A generous deck overlooking the backyard is perfect for relaxing or hosting friends. The first floor private office with full bath also serves as a guest bedroom. Upstairs, the primary bedroom features a fireplace and a sumptuous bath that opens to an outdoor deck. The third floor offers an entertainment center with full bath and an additional office space. New additions include a full house generator, outdoor lighting, a fire pit and patio. Nearby is the Shorehaven Country Club as well as The Shore and Country Club, a private club on Long Island Sound offering members a 25 yard pool, a separate wading pool, 10 tennis courts, beach areas on the Sound, a marina with boat slips, as well as dining and social areas for events, meals and gatherings. 3 Shorehaven is just minutes to Norwalk's famous SoNo district for great restaurants and entertainment. Room for a pool. Within one hour to NYC.

5 Beds ⋅ 6 Baths ⋅ 24163499 MLS

Welcome home to the Gold Coast of Norwalk. Location, space and timeless design come together in this stunning turn-key colonial with waterviews of Long Island Sound. Set on one acre in Norwalk's coveted Shorehaven neighborhood, it's just a short walk to Sandy Beach and the Sprite Island Yacht Club boat launch. Custom features and 10-foot ceilings elevate the main level and make it ideal for both everyday living and entertaining. The family room flows seamlessly into the eat-in kitchen. A generous deck overlooking the backyard is perfect for relaxing or hosting friends. The first floor private office with full bath also serves as a guest bedroom. Upstairs, the primary bedroom features a fireplace and a sumptuous bath that opens to an outdoor deck. The third floor offers an entertainment center with full bath and an additional office space. New additions include a full house generator, outdoor lighting, a fire pit and patio. Nearby is the Shorehaven Country Club as well as The Shore and Country Club, a private club on Long Island Sound offering members a 25 yard pool, a separate wading pool, 10 tennis courts, beach areas on the Sound, a marina with boat slips, as well as dining and social areas for events, meals and gatherings. 3 Shorehaven is just minutes to Norwalk's famous SoNo district for great restaurants and entertainment. Room for a pool. Within one hour to NYC.

3 Shorehaven Rd, Norwalk

$3,550,000

In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. The main level flows beautifully and showcases dramatic interiors with large gathering spaces, gourmet kitchen facilities and incredible entertaining capabilities. The main floor primary suite serves as a luxurious private retreat with his and her bathrooms and separate sitting room/office. Upstairs, three additional bedrooms continue the home's commitment to comfort and privacy. The finished lower level extends the home's appeal with numerous recreational spaces and a full bath. Beyond the impressive interiors, the grounds are truly breathtaking. A rhythm of blooming flowers and mature landscaping creates a sense of beauty throughout all four seasons, thoughtfully designed to offer year-round color and serenity. Located on a private cul-de-sac, this home is a true compound-balanced, gracious, and masterfully executed, offering unparalleled living inside and out. Once you have arrived, it will be hard to leave!

6 Beds ⋅ 7 Baths ⋅ 24191286 MLS

In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. The main level flows beautifully and showcases dramatic interiors with large gathering spaces, gourmet kitchen facilities and incredible entertaining capabilities. The main floor primary suite serves as a luxurious private retreat with his and her bathrooms and separate sitting room/office. Upstairs, three additional bedrooms continue the home's commitment to comfort and privacy. The finished lower level extends the home's appeal with numerous recreational spaces and a full bath. Beyond the impressive interiors, the grounds are truly breathtaking. A rhythm of blooming flowers and mature landscaping creates a sense of beauty throughout all four seasons, thoughtfully designed to offer year-round color and serenity. Located on a private cul-de-sac, this home is a true compound-balanced, gracious, and masterfully executed, offering unparalleled living inside and out. Once you have arrived, it will be hard to leave!

9 N Ridge Rd, Westport

Where the river meets the ocean, an extraordinary waterfront legacy awaits. Discover The River Estate at Shawandassee, one of the region's most captivating riverfront estates, where 1.06 acres of meticulously manicured, park-like grounds and more than 200 feet of pristine waterfront create an unparalleled coastal sanctuary. Launch your boat from the private deep-water dock and cruise effortlessly to Long Island Sound, Fishers Island, and beyond, or spend the day enjoying the rare grandfathered waterfront boathouse complete with electricity and running water, and a private beach. Spend your days sport fishing, shellfishing, kayaking, paddleboarding, boating or simply soaking in the serenity of life on the water. Complementing this remarkable setting is a charming pony barn attached to a two-car garage and a beautifully updated 2,700-square-foot residence offering three bedrooms and three full baths. This is far more than an exceptional property-it is a once-in-a-lifetime waterfront estate where luxury, privacy, and the timeless beauty of New England's coastline come together to create a lifestyle few will ever experience. Inside, timeless craftsmanship and warmth welcome you home. The inviting living room welcomes you with hardwood floors, a classic wood-burning fireplace and a picturesque window seat perfectly, positioned to take in the patio, beautifully landscaped grounds and tranquil water views.

3 Beds ⋅ 3 Baths ⋅ 24196231 MLS

Where the river meets the ocean, an extraordinary waterfront legacy awaits. Discover The River Estate at Shawandassee, one of the region's most captivating riverfront estates, where 1.06 acres of meticulously manicured, park-like grounds and more than 200 feet of pristine waterfront create an unparalleled coastal sanctuary. Launch your boat from the private deep-water dock and cruise effortlessly to Long Island Sound, Fishers Island, and beyond, or spend the day enjoying the rare grandfathered waterfront boathouse complete with electricity and running water, and a private beach. Spend your days sport fishing, shellfishing, kayaking, paddleboarding, boating or simply soaking in the serenity of life on the water. Complementing this remarkable setting is a charming pony barn attached to a two-car garage and a beautifully updated 2,700-square-foot residence offering three bedrooms and three full baths. This is far more than an exceptional property-it is a once-in-a-lifetime waterfront estate where luxury, privacy, and the timeless beauty of New England's coastline come together to create a lifestyle few will ever experience. Inside, timeless craftsmanship and warmth welcome you home. The inviting living room welcomes you with hardwood floors, a classic wood-burning fireplace and a picturesque window seat perfectly, positioned to take in the patio, beautifully landscaped grounds and tranquil water views.

7 Shawandassee Rd, Waterford

This stunning 1874 Federal house sits on a 3.93-acre lot and backs up to land-trust property. It was fully renovated and designed by Percy Steinhart, the design maven who created Stubbs & Wooton shoes. The estate contains a 6,641 square foot Main House, plus a wonderful Pool House and Carriage House. In the Main House, the spacious Entry Hall leads to the Living Room with a fireplace and a charming bay window. A large Library with a fireplace opens into a spacious Garden Room. The elegant Dining Room has a corner fireplace and double exposures. Adjacent is a gourmet Kitchen with a large island, high-end appliances, and a sizeable breakfast area with a spacious Cloak and Powder Room nearby. The front and back staircases lead to the second floor and a Primary Suite consisting of a large bedroom with a bay window and fireplace, and an elegant en-suite Bath. A second Bedroom with a fireplace is adjacent to the Primary. Two additional Bedrooms with en-suite Baths, and a Laundry Room, complete the second floor. On the third floor is a center gathering room plus two large Bedrooms and Baths. A large, unrenovated room has potential for use as an additional Bedroom, Gym, or Office. The Basement has a two-car garage with a Half Bath and generous storage rooms. The property is beautifully landscaped with a Croquet Lawn, a large pool, and Pool House with an outdoor fireplace for cooking, and a Greenhouse. The Main House and Pool House have updated HVAC systems with Central Air.

7 Beds ⋅ 6 Baths ⋅ 24169503 MLS

This stunning 1874 Federal house sits on a 3.93-acre lot and backs up to land-trust property. It was fully renovated and designed by Percy Steinhart, the design maven who created Stubbs & Wooton shoes. The estate contains a 6,641 square foot Main House, plus a wonderful Pool House and Carriage House. In the Main House, the spacious Entry Hall leads to the Living Room with a fireplace and a charming bay window. A large Library with a fireplace opens into a spacious Garden Room. The elegant Dining Room has a corner fireplace and double exposures. Adjacent is a gourmet Kitchen with a large island, high-end appliances, and a sizeable breakfast area with a spacious Cloak and Powder Room nearby. The front and back staircases lead to the second floor and a Primary Suite consisting of a large bedroom with a bay window and fireplace, and an elegant en-suite Bath. A second Bedroom with a fireplace is adjacent to the Primary. Two additional Bedrooms with en-suite Baths, and a Laundry Room, complete the second floor. On the third floor is a center gathering room plus two large Bedrooms and Baths. A large, unrenovated room has potential for use as an additional Bedroom, Gym, or Office. The Basement has a two-car garage with a Half Bath and generous storage rooms. The property is beautifully landscaped with a Croquet Lawn, a large pool, and Pool House with an outdoor fireplace for cooking, and a Greenhouse. The Main House and Pool House have updated HVAC systems with Central Air.

148 North St, Litchfield

Opportunities like this are exceedingly rare. Betts Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a canvas for imagination. Located approximately one mile offshore, the island is distinguished by its natural land bridge, which connects its two halves and creates a protected cove long favored by boaters. A small bungalow currently sits on the island, and future development options may be explored. Shaped by retreating glaciers more than 17,000 years ago, the Norwalk Islands form a remarkable archipelago scattered across Long Island Sound. For generations, they have attracted boaters, kayakers, and those drawn to a quieter, more adventurous relationship with the coast. Rich in maritime history and surrounded by protected waters, portions of the island chain are preserved within the Stewart B. McKinney National Wildlife Refuge, helping maintain the natural beauty, wildlife, and sense of escape that define this rare environment. A setting for those who appreciate that true privacy often lies just beyond easy reach. Also for sale is Calf Pasture Island which is MLS #24147619.

2 Beds ⋅ 1 Baths ⋅ 24148140 MLS

Opportunities like this are exceedingly rare. Betts Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a canvas for imagination. Located approximately one mile offshore, the island is distinguished by its natural land bridge, which connects its two halves and creates a protected cove long favored by boaters. A small bungalow currently sits on the island, and future development options may be explored. Shaped by retreating glaciers more than 17,000 years ago, the Norwalk Islands form a remarkable archipelago scattered across Long Island Sound. For generations, they have attracted boaters, kayakers, and those drawn to a quieter, more adventurous relationship with the coast. Rich in maritime history and surrounded by protected waters, portions of the island chain are preserved within the Stewart B. McKinney National Wildlife Refuge, helping maintain the natural beauty, wildlife, and sense of escape that define this rare environment. A setting for those who appreciate that true privacy often lies just beyond easy reach. Also for sale is Calf Pasture Island which is MLS #24147619.

Betts Island, Norwalk

Opportunities like this are rare. Calf Pasture Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a blank canvas for imagination. Properties like this remain in the same hands for many decades and do not come up for sale often. Located approximately a half mile offshore, it is among the closest islands to the mainland and takes its name from the cattle once kept there. The island is easily accessible from Norwalk Harbor and the Saugatuck River, making it a convenient yet distinctly separate retreat. A small A-frame structure currently sits on the island, and future development options may be explored. Shaped by retreating glaciers more than 17,000 years ago, the Norwalk Islands form a rare archipelago scattered across Long Island Sound. For generations, they have attracted boaters, kayakers, and those drawn to life just beyond the shoreline. Rich in maritime history and surrounded by protected waters, portions of the island chain fall within the Stewart B. McKinney National Wildlife Refuge, helping preserve the natural beauty, wildlife, and sense of escape that define this remarkable setting. A place for those who appreciate that true privacy often lies just beyond easy reach. Also for sale is Betts Island which is MLS #24148140.

3 Beds ⋅ 4 Baths ⋅ 24147619 MLS

Opportunities like this are rare. Calf Pasture Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a blank canvas for imagination. Properties like this remain in the same hands for many decades and do not come up for sale often. Located approximately a half mile offshore, it is among the closest islands to the mainland and takes its name from the cattle once kept there. The island is easily accessible from Norwalk Harbor and the Saugatuck River, making it a convenient yet distinctly separate retreat. A small A-frame structure currently sits on the island, and future development options may be explored. Shaped by retreating glaciers more than 17,000 years ago, the Norwalk Islands form a rare archipelago scattered across Long Island Sound. For generations, they have attracted boaters, kayakers, and those drawn to life just beyond the shoreline. Rich in maritime history and surrounded by protected waters, portions of the island chain fall within the Stewart B. McKinney National Wildlife Refuge, helping preserve the natural beauty, wildlife, and sense of escape that define this remarkable setting. A place for those who appreciate that true privacy often lies just beyond easy reach. Also for sale is Betts Island which is MLS #24148140.

Calf Pasture Island, Norwalk

$3,499,000

"MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house & the barn, and the stunning setting makes an enduring impression. The glamorous echoes of a Hollywood-style estate combine w/incredible updates throughout the transformed interiors. The front-to-back LR has a distinctive bay window & dual doors to a serene porch that gazes across the expansive grounds. The incredible great room is the focal point of this expertly-designed floorplan, combining a Chef's kitchen w/expansive island, endless storage, Thermador appliances, breakfast/casual dining area, all leading to the incredible DR & fam rm which has a wall of folding glass doors creating an effortless flow between the gorgeous interior & exterior spaces while preserving open views across the property. A BR suite w/private access, large laundry rm, mudrm, garage & powder rm complete this level. Upstairs, well-appointed BRs w/designer baths await. The primary suite is an exquisite space w/tray ceiling, fpl, plush bth, walk-in dressing rm & an amazing balcony that spans much of the rear of the home. An elegant patio lines the heated pool. The barn is a dream for auto enthusiasts.

5 Beds ⋅ 5 Baths ⋅ 24181944 MLS

"MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house & the barn, and the stunning setting makes an enduring impression. The glamorous echoes of a Hollywood-style estate combine w/incredible updates throughout the transformed interiors. The front-to-back LR has a distinctive bay window & dual doors to a serene porch that gazes across the expansive grounds. The incredible great room is the focal point of this expertly-designed floorplan, combining a Chef's kitchen w/expansive island, endless storage, Thermador appliances, breakfast/casual dining area, all leading to the incredible DR & fam rm which has a wall of folding glass doors creating an effortless flow between the gorgeous interior & exterior spaces while preserving open views across the property. A BR suite w/private access, large laundry rm, mudrm, garage & powder rm complete this level. Upstairs, well-appointed BRs w/designer baths await. The primary suite is an exquisite space w/tray ceiling, fpl, plush bth, walk-in dressing rm & an amazing balcony that spans much of the rear of the home. An elegant patio lines the heated pool. The barn is a dream for auto enthusiasts.

240 North Ave, Westport

Rich with classic character this 1918 Colonial sits on one of the most coveted streets in Old Greenwich. With an expansive 3,670 square feet, this charm filled home pairs timeless architectural details. A quintessential wide wraparound front porch greets you, opening into a spacious entry hall that connects the formal living room with high ceilings and into the warm flexible layout., coffered ceiling in the dining room and inviting family room with elevated half cathedral ceiling and skylights. At the center of the home, the family kitchen offers informal dining, a built in family office space and casual seating area, all flowing effortlessly onto an expansive back deck and stone patio. The Perfect private space for indoor-outdoor entertaining and to escape the day. The second floor hosts four light-filled bedrooms and a full bath, while the third level provides a private fifth bedroom suite with its own bath. Set on a .3 acre lot backing up to the scenic grounds of Innis Arden Golf Club, the property offers exceptional privacy. Unbeatable coastal lifestyle offering. Work in NYC? it's a 7 minute walk to the Old Greenwich Train Station or 2 minute drive. Effortless stroll to the village, local favorite King's Market, Binney Park and the seasonal outdoor concert series, living at 14 Highview, including short 9 minute bike ride to Tod's Point beach. Location is everything, start your next chapter of your story here in the heart of Old Greenwich at 14 Highview Avenue!

4 Beds ⋅ 3 Baths ⋅ 24203497 MLS

Rich with classic character this 1918 Colonial sits on one of the most coveted streets in Old Greenwich. With an expansive 3,670 square feet, this charm filled home pairs timeless architectural details. A quintessential wide wraparound front porch greets you, opening into a spacious entry hall that connects the formal living room with high ceilings and into the warm flexible layout., coffered ceiling in the dining room and inviting family room with elevated half cathedral ceiling and skylights. At the center of the home, the family kitchen offers informal dining, a built in family office space and casual seating area, all flowing effortlessly onto an expansive back deck and stone patio. The Perfect private space for indoor-outdoor entertaining and to escape the day. The second floor hosts four light-filled bedrooms and a full bath, while the third level provides a private fifth bedroom suite with its own bath. Set on a .3 acre lot backing up to the scenic grounds of Innis Arden Golf Club, the property offers exceptional privacy. Unbeatable coastal lifestyle offering. Work in NYC? it's a 7 minute walk to the Old Greenwich Train Station or 2 minute drive. Effortless stroll to the village, local favorite King's Market, Binney Park and the seasonal outdoor concert series, living at 14 Highview, including short 9 minute bike ride to Tod's Point beach. Location is everything, start your next chapter of your story here in the heart of Old Greenwich at 14 Highview Avenue!

14 Highview Ave, Greenwich

This luxury custom designed home in a private country setting offers maximum privacy and comfortable living. The main level offers single floor living featuring a private primary suite with dressing room, full bath and French doors to a full screened porch with fireplace. The living room under a cathedral ceiling with fireplace and its own terrace access. An eat in kitchen with bay windows, breakfast nook, granite counters, Sub-Zero and Wolf range, powder room. A private office with bay windows. Laundry off a stone floored mudroom with built ins. Upstairs, a loft family room under a vaulted ceiling. Additional 2nd floor space includes a bedroom with full bath, and recreation room with adjoining bedroom and full bath that functions as a self-contained guest suite. The lower level adds a media room with wet bar, built ins and half bath, plus a second recreation room. Each room thoughtfully designed without compromise. Geothermal heating and cooling, whole house generator, noise reduction windows, cedar siding, stone exterior, wood shingle roof, three car attached heated garage and two fireplaces set the stage for effortless living.

3 Beds ⋅ 5 Baths ⋅ 24200998 MLS

This luxury custom designed home in a private country setting offers maximum privacy and comfortable living. The main level offers single floor living featuring a private primary suite with dressing room, full bath and French doors to a full screened porch with fireplace. The living room under a cathedral ceiling with fireplace and its own terrace access. An eat in kitchen with bay windows, breakfast nook, granite counters, Sub-Zero and Wolf range, powder room. A private office with bay windows. Laundry off a stone floored mudroom with built ins. Upstairs, a loft family room under a vaulted ceiling. Additional 2nd floor space includes a bedroom with full bath, and recreation room with adjoining bedroom and full bath that functions as a self-contained guest suite. The lower level adds a media room with wet bar, built ins and half bath, plus a second recreation room. Each room thoughtfully designed without compromise. Geothermal heating and cooling, whole house generator, noise reduction windows, cedar siding, stone exterior, wood shingle roof, three car attached heated garage and two fireplaces set the stage for effortless living.

700 N Wilton Rd, New Canaan

Direct Waterfront with unobstructed views of The Mystic Seaport Museum and a Private Fixed Dock. Exceptional opportunity offering an impressive 176 linear feet of seamless direct waterfront on the Mystic River, with unobstructed panoramic views across the river to the Mystic Seaport Museum with its iconic tall ships and lighthouse. 5 Bedrooms with 2 Full and 2 Half Bath Home, this charming 3,176 square foot shingled shore home is beautifully positioned on a private dead-end street just moments from Long Island Sound, this distinctive property offers and extraordinary waterfront lifestyle with boating, sailing and kayaking directly from your own shoreline. Filled with character and timeless New England Coastal Charm, the 5 bedroom residence offers a gracious and comfortable floor plan designed for both every day living and entertaining. A highly desirable FIRST FLOOR PRIMARY SUITE enjoys beautiful water views while the homes inviting living space takes full advantage of its remarkable setting. Spacious water front decks extend the living and entertaining areas outdoors, while providing and idyllic setting for dining Al Fresco, hosting waterfront cocktail parties and simply relaxing while watching the boats sail by. From sunrise over the Mystic River, to the Majestic Tall Ships of Mystic Seaport Museum, the ever-changing views provide a spectacular backdrop throughout the seasons. Live a Dream!

5 Beds ⋅ 4 Baths ⋅ 24197086 MLS

Direct Waterfront with unobstructed views of The Mystic Seaport Museum and a Private Fixed Dock. Exceptional opportunity offering an impressive 176 linear feet of seamless direct waterfront on the Mystic River, with unobstructed panoramic views across the river to the Mystic Seaport Museum with its iconic tall ships and lighthouse. 5 Bedrooms with 2 Full and 2 Half Bath Home, this charming 3,176 square foot shingled shore home is beautifully positioned on a private dead-end street just moments from Long Island Sound, this distinctive property offers and extraordinary waterfront lifestyle with boating, sailing and kayaking directly from your own shoreline. Filled with character and timeless New England Coastal Charm, the 5 bedroom residence offers a gracious and comfortable floor plan designed for both every day living and entertaining. A highly desirable FIRST FLOOR PRIMARY SUITE enjoys beautiful water views while the homes inviting living space takes full advantage of its remarkable setting. Spacious water front decks extend the living and entertaining areas outdoors, while providing and idyllic setting for dining Al Fresco, hosting waterfront cocktail parties and simply relaxing while watching the boats sail by. From sunrise over the Mystic River, to the Majestic Tall Ships of Mystic Seaport Museum, the ever-changing views provide a spectacular backdrop throughout the seasons. Live a Dream!

8 Park Pl, Groton

Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

4 Beds ⋅ 5 Baths ⋅ 24201025 MLS

Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

35 Schoolhouse Rd, Roxbury

Hermitswood is a gracious French Norman-style country estate set on eight spectacular acres, features a natural swimming pool, extensive gardens, and two-bedroom guest suite. Originally renovated by renowned architect Theo Muller, the home has been reimagined by Charles Hilton Architects, transforming it into an exceptional country retreat offering 6,321 square feet of elegant living space. The award-winning landscape design is spectacular, with beautifully curated gardens, patios, terraces, a lily pond, and two sweeping grass stairways leading to the breathtaking 30' x 95' chemical-free swimming pool. The interior is highlighted by the award-winning chef's kitchen, featuring a 48" Sub-Zero, a Lacanche range with custom hood and limestone backsplash, Waterstone fixtures, and two impressive 11' islands topped with Calacatta marble. Exceptional craftsmanship is evident throughout, including custom millwork and moldings, hardwood floors with brass inlays, a 17th-century French fireplace, antique French stone flooring, and coffered ceilings. Designed for seamless indoor-outdoor living, a spacious new terrace just off the kitchen provides the perfect setting for dining and entertaining. An upper-level deck, and an additional main-level deck, offers peaceful spaces to relax and enjoy the surrounding landscape. Rarely does a property combine architectural pedigree, extraordinary craftsmanship, and such breathtaking natural beauty. Hermitswood is truly a one-of-a-kind country estate.

6 Beds ⋅ 9 Baths ⋅ 24196787 MLS

Hermitswood is a gracious French Norman-style country estate set on eight spectacular acres, features a natural swimming pool, extensive gardens, and two-bedroom guest suite. Originally renovated by renowned architect Theo Muller, the home has been reimagined by Charles Hilton Architects, transforming it into an exceptional country retreat offering 6,321 square feet of elegant living space. The award-winning landscape design is spectacular, with beautifully curated gardens, patios, terraces, a lily pond, and two sweeping grass stairways leading to the breathtaking 30' x 95' chemical-free swimming pool. The interior is highlighted by the award-winning chef's kitchen, featuring a 48" Sub-Zero, a Lacanche range with custom hood and limestone backsplash, Waterstone fixtures, and two impressive 11' islands topped with Calacatta marble. Exceptional craftsmanship is evident throughout, including custom millwork and moldings, hardwood floors with brass inlays, a 17th-century French fireplace, antique French stone flooring, and coffered ceilings. Designed for seamless indoor-outdoor living, a spacious new terrace just off the kitchen provides the perfect setting for dining and entertaining. An upper-level deck, and an additional main-level deck, offers peaceful spaces to relax and enjoy the surrounding landscape. Rarely does a property combine architectural pedigree, extraordinary craftsmanship, and such breathtaking natural beauty. Hermitswood is truly a one-of-a-kind country estate.

148 Taunton Hill Rd, Newtown

Sun-filled Colonial set on 2 private acres with desirable east/west exposures, offering exceptional privacy and natural beauty. Thoughtfully updated throughout, the home features a renovated gourmet kitchen with premium appliances, breakfast area, and seamless connection to the family room. French doors open to a terraced deck overlooking lush grounds, mature landscaping, a charming bridge, and tranquil lush green views. The second floor offers four bdrms including a spacious primary suite with luxury bath, dressing area, and custom closets.The finished walkout lower level with full bath provides flexible space for guests, recreation, home office, gym, nanny, or in-law suite. Recent improvements include Andersen windows and doors, generator, updated mechanicals, irrigation, security system and more!

5 Beds ⋅ 6 Baths ⋅ 24185738 MLS

Sun-filled Colonial set on 2 private acres with desirable east/west exposures, offering exceptional privacy and natural beauty. Thoughtfully updated throughout, the home features a renovated gourmet kitchen with premium appliances, breakfast area, and seamless connection to the family room. French doors open to a terraced deck overlooking lush grounds, mature landscaping, a charming bridge, and tranquil lush green views. The second floor offers four bdrms including a spacious primary suite with luxury bath, dressing area, and custom closets.The finished walkout lower level with full bath provides flexible space for guests, recreation, home office, gym, nanny, or in-law suite. Recent improvements include Andersen windows and doors, generator, updated mechanicals, irrigation, security system and more!

11 Butternut Hollow Rd, Greenwich