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

$199,900

2 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24195105 MLS ⋅ Hamlin Court BLDG.

Welcome to Hamilton Court! This beautifully remodeled 2 bedroom, 1.5 bath townhouse offers stylish updates, low-maintenance living, and an unbeatable location just one block from Wesleyan University. Renovated within the last year, this move-in-ready home features a remodeled kitchen with updated appliances, renovated bathrooms, new flooring, brand-new carpeting, freshly painted walls and trim, and modern finishes throughout. The bright and inviting main level offers an open layout with a spacious living room flowing into the dining area and kitchen, creating the perfect space for everyday living and entertaining. A convenient half bath and private front terrace add to the home's appeal. Upstairs, you'll find two generously sized bedrooms, including a primary suite with a walk-in closet and en-suite bathroom. An in-unit washer and dryer provide added convenience. Enjoy one assigned parking space and a prime location within walking distance to downtown Middletown, Middlesex Hospital, restaurants, shopping, parks, and entertainment, with easy access to major commuter routes. Whether you're looking for a primary residence or an investment opportunity near Wesleyan University, this turnkey townhouse is one you won't want to miss. Property is being sold AS IS, WHERE IS.

201 College St Unit 22, Middletown

$245,000

2 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24191054 MLS ⋅ Trolley Crossing BLDG.

Welcome to this beautifully maintained 2-bedroom, 1.5-bath townhouse-style condominium offering the perfect blend of comfort, convenience, and low-maintenance living. Featuring 1,206 square feet of inviting living space, this well-cared-for condo offers central air, natural gas heat, and an attached 2-car garage. The kitchen was updated approximately 3 years ago with cabinets, countertops, flooring, and appliances. Enjoy added peace of mind with a central air system approximately 3 years old, a hot water heater approximately 5 years old, a brand-new architectural shingle roof installed in 2025, and a special assessment that has been paid in full. Relax and unwind at the community's in-ground pool, or enjoy the convenience of being just minutes from shopping, restaurants, schools, parks, major highways, and nearby walking, biking, and hiking trails. Move right in and enjoy the comfort, convenience, and lifestyle this exceptional condominium has to offer. Schedule your private showing today!

79 Trolley Crossing Ln Unit 79, Middletown

$334,500

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24194926 MLS

Welcome to 67 Butternut, a charming home that offers comfort, character, and convenience. The main level features a bright, open kitchen with stainless steel appliances that flows seamlessly into the inviting living room, creating the perfect space for everyday living and entertaining. Beautiful hardwood floors extend throughout the home, adding warmth and timeless appeal. Upstairs, you'll find the comfortable bedrooms and a full bathroom. Ideally located just minutes from grocery stores, parks, shopping, dining, and major conveniences, this home combines charm with an unbeatable location.

67 Butternut St, Middletown

$489,000

5 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24194393 MLS

PROFESSIONAL PHOTOS COMING SOON! 98 S Front Street, Middletown Welcome home to this lovingly maintained and meticulously cared-for Cape, ideally situated on a quiet and welcoming neighborhood. Offering a wonderful blend of comfort, functionality, and quality updates, this move-in-ready home has been thoughtfully maintained both inside and out. The inviting floor plan features a bright eat-in kitchen that flows seamlessly into the cozy family room with a fireplace, creating the perfect gathering space for everyday living and entertaining. Just beyond, a sun-filled four-season room provides additional year-round living space with easy access to the deck and private backyard. A dedicated first-floor laundry room adds everyday convenience. The flexible layout includes a spacious primary en suite on the main level, along with an additional bedroom and a convenient half bath. Upstairs, you'll find two generously sized bedrooms and a third smaller room, ideal as a home office, nursery, or hobby space. Every bedroom offers excellent closet space, providing abundant storage throughout the home. The walk-out lower level offers exceptional storage and workshop space, with the potential to be finished for additional living area.

98 S Front St, Middletown

$449,900

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24194846 MLS

Welcome to this beautifully maintained, original-owner Colonial, perfectly nestled on a quiet cul-de-sac in Middletown's highly sought-after Westfield neighborhood! From the moment you step inside, you'll be welcomed by an abundance of natural light, gleaming hardwood floors, and a bright, open floor plan designed for both comfortable everyday living and effortless entertaining. The main level offers spacious gathering areas, convenient first-floor laundry, a half bath, and a flexible room that can easily serve as a home office, playroom, den, or additional living space to fit your lifestyle. Upstairs, you'll find three generously sized bedrooms and two full bathrooms, including an exceptional primary suite featuring an oversized bedroom, an expansive walk-in closet, and a private en-suite bath-your own peaceful retreat at the end of the day. Step outside and enjoy the beautiful deck beneath the gazebo while overlooking the large, level yard-perfect for entertaining, gardening, pets, or creating lasting memories with family and friends. The full unfinished basement offers approximately 1,000sq.ft of potential, giving you the opportunity to create a home gym, media room, recreation space, or whatever you've been dreaming of. Lovingly cared for by its original owners, this home offers the perfect combination of pride of ownership, timeless charm, and endless possibilities. Schedule your private showing today and experience everything this exceptional home has to offer!

279 Congdon St, Middletown

$264,900

2 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24192644 MLS ⋅ Newfield Commons BLDG.

Lovely 2-bed townhouse in a quiet complex near shopping, coffee, restaurants and the high school. You'll enjoy a peaceful spot to sip your coffee on the upgraded trex deck & with a view of the woods. Heat pump is under 10yrs, CAIR, Low HOA cost includes trash and snow removal. Finish the basement for even more space. This is the perfect place to start out. Some upgrades will make this home shine, but well-loved for years. Stair chairs will be removed, some furniture can stay. Visitor parking is a plus too!

675 Newfield St Unit 9, Middletown

$180,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$395,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24194117 MLS

Welcome home to this charming property located at the end of a peaceful cul-de-sac. This residence features three bedrooms, including a primary bedroom with an ensuite full bathroom. There are two updated full bathrooms in total, along with a convenient half bath. As you enter, you'll notice the gleaming hardwood floors that flow throughout the main living areas. The kitchen is thoughtfully designed with granite countertops, maple wood cabinets, and stainless steel appliances, offering a great setup for everyday cooking. The dining area seamlessly connects to the cozy living space, which features a gas fireplace and a mini-split system, providing an additional heating and cooling option for year-round comfort. From the dining area, sliding doors open to a patio with Trex decking, complete with a retractable awning, perfect for providing shade when needed and easily rolled back for sunny days. The two-car garage provides direct access to a finished basement area that includes a half bathroom and laundry facilities, enhancing the home's functionality. Energy-efficient solar panels ensure excellent coverage, leading to no current electric bill. Step outside to discover a private walking path accessible right from your backyard. This home is fully move-in ready, waiting for you to create lasting memories.

3 Yellow Pine Cir, Middletown

$539,999

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191099 MLS

Welcome to this beautifully updated 3-bedroom Contemporary retreat, perfectly situated on a lush, private lot. A charming wraparound covered front porch welcomes you home and offers the perfect space to relax, unwind, or gather with family and friends. Inside, you'll find freshly painted 1,600 plus sqft of above grade thoughtfully designed living space featuring soaring vaulted ceilings, abundant natural light, NEW beautiful (LVT) flooring, 2 1/2 bathrooms, and a spacious primary suite with an updated en-suite bathroom complete with a relaxing Jacuzzi tub. More than $60K in renovations have been completed within the past year, including new rear siding, new balcony, a freshly stained deck, and numerous additional updates, making this home truly move-in ready. The finished lower level expands your living space with a cozy family room centered around a fireplace. Adjacent to the family room is a space already equipped with plumbing, offering a true blank canvas for your vision. Whether you dream of a future kitchenette, home office, guest suite, multigenerational living space, or a potential in-law setup, the possibilities are endless.Step outside to your own backyard oasis. Surrounded by mature trees & lush greenery, the expansive deck, brand-new above-ground pool, and newly built balcony create a private, resort-like setting that's perfect for morning coffee, summer pool parties,or relaxing evenings under the stars..

1512 Country Club Rd, Middletown

$688,000

4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24193869 MLS

Welcome home to this beautifully maintained 5-bedroom, 2.5-bath Colonial, ideally located in the heart of vibrant Middletown. Enjoy easy access to Middletown's many wonderful restaurants and downtown charm, with Middlesex Health, Wesleyan University, and the scenic CT River all just minutes away. Freshly painted throughout, this turn-key home is ready for you to move right in! The main level offers a wonderful flow for both everyday living and entertaining. The spacious eat-in kitchen features a center island and a sunlit breakfast nook with a skylight, creating the perfect spot to enjoy your morning coffee or casual meals. The kitchen opens seamlessly into the inviting great room, complete with a cozy fireplace and a built-in sound system, creating the ideal setting for gatherings, movie nights, or relaxing at home. A separate living room and formal dining room provide additional space for hosting family and friends. A standout feature of this home is the impressive 500-square-foot first-floor fifth bedroom, traditionally designed as a media room. Complete with surround sound and a projector, this exceptional space is perfect for movie nights and entertaining. Its generous size also makes it an ideal primary or guest bedroom, home office, playroom, or recreation room-offering incredible flexibility. Upstairs, you'll find four generously sized bedrooms and well-appointed bathrooms, providing plenty of room for family, guests, or additional workspace.

166 Mccormick Ln, Middletown

$209,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193843 MLS ⋅ Hamlin Court BLDG.

This freshly painted townhouse-style condo offers 2 bedrooms, 1.5 bathrooms, newer windows, updated appliances, newer flooring throughout, and an open-concept layout. The main level features a spacious living room that flows into the dining area and kitchen, along with access to a private terrace. The kitchen includes tile flooring, a mosaic tile backsplash, and appliances replaced within the past three years. Upstairs are two bedrooms with spacious closets, a full bathroom, and convenient in-unit laundry with a new washer and dryer. Previously rented for $1,900 per month, this investor-friendly unit offers strong income potential. Additional features include a dedicated storage unit, one assigned parking space, and visitor parking. Ideally located within walking distance of Downtown Middletown, Wesleyan University, and Middlesex Hospital, with easy access to restaurants, shopping, and major commuter routes.

201 College St Unit 20, Middletown

$85,000

ACTIVE Status ⋅ 24192347 MLS

Approved 0.42-acre building lot offering the opportunity to build your custom single family or two family home. Public water, public sewer, and natural gas are available at the street. Ideally located just minutes from downtown Middletown, shopping, restaurants, parks, and major highways, this property offers the perfect combination of convenience and potential. Don't miss this opportunity to bring your vision to life!

672 E Main St, Middletown

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