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$429,000
3 Beds 2 Baths 24196637 MLS
Welcome to 76 George St, Middletown! This 1,600 SF home offers 3 bedrooms, a spacious kitchen, and plenty of potential to make the property your own. The walk-out lower level features roughed-in plumbing, creating an exciting opportunity for additional living space, a recreation area, or a possible in-law apartment. Set on nearly one acre of land, the property offers additional road frontage on Boston Rd and the potential for an additional structure, subject to zoning and approvals. With generous land, flexible space, and multiple possibilities for future use, this property offers an excellent opportunity for homeowners, investors, or those looking to create additional living space. A lease-to-own option is also available. Don't miss this unique opportunity-bring your vision and explore the possibilities!

76 George St, Middletown

$450,000
2 Beds 2 Baths 24196263 MLS
Welcome to 1511 Country Club Rd, a charming 2-bedroom Cape with the posability of 5- bedrooms offering comfort, character, and exceptional versatility. This inviting home features a flexible layout with a private in-law suite or separate living space-perfect for multi-generational living, guests, a private home office or income possibility. Step outside to enjoy the expansive backyard, offering plenty of room for entertaining, gardening, or relaxing. A fenced-in area provides a safe and secure space for people or pets to play, while the rest of the large yard offers endless opportunities to enjoy the outdoors. Whether you're looking for your first home, room to grow, or a property with flexible living options, this charming Cape is a wonderful place to make your next home.

1511 Country Club Rd, Middletown

$699,000
4 Beds 3 Baths 24197740 MLS
Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.

20 Chimney Hill Rd, Middletown

$299,900
2 Beds 3 Baths 24197288 MLS
Welcome to 824 Randolph Rd, Middletown! You'll fall in love with this beautiful ranch offering the convenience of one-floor living, a two-car garage, and an inviting in-ground pool with patio that's perfect for relaxing or entertaining. Step inside to find a bright, spacious living room with a beautiful fireplace, an eat-in kitchen with stainless steel appliances, and a dining room featuring a cozy wood stove. Most of the interior has been freshly painted, giving the home a fresh, welcoming feel throughout. The home offers two full bathrooms, plus a convenient half bath located just off the primary suite and with easy access to the pool-perfect for guests while entertaining. The expansive basement offers endless possibilities for a home gym, office, media room, or additional living space. Complete with energy-efficient solar panels, this home truly has something for everyone!

824 Randolph Rd, Middletown

$425,000
4 Beds 2 Baths 24197069 MLS
Welcome to 104 Bell Street - a rare find on 2.6 private acres in the heart of Middletown. This 4-bedroom, 2 full bath home offers a truly unique setting where you drive down a long, secluded driveway and cross a bridge over Sawmill Brook to arrive at your own private oasis. Fully updated throughout, this home features a renovated kitchen, updated bathrooms, new flooring, new 200-amp electrical service, new AC unit and furnace, new oil tank, an updated well system, and a resurfaced bridge. The wooded, incredibly private lot offers endless potential - whether you envision expanded outdoor living, gardens, or simply the peace and quiet of your own retreat tucked away from the world. Despite the secluded feel, the property is easy to show and conveniently located with quick access to I-91, Wesleyan University, and downtown Middletown. With so much already done, this is a move-in ready home with room to dream on 2.6 acres. Buyer to verify flood zone designation and obtain flood insurance quotes prior to purchase. Agent/Owner.

104 Bell St, Middletown

$554,900
3 Beds 3 Baths 24196131 MLS
Beautifully updated Saltbox Colonial in Middletown's Westfield neighborhood! This 3-bedroom, 2.5-bath home offers a spacious, open floor plan with the perfect balance of classic charm and modern updates. The updated kitchen featuring granite countertops, stainless steel appliances, and a bright eat-in dining area with cathedral ceilings and a slider leading to the expansive deck-ideal for indoor and outdoor entertaining. The kitchen flows seamlessly into the impressive family room with soaring cathedral ceilings, a custom fireplace with a pellet stove, and a second slider providing even more access to the deck and backyard. Hardwood floors run throughout the first floor, which also features a formal living room and formal dining room, offering flexible spaces for gatherings and everyday living. Upstairs, the spacious primary suite is a true retreat with an updated full bath, and dual closets. An open hallway overlooks the family room below, adding to the home's bright and airy feel. Two additional generously sized bedrooms and a full bath complete the second floor. The fully finished lower level provides exceptional space, perfect for a playroom, recreation room, home office, gym, or media room. You'll also find a dedicated laundry room and a cedar closet for additional storage. Outside, enjoy the expansive deck overlooking the fully fenced backyard-perfect for summer entertaining. Enjoy evening strolls or bike rides through the 3 cul-de-sacs of Sylvan Run.

897 East St, Middletown

$394,500
3 Beds 2 Baths 24195917 MLS
Welcome to 45 Annette Place! This beautifully maintained home is truly move-in ready and has so much to offer. The updated kitchen features granite countertops, stainless steel appliances, and recessed lighting, creating a bright and modern space. Hardwood floors flow throughout the living room and bedrooms, adding warmth and timeless appeal. The partially finished basement provides additional living space and is complete with a cozy pellet stove-perfect for relaxing year-round. Need room for vehicles, hobbies, or storage? The impressive 3-car garage offers endless possibilities. Outside, you'll be welcomed by beautifully landscaped grounds that add exceptional curb appeal and create a wonderful outdoor setting to enjoy. This is a home you'll be proud to own!

45 Annette Pl, Middletown

$465,000
2 Beds 3 Baths 24195232 MLS
Experience elevated living in this brand-new luxury townhome, thoughtfully designed with quality craftmanship, modern finishes, and an open concept layout ideal for everyday living and entertaining. This is a spacious 2 bedroom 2.5 bath home. The chef-inspired kitchen showcases GE stainless steel appliances, white shaker cabinetry, premium quartz countertops, sleek black hardware, and coordinating designer fixtures throughout. Beautifully finished bathrooms, spacious living areas, prefinished engineered hardwood flooring, and abundant natural light creates a sophisticated yet inviting atmosphere. Additional features include central air, city water and sewer, washer and dryer hookups, an attached one car garage with dedicated storage, and professionally designed landscaping with blue stone steppingstones leading to the sidewalk. Ideally located in desirable Middletown, this exceptional new construction community offers low maintenance luxury living just minutes from vibrant downtown, Weslyn University, Wadsworth Falls State Park, the Connecticut River, restaurants, shopping, entertainment and major highways.

61 W St Unit 15, Middletown

$419,900
1 Beds 2 Baths 24195008 MLS
Experience elevated living in this brand-new luxury townhome, thoughtfully designed with quality craftsmanship, modern finishes, and an open-concept layout ideal for everyday living and entertaining. This spacious 1-bedroom, 1.5-bath home features a versatile loft perfect for a home office, den, or flex space. The chef-inspired kitchen showcases GE stainless steel appliances, white shaker cabinetry, premium quartz countertops, sleek black hardware, and coordinating designer fixtures throughout. Beautifully finished bathrooms, spacious living areas, and abundant natural light create a sophisticated yet inviting atmosphere. Additional features include central air, city water and sewer, washer and dryer hookups, an attached one-car garage with dedicated storage, and professionally designed landscaping with bluestone stepping stones leading to the sidewalk. Ideally located in desirable Middletown, this exceptional new construction community offers low-maintenance luxury living just minutes from vibrant downtown, Wesleyan University, Wadsworth Falls State Park, restaurants, shopping, entertainment, and major highways.

61 W St Unit 13, Middletown

$385,000
3 Beds 2 Baths 24193289 MLS
Welcome home to this beautifully remodeled 3 bedroom, 2 full bath home that's truly move in ready! Enjoy relaxing on the inviting front porch or entertaining in the fenced backyard. The updated kitchen features stainless steel appliances, plenty of cabinet and counter space, and room for meal preparation. The spacious living room offers a cozy fireplace and new flooring, creating a warm and inviting atmosphere. The finished lower level provides additional living space with two finished rooms, a full tiled bathroom, and a laundry area with washer and dryer. Perfect for a family room, home office, gym, playroom, or guest space. Recent updates include central air, windows, flooring, fenced backyard, along with many additional improvements. This home is conveniently located near shopping, restaurants and parks and offers the perfect combination of comfort, style, and convenience. Don't miss your opportunity to make this beautiful home yours!

49 George St, Middletown

$425,000
3 Beds 1 Baths 24195038 MLS
Welcome to this charming 3-bedroom, 1-bath ranch nestled on the highly sought-after Higby Road. Set on a generous half-acre lot, this home offers the perfect opportunity for first-time buyers, downsizers, or anyone looking to add their personal touch. Inside, you'll find comfortable one-level living with a functional layout, hardwood floors, and a cozy fireplace. Additional features include an attached garage, partially finished basement for extra living or storage space, and a peaceful backyard with plenty of room to relax or entertain. Conveniently located near shopping, dining, parks, and major commuter routes, this home combines a desirable location with endless potential. Don't miss your chance to make this Higby Road gem your own!

104 Higby Rd, Middletown

$395,000
3 Beds 3 Baths 24194117 MLS
Welcome home to this charming property located at the end of a peaceful cul-de-sac. This residence features three bedrooms, including a primary bedroom with an ensuite full bathroom. There are two updated full bathrooms in total, along with a convenient half bath. As you enter, you'll notice the gleaming hardwood floors that flow throughout the main living areas. The kitchen is thoughtfully designed with granite countertops, maple wood cabinets, and stainless steel appliances, offering a great setup for everyday cooking. The dining area seamlessly connects to the cozy living space, which features a gas fireplace and a mini-split system, providing an additional heating and cooling option for year-round comfort. From the dining area, sliding doors open to a patio with Trex decking, complete with a retractable awning, perfect for providing shade when needed and easily rolled back for sunny days. The two-car garage provides direct access to a finished basement area that includes a half bathroom and laundry facilities, enhancing the home's functionality. Energy-efficient solar panels ensure excellent coverage, leading to no current electric bill. Step outside to discover a private walking path accessible right from your backyard. This home is fully move-in ready, waiting for you to create lasting memories.

3 Yellow Pine Cir, Middletown

$539,999
3 Beds 3 Baths 24191099 MLS
Welcome to this beautifully updated 3-bedroom Contemporary- ranch style home, privately set on a lush .92-acre lot. A charming wraparound covered porch creates an inviting first impression and a wonderful place to relax. Inside, vaulted ceilings, abundant natural light, fresh paint and new luxury vinyl flooring enhance more than 1,600 square feet of above-grade living space, with an additional 800+ square feet on the lower level. The home offers 2 full and 1 half baths, including a primary bathroom upgraded in 2022. More than $70,000 in recent improvements include a new upper-level balcony, siding, refinished deck, Driveway, new appliances and a washing machine installed in 2025. Additional updates include a 30-year architectural roof installed in 2004, replacement shingles adjacent to the rear balcony in 2026, a new central-air condenser installed in 2016 and two 100-amp electrical panels, including one installed in 2018. The versatile lower level features a heated family room with a fireplace, a new sliding door and existing plumbing, creating exciting possibilities for an en-suite guest area, potential in-law, home office, studio or salon. Buyers should perform their own diligence regarding any intended use and applicable municipal requirements and approvals. The outdoor space has been beautifully refreshed with more than $5,000 in new landscaping and a brand-new saltwater above-ground pool installed just three weeks ago...

1512 Country Club Rd, Middletown

$677,000
4 Beds 3 Baths 24193869 MLS
Welcome to this beautifully maintained 4+-bedroom, 2.5-bath Colonial conveniently located in the heart of Middletown. Freshly painted and move-in ready, this home offers the rare combination of generous living space, flexible room options, entertaining areas, and valuable recent updates-including a new roof in 2025. The spacious eat-in kitchen features a center island and bright breakfast nook with skylight, opening directly into a welcoming great room with a fireplace and built-in sound system. It's an ideal layout for both everyday living and entertaining. But the feature you'll want to see is the approximately 500-square-foot first-floor fifth bedroom/media room. With a projector and surround sound already in place, it's perfect for movie nights, watching the big game, or hosting friends. Because of its size and location, it can easily be transformed into a first-floor primary suite, guest suite, home office, gym, playroom, or recreation space. Upstairs, four generously sized bedrooms provide plenty of room for family, guests, or dedicated work-from-home space. A separate living room and formal dining room offer even more flexibility for entertaining.

166 Mccormick Ln, Middletown

$229,900
3 Beds 1 Baths 24192281 MLS
Welcome to 21 Inverness Ln. Make this spacious 3 bedroom your new home. This home is nestled in the sought-after Highland Lake Community. The home features an open floor plan with generous sized rooms. Upon entering, you'll be met with an updated kitchen and a comfortable dining area. The adjacent family room features laminate flooring and sliders to a private fenced in patio complete with a pergola to shield you from the sun on scorching hot summer days. The upstairs features 3 spacious bedrooms, updated full bathroom, laundry nook and an area for den, office or media play. The 2-car garage also has an additional storage area off the back. You can enjoy single family home living without the extensive yard work. This home is waiting for your next summer party. Highest and best Sunday, 7/26 by 5:00 PM.

21 Inverness Ln, Middletown

$759,000
3 Beds 3 Baths 24189442 MLS
Welcome to South Farms, where "staycation" is a way of life. This custom-built home is made for lazy mornings on the wraparound porch and sunny afternoons by the pool - all behind a brand-new full privacy fence with an acre of land. The grounds bloom spring through fall, and a charming chicken coop with its own shed adds hobby-farm charm. Inside, an open-concept layout shines with soaring cathedral ceilings, skylights, and a dramatic floor-to-ceiling fireplace. The kitchen boasts new appliances and flows into a breakfast bar and dining area made for gathering. A flexible downstairs den works as a fourth bedroom, playroom, office, or media room. Spacious full sized unfinished basement perfect for pool table and endless storage. The main floor primary bedroom suite offers a fully renovated bathroom and French doors leading to your own backyard oasis. A heated in-ground pool, lush plantings, and a footbridge over a koi pond to a pool house complete with a half bath! Upstairs, a sunny loft overlooks the living room; two bedrooms feature built-in window seats, and a huge room ready for anything; gym, playroom, extra bedroom; you name it. City sewer means no septic to worry about. Homes like this don't come around often. Come make it yours.

236 Maple Shade Rd, Middletown

$399,900
3 Beds 3 Baths 24190665 MLS
Classic Colonial on a picture-perfect lot with sweeping pastoral views in one of Middletown's most scenic settings! This home offers solid bones, generous room sizes, and loads of potential for anyone ready to add their own touches. The sun-filled living room offers oversized windows and flows easily into the dining area, while the beamed family room delivers warmth and character with wood paneling and a brick fireplace. The eat-in kitchen features ample counter space, stainless appliances, and a picture window overlooking the private backyard. A main-level laundry room and half bath add everyday convenience. Upstairs you'll find three comfortable bedrooms, including a spacious primary suite with its own private bath and double closets, plus a second full bath off the hall. The finished lower level adds fantastic flexible space with a large recreation room and dry bar - perfect for movie nights, a home office, or gym. Step outside and this property truly shines: an expansive deck with covered gazebo overlooks a sprawling, level backyard bordered by mature trees and open field views - a wonderful setting for entertaining or simply unwinding at the end of the day. Additional highlights include a two-car garage, mini-split systems for efficient heating and cooling, and a peaceful country feel just minutes from shopping, schools, and Route 9. Opportunities to own this view, space, and charm don't come along often. Bring your vision and make it home!

9 Round Hill Rd, Middletown

$898,000
4 Beds 5 Baths 24187393 MLS
Lakeshore Realty is proud to present 49 Partridge Lane, a beautifully maintained home tucked away on a quiet cul-de-sac in one of Middletown's most desirable neighborhoods. Designed for both everyday living and entertaining, this exceptional home features a bright, open floor plan, spacious living areas, and a beautifully appointed kitchen complete with premium Viking stainless steel appliances, offering both luxury and performance for the home chef. One of the property's most unique features is its location abutting the Mt. Higby Reservoir, providing a peaceful natural backdrop, enhanced privacy, and picturesque views. Enjoy direct access to nature while relaxing in your private backyard, perfect for entertaining, gardening, or unwinding after a long day. Generously sized bedrooms, well-designed living spaces, and meticulous upkeep make this home truly move-in ready. Conveniently located just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, golf courses, and major highways, you'll enjoy the perfect combination of tranquility and accessibility. With high-end finishes, a sought-after location, and the rare benefit of bordering protected natural surroundings, 49 Partridge Lane offers an outstanding opportunity to own a home that blends comfort, quality, and lifestyle. Schedule your private showing today!

49 Partridge Ln, Middletown

$1,295,000
4 Beds 4 Baths 24187574 MLS
Nestled on an extraordinary 39-acre estate with breathtaking panoramic views, this stunning custom log home offers the perfect blend of rustic elegance, modern comfort, and exceptional investment potential. Originally built in 2005 with an addition completed in 2014, the home features 4 bedrooms and 3 full bathrooms. The interior showcases soaring cathedral ceilings, beautiful tile flooring, ceiling fans throughout, and a dramatic two-sided fireplace that serves as a focal point for multiple living areas. German-engineered windows with roll shutters & premium German doors provide exceptional quality. Kitchen features new appliances & an open concept. 2 bedrooms with full bathrooms on the main level offer one-floor living options. The lower level includes 2 oversized garages providing abundant storage, workshop space, and room for recreational equipment. A wood/storage shed adds even more utility. This home is in pristine condition with brand new well, new water heater, and 2 central air units. The property consists of three separately deeded parcels presenting a rare opportunity for future investment, development, or resale. The land features rolling acreage, mature trees, open spaces, and a picturesque man-made pond. Whether you're seeking a private retreat, recreational haven, family compound, or property with investment upside, this one-of-a-kind estate delivers stunning natural beauty, exceptional craftsmanship, and limitless possibilities.

1409 Millbrook Rd, Middletown

$649,900
4 Beds 4 Baths 24183475 MLS
Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and solid wood doors throughout. The floor plan provides plenty of flexibility for everyday living, entertaining, working from home, or accommodating changing needs over time. The partially finished walkout lower level adds valuable bonus space and offers a variety of potential uses, including a recreation room, home office, gym, hobby area, or possible in-law setup. Direct access to the yard makes the space feel like a natural extension of the home. Conveniently located near Middletown's amenities while offering a quieter setting, this property provides space, functionality, and quality construction in a sought-after area of town. Estate sale subject to probate court approval.

76 Thimble Rock Rd, Middletown

$224,900
3 Beds 2 Baths 24175733 MLS
Beautifully updated home tucked away on a quiet cul-de-sac offering the perfect blend of comfort, functionality & major recent improvements. The open floor plan creates a bright, inviting feel, complemented by hardwood floors throughout the main level. The kitchen was updated in 2022 with new cabinetry, quartz countertops & a clean modern look ideal for everyday living. The flexible layout includes a convenient first-floor bedroom, while upstairs offers two generously sized bedrooms. Both bathrooms were tastefully renovated in 2022. Additional updates completed in 2022 include the roof, gutters, siding, electrical panel, water heater & fresh interior paint throughout the entire home, providing peace of mind for years to come. Move-in ready with modern updates in a desirable cul-de-sac setting.

2 Hillside Ct, Middletown

$599,900
4 Beds 2 Baths 24162489 MLS
Historic 1868 South Farms area of Middletown Home with Exceptional Outbuildings Step back in time while enjoying the comfort of modern updates in this distinctive 1868 home, set on a property filled with character, history, and functionality. The home features three bedrooms, 1 1/2 baths, an upstairs office, and a completely remodeled kitchen area. The full-height basement has a granite foundation, poured concrete floor, and floor drains, while an updated electrical box adds peace of mind. The property is framed by magnificent pine trees believed to be among some of the oldest in Middletown, creating a truly memorable setting at the front of the home. The outbuildings offer an exceptional amount of space and versatility: * Three-story barn with an insulated bonus room on the third floor * Heated one-car garage with a concrete floor and insulated office- ideal for a workshop, studio, or home business. * Second one-car garage with a concrete floor, attic storage, and a gardening area with shelving on the first level. * Three-bay open shed, including one bay with a concrete slab.

110 Freeman Rd, Middletown

$209,900
3 Beds 2 Baths 24163396 MLS
This classic 1900 Colonial at 103 Prospect Street offers a chance to bring new life to a well-loved home in a convenient Middletown location. With 1,160 square feet of living space, three bedrooms, and two full baths, the layout is simple and functional, ready for someone with vision to make it their own. The home does require work, making it a great project for investors, renovators, or buyers looking to build equity over time. Set on a manageable lot, this property is part of an estate and is being sold as-is. If you've been waiting for an opportunity to create something from the ground up, this could be the one worth exploring! as is, where is, with remaining contents at closing. Subject to probate approval

103 Prospect St, Middletown

$289,609
4 Beds 2 Baths 24158805 MLS
Welcome to this inviting contemporary home in Middletown offering the perfect blend of comfort, style, and convenience. This well maintained 4 bedroom, 2 bath residence features 1,328 square feet of thoughtfully designed living space ideal for today's lifestyle. Step inside to discover an updated kitchen with modern finishes, providing a functional and attractive space for everyday living and entertaining. Both bathrooms have been tastefully updated, adding a fresh, move in ready feel throughout the home. The flexible floor plan offers four bedrooms, giving plenty of room for family, guests, or a home office. One of the home's most convenient features is the second floor laundry, making daily chores easier and more efficient. With its contemporary style, smart layout, and desirable updates, this home offers a fantastic opportunity to enjoy comfortable living in a convenient location close to shopping, dining, parks, and major commuting routes. Don't miss your chance to make this beautiful Middletown home your own.

34 Inverness Ln, Middletown

$675,000
2 Beds 2 Baths 24133669 MLS
Experience Carefree Living at Founders' Ridge - the Premier 55+ Award-Winning Community! Introducing our newest Model Home -our sought after "KIRBY II", now available for early 2027 occupancy! This is the last Kirby at this price point! Nestled in the highly desirable Westfield section of Middletown, this thoughtfully designed 1,555 sq. ft. single-level home offers both luxury and ease in one perfect package. Elegant Interior Features include stunning white cabinetry, quartz countertops, and a walk-in pantry for style and function. Hardwood flooring throughout the main living areas, with tile in baths and laundry for durability. A bright bay window in the front room offers sweeping views and a private rear patio is ideal for relaxing or entertaining. Comfort All Year Long: Enjoy the convenience of natural gas heating and central A/C. Some photos shown are of similar homes and may include upgrades. Agent/Owner related.

145 Webster Ln Unit 2-41, Middletown

$589,900
2 Beds 2 Baths 24123204 MLS
Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "MARTIN II," Under CONSTRUCTION! Now with many new UPGRADES - available for occupancy in early 2027 Located in the highly sought-after Westfield section of Middletown, this beautiful 1,430 sq. ft. home has the convenience of single-floor living with top-of-the-line features and Elegant Design: Enjoy the sophistication of wood cabinetry with granite countertops and a walk-in pantry. Hardwood floors flow through out the main living areas, while tile flooring is featured in the baths and laundry room. A deck at the rear of the home creates the perfect space to relax and entertain. The home is equipped with natural gas and central A/C for year-round comfort. Some photos similar and depict some upgrades. Agent/Owner related. Come see why our motto is "Choose a Carefree Lifestyle!"

137 Webster Ln Unit 2-42, Middletown

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