Middletown Homes for Sale

Welcome to Middletown, Connecticut—a charming city nestled in the heart of Middlesex County that perfectly blends rich history with modern living. Known for its vibrant community and picturesque landscapes, Middletown offers residents a unique lifestyle that balances urban conveniences with suburban tranquility. With its historic downtown area buzzing with shops, restaurants, and cultural venues, there’s always something to explore. The Connecticut River meanders through the city, providing stunning views and outdoor activities that are perfect for nature enthusiasts.

Middletown is not just a beautiful place to live; it’s also a thriving hub for education and innovation, home to the renowned Wesleyan University. This academic presence adds a youthful energy to the city and fosters a diverse, engaged community. Families will appreciate the top-rated schools and the abundance of parks and recreational facilities, making it an ideal spot for raising children.

For those looking to call Middletown home, there are numerous homes for sale that cater to a variety of tastes and budgets. From charming historic houses with character to modern townhouses and spacious family homes, the real estate market here is as diverse as the community itself. Whether you're a first-time buyer, looking to downsize, or seeking a family-friendly neighborhood, Middletown has something for everyone.

Explore the possibilities and find your perfect home in this delightful city where history meets modern living. Let Middletown’s warmth and charm welcome you into a new chapter of your life!

Newest Middletown Homes for Sale

$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

$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

$229,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24192281 MLS

Welcome to 21 Inverness Ln. Make this spacious 3 bedroom your new home. This home is nestled in the sought-after Highland Lake Community. The home features an open floor plan with generous sized rooms. Upon entering, you'll be met with an updated kitchen and a comfortable dining area. The adjacent family room features laminate flooring and sliders to a private fenced in patio complete with a pergola to shield you from the sun on scorching hot summer days. The upstairs features 3 spacious bedrooms, updated full bathroom, laundry nook and an area for den, office or media play. The 2-car garage also has an additional storage area off the back. You can enjoy single family home living without the extensive yard work. This home is waiting for your next summer party. Highest and best Sunday, 7/26 by 5:00 PM.

21 Inverness Ln, Middletown

$299,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191998 MLS

Are you looking for a charming 3 bedroom, 1.5 bath Colonial that is located on a quiet street in a desirable neighborhood, offering convenient location just minutes from the shops, restaurants, Wesleyan University, hospitals, and major healthcare centers? This is an excellent choice for anyone seeking an easy commute and access to everyday amenities. Filled with warmth and character, this inviting home is ready for its next chapter. Whether you're a first-time homebuyer, looking to make it your forever home, or searching for a great investment opportunity, this property offers endless potential. Add your personal touch and some TLC to make this charming Colonial truly your own while creating lasting memories for years to come. City water and city sewer. Don't miss the opportunity to own a home in a convenient and quiet location. Schedule your showing today and discover all that 153 Eastern Drive has to offer!

153 Eastern Dr, Middletown

$759,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24189442 MLS

Welcome to South Farms, where "staycation" is a way of life. This custom-built home is made for lazy mornings on the wraparound porch and sunny afternoons by the pool - all behind a brand-new full privacy fence with an acre of land. The grounds bloom spring through fall, and a charming chicken coop with its own shed adds hobby-farm charm. Inside, an open-concept layout shines with soaring cathedral ceilings, skylights, and a dramatic floor-to-ceiling fireplace. The kitchen boasts new appliances and flows into a breakfast bar and dining area made for gathering. A flexible downstairs den works as a fourth bedroom, playroom, office, or media room. Spacious full sized unfinished basement perfect for pool table and endless storage. The main floor primary bedroom suite offers a fully renovated bathroom and French doors leading to your own backyard oasis. A heated in-ground pool, lush plantings, and a footbridge over a koi pond to a pool house complete with a half bath! Upstairs, a sunny loft overlooks the living room; two bedrooms feature built-in window seats, and a huge room ready for anything; gym, playroom, extra bedroom; you name it. City sewer means no septic to worry about. Homes like this don't come around often. Come make it yours.

236 Maple Shade Rd, Middletown

$430,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190665 MLS

Classic Colonial on a picture-perfect lot with sweeping pastoral views in one of Middletown's most scenic settings! This home offers solid bones, generous room sizes, and loads of potential for anyone ready to add their own touches. The sun-filled living room offers oversized windows and flows easily into the dining area, while the beamed family room delivers warmth and character with wood paneling and a brick fireplace. The eat-in kitchen features ample counter space, stainless appliances, and a picture window overlooking the private backyard. A main-level laundry room and half bath add everyday convenience. Upstairs you'll find three comfortable bedrooms, including a spacious primary suite with its own private bath and double closets, plus a second full bath off the hall. The finished lower level adds fantastic flexible space with a large recreation room and dry bar - perfect for movie nights, a home office, or gym. Step outside and this property truly shines: an expansive deck with covered gazebo overlooks a sprawling, level backyard bordered by mature trees and open field views - a wonderful setting for entertaining or simply unwinding at the end of the day. Additional highlights include a two-car garage, mini-split systems for efficient heating and cooling, and a peaceful country feel just minutes from shopping, schools, and Route 9. Opportunities to own this view, space, and charm don't come along often. Bring your vision and make it home!

9 Round Hill Rd, Middletown

$349,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189620 MLS

Bring your growing family to this spacious colonial! 4 bedrooms with two on first floor. 2 full baths. Eat in kitchen. Living room with fireplace. Spacious room at top of staircase can potentially be 5th bedroom! Hardwood floors thru-out. Walk out basement to level yard. Deck. Whether you are a car enthusiast or need a lot of storage space, you will love the oversized detached 2 car heated garage with steel beam and loft area. Solar panels...see attachment

125 Stevens Ln, Middletown

$480,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188018 MLS

Nestled in the highly desirable South Farms neighborhood, this well-maintained home is filled with quality features and timeless appeal. Car enthusiasts and hobbyists will appreciate the impressive 4-car garage, offering exceptional space for vehicles, storage, or the perfect workshop. The spacious eat-in kitchen features granite countertops, abundant cabinetry, and generous workspace for cooking and entertaining. Throughout the home, you'll find an abundance of closet space in each of the 3 bedrooms. Hardwood floors lie beneath the carpeting, offering the opportunity to restore their original beauty. The expansive finished basement, complete with a full bath, additional laundry room, and cozy gas fireplace, provides the perfect setting for entertaining, relaxing, or creating the ultimate recreation space. The sunroom off the kitchen can also be used for a home office. A second gas fireplace in the living room adds warmth and charm, making this home inviting in every season. Step outside to enjoy the deck, complete with a retractable awning for shade on sunny days. Additional highlights include a full-house generator, walk-up attic, central A/C, laundry on the main floor and exceptional storage space throughout the home. Take advantage of all that Middletown has to offer with its many restaurants, cultural centers, and shopping. Close to I-91 and Rt 9. This home presents an exceptional opportunity for its next owner. Don't miss your chance to make it yours!

779 Ridge Rd, Middletown

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