Middletown Homes for Sale

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

9 Burr Ave, Middletown
$314,900
3 Beds ⋅ 1 Baths ⋅ 24216947 MLS
Open house November 2nd 5pm-6pm Welcome to 9 Burr Avenue! This charming Colonial offers 3 bedrooms, 1 full bathroom, and 1,344 square feet of living space per public records. The home features a recently remodeled kitchen, updated within the past year, along with a finished walk-up attic that provides versatile additional space, ideal for a home office, hobby room, or bonus area. Additional improvements include a newer hot water heater, approximately one year old. Outside, enjoy a fully fenced backyard offering privacy and plenty of room for entertaining, outdoor gathering, or simply relaxing. This home is ready for its new owners! Property is being sold AS-IS

9 Burr Ave, Middletown
1511 Country Club Rd, Middletown
$410,000
4 Beds ⋅ 2 Baths ⋅ 24216990 MLS
Welcome to 1511 Country Club Road, a remarkably versatile property offering 4-bedroom functionality situated on an expansive 1.25-acre parcel on a peaceful, non-through street. A charming entry introduces the main Cape, which features two comfortable bedrooms, a full bath, and an upper loft ready to serve as a home office, recreation room, or potential third bedroom. Seamlessly connected yet private, the dedicated in-law/secondary living quarters boast their own bedroom and an additional loft space currently utilized as a primary suite-ideal for multi-generational living, extended guests, or a dedicated private wing. Peace of mind comes built-in with a brand-new septic system. Outside, the sprawling acre-and-a-quarter grounds provide mature greenery, a fenced-in play/pet area, and boundless room for entertaining, gardening, or outdoor expansion. A rare combination of privacy, acreage, and adaptable living space.

1511 Country Club Rd, Middletown
360 Chauncey Rd, Middletown
$345,000
3 Beds ⋅ 2 Baths ⋅ 24216264 MLS
Do you love downtown Middletown, but want to live in a quieter area? 360 Chauncey Road is the answer you're looking for! Enjoy what Middletown has to offer while being tucked away in a quiet area. This property offers 3-4 bedrooms, two full bathrooms, hardwood floors, harvey windows and a yard to enjoy. Throughout the home you'll find pockets of character that make it unique; the wood paneling on the ceilings, the bathroom trim, or the covered porch paired with a charming blue door. The eat-in kitchen has plenty of counter and cabinet space, all your needed appliances, and access to the brand new deck. The main floor bedroom is accompanied with a full bath and another potential bedroom, study, rec room, or dining room. Upstairs are the two spacious bedrooms with another full bath and crawl space storage. In the basement you'll find a ton of storage and future expandable space. Enjoy dedicated laundry space & shelving with access to outside. Outside, the back deck overlooks the level yard with plenty of tree cover for the Summer months and offering beautiful views in the Fall. Come check out 360 Chauncey Road and then head downtown to enjoy some of the incredible restaurants and shops Middletown has to offer, or hit the nearby hiking trails at Millers Pond or Crystal Lake! Updates include Brand new 2026 deck, 2021 plastic septic tank, 2022 well pump, 2026 well tank & water softener, 2019 roof, and AO Smith 2021 water heater. Take advantage of this well maintained home!

360 Chauncey Rd, Middletown
368 Bow Ln, Middletown
$399,000
2 Beds ⋅ 1 Baths ⋅ 24217601 MLS
Antique 2-Bedroom Cape with Country Charm, 15+ Acres of Land and Endless Potential! Looking for a home with character, charm, over 15 acres of land, and the opportunity to make it your own? This quaint antique 2-bedroom Cape is nestled in a peaceful country setting, with beautiful views from the front porch and backyard that truly make this property special! This antique home received a new roof in the Spring, but it needs your vision and creativity to make the space your own while exploring its potential. The first floor includes an eat-in- kitchen, a laundry room, a full bathroom, and a bonus room. Upstairs, you'll find two bedrooms and a storage area. The bonus on the main level that could serve as a 1st floor bedroom, office or a library, or simply be considered flex space? Enjoy a peaceful country setting while remaining conveniently close to Route 9, Middlesex Health, Middlesex Community College, Wesleyan University, shopping, and the restaurants and amenities of downtown Middletown. If you're looking for an antique home with character and the opportunity to add your personal touch, this could be the one for you!

368 Bow Ln, Middletown
150 Millbrook Rd, Middletown
$340,000
4 Beds ⋅ 1 Baths ⋅ 24203998 MLS
Set on approximately 5.2 acres in Middletown, this historic 4-bedroom home offers a unique opportunity to enjoy space, privacy, and the character of an older property. Built in 1760, the home offers approximately 1,680 square feet of living space and plenty of room to explore the possibilities. The expansive parcel provides a peaceful setting with ample outdoor space for gardening, recreation, entertaining, or simply enjoying the privacy of your own property. Inside, the home offers four bedrooms and one full bath, providing a flexible layout with plenty of potential to make the space your own. The generous acreage creates opportunities for those looking for more land while still being conveniently located in Middletown. Whether you're looking for a property with history, land, or the opportunity to bring your own vision to life, 150 Millbrook Road is worth a look. Come see the property and discover its potential for yourself.

150 Millbrook Rd, Middletown
404 Newfield St, Middletown
$450,000
3 Beds ⋅ 3 Baths ⋅ 24217472 MLS
One level living with room for expansion in this spacious ranch. Three bedrooms and 3 full baths with and oversize mudroom between the house and garage give you lots of options. Oversized 2 car garage gives you plenty of room for storage in the event you may want to finish off the lower level of this home. Completely remodeled home allows you peace of mind knowing all you have to do is move in. New Windows, new roof, new gutters, new flooring in kitchen and living room and remaining floors refinished The kitchen offers lots of countertop space, cabinets, quartz countertops, island, stainless steel appliances and room for the dining table. Recessed lighting and tile back splash finish off the detail. All three bedrooms are roomy and the master bedroom offers a fully renovated master bath with tiled walk in shower. Keep the open fireplace or add a pellet or wood stove to give you that New England feel while keeping the chill off. The basement would make for great additional living space as there is already a full bath there. New Bilco door and steps to basement. Updated mechanicals including new gas boiler, city water and sewer will give you peace of mind. New roof, windows and fresh paint throughout. There is a shared driveway however there is room from survey (in photos) that was done to have a private driveway. Located near the heart of Middletown, with so many options when it comes to dining, shopping or entertainment.

404 Newfield St, Middletown
9 Magnolia Ave, Middletown
$285,000
4 Beds ⋅ 1 Baths ⋅ 24217261 MLS
Welcome to 9 Magnolia Place, a charming and well-maintained Middletown home offering an impressive list of thoughtful updates inside and out. Tucked along a quiet dead end, this 4-bedroom home combines character, comfort and many of the major improvements buyers appreciate. Recent updates include new kitchen cabinetry, new quartz countertops, sink and faucet, a metal range hood, and fresh interior paint throughout nearly every room, both hallways and the upper staircase. Approximately a year and a half ago, the first 10 feet of the exterior sewer line were replaced, another valuable improvement to the property. Additional improvements over the years include newer vinyl siding with insulation, energy-efficient double-pane replacement windows, a designer front entry door and surrounding structure, added attic/crawl-space and ceiling insulation, and an updated large shower/bath with generous built-in shelving. The home is equipped with an oil-fired Crown heating system, an above-ground oil tank, a newer A.O. Smith water heater and solar panels. The roof features high-performance asphalt shingles, reported by the seller to carry a 50-year rating and designed for winds up to 130 mph, along with updated gutters. Outside, enjoy a partially fenced backyard, storage shed and a wonderful covered rear deck overlooking the yard-a comfortable spot for morning coffee, outdoor dining or simply relaxing. A full unfinished basement with hatchway access provides additional storage

9 Magnolia Ave, Middletown
2 Sonoma Ln Unit 2, Middletown
$549,900
2 Beds ⋅ 3 Baths ⋅ 24217347 MLS
Your Next Chapter Starts at 2 Sonoma Lane! Looking for low-maintenance living without sacrificing space, style, or flexibility? Welcome to Sonoma Woods, one of Middletown's sought-after 55+ communities! This beautifully maintained detached home offers approximately 1,903 sq. ft., 2 bedrooms, 2.5 baths, and a layout full of surprises! Step inside to soaring cathedral ceilings, hardwood floors, and a spacious living room with a cozy gas fireplace. The inviting kitchen features granite countertops, abundant cabinetry, and a breakfast nook, while the dining area opens to a private deck, perfect for morning coffee or entertaining. The main-level primary suite offers a walk-in closet and full bath with double vanities and a tiled shower. First-floor laundry adds everyday convenience. Upstairs, discover a second bedroom, full bath, bonus room, and loft offering incredible flexibility. But here's the fun part! Behind charming bookshelf barn doors awaits a hidden retreat that's anything but ordinary! Create your own private speakeasy-inspired lounge, movie hideaway, reading sanctuary, or creative studio. The possibilities are limited only by your imagination! A full basement offers exceptional storage, while the attached two-car garage adds convenience. Enjoy central air, a community clubhouse, and more time for the things you love. Less upkeep, more freedom, and a secret space all your own. Welcome home to 2 Sonoma Lane!

2 Sonoma Ln Unit 2, Middletown
5 Castanea Ct, Middletown
$375,000
2 Beds ⋅ 1 Baths ⋅ 24217229 MLS
Charming ranch sitting on a corner lot in a pretty cul-de-sac neighborhood! Hardwood floors, central a/c and a finished basement! The living room with hardwood floors leads to the dining room and kitchen with new flooring and dishwasher. Two bedrooms with hardwood floors and a full bath finishes the main level. Downstairs is large den with new carpeting and a dry bar, perfect for entertaining! The one car attached garage is spacious and offers more storage! The deck overlooks the pretty lot that boarders a babbling brook (no flood insurance required). Roof and central air are approximately 10 years old. Come enjoy one-level living just minutes from bustling downtown with numerous restaurant, shops and activities! Welcome Home!

5 Castanea Ct, Middletown
400 Coleman Rd, Middletown
$425,000
3 Beds ⋅ 2 Baths ⋅ 24216846 MLS
Don't miss this pristine and charming Gambrel Colonial on a perfect level half acre, offering a quiet setting, gorgeous views, generous outdoor living spaces, and tasteful renovations in every room. Infused with beautiful natural light, this right-sized home offers 1718 sf with loads of windows (11 have been replaced by this owner), 3 bedrooms, and 2 bathrooms. The main floor space takes full advantage of its front-to-back design with two living/family rooms anchored by a central combined kitchen and dining room. The kitchen was renovated in 2026 with new LifeProof flooring, solid surface counters, subway tile backsplash, paint, and lighting. With separate coffee bar area and pantry and cool exposed brick, the kitchen offers great storage and is large enough for a long dining table, and can accommodate an island too! The family room features a wood-burning fireplace for cozy nights. The second floor offers a full bathroom and 3 generously sized bedrooms and spacious hallway, all updated with paint and featuring new flooring. The large remodeled full bath (2024) features marble tile tub surround and gorgeous hexagonal floor tile. More to love: half bath (remodeled 2023); new A/C (2023); new paver patio, garage doors, and shed (2021); new siding (2020); full basement; underground pet fence; and generator-ready.

400 Coleman Rd, Middletown
126 Rolling Grn, Middletown
$474,900
3 Beds ⋅ 3 Baths ⋅ 24215505 MLS
Welcome to 126 Rolling Green in Middletown! This spacious Ranch-style home combines comfortable one-level living with versatile additional space and an inviting setting in a fantastic neighborhood. The main level features three bedrooms, two full baths and a convenient laundry room, offering an easy and functional layout for everyday living. Step inside to discover abundant natural light and a formal dining room with vaulted ceilings and an elegant Palladian-style window. The spacious eat-in kitchen offers extensive cabinetry, recessed lighting, and a large pantry, opening to a versatile adjoining room with vaulted ceilings, a wine rack, and beverage refrigerator - perfect for entertaining or everyday relaxation. The living room features a natural gas fireplace, creating a warm and welcoming gathering space. The primary bedroom offers a large walk-in closet and an en-suite bathroom with a stand-up shower and Jacuzzi-style tub. Two additional bedrooms and two full bathrooms complete the main-level living space.

126 Rolling Grn, Middletown
55 Berkeley Rd, Middletown
$370,000
3 Beds ⋅ 2 Baths ⋅ 24216927 MLS
Welcome to 55 Berkeley Road, a charming New England Cape nestled on a quiet, low-traffic street in Middletown. Offering 3 bedrooms, 1.5 baths, and approximately 1,386 square feet of living space, this inviting home blends classic character with modern updates and a versatile floor plan. The living room features a cozy fireplace, while the formal dining room provides an ideal setting for everyday meals and entertaining. The beautifully updated kitchen boasts quartz countertops, a farmhouse sink, and a subway tile backsplash, combining style and functionality. A main-level bedroom offers added convenience and flexibility, while the partially finished lower level features a spacious family room with a second fireplace that is perfect for recreation, entertaining, or relaxing. Outside, the .32-acre lot provides plenty of room for gardening, outdoor gatherings, and recreation. A detached one-car garage and ample off-street parking add to the home's appeal. Additional highlights include public water and sewer and a convenient location just minutes from Wesleyan University, downtown Middletown's vibrant shops and restaurants, and Route 9. With its timeless Cape Cod charm, thoughtful updates, and desirable location, 55 Berkeley Road is ready to welcome you home!

55 Berkeley Rd, Middletown
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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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