Middletown Homes with Window/Wall Cooling

Welcome to Middletown, Connecticut – a charming city nestled in the heart of Middlesex County, where small-town warmth meets vibrant community spirit. Known for its rich history, picturesque landscapes, and a thriving arts scene, Middletown offers a unique blend of suburban charm and urban convenience. With a population that values both heritage and progress, residents enjoy a variety of local shops, restaurants, and recreational opportunities that make this city a delightful place to call home.

One of the many appealing features of Middletown’s real estate market is the availability of homes equipped with window and wall cooling systems. These homes are designed to provide you with comfort during the warm summer months, ensuring that you can relax and enjoy your living space without the sweltering heat. Whether you're looking for a cozy bungalow or a spacious family home, you'll find a range of properties that cater to your cooling preferences.

Middletown is also home to an array of parks, trails, and outdoor spaces, perfect for those who love to explore nature or engage in recreational activities. The nearby Connecticut River offers opportunities for boating and fishing, while the city’s vibrant downtown area is brimming with cultural attractions, including theaters and art galleries.

With its welcoming atmosphere and diverse housing options, Middletown stands out as a fantastic choice for anyone seeking a place to settle down. Experience the charm of this lovely city and discover the perfect home equipped with all the comforts you desire!

Newest Middletown Homes with Window/Wall Cooling

$119,000

1 Beds ⋅ 1 Baths ⋅ 24204389 MLS

*** BRAND NEW MOBILE HOME - Modern, Stylish & Ready for You! *** Be the first to call 500 Washington Street #9 home! Located in Middletown Mobile Home Park, this brand-new 1-bedroom, 1-full-bath mobile home offers fresh, modern living with everything new from the start. A welcoming 6' front porch adds charm and the perfect spot to relax outdoors. Inside, enjoy a bright, thoughtfully designed interior featuring a beautiful kitchen with new stainless steel appliances, including refrigerator, dishwasher, microwave/hood vent, and upgraded smooth-top electric range. With 200-amp electrical service and an efficient, easy-to-maintain layout, this home offers comfort, convenience, and the peace of mind that comes with owning brand new. Mobile home scheduled to be delivered onsite October 9, 2026, with anticipated move-in availability October 30, 2026. Why renovate when you can start fresh? Don't miss this opportunity to be the very first owner-schedule your showing and make #9 yours! ***Note: Home to be delivered and installed onsite. Sketch is a rendering of the New Mobile Home Model. Colors and Details may differ. New Mobile Home on Pad Site - Taxes to be determined. Purchaser to verify with local municipality.***

500 Washington St Unit #9, Middletown

$189,900

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

$499,999

3 Beds ⋅ 3 Baths ⋅ 24203636 MLS

This Dutch style Colonial offers a perfect blend of traditional charm and the airy feel everyone is looking for. From the moment you step inside, you see the open floor plan, creating a seamless flow that's well suited for quiet weeknights or for hosting a crowd. Access the multi-level deck off the back of the family room for outdoor enjoyment. The beautifully updated kitchen features stylish finishes and plenty of prep space for the home chef. The first floor is complete with an oversized full bathroom, and convenient mudroom space between kitchen and garage. On the second floor, a generous primary bedroom with great closet space is on one side of the hallway, with 2 secondary bedrooms on the other. A large bathroom with jetted tub and double sinks allows space for everyone's morning routine. The layout provides incredible flexibility, including a fourth bedroom located in the finished walkout lower level. With access to a full bath, this space serves as a private and comfortable guest suite or home office. The lower level adds significant versatility to the home with its laundry area, rec room with wet bar and slider that walks out to the lower-level patio with hot tub. Situated in a prime Middletown location, you're just moments away from the local park and Moody elementary school. With quick access to the highway the commute to work is a breeze. This home is ready for its next chapter!

141 Cimarron Rd, Middletown

$330,000

3 Beds ⋅ 2 Baths ⋅ 24201680 MLS

Welcome to 19 Kent Court, a charming Colonial tucked away on a quiet cul-de-sac in Middletown. This inviting home offers comfortable living space, thoughtful updates. The main level features a spacious living room with a large picture window and wood-burning fireplace, creating a warm and welcoming atmosphere. The updated kitchen offers granite countertops, ample cabinet space, and easy access to the deck-perfect for outdoor dining and entertaining. A formal dining room and convenient half bath complete the first floor. Upstairs, the spacious primary bedroom features a walk-in closet, along with two additional bedrooms and an updated full bathroom. The finished basement provides valuable additional living space that can be used as a home office, gym, recreation room, or additional living area. Recent improvements include a 1-year-old HVAC system, Mini split system, newer roof and boiler, and energy-efficient 2-year-old solar panels, helping provide greater energy efficiency and potentially lower utility costs. The property also includes a one-car garage.

19 Kent Ct, Middletown

$349,900

3 Beds ⋅ 2 Baths ⋅ 24201520 MLS

Located in desirable South Farms, this charming 3 bed, 1.5 bath Cape offers a comfortable and versatile floor plan with the convenience of a 1st floor primary bedroom. Warm hardwood flooring and abundant natural light create an inviting atmosphere throughout the main living areas, while the 1st floor layout provides the ease of one-level living where it matters most. The spacious primary bedroom boasts a large walk-in closet and is conveniently located just off the living area next to the recently renovated full bathroom with tub and modern shower tile. The recently renovated kitchen features modern, soft-close cabinets, stainless steel appliances, timeless subway tile backsplash, granite composite sink and an abundance of cabinet and counter space. Step outside the slider from the dining room to enjoy the rear deck overlooking the fenced-in backyard, offering a great space for relaxing, grilling, or outdoor entertaining. A mudroom with laundry brings the house, garage and backyard access conveniently together. The upper level offers 2 spacious bedrooms and a large half bath. An oversized garage provides additional storage with a workbench and room to work as well. Additional features include a newer roof, new hot water heater, newer vinyl fence, a driveway that fits 4 cars, lots of storage space in the basement and located just minutes from thriving downtown, Middlesex hospital, Wesleyan and convenient access to the highway yet tucked away in an established neighborhood.

34 Overlook Ave, Middletown

$349,000

5 Beds ⋅ 2 Baths ⋅ 24201926 MLS

Welcome to this spacious 1952 Middletown Colonial, where classic charm meets low-maintenance living in a quiet neighborhood. Step inside a welcoming foyer with an entry closet that opens into a sun-drenched living area highlighted by a large bay window. The home features stunning hardwood floors throughout, flowing into a functional kitchen complete with natural wood cabinets, Corian countertops, a matching backsplash, and durable laminate flooring. Designed for effortless lifestyle flexibility, the main level hosts two bedrooms, including the primary bedroom, alongside a full bathroom with a tub/shower. Upstairs, you will find three additional bedrooms, perfect for a home office or private gym, and a second full bathroom with a tub/shower. The expansive basement is perfect for a hobbyist equipped with a dedicated tool workbench, storage shelving, and a laundry area with a washer and dryer. Outside, the home has low-maintenance vinyl siding and a cleared, level rear yard with mature landscaping and a handy tool shed. This prime location keeps you tranquil at home while placing you just minutes from Wesleyan University, downtown restaurants, nightlife, and scenic walks at Harborpark or Wadsworth Falls State Park. Commuting is a breeze with instant access to Route 9 and Route 66. This turn-key five-bedroom gem blends comfort, space, and ultimate Connecticut convenience.

130 Spencer Dr, Middletown

$339,900

3 Beds ⋅ 1 Baths ⋅ 24200402 MLS

Welcome to 100 Jacobs Terrace, an adorable, move-in-ready, one-floor home, tucked away at the end of a quiet dead-end street with a convenient turnaround. Offering easy single-level living, this home features three bedrooms and one full bath with a comfortable and practical layout. Step outside to the fully fenced yard, where a nice deck and pergola create the perfect setting for morning coffee, outdoor dining, entertaining, or simply relaxing. While the home does not have a basement, there is a shed and attic space to provide additional storage. Ideally located in a peaceful residential setting while still close to all that Middletown has to offer, this home is convenient to shopping, dining, parks, schools, downtown Middletown, Wesleyan University, and major highways. Whether you're a first-time buyer, downsizing, or simply looking for the ease of one-floor living, 100 Jacobs Terrace is a wonderful place to call home.

100 Jacobs Ter, Middletown

$364,900

5 Beds ⋅ 3 Baths ⋅ 24199686 MLS

This well maintained colonial, located just steps from the bustling downtown of Middletown, is ready for its new owner! Three units, all on different floors, offer flexible plans for owner-occupants and investors alike! The first and second floor units are comfortably controlled with high efficiency Navien units, both with a 2 bed/1 bath layout. The third unit is also natural gas, and provides a generous sized 1 bed/1 bath unit. The units themselves are mostly updated, some with fresh paint and tile work tastefully done. A two car garage and off street parking provide ultimate convenience for owners and/or tenants. Lively flower beds decorate the front walkway, adding to the curb appeal. A back staircase seconds as small deck platforms overlooking the backyard. Whether living in one unit and renting the others for residual income, or adding this wonderful opportunity to your investment portfolio, this one is NOT to miss. Schedule your private showing today!

53 Spring St, Middletown

$649,900

9 Beds ⋅ 6 Baths ⋅ 24199960 MLS

Exceptional 3-Unit Mixed-Use Investment Opportunity A rare opportunity to own a well-maintained three-unit property offering townhouse-style living, private garages, excellent parking, and strong income-producing potential in the heart of Middletown. 227 East Main Street is an attractive investment opportunity for both seasoned investors and owner-occupants looking to build equity while generating rental income. The property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bathroom, and 1 half bathroom. The desirable layouts include bright, comfortable living spaces and eat-in kitchens, creating a residential feel that appeals to a broad range of tenants. One of the property's most compelling features is the private under-building garage for each unit, complete with direct access. This added convenience provides residents with the feel and functionality of a single-family home-an especially desirable feature in a multi-family property. Additional highlights include separate utilities, hardwood flooring, abundant natural light, basement storage, Washer dryer hook-ups in each unit, ample off-street parking, and a rear driveway providing convenient access behind the building. Separate utilities offer practical advantages for ownership and day-to-day management. Situated near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. Property being sold As Is. Agent owner related.

227 E Main St, Middletown

$400,000

3 Beds ⋅ 2 Baths ⋅ 24192947 MLS

Tastefully updated and move-in ready, this charming 3-bedroom, 2-bath home is located in Middletown's desirable South Farms area. The spacious family room features a vaulted ceiling and brand-new skylights, creating a bright and welcoming gathering space. The updated kitchen offers abundant cabinet storage, granite countertops, stainless steel appliances, and a center island. The dining room showcases hardwood flooring, a wood-burning fireplace, and access to a four-season sunroom complete with a custom-built bar, perfect for entertaining year-round. The first floor includes a bedroom with hardwood floors, a full bath, and an additional flex room ideal for a home office, playroom, or hobby space. Upstairs you'll find two additional bedrooms and a second full bath with a stand-up shower. Relax outdoors on the back deck under the gazebo overlooking the yard. Additional highlights include a one-car under-house garage, additional room in basement perfect for workout room or storage, brand-new roof with 50 year transferable warranty, and numerous updates throughout. Conveniently located within walking distance to schools and just minutes from Main Street Middletown, shopping, dining, and major highways.

25 Garfield Ave, Middletown

$449,900

3 Beds ⋅ 2 Baths ⋅ 24199578 MLS

Welcome to 147 Ridge Rd, a stunning, completely remodeled home located in the highly desirable South Farms district of Middletown! This beautifully updated property has been renovated from top to bottom and is truly move-in ready. The heart of the home is the spectacular open-concept kitchen, featuring beautiful quartz countertops and seamless flow into a bright, light-filled living room with a decorative stone fireplace. Throughout the home, you'll find beautifully refinished hardwood floors and two beautifully updated bathrooms, each featuring elegant inlaid tile showers. The dining room features a slider to an impressive 16-foot deck, creating the perfect setting for indoor and outdoor entertaining, relaxing, and enjoying the private surroundings. Major updates include a new roof and windows, a newer furnace, and new electrical wiring and electrical panel. Every detail has been thoughtfully updated to create a comfortable, stylish, and modern home. This is a must-see property! Schedule your private showing today and experience everything 147 Ridge Rd has to offer.

147 Ridge Rd, 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

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