Middletown Homes under $400,000

Welcome to Middletown, Connecticut, a charming city nestled in the heart of Middlesex County. Known for its rich history, vibrant arts scene, and picturesque landscapes, Middletown offers a unique blend of urban conveniences and small-town charm. With a population that embraces diversity and community spirit, residents enjoy a range of amenities, including delightful parks, local shops, and a variety of dining options that cater to every palate.

Middletown is also home to several educational institutions, including the renowned Wesleyan University, which adds a youthful energy to the city. The scenic Connecticut River runs alongside the city, providing opportunities for outdoor activities like kayaking, fishing, and leisurely riverside strolls. Whether you're exploring the historic downtown area or attending one of the many local festivals, there’s always something happening in Middletown.

For those seeking affordable housing options, Middletown is an excellent choice. The real estate market features a variety of homes under $400,000, making it an attractive destination for first-time buyers, families, and retirees alike. From charming single-family homes to cozy condominiums, you’ll find properties that fit your lifestyle and budget.

With its welcoming atmosphere, rich cultural offerings, and affordable housing, Middletown is more than just a place to live; it’s a community where you can thrive. Explore the possibilities and discover your dream home in this delightful city today!

Newest Middletown Homes under $400,000

$339,900

4 Beds ⋅ 2 Baths ⋅ 24210969 MLS

This is home is located convenient to Shopping center and route 9. First floor main bedroom. Addition four bedrooms on the upper level and a full bath one of the bedroom does not have a closet. Builtin hutch in the dinning area. Living room with fireplace. (never used) Hardwood floors under carpeting. Handicap Ramp A detached two car garage. Property to be sold in "as is" condition, Contingent upon probate approval. Easy to show

42 Saybrook Rd, Middletown

$274,900

3 Beds ⋅ 1 Baths ⋅ 24211027 MLS

Welcome home to 6 Johnson Street, Middletown! This charming dollhouse colonial boasts timeless architectural features, including elegant arches, stained glass accents, and classic wall paneling that exude character and warmth. Inside, enjoy the cozy yet functional layout, with inviting living and dining areas perfect for relaxing or entertaining. The bright kitchen provides plenty of space for meal preparation, including a new pantry and stainless steel appliances. The front enclosed porch offers a versatile retreat for sipping coffee or unwinding after a long day. With inviting updated paint hues, new light fixtures throughout and a redone staircase, the charm of this home has been lovingly preserved! A fully remodeled bathroom also offers a serene place to get away after a long day. The backyard is a true highlight, providing ample space for outdoor activities and gatherings. The outdoor space has been equally as cared for as the interior- with new flower plantings, a privacy fence added and a two-tiered backyard that exudes relaxation and ease in its use of space. Located in a quiet neighborhood, this home is just seconds away from the heart of Middletown, offering easy access to shopping, dining, and all the conveniences of city living all within walking distance!

6 Johnson 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

$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

$393,000

3 Beds ⋅ 2 Baths ⋅ 24210439 MLS

Welcome to this inviting contemporary-style single-family home offering 3 bedrooms, 2 full bathrooms, and approximately 1,963 square feet of living space. Situated on a level .45-acre lot, this well-maintained 1975 home offers comfortable living spaces, desirable updates, and exceptional versatility. The spacious living room features a striking cathedral ceiling, creating an open and airy atmosphere. The kitchen has been updated with new appliances, while newer carpeting adds a fresh, updated feel throughout the home. A standout feature is the finished basement, complete with its own kitchen, offering excellent additional living space and flexibility. This area is ideal for an in-law suite, extended family, guests, home office, or recreation space, providing numerous possibilities to suit your needs. Enjoy outdoor living from both the front and rear decks, perfect for relaxing, entertaining, or enjoying the generous level property. Additional features include a two-car attached garage and central air conditioning. With its spacious layout, flexible finished lower level, updated kitchen appliances, outdoor living spaces, and convenient attached garage, this contemporary home offers a wonderful combination of comfort and versatility. **This is a short sale. **

63 Millbrook Rd, 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

$369,900

6 Beds ⋅ 2 Baths ⋅ 24208513 MLS

Ideal for an investor or owner occupant this 2 family home offers 2 units 5 rooms with 3 bedrooms each. The first floor unit with hardwood floors 3 spacious bedrooms, refreshed bath, and a kitchen with a walk in pantry. The second floor has been remodeled with 3 bedrooms and the primary bedroom with a large walk in closet or storage room. Updated kitchen, laminate floor, white cabinets and walk in pantry and refreshed full bath with tile tub surround and floor. This property has a front porch and a rear porches. A walk up attic offers additional space with an option for future expansion. A full basement with a full bath and a finished room. Furnaces and Hot water heaters replaced in 2021. Driveway which will allow for 2 cars of off street parking. Great opportunity to add to a portfolio.

42 Grand St, Middletown

$369,900

3 Beds ⋅ 1 Baths ⋅ 24207903 MLS

Beautifully updated and ideally located just steps away from Wesleyan University and minutes from Downtown Middletown! This move-in-ready home features three spacious bedrooms plus a flexible bonus room with potential for a fourth-bedroom or home office with its own entrance ideal for renters, or in-law space. Enjoy hardwood floors, a large living room with fireplace, and a completely remodeled eat-in kitchen opening to the dining room with sliders to the backyard and a full bath. Lower level is not finished but features the homes 2nd fireplace already creating an inviting space should you decide to finish this space for more living area. Outside, a large deck overlooks the level backyard, perfect for entertaining or relaxing. A two-car tandem garage provides additional parking and storage. A fantastic combination of updates, space, and location! **INVESTORS TAKE NOTE: Great investment to rent out to college students with potential four bedrooms.

133 Highland Ave, Middletown

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