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$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
$689,000
2 Beds ⋅ 2 Baths ⋅ 24205132 MLS
Expect the best! Carefree living at Founders' Ridge, the premier award-winning 55+ community in Central Connecticut! Introducing the highly sought-after Kirby II model home, now available for IMMEDIATE occupancy. This is the last Kirby II available at this price point. Located in Middletown's desirable Westfield section, this thoughtfully designed 1,555-square-foot, single-level home offers an ideal blend of comfort, style, and convenience. Inside, you'll find elegant white cabinetry, quartz countertops, and a spacious walk-in pantry that combine beauty with functionality. Hardwood flooring flows throughout the main living areas, while the bathrooms and laundry room feature durable tile flooring. A bright bay window in the front room fills the space with natural light and offers sweeping views. Outside, the private rear patio provides the perfect setting for relaxing or entertaining. Additional highlights include natural gas heating and central air conditioning for year-round comfort. Some photos are of similar homes and may include optional upgrades. Agent/owner related.

Unit 2-41 Webster Ln Unit 145, 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
$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
$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
$649,900
9 Beds ⋅ 6 Baths ⋅ 24199960 MLS
Exceptional 3-Unit Mixed-Use Investment Opportunity A rare opportunity to own a well-maintained three-unit property offering townhouse-style living, private garages, excellent parking, and strong income-producing potential in the heart of Middletown. 227 East Main Street is an attractive investment opportunity for both seasoned investors and owner-occupants looking to build equity while generating rental income. The property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bathroom, and 1 half bathroom. The desirable layouts include bright, comfortable living spaces and eat-in kitchens, creating a residential feel that appeals to a broad range of tenants. One of the property's most compelling features is the private under-building garage for each unit, complete with direct access. This added convenience provides residents with the feel and functionality of a single-family home-an especially desirable feature in a multi-family property. Additional highlights include separate utilities, hardwood flooring, abundant natural light, basement storage, Washer dryer hook-ups in each unit, ample off-street parking, and a rear driveway providing convenient access behind the building. Separate utilities offer practical advantages for ownership and day-to-day management. Situated near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. Property being sold As Is. Agent owner related.

227 E Main St, 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
$625,000
3 Beds ⋅ 3 Baths ⋅ 24201081 MLS
Welcome to 23 Brookview Lane, a spacious Colonial tucked into the desirable Westfield section of Middletown. Set in a beautiful residential community, this home offers a great combination of space, privacy, and a comfortable layout with plenty of room to grow. Inside, beautiful hardwood floors run through much of the main living area, while the fireplace creates a warm focal point and a perfect place to gather. The kitchen and dining areas offer plenty of room for everyday living and entertaining, with direct access to the rear deck overlooking the backyard. Upstairs, you'll find spacious bedrooms and a primary suite complete with its own private full bathroom and walk-in closet, giving the homeowners a comfortable space of their own. The additional bedrooms offer plenty of flexibility for family, guests, or a home office. Downstairs, the fully finished walk-out lower level adds another dimension to the home and can easily serve as a second family room, recreation space, office, gym, or playroom. One of the highlights of the property is the outdoor setting. Step out onto the deck and enjoy views of the private, lightly wooded backyard, creating a peaceful setting for morning coffee, summer gatherings, or simply relaxing at the end of the day. The attached two-car garage and sizable private driveway provide ample parking and additional convenience. Located just minutes from Spencer School, Middletown High School, shopping, restaurants, parks, and major commuter routes, Broo

23 Brookview Ln, Middletown
$605,000
4 Beds ⋅ 3 Baths ⋅ 24198723 MLS
Welcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable Middletown neighborhood, privately set back from the road. Featuring an updated kitchen, new windows throughout, remodeled baths and a finished walk-out basement with a full bathroom this home offers space, flexibility and privacy. The finished lower level provides potential for an in-law apartment or separate living space, subject to town approval, making it ideal for extended family, guests, a home office or recreation. The expansive deck overlooks a beautiful yard for entertaining, a game of catch or running with your favorite four legged pal. Close to major highways, 20 minutes from Downtown Hartford, 35 minutes to New Haven, 45 minutes to CT Casinos, a little over an hour to the Rhode Island line and minutes from Wesleyan University, great shopping and restaurants in downtown Middletown! Major updates include: Brand New Septic- 2019 Kitchen remodeled - 2024 All windows replaced - 2024 Basement remodeled - 2023 Garage doors replaced - 2023 Full bathroom remodeled - 2022 AC air handler & condenser - 2021 Electrical upgrades & generator hookup - 2021 Well pump - 2021 Front door - 2021 Paver walkway & gutter/fascia improvements - 2020 Chimney repair & cap - approx. 2019 Boiler -2014 With a private setting, extensive updates, 4 bedrooms, 2.5 baths and a versatile walk-out lower level, this Middletown Colonial is ready to welcome its next owner!

85 Oakcliff Rd, Middletown

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