Middletown Real Estate

Welcome to Middletown, Connecticut – a charming city where rich history meets vibrant community spirit. Nestled in Middlesex County, Middletown offers a unique blend of small-town warmth and urban convenience, making it an ideal place to call home.

Middletown is steeped in history, with roots dating back to the 17th century. Its picturesque downtown area boasts beautifully preserved architecture, quaint shops, and delightful eateries that cater to every palate. Stroll along Main Street and discover local boutiques, art galleries, and cozy cafes, all contributing to the city’s inviting atmosphere.

For nature enthusiasts, Middletown offers an array of outdoor recreational opportunities. The nearby Connecticut River provides stunning views and a perfect backdrop for kayaking, fishing, or simply enjoying a leisurely walk along the waterfront. Parks like Wadsworth Falls State Park invite families and individuals alike to explore hiking trails, picnic areas, and breathtaking waterfalls.

Education is a cornerstone of the Middletown community, with a range of public and private schools that prioritize academic excellence. Home to Wesleyan University, the city is also a hub for cultural and intellectual activities, hosting art exhibits, theater performances, and community events throughout the year.

With its strategic location, Middletown provides easy access to major highways, making commuting to nearby cities like Hartford and New Haven a breeze. Whether you’re a first-time homebuyer, a growing family, or looking to retire, Middletown offers a welcoming environment that is sure to capture your heart. Come and experience the charm of Middletown – where community, history, and opportunity converge!

Newest Listings in Middletown

$389,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205251 MLS

You'll fall in love with this move-in condition colonial located at the end of a cul-de-sac. The yard is level and partially fenced with a large deck ideal for three-season cookouts and relaxation. The bright interior has plenty of room for hosting gatherings. The recently remodeled kitchen adjoins the dining room so the cook can join the conversation. Upstairs are two bedrooms each with hardwood floors and their own newly remodeled baths. There's a full basement for exercising and storage ideal for future finishing. All this convenient to highways, shopping, and recreation. Don't miss this one!

46 Clarence Ct, Middletown

$280,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206413 MLS

Beautifully renovated and ready for its next chapter, this charming 3-bedroom, 2-bath home offers comfortable living with modern updates throughout. The main living spaces provide a warm and inviting setting, while three bedrooms upstairs offer privacy and plenty of room to spread out. The spacious primary bedroom features vaulted ceilings, adding an open and airy feel. Conveniently located near major highways, this home is an excellent choice for commuters while still being close to shopping, dining, and everyday conveniences. With thoughtful renovations already completed, there's nothing left to do but move in and enjoy!

6 Hillside Ct, Middletown

$379,900

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24205306 MLS

Well maintained 3 bedroom home with flexible floor plan. 1 bedroom on the first floor, as well as 2 full baths, Living room, and eat-in kitchen. The second floor has 2 additional bedrooms. 1st Floor Laundry. New Furnace. Splits for air condioning. 200 amp elec. Panel w/ Generator hook up. New detached 3 car garage with loft are above.

64 Ryan St, Middletown

$379,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206199 MLS

FULLY UPDATED & TURN KEY! Welcome to 672 East Main Street, a beautifully renovated home offering extensive update inside and out. This meticulously maintained property features a new roof, siding, windows, front door, flooring, interior paint, kitchen cabinets, updated kitchen and bathrooms, and so much more. Enjoy the convenience of a dedicated washer and dryer located on the main floor, making everyday living easy and convenient without the need to go up or down. Outside, enjoy new landscaping, a new concrete walkway, and a new back patio, creating a fresh and welcoming exterior. Located close to everything, with easy access to Route 9 and just minutes from Downtown Middletown, you'll enjoy convenient access to shopping, dining, entertainment, and everyday amenities. With so many major improvements already completed, this home is truly move-in ready and turn-key. Just unpack, settle in, and enjoy!

672 E Main St, Middletown

$199,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ COMING SOON Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$289,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205925 MLS ⋅ Laurel Ridge BLDG.

Rare Laurel Ridge Opportunity! This beautifully updated, and move in condition unit is located in a small quiet complex in the Wesleyan Hills section of town. No work to do Just enjoy your space featuring a modern style updated kitchen with dark wood cabinetry, granite counters and stainless appliances. Sit back and relax in the living room with French door access to your private deck with views of a treed yard or sit by the wood burning fireplace in cooler weather which is right around the corner. A stackable full sized washer and dryer are conveniently located on the upper level along with 2 generous size bedrooms. NO CARPET! All engineered hardwood flooring throughout the entire living space. Need more space? The basement is unfinished and ready for expansion ideas. The complex has nearby walking trails and Wadsworth State Park for outdoor fun. Not far from all that Middletown has to offer. Additionally this is part of the Wesleyan Hills Association which includes the ponds, the lawns around the ponds, the three miles of footpaths, the four bridges on the paths, and the Barns complex.

1 Canterbury Ct Unit 2, Middletown

$689,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205132 MLS

Expect the best! Carefree living at Founders' Ridge, the premier award-winning 55+ community in Central Connecticut! Introducing the highly sought-after Kirby II model home, now available for IMMEDIATE occupancy. This is the last Kirby II available at this price point. Located in Middletown's desirable Westfield section, this thoughtfully designed 1,555-square-foot, single-level home offers an ideal blend of comfort, style, and convenience. Inside, you'll find elegant white cabinetry, quartz countertops, and a spacious walk-in pantry that combine beauty with functionality. Hardwood flooring flows throughout the main living areas, while the bathrooms and laundry room feature durable tile flooring. A bright bay window in the front room fills the space with natural light and offers sweeping views. Outside, the private rear patio provides the perfect setting for relaxing or entertaining. Additional highlights include natural gas heating and central air conditioning for year-round comfort. Some photos are of similar homes and may include optional upgrades. Agent/owner related.

Unit 2-41 Webster Ln Unit 145, Middletown

$245,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 and 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

$119,000

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

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