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$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
$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
$220,000
24188906 MLS
An exceptional opportunity to acquire a well-established restaurant that has successfully served the Middletown community for 26 years. This turnkey operation is strategically positioned in a high-traffic corridor surrounded by schools, office parks, medical facilities, and densely populated residential neighborhoods, generating consistent customer traffic and strong year-round demand. The business benefits from an efficient operating model, a loyal repeat customer base, and a fully trained, long-tenured staff already in place. With decades of successful operation, the restaurant has earned a strong reputation within the community and offers a proven foundation for continued growth and profitability. Recent renovations and upgraded kitchen equipment enhance the property's appeal and operational efficiency. The business is designed for smooth day-to-day management with minimal owner oversight, making it an ideal opportunity for an owner-operator or an experienced restaurant group seeking to expand its portfolio. To ensure a seamless transition, the current owner will provide comprehensive training and support at no additional cost.

280 Main St, Middletown
$215,000
2 Beds ⋅ 2 Baths ⋅ 24188722 MLS ⋅ Carriage Crossing BLDG.
Welcome home to this sought-after condo complex at Carriage Crossing, where you will find this two bedroom two full bath unit, with open concept space. The galley kitchen has pantry. Both bathrooms have granite countertops and soft close cabinetry. In unit washer and dryer. Living room has a cozy wood-burning fireplace. Primary bedroom has a walk-in closet, and both bedrooms have their own full baths, and offer plenty of room. Unit offers recently replaced washer/dryer, water heater and the microwave. HVAC replaced 4 years ago. Take advantage of the incredible amenities, including an inground pool, clubhouse, basketball court, fitness center, racquetball, and tennis courts, and clubhouse available for events. This association is Pet friendly (allowing up to two pets small dogs only and/or cats) Conveniently located near shopping, dining, major highways and downtown Middletown. Also located near major employers and Medical centers, including Middlesex Hospital, and easy commutes to Yale New Haven Hospital and Harford Hospital, and near Wesleyan University. Property is ideal for owner occupants or investors seeking low maintenance living in a well managed community.

93 Carriage Crossing Ln Unit 93, 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
$229,900
2 Beds ⋅ 2 Baths ⋅ 24184158 MLS ⋅ River's Edge BLDG.
Come see this beautiful freshly painted two bedroom, 2 bath remodeled unit which has Corian countertops and white cabinetry for a bright and light kitchen. All kitchen appliances are stainless steel and the flooring is tile. Walk into the dining room/living room with tile flooring and overhead fan to the slider for some extra views of the CT. River! Both bedrooms have Bamboo wood flooring with large windows and closets. The washer and dryer are in the unit. The HOA covers heat, hot water, water and sewer, air conditioning, trash, heated indoor pool, fitness room, community room, plowing, renovated elevator and ground maintenance. The fob opens the pool, fitness, storage and community room to enter. Each unit has it's own storage in the basement of this complex. It's close to Middlesex Hospital, Wesleyan University, Tates (riverfront restaurant) and downtown Middletown with shops and restaurants.

111 Dekoven Dr Unit 609, 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
$4,500,000
4 Baths ⋅ 24182009 MLS
Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts.

423 Main St, Middletown
$249,000
3 Beds ⋅ 2 Baths ⋅ 24176493 MLS ⋅ Ridgely Condo BLDG.
Nestled in the highly sought-after Wesleyan Hills community, this well-maintained and affordable 3-bedroom condo offers the perfect blend of comfort, convenience, and privacy. Featuring an open floor plan, the home boasts an updated kitchen that flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. A sliding glass door leads to your own private deck overlooking a peaceful, quiet setting. The finished walk-out lower level provides additional flexible living space ideal for a family room, home office, or gym. Conveniently located just minutes from downtown Middletown, Wesleyan University, Middlesex Hospital, shopping, restaurants, and major highways, this property offers easy access to everything while still enjoying a serene neighborhood atmosphere. Enjoy nearby parks, hiking trails, golf courses, and the Connecticut River waterfront. A wonderful opportunity to own in one of Middletown's most desirable communities

714 Long Hill Rd Unit 714, Middletown
$679,900
24175820 MLS
Exceptional opportunity to own a beautifully maintained commercial property in one of Middletown's most desirable and visible locations. Currently operating as a professional attorney's office, this versatile building offers endless potential for professional, medical, office, boutique, or mixed-use possibilities. Perfectly positioned across from the historic town green and hospital, and just moments from downtown restaurants, shops, and major commuter routes, the location offers outstanding convenience and exposure. Blending timeless historic charm with modern updates, the property features an inviting entrance, impressive grand staircase, and a tastefully updated interior that preserves elements of the home's original character while incorporating modern finishes and functionality. Dedicated off-street parking, with charging for your EV, provides added convenience for clients and staff. The upper level offers exceptional flexibility with an updated full kitchen featuring quartz countertops, a luxurious full bath with a full tile shower, and two bedrooms. Ideal for an owner-occupant or live/work setup, you can simply walk downstairs to work each day. The sellers have also obtained city approval for a future rooftop expansion, creating the opportunity for an upscale rooftop terrace or executive entertaining space overlooking the downtown setting. A rare landmark-style property combining character, convenience, and future potential in an unbeatable location.

27 Pleasant St, Middletown
$650,000
3 Baths ⋅ 24173282 MLS
Industrial condo unit 5 located at 362 Industrial Park Road in Middletown offering a total of 8545 square feet, including 5,000+ square feet of office space and 3,000+ square feet of warehouse space. The property features 15 private offices, three bathrooms, ADA accessibility, and 440 amp three phase power to support a wide range of operations. The warehouse area includes two loading docks for efficient distribution. Gas central heating and cooling serve the space. Situated within a well maintained industrial park with convenient access to I-91, this clean and move in ready property is zoned IT (Interstate Trade) and is available for both sale and lease.

362 Industrial Park Rd Unit 5, Middletown
$1,695,000
1 Baths ⋅ 24157523 MLS
The perfectly situated and meticulously maintained medical/office campus at 51 & 57 South Main Street in Middletown is now being offered for sale. The properties will have 6,618sf available for occupancy at the time of sale leaving ample room for a new owner and their medical practice or an investor bringing a new tenant/tenants with them. The properties are located directly across the street from Middlesex Hospital offering healthcare providers the convenience of just a quick walk to and from their procedures. The shared 30+ car parking area was freshly paved and striped less than a year ago and there is no deferred maintenance to speak of. The lone tenant at the properties is on a triple net lease relieving ownership of a portion of the maintenance, property tax and insurance burden. Financials and interior photos are available upon request. -Location: The properties are located directly across from Middlesex Hospital's main campus -Well Maintained: The current owner operated his ENT practice here for decades and has taken meticulous care and great pride in the upkeep of the properties -Income: The lone medical tenant pays good rent on a landlord-friendly triple net lease -Convenience: The campus is located just off of CT Route 9 which connects to I-91, I-95 and I-84 -Value-Add: 1,772sf basement at 57 South Main can be converted to paid tenant storage or possibly addit

51-57 S Main St, 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
$399,900
2 Baths ⋅ 24131954 MLS
Location, Location, Location! Nice 1482sf retail building in the heart of Main St. Middletown. High traffic area, property currently being used as smoke shop, but can fit many other retail needs. Building is Zoned B-1. Currently being leased until Nov.2026

346 Main St, Middletown
$999,999
24130767 MLS
Position your business for success at 575 Main Street, a full-floor office condominium offering over 7,800 square feet of modern, light-filled workspace in downtown Middletown. This suite thoughtfully balances private offices, open collaboration areas, and meeting rooms, all serviced by an elevator and ADA-compliant restrooms. Meticulously maintained by a single tenant since 2008, it combines immediate professional appeal with long-term reliability. Ideally located just minutes from Middlesex Hospital, Wesleyan University, Pratt & Whitney, and the Superior Court, the property is part of a federally designated Opportunity Zone and sits within Middletown's Riverfront Redevelopment, offering both strategic value and growth potential. With a Walk Score of 93, vibrant downtown amenities, and convenient access to Route 9, 575 Main Street represents a rare opportunity to secure a premier office condominium in one of Connecticut's most dynamic markets. Owner Financing Available

575 Main St Unit STE 2, Middletown
$479,900
2 Baths ⋅ 24053933 MLS
*** Prime Commercial Property for Sale - 110 Coe Ave, Middletown, CT *** Discover an exceptional investment opportunity with this versatile commercial property. Ideal for a wide range of business ventures, this property allows both flexibility and prime location appeal. Featuring a spacious interior, ample parking, and excellent visibility, it's perfectly suited for retail, office, or mixed-use development. Ideally positioned in Middletown with easy access to I-91 and so close to Route 9. Conveniently located near Middlesex Hospital, one of the top medical facilities in the region, providing heathcare and attracting a steady flow of traffic. In close proximity to Wesleyan University, Middlesex Community College, Xavier High School and local Middletown schools, offering potential customer base and employee convenience. Directly next to Tradewinds Shopping Center with Restaurants, Retail Shops and Car Wash. This property is perfect for retail stores, medical offices, a professional facility, or a mixed-use development. Take advantage of this rare opportunity to own a prime piece of Middletown's commercial real estate. Whether you're expanding your business or looking for a new investment, 110 Coe Ave has the perfect blend of location, flexibility, and potential.

110 Coe Ave, Middletown

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