Middletown Homes under $250,000

Welcome to Middletown, Connecticut, a charming city nestled in the heart of Middlesex County! Known for its rich history, vibrant community, and stunning natural landscapes, Middletown offers a unique blend of small-town charm and urban convenience. With a population of just over 47,000 residents, this city is a welcoming place where neighbors become friends and families thrive.

Middletown boasts a variety of recreational opportunities, including beautiful parks, scenic walking trails, and access to the Connecticut River, perfect for kayaking and fishing enthusiasts. The city is also home to a thriving arts scene, highlighted by the renowned Wesleyan University, which hosts numerous cultural events and performances throughout the year.

For those looking to settle down in this delightful city, Middletown offers a range of affordable housing options, including homes priced under $250,000. Whether you're a first-time homebuyer, a young family, or someone looking to downsize, you'll find a variety of charming single-family homes, cozy townhouses, and inviting condominiums that fit your budget. These properties are often characterized by their unique architectural styles and well-maintained neighborhoods, providing a perfect backdrop for creating lasting memories.

With its excellent schools, diverse dining options, and a strong sense of community, Middletown is an ideal place to call home. Explore our listings today and discover the perfect property that fits your lifestyle and budget in this wonderful city!

Newest Middletown Homes under $250,000

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

$215,000

2 Beds ⋅ 1 Baths ⋅ 24210298 MLS ⋅ Quail Run Village BLDG.

Why rent when you can own this immaculate 2-bedroom townhouse in great location at Quail Run. The open floorplan which includes the kitchen with all stainless-steel appliances, dining area and living room with newer laminate flooring for easy maintenance. There is a slider to deck overlooking wooded area from the kitchen. The 2nd floor has a primary bedroom with double closets, a guest bedroom and a recently remodeled bathroom. Unit includes an oversized heated under garage with laundry area. There is a pool for summer enjoyment.

163 Cynthia Ln Unit D5, Middletown

$195,000

2 Beds ⋅ 1 Baths ⋅ 24202808 MLS ⋅ Woodgate BLDG.

An airy sense of scale and an exceptional outdoor setting define this spacious second-level residence at the Woodgate condo complex in Middletown. A thoughtfully added entry area provides a convenient place for coats and shoes before leading into the main living space. Beautiful natural light and a soaring cathedral ceiling enhance the combined living and dining area, which opens to the kitchen for a welcoming setting to relax or gather with guests. An oversized loft adds another dimension to the home, offering generous space for a dedicated office, bonus bedroom, creative studio, or additional lounge. Both bedrooms feature sliding glass doors to one of the home's signature features: an expansive Trex deck overlooking a peaceful, treed view. This outdoor retreat offers a lovely place for morning coffee or unwinding at the end of the day, with stairs providing direct access to the rear grounds. In-unit laundry with an all-in-one washer/dryer adds everyday convenience. Nearby Washington Street shopping, downtown Middletown's restaurants and boutiques, and the trails and waterfalls of Wadsworth Falls State Park enrich the location. Route 66 connects to I-91 and Route 9. Discover the space you've been looking for and a deck you'll want to linger on, schedule your private showing and experience this home firsthand.

1231 Washington St Unit 12, Middletown

$250,000

2 Beds ⋅ 2 Baths ⋅ 24208721 MLS

Beautifully updated 1895 Colonial in the heart of Middletown, offering 735 square feet of thoughtfully renovated living space. Both full bathrooms have been tastefully redone with new vanities, tile surrounds, and modern fixtures. Throughout the home you'll find fresh paint, new flooring, and updated light fixtures, plus a new central heating system for year-round comfort. Outside, enjoy a fenced yard, off-street parking, and a storage shed - all on a low-maintenance lot just a mile from downtown Middletown, Wesleyan University, museums, libraries, grocery stores, and Middlesex Hospital. A move-in ready opportunity in a walkable, convenient location.

3 Prospect Pl, Middletown

281 Burgundy Hill Ln Unit 281, Middletown

$149,000

2 Beds ⋅ 1 Baths ⋅ 24207692 MLS ⋅ Peppermill Village BLDG.

Welcome to this well-maintained condo in Middletown, offering comfortable living with a convenient layout. The main level features an open kitchen and living area, primary bedroom, and full bathroom. Head upstairs via the spiral staircase to the loft-style second bedroom, creating a unique and flexible space. Enjoy your own balcony with additional outdoor storage, along with the convenience of in-unit laundry. Situated on the top floor, this condo offers a comfortable setting while remaining conveniently located for commuters, with easy access to Route 9 and I-91. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home, this condo is ready for its next owner. Come take a look and see all it has to offer!

281 Burgundy Hill Ln Unit 281, 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

87 Carriage Crossing Ln Unit 87, Middletown

$249,000

2 Beds ⋅ 2 Baths ⋅ 24208127 MLS ⋅ Carriage Crossing BLDG.

Enjoy comfort, convenience, and low-maintenance living at Unit 87, ideally situated with a courtyard view in the sought-after Carriage Crossing community. This open-concept home features vaulted ceilings, soaring windows, and a living room fireplace. The kitchen, complete with a breakfast nook, opens to the main living space for easy everyday living and entertaining. Two bedrooms, each with its own bathroom, offer privacy and flexibility, while in-unit laundry and central air add everyday convenience. Sliding doors lead to an outdoor patio-an inviting spot for morning coffee-and additional exterior storage adds functionality. This pet-friendly community offers impressive amenities, including a clubhouse, swimming pool, fitness center, and tennis and racquetball facilities. Brand-new exterior security cameras have been installed throughout the complex. Conveniently located near shopping, restaurants, Wesleyan University, Route 9, and I-91, with access to Middlesex Hospital, Yale New Haven Hospital, and Hartford Hospital. Whether you're purchasing your first home, downsizing, or seeking a low-maintenance lifestyle, Unit 87 is ready to welcome you.

87 Carriage Crossing Ln Unit 87, Middletown

$215,000

3 Beds ⋅ 2 Baths ⋅ 24201724 MLS ⋅ Beacon Hill Towne Homes BLDG.

Welcome to 3 Rising Trail Court, a spacious 3-bedroom townhouse tucked within the private Beacon Hills community of Middletown. One of this home's standout features is its location within the complex, backing to a peaceful wooded area that provides a wonderful sense of privacy and a natural backdrop. Inside, the open living and dining areas offer plenty of room to spread out, while a charming brick fireplace creates a warm and inviting focal point. The updated kitchen features abundant cabinetry, tile backsplash and plenty of workspace. Upstairs, you'll find three generously sized bedrooms, along with the convenience of in-unit laundry. A private carport adds everyday ease and additional protection from the elements. When warmer weather arrives, take advantage of the community swimming pool and enjoy the low-maintenance lifestyle Beacon Hills has to offer. Conveniently located near shopping, dining, highways and everything Middletown has to offer, 3 Rising Trail Court combines space, privacy and community amenities in one inviting package.

3 Rising Trail Ct Unit 3, 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

$220,000

2 Beds ⋅ 1 Baths ⋅ 24206382 MLS ⋅ Forest Glen BLDG.

"WOW" Run - do not walk to see this spectacular 2nd floor Forest Glen condo! One floor living at its best. The open concept will impress with large great room with fireplace, oversized galley kitchen with breakfast bar, stainless steel appliances including brand new refrigerator, and dining area. Sliders leading to your fantastic-sized deck to enjoy the summer months and outdoor space. Large windows throughout makes this home exceptionally bright and sunny. Good-sized primary bedroom with plenty of closet space. Second bedroom or office. Recent updates include top of the line entire new heating and cooling system with smart thermostat, brand new sliders, new flooring in kitchen, freshly painted. Just bring yourself and all your things and move right in! Convenient location on Cromwell border with easy access to major highways, shopping and dining. Just a short 5-minute drive to downtown Middletown offering an array of restaurants from fine dining to pizza, Main Street shopping and picturesque CT River boardwalk. An easy 25-minute ride to some of CT's most beautiful shoreline towns and beaches.

14 Forest Glen Cir Unit 13, Middletown

316 Carriage Crossing Ln Unit 316, Middletown

$199,900

2 Beds ⋅ 2 Baths ⋅ 24197276 MLS ⋅ Carriage Crossing BLDG.

Welcome to this bright and inviting condo offering comfortable, low-maintenance living! The open living and dining area features soaring vaulted ceilings, oversized windows that fill the space with natural light, and a cozy, wood burning fireplace with built-in shelving. Off the living room is a private outdoor space, perfect for enjoying your morning coffee or relaxing at the end of the day. The kitchen offers ample cabinet and counter space, a convenient breakfast bar, tile flooring, and in-unit laundry. The 2 spacious bedrooms feature a walk-in closet in one and a double closet in the other, both with direct access to their private full bathroom. Neutral finishes and new carpeting throughout showcase a clean canvas ready for your personal style. The new heat pump for the central air and forced hot air provide efficiency and energy savings. Abundant storage including an exterior storage unit right outside your door add to the everyday convenience. Amenities just a short walk away include a pool, jacuzzi, sauna, tennis court, basketball court, racketball court, and clubhouse with kitchen to host larger gatherings at no additional cost. All while centrally located on the Middletown/Cromwell line with easy access to major highways, shops and restaurants. New features include heat pump, hot water heater 2022 and dishwasher 3-4 years old. Just bring your finishing touches and make this well-designed condo your own!

316 Carriage Crossing Ln Unit 316, 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

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