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1 Forest Glen Cir Unit 6, Middletown
$250,000
2 Beds ⋅ 2 Baths ⋅ 24215771 MLS ⋅ Forest Glen BLDG.
Lovely first-floor, end-unit condo with zero steps for easy entry! This surprisingly spacious home has an open-concept design, offering a roomy heart-of-the-house while keeping the bedrooms nicely separated. Step into the dining and family room, featuring a cozy fireplace and a slider to the patio with a private, locked storage closet. Down the hall at the back, you'll find a large primary suite with a walk-in closet, en suite bath, and a window seat with storage. There's also a large second bedroom, a hallway/guest bath, and a laundry room. Bedrooms are carpeted wall-to-wall, while the rest of the space has rich vinyl plank flooring. Updates include kitchen appliances (2018), hot water heater (2018), primary bath with walk-in shower (2018), washer/dryer (2021), brand-new windows and slider (2025/2026), and dishwasher (2026). Well maintained and full of upgrades-New windows and sliding glass door is WOW! Move in and enjoy easy living! One assigned parking space plus plenty of visitor spots.

1 Forest Glen Cir Unit 6, Middletown

27 Fairview Ave, Middletown
$244,900
4 Beds ⋅ 1 Baths ⋅ 24205927 MLS
Set on a quiet dead-end street near Wesleyan University and downtown Middletown, 27 Fairview Ave is a classic 1934 Colonial with character, convenience, and potential. This estate property features 1,235 sq ft, 4 bedrooms, 1 full bath, (with room for a 2nd bath on the upper level) and walk-in attic space. MAJOR RECENT IMPROVEMENTS INCLUDE: NEW ROOF IN 2024 (stripped & reroofed=1 layer), NEW 200 AMP ELECTRICAL SERVICE IN 2025, a NEW OIL BOILER AND OIL TANK in 2025 as well as a NEW CEILING IN both the LIVING ROOM and ONE BEDROOM, all of which creates a strong starting point for a remodel. Seller believes there to be oak hardwood under the carpets. The traditional layout offers defined living spaces, a manageable footprint, and room to bring fresh ideas to the kitchen, bath, finishes, and overall design. Its central Middletown location provides easy access to nearby campus, downtown shops, restaurants, parks, and commuter routes. Best suited for an investor or contractor. This property will not qualify for FHA or VA financing. Cash, renovation loan or conventional financing only. This home to be sold strictly AS-IS. Seller will not make any repairs. Sale is subject to Probate Court approval.

27 Fairview Ave, Middletown

52 Trolley Crossing Ln Unit 52, Middletown
$240,000
3 Beds ⋅ 2 Baths ⋅ 24204011 MLS ⋅ Trolley Crossing BLDG.
THIS CONDO BUILDING IS FHA APPROVED! SELLER WILLING TO OFFER $5000 CREDIT TO BUY DOWN THE RATE. Welcome to Trolley Crossing in Middletown! This well-maintained three-bedroom, one-and-a-half-bath townhouse offers a comfortable layout with generously sized bedrooms and a spacious living room. The first floor features a convenient laundry room, half bath, and a well-equipped kitchen with an updated microwave and oven, dishwasher, and refrigerator replaced approximately two years ago. Major improvements include a 2022 furnace, newer water heater, brand-new windows with a lifetime warranty, and a new roof. Step outside and enjoy the private deck, perfect for relaxing or entertaining. The association also includes water and sewer, adding even more convenience to this move-in-ready home.

52 Trolley Crossing Ln Unit 52, Middletown

15 Rising Trail Dr Unit 15, Middletown
$239,900
3 Beds ⋅ 2 Baths ⋅ 24209015 MLS ⋅ Beacon Hill Towne Homes BLDG.
Experience the timeless elegance in this beautiful 3-bedroom, 1.5-bath townhome offering 1,232 sq. ft. of bright, comfortable living space. This refined residence features three spacious bedrooms plus a versatile Flex room with skylight on the 3rd floor, seamlessly blending classic architectural details with modern, open-concept living.. This unit also includes a 1-car under unit garage, adding convenience with additional storage and a new roof. Enjoy private outdoor living on your own personal deck and take advantage of the community pool just around the corner on warm summer days. Conveniently located close to a variety of popular restaurants, shopping and biking trails all within a prime Middletown location. Perfectly positioned close to Route 9 and I-91, this home offers the ultimate lifestyle of comfort, convenience, and commuter ease, all within a well-maintained association with a low HOA of only $450 per month. Ready to schedule your showing today.

15 Rising Trail Dr Unit 15, Middletown

714 Long Hill Rd Unit 714, Middletown
$225,000
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

1231 Washington St Unit 2, Middletown
$224,500
3 Beds ⋅ 1 Baths ⋅ 24205455 MLS ⋅ Woodgate BLDG.
Enjoy one of a select few of the largest townhouse end units in the complex offering 1,109 square feet of vast living space. Nestled in a popular, well-maintained community, this home combines convenience, comfort and peace of mind with nothing to do but unpack and enjoy. Recent complex-wide improvements include new roads with abundant guest parking, new siding, roofs, and decks giving the community a fresh, updated appearance. Additional highlights include a private entrance, in-unit washer and dryer, 6 panel doors, and hot water heater only four months old. Step inside to discover an inviting open floor plan featuring a spacious living room with soaring vaulted ceilings that fill the space with natural light and create an airy, welcoming atmosphere. The main level offers a remodeled kitchen with newer cabinetry, appliances and tile flooring. Enjoy an updated full bath with deep tub / shower combination, newer glass doors, plus two generously sized bedrooms, each with sliding glass doors leading to an oversized deck-perfect for morning coffee, outdoor dining, or simply relaxing. Upstairs, a third bedroom provides flexible space ideal for guests, a home office, workout room, or additional living area. Conveniently located near shopping, restaurants, major commuter routes, and just 2.2 miles to Wesleyan University, this home presents an excellent opportunity for owner-occupants and investors alike. Cash, Conventional and CHFA Conv Financing only. Special Assessment ends 10/38.

1231 Washington St Unit 2, Middletown

280 Main St, 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

296 Carriage Crossing Ln Unit 296, Middletown
$217,500
2 Beds ⋅ 2 Baths ⋅ 24209330 MLS ⋅ Carriage Crossing BLDG.
Welcome to the desirable Carriage Crossing community, offering comfortable, low-maintenance living. The open-concept living and dining area features vaulted ceilings, oversized windows that fill the space with natural light, and a wood burning fireplace creating the perfect setting for relaxing. The kitchen well-appointed with stainless steel appliances and a breakfast bar. This layout creates an easy flow into the main living area with hardwood floors perfect for entertaining! BRAND NEW HVAC MAY 2026! Enjoy your own outdoor space, perfect for morning coffee, fall and summer evenings, or relaxing at the end of the day. The two spacious bedrooms provide comfortable retreats with closet spaces and a full private bathroom in each. In-unit laundry off the kitchen and exterior storage add everyday convenience. Carriage Crossing offers an array of amenities, including a swimming pool, clubhouse, fitness facilities, tennis and racquetball courts, and additional recreational spaces. Conveniently located near shopping, restaurants, Route 9, I-91, and the Cromwell area, this home combines an easy lifestyle with excellent everyday accessibility.

296 Carriage Crossing Ln Unit 296, Middletown

36 Rising Trail Dr Unit 36, Middletown
$217,500
3 Beds ⋅ 2 Baths ⋅ 24111633 MLS
Prime location near the pool & clubhouse - just in time for Summer! Welcome to 36 Rising Trail Drive, a beautifully maintained condo nestled in the desirable Westlake area of Middletown. This spacious unit offers a bright and open layout with generous living and dining areas, perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, ample counter space, and appliances. Upstairs, you'll find comfortably sized bedrooms, with plenty of closet space. Additional highlights include in-unit laundry, a private patio for outdoor relaxation, and convenient Carport. Located in a quiet, well-managed complex with easy access to shopping, restaurants, and major highways-this home offers the perfect blend of comfort, style, and location. Don't miss the opportunity to make it yours!

36 Rising Trail Dr Unit 36, Middletown

201 College St Unit 10, Middletown
$199,000
2 Beds ⋅ 2 Baths ⋅ 24205649 MLS ⋅ Hamlin Court BLDG.
Welcome to a bright and updated townhouse-style condo offering a comfortable layout and several features that set it apart. The first floor has been refreshed with luxury vinyl plank flooring and includes a spacious living area, dining space, and modern-style kitchen. Upstairs, two bedrooms are accompanied by a versatile bonus room featuring a vaulted ceiling and skylight, offering an ideal spot for a home office, reading room, gym, or creative space. Newer windows installed in 2020. One of the best highlights is the private composite deck overlooking the courtyard, creating an enjoyable outdoor space without the maintenance of a traditional yard. The unit also includes in-unit laundry, dedicated enclosed basement storage, 1 parking spot in the private lot and some overflow parking. With the association currently having capacity for rentals, this condo offers flexibility for an owner occupant or investor. Conveniently located next to Wesleyan's art building, near Downtown Middletown, Wesleyan University, shopping, dining, and major commuter routes. Cash buyers only.

201 College St Unit 10, Middletown

201 College St Unit 20, Middletown
$179,900
2 Beds ⋅ 2 Baths ⋅ 24193843 MLS ⋅ Hamlin Court BLDG.
This freshly painted townhouse-style condo offers 2 bedrooms, 1.5 bathrooms, newer windows, updated appliances, newer flooring throughout, and an open-concept layout. The main level features a spacious living room that flows into the dining area and kitchen, along with access to a private terrace. The kitchen includes tile flooring, a mosaic tile backsplash, and appliances replaced within the past three years. Upstairs are two bedrooms with spacious closets, a full bathroom, and convenient in-unit laundry with a new washer and dryer. Previously rented for $1,900 per month, this investor-friendly unit offers strong income potential. Additional features include a dedicated storage unit, one assigned parking space, and visitor parking. Ideally located within walking distance of Downtown Middletown, Wesleyan University, and Middlesex Hospital, with easy access to restaurants, shopping, and major commuter routes.

201 College St Unit 20, Middletown

170 Rising Trail Dr Unit 170, Middletown
$175,000
3 Beds ⋅ 2 Baths ⋅ 24203716 MLS ⋅ Beacon Hill Towne Homes BLDG.
Opportunity awaits in this spacious three-bedroom, one-and-a-half-bath townhouse offering three levels of flexible living space and immediate occupancy. Enjoy the convenience of your own private entrance and a covered carport that helps protect your vehicle from the elements year-round. The main level features a functional kitchen and an open living and dining area with sliders leading to outdoor space-perfect for relaxing or entertaining. Upstairs, you'll find two comfortable bedrooms, a full bath, and conveniently located second-floor laundry. The private third-floor bedroom offers separation from the rest of the home and includes a dedicated storage area, making it ideal for a bedroom, home office, or quiet retreat. Pets are allowed, giving pet owners the freedom to truly feel at home. With its practical layout, valuable amenities, immediate availability, and attractive price, this townhouse is ready for its next owner. Schedule your showing today!

170 Rising Trail Dr Unit 170, Middletown

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