Middletown Condos for Sale

Welcome to Middletown, Connecticut, a vibrant city nestled in the heart of Middlesex County. Known for its rich history, diverse culture, and picturesque landscapes, Middletown offers a unique blend of urban conveniences and small-town charm. With its bustling downtown, adorned with eclectic shops, delightful eateries, and cultural venues, residents enjoy a lively atmosphere that fosters community engagement and creativity. The city is also home to Wesleyan University, which enriches the area with a youthful energy and a variety of cultural events throughout the year.

For those considering a move to this enchanting city, our selection of condos for sale in Middletown presents an exceptional opportunity to embrace a modern lifestyle while being surrounded by the beauty of Connecticut. These condos offer a perfect balance of comfort and convenience, featuring contemporary designs, spacious layouts, and amenities that cater to today’s discerning buyers. Whether you’re looking for a cozy one-bedroom retreat or a larger unit for entertaining guests, there’s something for everyone in Middletown’s thriving condo market.

Imagine waking up to stunning views, enjoying morning coffee on your private balcony, or taking a leisurely stroll along the Connecticut River. With easy access to parks, recreational activities, and a robust public transportation system, you’ll find that Middletown is not just a place to live, but a place to thrive. Explore our listings today and discover your dream condo in this inviting city where community spirit and modern living harmoniously intertwine. Welcome home to Middletown!

Newest Middletown Condos for Sale

$234,999

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

$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

$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

$245,000

3 Beds ⋅ 2 Baths ⋅ 24204011 MLS ⋅ Trolley Crossing BLDG.

Welcome to Trolley Crossing in Middletown! This well-maintained two-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

$199,900

2 Beds ⋅ 2 Baths ⋅ 24205044 MLS ⋅ Trolley Crossing BLDG.

This townhouse style condo is in a great location with easy access to both Hartford and New Haven. Close to the Rt 9 and I-91 highway ramps. This 2 bedroom 1 1/2 bath unit is in need of updating but well worth the efforts. Ready for your upgrades, along with a private deck in the complex. Key features include: - Parking: 2-car garage plus 2 dedicated driveway spaces in front of the garage, providing ample parking. - Included Amenities: Newer washer and dryer, plus a 65" wall-mounted TV. Stereo rack system 200 AMP electric Service - Updates: Roof was replaced in 2025. AC unit and Furnace were all replaced in 2013. Swimming pool in the complex. Low H.O.A cost compared to other area condo's - Exterior: Assessment repairs are underway, with new siding and painting scheduled for completion soon. Driveway repairs.

95 Trolley Crossing Ln Unit 95, Middletown

$329,900

3 Beds ⋅ 2 Baths ⋅ 24201404 MLS ⋅ Arawana Estates BLDG.

Welcome to Arawana Estates, where historic charm meets modern comfort in a truly unique setting! Located within a beautifully converted mansion, this rarely available penthouse-style condo offers a spacious & distinctive layout filled with character & natural light. High ceilings, hardwood floors, recessed lighting, oversized windows & custom built-ins create a warm & inviting atmosphere throughout. The updated kitchen features crisp white cabinetry, leathered granite countertops with breakfast-bar seating, stainless steel appliances & a new Bosch dishwasher. Beautifully appointed baths offer granite finishes, subway tile & a relaxing soaking tub. The impressive primary bedroom is a standout, offering generous proportions, beautiful hardwood flooring, a fireplace & extensive custom built-in cabinetry & shelving. In-unit laundry & abundant storage add everyday convenience. Set within an intimate 6-unit community, Arawana Estates is surrounded by expansive lawns, mature trees, distinctive stonework & picturesque views, creating a peaceful & private setting just minutes from everything Middletown has to offer. Conveniently located near Wesleyan University, downtown Middletown, restaurants, shopping, parks, trails & public transportation. Veterans Memorial Park is also nearby, offering a community pool, splash pad & walking trails. A rare opportunity to own a one-of-a-kind residence combining historic architecture, modern updates, generous living space & beautiful surroundings.

122 Newfield St Unit 3A, 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

$219,900

3 Beds ⋅ 2 Baths ⋅ 24203872 MLS ⋅ Ridgely Condo I BLDG.

MULTIPLE OFFERS RECEIVED - PLEASE SUBMIT HIGHEST AND BEST BY END OF DAY MONDAY SEPT 7, 2026. Bring Your Vision to Wesleyan Hills! This is the kind of opportunity buyers love-a 3-bedroom, 11/2-bath townhouse in the desirable Wesleyan Hills community, priced more than $70,000 below other condos in the complex. If you've been looking for a home where you can put your own stamp on things and build equity along the way, this could be the one. Freshly painted from top to bottom, the home gives you a clean starting point for your updates and ideas. The living room features a cozy fireplace, perfect for gathering on chilly evenings, while the generously sized deck is ready for morning coffee, afternoon relaxing, or summer entertaining. And then there's Wesleyan Hills itself. Set on 288 beautifully planned acres, the community offers an uncommon connection to nature, with about 30 acres of woods, fields, ponds, and two miles of walking paths winding through the property, complete with bridges and tunnels. It feels like a peaceful retreat while still being close to everything you need. Downtown Middletown is less than 10 minutes away, with restaurants, shopping, and the energy of Wesleyan University nearby. Easy access to Route 9 and Route 17 makes commuting toward Hartford or New Haven convenient as well. Sold as-is and priced with the opportunity in mind, this is your chance to create the home you've been imagining-at a price that gives you room to make it your own.

868 Long Hill Rd Unit 868, Middletown

$220,000

1 Beds ⋅ 1 Baths ⋅ 24202361 MLS ⋅ Carriage Crossing BLDG.

Welcome to 277 Carriage Crossing Lane, where soaring ceilings, a charming loft, and a beautiful fireplace create a home you'll love coming back to. The inviting layout offers a comfortable, open feel with a cozy kitchen and versatile loft space perfect for a home office, reading nook, creative space, or relaxing retreat. Curl up by the fireplace on a cool evening or step outside and enjoy the community pool and hot tub when it's time to unwind. Warm, welcoming, and full of character, this is a home that truly feels like your own. Come see it and imagine yourself here!

277 Carriage Crossing Ln Unit 277, Middletown

$299,900

3 Beds ⋅ 2 Baths ⋅ 24201757 MLS ⋅ Ridgely Condo Ii BLDG.

Welcome to 774 Long Hill Road, a meticulously maintained 3-bedroom, 1.5-bath townhouse in the desirable Wesleyan Hills community. Lovingly cared for by the same owner for the past 20 years, this home offers durable, easy-care laminate flooring throughout and annually serviced mechanicals for added peace of mind. The spacious eat-in kitchen opens through sliding doors to a large private deck, perfect for outdoor dining and relaxation. A finished lower level provides additional flexible living space for a recreation room, home office or gym. Additional highlights include a new washer, thermal windows, low-maintenance vinyl siding, two parking spaces and a roof approximately 10 years old. Set across 288 scenic acres, Wesleyan Hills offers a truly special neighborhood setting with ponds, fields, wooded open spaces and approximately two miles of walking paths connected by charming footbridges and tunnels. The community is also home to the historic Barns at Wesleyan Hills, a picturesque event venue overlooking the water. Just moments away, the beautiful Wadsworth Mansion and surrounding parklands offer miles of additional trails, seasonal events and popular outdoor summer concerts. Enjoy peaceful surroundings and a wonderful sense of community, all just three miles from vibrant downtown Middletown.

774 Long Hill Rd Unit 774, Middletown

$249,900

2 Beds ⋅ 2 Baths ⋅ 24198658 MLS ⋅ Carriage Crossing BLDG.

Welcome to 210 Carriage Crossing Lane, a desirable end-unit condo offering comfort, convenience, and low-maintenance living in the popular Carriage Crossing community. This bright and inviting 2-bedroom, 2-bath home features an open floor plan with a vaulted ceiling and fireplace in the living room, creating a spacious and comfortable gathering area. The kitchen opens easily to the main living space, while in-unit laundry adds everyday convenience. Step outside to your private patio, perfect for relaxing or enjoying your morning coffee, with additional exterior storage for added functionality. Carriage Crossing offers an impressive selection of amenities, including a clubhouse, swimming pool, fitness center, and tennis/racquetball facilities. Conveniently located near shopping, restaurants, Route 9 and I-91, this end unit combines a great location with easy condo living. Whether you're looking for your first home, downsizing, or simply seeking a low-maintenance lifestyle, 210 Carriage Crossing is one you won't want to miss!

210 Carriage Crossing Ln Unit 210, Middletown

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