Middlesex County Homes for Sale

Welcome to Middlesex County, Connecticut – a hidden gem nestled in the heart of New England! Known for its picturesque landscapes and vibrant communities, Middlesex County offers a unique blend of small-town charm and modern amenities. With its rich history, diverse recreational opportunities, and a strong sense of community, it’s no wonder that this area is a sought-after destination for homebuyers.

Middlesex County is home to a variety of charming towns, each with its own distinct character. From the scenic waterfront views of Old Saybrook to the historic charm of Middletown, residents enjoy a lifestyle that balances tranquility with access to urban conveniences. The county boasts excellent schools, beautiful parks, and a plethora of dining and shopping options, making it perfect for families, young professionals, and retirees alike.

For those looking to buy a home, Middlesex County has an impressive selection of properties for sale. Whether you’re in the market for a cozy cottage, a contemporary condo, or a spacious family home, you’ll find a range of options to suit your needs. Many homes feature beautiful outdoor spaces, ideal for entertaining or simply enjoying the serene surroundings. With an array of price points and styles, there’s something for everyone in this vibrant community.

Explore the charm of Middlesex County and discover your dream home today! With its welcoming neighborhoods and rich local culture, you’ll find that this area is not just a place to live, but a place to thrive. Don’t miss out on the opportunity to be part of this wonderful community!

Newest Middlesex County Homes for Sale

$1,850,000

3 Beds ⋅ 4 Baths ⋅ 24217721 MLS

A distinctive waterfront residence overlooking the Hammonasset River, 98 Pratt Road brings together contemporary architecture, refined interiors, and an extraordinary natural setting. Built in 2024 and situated on nearly an acre, this thoughtfully designed home offers an effortless balance of sophistication and comfort. At its heart, a beautifully appointed kitchen features Cambria quartz countertops, an expansive center island, Bosch appliances, and a generous walk-in pantry. White oak flooring, custom millwork, and carefully selected finishes lend warmth and continuity to the open living spaces, where a gas fireplace creates an inviting focal point. Expansive doors open to a covered deck overlooking the river and surrounding marshland, creating a seamless connection between indoor and outdoor living. The main level primary suite enjoys private deck access, dual walk-in closets, and a beautifully finished bath with radiant heated floors, soaking tub, and oversized shower. Two additional bedrooms, a dedicated office, and a four car garage complete the home's exceptional design. A private dock provides a wonderful opportunity to enjoy life along the water, with access toward Long Island Sound. A compelling expression of modern coastal living.

98 Pratt Rd, Clinton

$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

$299,900

4 Beds ⋅ 1 Baths ⋅ 24217621 MLS

Antique 4 Bedroom colonial just steps to the CT River and a short walk to town. First floor bedroom and full bath. Small manageble yard. 1 Car Detached oversized garage. Distance from school. Great potential. Generator hook up. Needs work. Ready for your updating!

147 River St, Deep River

$649,900

4 Beds ⋅ 3 Baths ⋅ 24217291 MLS

Welcome to 5 Skyline Drive, where spacious living, natural light, and endless possibilities come together! Offering 2,800 sq ft, this 4-bedroom, 2.5-bath home sits on a beautiful 1-acre lot in Skyline Estates in East Hampton. Step inside to a stunning two-story living room filled with natural light, creating an open and inviting atmosphere. The kitchen features maple cabinetry, granite countertops, an eat-in area, and access to a deck perfect for outdoor dining. The spacious primary suite offers a walk-in closet, full bath with soaking tub and heated floor, plus a generous sitting area ideal for an office, fitness space, or private lounge. Three additional bedrooms provide plenty of flexibility. The unfinished walk-out lower level offers approximately 1,200 sq ft of potential, with framing and plumbing for a future bathroom, and a mini-split for heating and cooling already in place. A slider leads to an outdoor patio, adding another space to relax or entertain. Additional highlights include a 3-car garage, generator hookup, and a roof approximately 5 years old. Conveniently located near Lake Pocotopaug, the Airline Trail, and East Hampton's charming village center, this home offers a wonderful combination of space, comfort, and opportunity!

5 Skyline Dr, East Hampton

$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

$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

$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

$274,900

2 Beds ⋅ 1 Baths ⋅ 24214510 MLS

Welcome to New England Village Sun - A 55+ Community! This beautifully remodeled ranch-style home welcomes you with a bright, open floor plan filled with natural light. Enjoy all the modern updates, including new flooring throughout, a stunning new kitchen featuring granite countertops, All new appliances, ample storage, and an island perfect for meal preparation, casual dining, or enjoying your morning coffee. The open living room creates a comfortable space for relaxing or entertaining, while the propane heater provides added warmth on chilly evenings. Just off the kitchen area, there are Sliders to a wonderful new sunporch with walls of windows that invite in the sunshine and fresh coastal breezes while overlooking the pretty, private backyard. This inviting space is sure to become your favorite spot to unwind! The home offers two bedrooms and a nicely updated bathroom featuring tile and glass shower doors. Additional conveniences include a stackable washer and dryer, New Siding a large storage shed, and, last but certainly not least, an attached carport-a true bonus and a standout feature of this home! Enjoy the best of coastal living in Westbrook, with the town beach on Seaside Avenue just minutes away.The nearby Water's Edge Resort offers dining throughout the week, weekend music, and a seasonal outdoor patio with exceptional views. Explore the many restaurants along the shoreline in Westbrook and neighboring Old Saybrook,or enjoy the excellent shopping opportunities at

15 Old Forge Rd, Westbrook

$839,000

4 Beds ⋅ 3 Baths ⋅ 24217096 MLS

Enjoy the best of shoreline living in this newly renovated four-bedroom home located in the sought-after Cornfield Point community of Old Saybrook! Featuring a bright, open floor plan, with a new kitchen, new stainless steel appliances, new split systems, new hot water heater, and a new deck. First floor bedroom, a full bath and laundry are all located on the main floor. This inviting home offers a wonderful blend of modern updates, comfortable living, and coastal charm. The open layout creates an ideal setting for entertaining family and friends, while four bedrooms provide plenty of space for guests and everyday living. As a member of the Cornfield Point Beach Association, you'll enjoy an exceptional array of community amenities, including beautiful beaches, a boat launch, a tennis court, a clubhouse, and a playground. Experience the relaxed coastal lifestyle that makes Cornfield Point such a special place to call home. Whether you're looking for a year-round residence, a shoreline getaway, or a place to make lasting family memories, this updated home is an opportunity not to be missed!

3 Town Beach Rd, Old Saybrook

$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

$1,195,000

4 Beds ⋅ 2 Baths ⋅ 24217364 MLS

Experience the charm of coastal living in this beautifully renovated, year-round home with deeded beach access! Built in 2009 and thoughtfully updated, this delightful 4-bedroom, 2-full-bath home offers an exceptional seaside retreat with breathtaking views of the expansive sandy beach directly across the street, complete with beach rights.Inside, bright and inviting living spaces complement a gorgeous new kitchen featuring quartz countertops, a beautifully renovated first-floor full bath, and convenient first-floor laundry. Additional recent improvements include a new heating system, central air conditioning, fresh interior paint, and a new outdoor shower, providing all the comforts of modern living in a relaxed coastal setting. Spend your mornings strolling along the sandy shoreline, afternoons enjoying the water, and evenings unwinding on the spacious deck overlooking the peaceful marsh. Sheltered by Duck Island and the breakwater, the surrounding waters offer endless opportunities for paddleboarding, kayaking, boating, jet skiing, and sailing. Nearby marinas, boat mooring opportunities, bike rides for ice cream, and spectacular coastal sunsets capture the simple pleasures of a quintessential New England beach community.The property also features a garage with generous storage space and additional laundry facilities, perfect for accommodating beach gear, bicycles, and boating essentials. This special property offers the perfect combination of modern amenities and charm!

70 Old Mail Trl, Westbrook

$559,900

3 Beds ⋅ 2 Baths ⋅ 24209993 MLS

Prominently set on a desirable corner lot in historic Ivoryton, this custom three bedroom ranch is designed for the way we live today. From the moment you step onto the inviting front porch overlooking park-like grounds you will feel right at home. Move-in ready and offering desirable one floor living, the spacious open floor plan of this unique home features gleaming hardwood floors has been freshly painted throughout the main level. Truly a Chef's delight and the heart of the home is the well-appointed kitchen, featuring rich wood cabinetry, granite countertops, and a center island...perfect for enjoying your morning coffee. The light-filled dining area is ideal for everyday meals or those special occasions and a spacious living room with sliders opens directly to your private backyard retreat. The primary bedroom features a lovely updated bathroom and two well-appointed bedrooms with a shared bath are perfect for guests. The lower level bonus rooms adds an additional 638 sq. ft.and offers endless possibilities such as an in-home office, craft-room, media space or work-out area. A separate laundry area and easy access to the mechanicals will give buyers peace of mind. Ideal for entertaining, there is a casual outdoor dining area and a charming fire pit for gathering with friends and family. A handy garden shed is perfect for all of your storage needs. Whether you are looking for a full time residence or an ideal weekend retreat enjoy all historic Ivoryton has to offer.

3 Rachel Ln, Essex

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Middlesex County Homes for Sale

Newest Middlesex County Homes for Sale

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