Middletown Homes for Sale

Welcome to Middletown, Connecticut – a charming city nestled in the heart of Middlesex County, where rich history meets modern living! With its vibrant downtown, scenic parks, and a community spirit that welcomes all, Middletown offers a unique blend of suburban tranquility and urban convenience.

Middletown is renowned for its picturesque streets lined with historic homes and contemporary residences, making it an ideal place for families, professionals, and retirees alike. The city boasts a diverse range of homes for sale, from quaint colonial-style houses to modern condominiums and spacious single-family homes. Whether you're seeking a cozy starter home or a luxurious retreat, Middletown's real estate market has something to cater to every taste and budget.

The city's vibrant arts scene, highlighted by the renowned Wesleyan University, offers a plethora of cultural events, theaters, and galleries. Outdoor enthusiasts will appreciate the lush parks and the beautiful Connecticut River, perfect for kayaking, fishing, and leisurely strolls. With excellent schools, a variety of dining options, and convenient access to major highways, Middletown is not just a place to live; it’s a place to thrive.

If you’re considering a move to this delightful city, now is the perfect time to explore the homes for sale in Middletown. Discover the community that feels like home and experience the warmth of a city that truly embraces both its history and its future. Let us help you find your dream home in Middletown today!

Newest Middletown Homes for Sale

$600,000

4 Beds ⋅ 4 Baths ⋅ 24178710 MLS

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

$1,350,000

3 Beds ⋅ 4 Baths ⋅ 24196036 MLS

A one-of-a-kind custom-built new construction home that must be experienced in person to be appreciated. This modern contemporary farmhouse-style ranch sits on 2.38 acres of private land, positioned at the end of a cul-de-sac on a private road. From the moment you arrive, the exterior makes a lasting impression. Stone walls frame the driveway, guiding you past a thoughtfully designed approach w/a waterfall element & circular drive. The home's facade showcases board & batten siding, stone & striking black windows, gutters & trim. A covered front entry with a custom-built on-site front door & oversized 10-ft garage doors complete the curb appeal. Inside, every detail has been carefully designed & executed. Custom paneled walls conceal hidden features, including a discreet foyer closet & a hidden half bath accessed through the paneling along w/built-in storage for convenience. The open-concept living space is breathtaking, highlighted by soaring ceilings, exposed beams & a stunning central fireplace that anchors the home. The chef's kitchen is both beautiful & functional, featuring high-end cabinetry, a farmhouse sink, a large center island w/waterfall quartz edges & additional storage below. 1 wing of the home includes 2 guest bedrooms, a full bath & a cleverly enclosed laundry area finished walnut, keeping it completely out of sight. The primary suite offers a luxurious bath w/a walk-in shower, double vanities, walk-in closet, & a unique double-seater, lay-down soaking tub.

145 Monarca Dr, Middletown

$309,000

3 Beds ⋅ 2 Baths ⋅ 24194943 MLS

Move right in! 34 Franklin Street is a well-cared-for Middletown split-level offering 3 bedrooms, 1 fully renovated bath, and 966 sq ft of comfortable living. Highlights include hardwood flooring, an eat-in kitchen with sliders to a huge covered deck, and a spa-style bathroom with a walk-in shower, built-in seat, and skylight. Outside, enjoy a private, fenced 0.16-acre yard with mature trees and a storage shed - plenty of room to garden, play, or entertain. Forced-air heat, central air, and durable vinyl siding keep maintenance simple. Zoned for Farm Hill Elementary (0.5 mi) and Woodrow Wilson Middle School, with quick access to downtown Middletown and major routes. Priced to move and ready for its next owner - schedule a showing today.

34 Franklin St, Middletown

$394,500

3 Beds ⋅ 2 Baths ⋅ 24195917 MLS

Welcome to 45 Annette Place! This beautifully maintained home is truly move-in ready and has so much to offer. The updated kitchen features granite countertops, stainless steel appliances, and recessed lighting, creating a bright and modern space. Hardwood floors flow throughout the living room and bedrooms, adding warmth and timeless appeal. The partially finished basement provides additional living space and is complete with a cozy pellet stove-perfect for relaxing year-round. Need room for vehicles, hobbies, or storage? The impressive 3-car garage offers endless possibilities. Outside, you'll be welcomed by beautifully landscaped grounds that add exceptional curb appeal and create a wonderful outdoor setting to enjoy. This is a home you'll be proud to own!

45 Annette Pl, Middletown

$465,000

2 Beds ⋅ 3 Baths ⋅ 24195232 MLS

Experience elevated living in this brand-new luxury townhome, thoughtfully designed with quality craftmanship, modern finishes, and an open concept layout ideal for everyday living and entertaining. This is a spacious 2 bedroom 2.5 bath home. The chef-inspired kitchen showcases GE stainless steel appliances, white shaker cabinetry, premium quartz countertops, sleek black hardware, and coordinating designer fixtures throughout. Beautifully finished bathrooms, spacious living areas, prefinished engineered hardwood flooring, and abundant natural light creates a sophisticated yet inviting atmosphere. Additional features include central air, city water and sewer, washer and dryer hookups, an attached one car garage with dedicated storage, and professionally designed landscaping with blue stone steppingstones leading to the sidewalk. Ideally located in desirable Middletown, this exceptional new construction community offers low maintenance luxury living just minutes from vibrant downtown, Weslyn University, Wadsworth Falls State Park, the Connecticut River, restaurants, shopping, entertainment and major highways.

61 W St Unit 15, Middletown

$419,900

1 Beds ⋅ 2 Baths ⋅ 24195008 MLS

Experience elevated living in this brand-new luxury townhome, thoughtfully designed with quality craftsmanship, modern finishes, and an open-concept layout ideal for everyday living and entertaining. This spacious 1-bedroom, 1.5-bath home features a versatile loft perfect for a home office, den, or flex space. The chef-inspired kitchen showcases GE stainless steel appliances, white shaker cabinetry, premium quartz countertops, sleek black hardware, and coordinating designer fixtures throughout. Beautifully finished bathrooms, spacious living areas, and abundant natural light create a sophisticated yet inviting atmosphere. Additional features include central air, city water and sewer, washer and dryer hookups, an attached one-car garage with dedicated storage, and professionally designed landscaping with bluestone stepping stones leading to the sidewalk. Ideally located in desirable Middletown, this exceptional new construction community offers low-maintenance luxury living just minutes from vibrant downtown, Wesleyan University, Wadsworth Falls State Park, restaurants, shopping, entertainment, and major highways.

61 W St Unit 13, Middletown

$385,000

3 Beds ⋅ 2 Baths ⋅ 24193289 MLS

Welcome home to this beautifully remodeled 3 bedroom, 2 full bath home that's truly move in ready! Enjoy relaxing on the inviting front porch or entertaining in the fenced backyard. The updated kitchen features stainless steel appliances, plenty of cabinet and counter space, and room for meal preparation. The spacious living room offers a cozy fireplace and new flooring, creating a warm and inviting atmosphere. The finished lower level provides additional living space with two finished rooms, a full tiled bathroom, and a laundry area with washer and dryer. Perfect for a family room, home office, gym, playroom, or guest space. Recent updates include central air, windows, flooring, fenced backyard, along with many additional improvements. This home is conveniently located near shopping, restaurants and parks and offers the perfect combination of comfort, style, and convenience. Don't miss your opportunity to make this beautiful home yours!

49 George St, Middletown

$425,000

3 Beds ⋅ 1 Baths ⋅ 24195038 MLS

Welcome to this charming 3-bedroom, 1-bath ranch nestled on the highly sought-after Higby Road. Set on a generous half-acre lot, this home offers the perfect opportunity for first-time buyers, downsizers, or anyone looking to add their personal touch. Inside, you'll find comfortable one-level living with a functional layout, hardwood floors, and a cozy fireplace. Additional features include an attached garage, partially finished basement for extra living or storage space, and a peaceful backyard with plenty of room to relax or entertain. Conveniently located near shopping, dining, parks, and major commuter routes, this home combines a desirable location with endless potential. Don't miss your chance to make this Higby Road gem your own!

104 Higby Rd, Middletown

$334,500

3 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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 ⋅ 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

$395,000

3 Beds ⋅ 3 Baths ⋅ 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

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