Middletown Real Estate

Welcome to Middletown, Connecticut – a charming city that beautifully blends rich history with modern living. Nestled in the heart of Middlesex County, Middletown boasts a vibrant community and a picturesque setting along the Connecticut River. With its roots dating back to the 17th century, the city is steeped in history, reflected in its well-preserved architecture and historical landmarks.

Middletown is renowned for its diverse cultural scene, offering an array of art galleries, theaters, and music venues that cater to all tastes. The city is also home to Wesleyan University, which brings a youthful energy and a wealth of educational opportunities to the area. The university’s presence fosters a lively atmosphere, with various events and cultural activities that engage residents and visitors alike.

Outdoor enthusiasts will find plenty to love about Middletown. The city is surrounded by beautiful parks and nature reserves, perfect for hiking, biking, or simply enjoying a leisurely stroll. The scenic Connecticut River provides ample opportunities for boating and fishing, making it a delightful destination for those who appreciate the great outdoors.

Middletown’s downtown area is a hub of activity, featuring an eclectic mix of shops, restaurants, and cafes. Whether you're in the mood for a cozy coffee shop or a fine dining experience, you'll find it all within walking distance. The community is known for its friendly atmosphere and commitment to local businesses, making it a wonderful place to call home.

In summary, Middletown, CT, is a dynamic city that offers a perfect blend of history, culture, and natural beauty. Whether you're looking to settle down or simply explore, Middletown welcomes you with open arms.

Newest Listings in Middletown

$415,000

3 Beds ⋅ 2 Baths ⋅ 24204682 MLS

This home is located in a sought-after section of Westfield near the Cromwell town line convenient to highways.Vaulted ceilings in the living room/family room/dining area create a bright modern feeling perfect for entertaining. All are connected to an eat-in kitchen where you can sit at the island and keep the cook company. The two bedrooms are both comfortable retreats. The lower level has a large third bedroom with privacy for guests or teens. You'll enjoy the extra room with a full walk-out ideal for games, exercise, parties and gatherings. All this within minutes of commuter highways, shopping, and recreation. You'll love to call this home!

55 Moss Gln, Middletown

$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

$135,000

2 Beds ⋅ 2 Baths ⋅ 24204426 MLS

*** BRAND NEW 2-BEDROOM, 2-BATH MOBILE HOME - Fresh, Modern & Ready for You! *** Welcome to 500 Washington Street #6 in Middletown Mobile Home Park! Be the first to call this brand-new 2-bedroom, 2-full-bath mobile home yours. Designed with modern comfort and easy living in mind, this beautiful home offers a fresh, stylish interior and the peace of mind that comes with owning brand new. At the heart of the home is a beautifully appointed kitchen featuring elegant Glacier Quartzite countertops and new stainless steel appliances, including refrigerator, dishwasher, microwave/hood vent, and upgraded smooth-top electric range. The desirable 2-bedroom, 2-bath layout provides added privacy and flexibility-perfect for a guest room, home office, or additional living needs. Additional features include 200-amp electrical service and an efficient, low-maintenance design. Mobile home scheduled to be delivered onsite October 9, 2026, with anticipated move-in availability October 30, 2026. Everything is new, and all that's missing is you! Don't miss your opportunity to be the very first owner-schedule your showing and make #6 your new home! ***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 #6, 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

$349,000

3 Beds ⋅ 2 Baths ⋅ 24204544 MLS

Welcome home to this beautifully updated property tucked away on a quiet cul-de-sac offering privacy, ample parking, and a spacious backyard perfect for relaxing, entertaining, or enjoying the outdoors. Inside, you'll find an updated and upgraded kitchen and bathrooms, complemented by newer vinyl windows and a newer roof for added peace of mind. A large two-car garage provides plenty of room for vehicles along with valuable additional storage. Conveniently located near the Cromwell/Middletown line, this home is a commuter's delight with easy access to Route 9, Route 372, and I-91. Enjoy being just minutes from restaurants, shopping, supermarkets, Wesleyan University, Wadsworth Falls State Park, Powder Ridge Park and Resort and many other area amenities. Offering a great combination of privacy, convenience, updates, and accessibility, this home is ready for its next chapter. AS-IS sale. Inspection for buyers' information only.

17 E Lake Pl, Middletown

$749,900

4 Beds ⋅ 3 Baths ⋅ 24204169 MLS

NEW CONSTRUCTION MODERN COLONIAL Beautiful 4-bedroom, 21/2-bath Modern Colonial privately situated on 1.8 acres of rolling country hills. Currently under construction & not yet complete. Exterior features include vinyl siding, Harvey windows, architectural shingles, Trex front porch with white railings, & paved driveway not yet complete. The lot will be professionally graded, topsoiled, and seeded. The approximately 2,232 sq. ft. home features 31/4" natural-finish white oak flooring, tile baths, square-edge flat trim, recessed lighting, & inset floor registers. The kitchen offers white shaker cabinets, quartz counters, navy-blue eat-at island, stainless farmhouse sink, built-in hood, propane stove, & an appliance allowance. The family room features a gas fireplace. The primary suite includes a coffered ceiling with crown molding, walk-in closet with custom shelving,& bath with double vanity, quartz counter, and walk-in rain-head shower. Four bedrooms include a flexible 4th bedroom/bonus room, plus second-floor laundry. Additional features include white bathroom vanities, quartz bath counters, hydro-air heating/cooling, Insta-hot combination boiler/hot water system, 200-amp service, well & septic, oversized 2-car garage with openers, unfinished basement, and Trex rear deck. Adjacent 2.8-acre lot also available, with plans for a home in the same Modern Colonial style. AI-enhanced photos of anticipated finished home/landscaping- actual appearances may vary

85 Freeman Rd, 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

$1,000,000

24203918 MLS

PERMIT IN HAND - READY TO BUILD! Located in the heart of Middletown and within walking distance of an abundance of downtown amenities, 54 Washington Street presents an exceptional redevelopment opportunity in a highly desirable location. Formerly home to the Italian American Club, this distinctive property offers both character and history while being fully positioned for its next chapter. The property has received zoning approval for conversion from a community/event space into 18 residential units, with additional space incorporated for a superintendent. A tremendous amount of the development work has already been completed. The property includes professionally engineered 18-unit build-out plans, along with stamped electrical and plumbing plans. With major building systems professionally designed, code-compliant, and permit-ready, a new owner can move directly toward the construction phase-eliminating much of the time, cost, and uncertainty typically associated with the planning and approval process. Adding even greater value, the Town has approved 18 parking spaces directly across the street, adjacent to the police station. For the savvy investor or developer seeking a residential conversion opportunity with approvals, plans, parking, and a prime downtown location already in place, 54 Washington Street offers a rare opportunity to step into a project that is truly ready to build.

54 Washington St, Middletown

$219,900

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

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. Come see the possibilities and decide what you can make of this one.

868 Long Hill Rd Unit 868, 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

$309,900

5 Beds ⋅ 2 Baths ⋅ 24203700 MLS

Opportunity knocks in the heart of Middletown! This two-family home sits just minutes from Route 9, public transportation, and the Main Street corridor with its restaurants, shops, and year-round events. Live in one unit and have a tenant help pay your mortgage, or add a solid two-family to the portfolio - a great fit for owner-occupants and investors alike. Unit 1 has been freshly updated with new flooring, fresh paint, an updated kitchen and bath, and ceiling fans. Unit 2 offers a functional layout with an enclosed sun porch and its own private entry. Separate utilities, including two electrical panels and two heating systems, keep operating simple. Additional highlights include enclosed porches, new flooring and updates throughout, an open unfinished basement with plenty of storage, and off-street parking for multiple vehicles. Appliances will be provided with the right offer. Close to Wesleyan University, hospitals, parks, and commuter routes to Hartford and the shoreline. Easy to show - schedule today! Agent Owner

105 Spring St, Middletown

$369,999

3 Beds ⋅ 2 Baths ⋅ 24196726 MLS

Welcome to 123 Fisher Rd, a charming 3-bedroom, 2-bath Cape offering a flexible floor plan and plenty of space to suit today's lifestyle. One of the home's standout features is the main-level bedroom, which is currently being used as an additional living space. This versatile room provides an excellent opportunity for a family room, home office, den, or comfortable first-floor bedroom depending on your needs. The main level offers a welcoming flow between the living areas, kitchen, full bathroom, and flexible bonus space. Upstairs, you'll find additional bedrooms that provide privacy and room for family or guests. With two full bathrooms and a traditional Cape layout, the home offers both functionality and flexibility. Located in a convenient Middletown setting, 123 Fisher Rd is close to everyday amenities, shopping, dining, parks, schools, and major roadways. Schedule your showing today before it's too late!

123 Fisher Rd, Middletown

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