Browse All Middletown CT Properties with Pool for Sale

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

$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

$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

$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

$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

$199,900

3 Beds ⋅ 2 Baths ⋅ 24202713 MLS ⋅ Beacon Hill Towne Homes BLDG.

***Multiple offers received, deadline for final offers is Monday 9/7 at 5pm. ***Welcome to 27 Rising Trail Court, a spacious 3-bedroom, 1.5-bath townhouse-style condo offering three levels of living space, a two-car carport, and a desirable end-unit location! Step inside to an open-concept main level featuring luxury vinyl flooring throughout, where the recently updated kitchen overlooks the dining area and sunken living room. The kitchen features granite countertops, stainless steel appliances, recessed lighting, and plenty of workspace, with a convenient half bathroom nearby. Just beyond, the sunken living room is filled with natural light from sliding glass doors that lead directly to your private back deck. Upstairs, the second floor offers two generously sized bedrooms with wall-to-wall carpeting, a dedicated laundry area, and a remodeled full bathroom featuring tile flooring, a tiled tub/shower surround, and an updated vanity. Continue to the third floor where you'll find an additional bedroom along with a large unfinished storage area offering excellent potential for additional usable space. Additional highlights include a brand-new water heater installed earlier this year, two-car covered parking, pool access, and an end-unit location situated beside the community swing set. The association also allows one dog or one cat, making this a great option for pet owners. Offered at $199,900, this is a fantastic opportunity to make the move from renting to homeownership!

27 Rising Trail Ct, 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

$369,900

4 Beds ⋅ 1 Baths ⋅ 24198560 MLS

Back on Market, and meant to be for You!! This adorable Cape boasts 4 bedrooms, an Open Layout, Fully Finished Basement, and an Enchanting private, flat fenced yard with a pool, Magnificent Weeping Willow tree, Firepit, and Gazebo. The Main level welcomes a friendly open layout connecting the open kitchen to the living room with cozy wood burning fireplace, Primary bedroom, Full bathroom, and another bedroom which can be used as an office if a 4th is not needed, as well as a laundry area quietly tucked away. Enter the Breezeway with dramatic wood vaulted ceiling, and french doors looking out to the patio and pool, which is currently being used as a Romantic Dining Room. Upstairs you will find two ample sized bedrooms. The Fully Finished basement offers more room for an In-Law possibility complete with kitchen and full bath. The oversized Tandem garage will hold 3 compact cars, or two large trucks and motorcycles, or hobbies. The roof is 5 years old, and the solar panels are owned and convey with the home at no additional cost to save you money on your electric bill. Located in a convenient location for commuting close to 91, route 9, close to shopping, restaurants, golf courses and more. Must Come see!!

171 Smith St, Middletown

$299,900

2 Beds ⋅ 3 Baths ⋅ 24197288 MLS

Welcome to 824 Randolph Rd, Middletown! You'll fall in love with this beautiful ranch offering the convenience of one-floor living, a two-car garage, and an inviting in-ground pool with patio that's perfect for relaxing or entertaining. Step inside to find a bright, spacious living room with a beautiful fireplace, an eat-in kitchen with stainless steel appliances, and a dining room featuring a cozy wood stove. Most of the interior has been freshly painted, giving the home a fresh, welcoming feel throughout. The home offers two full bathrooms, plus a convenient half bath located just off the primary suite and with easy access to the pool-perfect for guests while entertaining. The expansive basement offers endless possibilities for a home gym, office, media room, or additional living space. Complete with energy-efficient solar panels, this home truly has something for everyone!

824 Randolph Rd, Middletown

$379,900

4 Beds ⋅ 2 Baths ⋅ 24196455 MLS

Welcome home to this charming Cape Cod-style house, offering 1,874 square feet of comfortable living space, plus an additional 150 square feet of finished space in the basement. This inviting four-bedroom, 2 full bath home is nestled in a wonderful neighborhood, combining timeless charm with everyday comfort. The updated kitchen is ready for cooking, gathering, and entertaining, while the spacious living room features a cozy fireplace-perfect for relaxing evenings at home. A one-car garage and an outdoor storage shed provide added convenience and plenty of room for tools, lawn equipment, or seasonal storage. Step outside to a spacious deck overlooking the backyard, creating a wonderful setting for morning coffee, outdoor dining, or simply enjoying the peaceful surroundings. The property also includes an above-ground pool that offers great potential and just needs a little TLC to be enjoyed again. The upper bathroom present an excellent opportunity to update and personalize the home to your own style, allowing you to add value while making the space uniquely yours. With its generous layout, desirable location, updated kitchen, classic Cape Cod character, and inviting outdoor living space, this home is ready to welcomes its next owners. VERY MOTIVATED SELLERS!

25 Morgan St, Middletown

$600,000

4 Beds ⋅ 4 Baths ⋅ 24178710 MLS

HIGHEST AND BEST OFFERS DUE WEDNESDAY AUG 12th by 10AM!! Exceptional 4 bedroom, 3.5 bath Split Level offering over 2,800 sq ft of beautifully maintained living space, perfectly situated on a quiet cul-de-sac in one of Middletown's desirable neighborhoods. Conveniently located just minutes from vibrant Main Street Middletown, you'll enjoy easy access to popular restaurants, shops, local amenities, & major highways for an effortless commute. The heart of the home is the spacious kitchen featuring a large center island, ideal for entertaining & gathering w/ family & friends. Hardwood floors flow throughout the home, leading to a dramatic living room w/ vaulted ceilings & a cozy gas fireplace. A formal dining room provides the perfect setting for holiday gatherings & special occasions. The expansive primary suite features vaulted ceilings, a walk-in closet w/ convenient laundry, & a luxurious ensuite bath complete w/ a soaking tub, separate shower, & double vanity. Three additional generously sized bedrooms include one w/ a private full bath, while a second full hallway bath serves the remaining bedrooms. Outdoor living is equally impressive w/ a large deck featuring an awning & propane hookup for grilling. The backyard is designed for summer enjoyment w/ an inground pool surrounded by brick pavers & a pool house for storage. The partially finished walk-out basement provides additional living space, 1/2 bath, & direct access to the pool area. Continued ...

51 Snipes Ter, Middletown

$180,000

3 Beds ⋅ 2 Baths ⋅ 24194531 MLS ⋅ Beacon Hill Towne Homes BLDG.

Investment Opportunity! This spacious condo is being sold as-is and offers excellent potential for investors or buyers looking to build sweat equity. The unit features gleaming hardwood floors throughout, a partially finished basement offering additional living or storage space, and a finished attic that adds even more usable square footage. A convenient 1.5 bath layout rounds out the floor plan. Enjoy community amenities including access to a sparkling in-ground pool. Conveniently located near I-91 and Route 9, offering easy access for commuters. With its combination of extra finished space, low-maintenance hardwood flooring, and community amenities, this unit presents a strong opportunity for value-add renovation or rental income. Sold as-is.

106 Rising Trail Dr Unit 106, Middletown

$539,999

3 Beds ⋅ 3 Baths ⋅ 24191099 MLS

Welcome to this beautifully updated 3-bedroom Contemporary- ranch style home, privately set on a lush .92-acre lot. A charming wraparound covered porch creates an inviting first impression and a wonderful place to relax. Inside, vaulted ceilings, abundant natural light, fresh paint and new luxury vinyl flooring enhance more than 1,600 square feet of above-grade living space, with an additional 800+ square feet on the lower level. The home offers 2 full and 1 half baths, including a primary bathroom upgraded in 2022. More than $70,000 in recent improvements include a new upper-level balcony, siding, refinished deck, Driveway, new appliances and a washing machine installed in 2025. Additional updates include a 30-year architectural roof installed in 2004, replacement shingles adjacent to the rear balcony in 2026, a new central-air condenser installed in 2016 and two 100-amp electrical panels, including one installed in 2018. The versatile lower level features a heated family room with a fireplace, a new sliding door and existing plumbing, creating exciting possibilities for an en-suite guest area, potential in-law, home office, studio or salon. Buyers should perform their own diligence regarding any intended use and applicable municipal requirements and approvals. The outdoor space has been beautifully refreshed with more than $5,000 in new landscaping and a brand-new saltwater above-ground pool installed just three weeks ago...

1512 Country Club Rd, Middletown

$759,000

3 Beds ⋅ 3 Baths ⋅ 24189442 MLS

Welcome to South Farms, where "staycation" is a way of life. This custom-built home is made for lazy mornings on the wraparound porch and sunny afternoons by the pool - all behind a brand-new full privacy fence with an acre of land. The grounds bloom spring through fall, and a charming chicken coop with its own shed adds hobby-farm charm. Inside, an open-concept layout shines with soaring cathedral ceilings, skylights, and a dramatic floor-to-ceiling fireplace. The kitchen boasts new appliances and flows into a breakfast bar and dining area made for gathering. A flexible downstairs den works as a fourth bedroom, playroom, office, or media room. Spacious full sized unfinished basement perfect for pool table and endless storage. The main floor primary bedroom suite offers a fully renovated bathroom and French doors leading to your own backyard oasis. A heated in-ground pool, lush plantings, and a footbridge over a koi pond to a pool house complete with a half bath! Upstairs, a sunny loft overlooks the living room; two bedrooms feature built-in window seats, and a huge room ready for anything; gym, playroom, extra bedroom; you name it. City sewer means no septic to worry about. Homes like this don't come around often. Come make it yours.

236 Maple Shade Rd, Middletown

$215,000

2 Beds ⋅ 2 Baths ⋅ 24188722 MLS ⋅ Carriage Crossing BLDG.

Welcome home to this sought-after condo complex at Carriage Crossing, where you will find this two bedroom two full bath unit, with open concept space. The galley kitchen has pantry. Both bathrooms have granite countertops and soft close cabinetry. In unit washer and dryer. Living room has a cozy wood-burning fireplace. Primary bedroom has a walk-in closet, and both bedrooms have their own full baths, and offer plenty of room. Unit offers recently replaced washer/dryer, water heater and the microwave. HVAC replaced 4 years ago. Take advantage of the incredible amenities, including an inground pool, clubhouse, basketball court, fitness center, racquetball, and tennis courts, and clubhouse available for events. This association is Pet friendly (allowing up to two pets small dogs only and/or cats) Conveniently located near shopping, dining, major highways and downtown Middletown. Also located near major employers and Medical centers, including Middlesex Hospital, and easy commutes to Yale New Haven Hospital and Harford Hospital, and near Wesleyan University. Property is ideal for owner occupants or investors seeking low maintenance living in a well managed community.

93 Carriage Crossing Ln Unit 93, Middletown

$229,900

2 Beds ⋅ 2 Baths ⋅ 24184158 MLS ⋅ River's Edge BLDG.

Come see this beautiful freshly painted two bedroom, 2 bath remodeled unit which has Corian countertops and white cabinetry for a bright and light kitchen. All kitchen appliances are stainless steel and the flooring is tile. Walk into the dining room/living room with tile flooring and overhead fan to the slider for some extra views of the CT. River! Both bedrooms have Bamboo wood flooring with large windows and closets. The washer and dryer are in the unit. The HOA covers heat, hot water, water and sewer, air conditioning, trash, heated indoor pool, fitness room, community room, plowing, renovated elevator and ground maintenance. The fob opens the pool, fitness, storage and community room to enter. Each unit has it's own storage in the basement of this complex. It's close to Middlesex Hospital, Wesleyan University, Tates (riverfront restaurant) and downtown Middletown with shops and restaurants.

111 Dekoven Dr Unit 609, Middletown

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Middletown Homes with Pool

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