Middlesex 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 Homes for Sale

$399,900

3 Beds ⋅ 2 Baths ⋅ 24205702 MLS

Welcome to 33 A P Gates Road, where privacy, space, and the natural beauty of East Haddam come together. Set on an expansive 8.25-acre parcel featuring a picturesque pond, this property offers a wonderful opportunity to enjoy the tranquility of a private setting while creating a home that reflects your lifestyle. With approximately 1,357 square feet of living space, the residence offers a comfortable footprint with room to make it your own. The generous acreage provides exceptional outdoor space for recreation, gardening, entertaining, or simply enjoying the peaceful surroundings. Whether you're looking for a private retreat, a place to put down roots, or a property with room to grow, this offering provides a rare combination of land and location. Situated in scenic East Haddam, the property offers the opportunity to enjoy the charm of the Connecticut countryside while remaining conveniently connected to area amenities and attractions. If you've been searching for a property where privacy and possibilities take center stage, 33 A P Gates Road is one to see.

33 A P Gates Rd, East Haddam

$609,000

3 Beds ⋅ 3 Baths ⋅ 24207436 MLS

Welcome to this gorgeous 3-bedroom, 3.5-bath Colonial nestled on a desirable cul-de-sac in a highly sought-after neighborhood. Filled with natural light, this beautifully updated home offers comfort, space, and functionality throughout. The home has been thoughtfully updated within the past two years.The inviting living room features beautiful flooring and flows seamlessly into the dining area, creating an ideal space for entertaining. The updated kitchen offers new appliances, abundant natural light, and convenient access to the sunroom-perfect for relaxing and enjoying the surroundings. The oversized family room provides plenty of space for quality time with family and friends.Upstairs, you'll find generously sized bedrooms, with updated carpeting throughout the second floor. The spacious primary suite features hardwood flooring, a ceiling fan, and a private bath with a Jacuzzi tub and separate standing shower. Additional ceiling fans throughout the home enhance comfort and airflow.The finished walkout basement adds valuable living space and includes a full bathroom, making it ideal for a media room, recreation area, home office, or entertaining space. Step outside to enjoy the beautiful backyard and patio, perfect for gatherings, outdoor dining, and summer celebrations.This wonderful home offers a great combination of updates, space, and location. The seller has spent $161,000 to keep the house updates. Don't miss the opportunity to make it your own dream home!

184 Rolling Grn, Middletown

$539,900

3 Beds ⋅ 3 Baths ⋅ 24207248 MLS

Welcome to Sylvan Run, a welcoming Westfield neighborhood where spacious homes, three cul-de-sacs and a convenient Middletown location come together. This beautifully updated Saltbox Colonial offers an impressive amount of living space with a layout designed for both everyday comfort and entertaining. Step inside to hardwood floors and a bright, inviting interior. The updated kitchen features granite countertops with stainless steel appliances. The open floor plan makes the stunning custom pellet stove fireplace the focal point of family room with vaulted ceilings adding to the spacious feel. Two sets of sliding doors connect the main living spaces to the expansive rear deck and fully fenced back yard. A formal dining room and living room provide even more flexibility on the main level. Upstairs, the spacious primary suite offers dual closets and an updated private bath. An open hallway overlooking the family room below enhances the homes bright, airy feel, while two additional generously sized bedrooms and full bath complete the second floor. Need even more space? The finished lower level offers exceptional versatility for a recreation room, home gym, office, media room or playroom along with a dedicated laundry room and cedar closet. Outside enjoy your evenings on the expansive deck overlooking the fenced backyard or take advantage of the Sylvan Run neighborhood - perfect for a stroll, bike ride or enjoy the picnic area.

897 East St, Middletown

$928,000

3 Beds ⋅ 4 Baths ⋅ 24207147 MLS

Born in 1835. Reimagined for life today. Expanded to over 2,950 sq. feet, the new floor plan emphasizes light, proportion, and seamless flow from one room to the next. At its center, a beautifully composed chef's kitchen pairs a waterfall island with white cabinetry and an oversized walk-in pantry, making entertaining feel wonderfully uncomplicated. The adjoining vaulted great room is the home's defining gesture: window-lined and grounded by dramatic millwork. Three en-suite bedrooms invite family and friends to settle in with privacy. The primary suite offers two walk-in closets, while a generous upstairs lounge can easily serve as a library, office, or media room. A second-floor laundry adds discreet modern practicality. Beneath the polished interiors of an 8-month transformation, including a new roof, siding, plumbing, kitchen, baths, hardwood floors, and a Trex deck. Set on .85 acres next to the protected landscape of Bushy Hill Preserve, the property feels quietly removed while remaining close to Essex shoreline marinas, beaches, and notable restaurants-a country house with a sense of occasion and history without compromise.

60 Blushy Hill Rd, Essex

$619,900

3 Beds ⋅ 3 Baths ⋅ 24207265 MLS

Lake Overlook Estates - an enclave of 12 homesites with stunning seasonal views of Lake Pocotopaug. Lot 4 - last home site available in Phase I. One floor living at its best. This beautiful Cape with first floor primary offers it all. First floor offers laundry room, mudroom, open great room concept with open balcony from above. Second floor offers 2 additional bedrooms and full bath. Options for finishing above the garage for additional space. Some additional standard features include granite counters, onsite finished hardwood floors throughout first floor except bathrooms, gas fireplace, deck and many cabinet options. The list goes on! Public sewer, public water. All situated on a beautiful level homesite with seasonal views of Lake Pocotopaug. Foundation is in, still time to make modifications. Estimated completion is end of April 2027. No association. Sewer/water connection fee $4500. Floor plan coming soon.

7 Freya Ln, East Hampton

$664,900

5 Beds ⋅ 3 Baths ⋅ 24207255 MLS

Lake Overlook Estates - an enclave of 12 homesites with stunning seasonal views of Lake Pocotopaug. Lot 4 - last home site available in Phase I. Expanded Colonial III - this stately home offers a spacious and dramatic first floor with two story entry. The large kitchen is open to eating area and large great room. One will enjoy a mudroom, first floor office and fantastic sized dining room. This amazing abode offers plenty of large windows throughout, letting the outside in. The upstairs continues to impress with an oversized primary bedroom with 2 large walk in closets, an en suite with soaking tub and oversized walk in tile shower. One will also enjoy a walk in laundry room with plenty of space also located on the second floor. Many upgrades available including a possibility of finishing above the garage for a luxurious primary suite or 5th bedroom or bonus room/game room. Some additional standard features include granite counters, onsite finished hardwood floors throughout first floor except bathrooms, gas fireplace, decks, cabinetry color choices. The list goes on! Public sewer, public water. Foundation is in, still time to make modifications. Estimated completion is end of April 2027. No association. Sewer/water connection fee $4500.

7a Freya Ln, East Hampton

$639,900

4 Beds ⋅ 3 Baths ⋅ 24207253 MLS

Lake Overlook Estates - an enclave of 12 homesites with stunning seasonal views of Lake Pocotopaug. Lot 4 - last home site available in Phase I. Expanded Colonial I - this stately home offers a spacious and dramatic first floor with two story entry. The large kitchen is open to eating area and large great room. One will enjoy a mudroom, first floor office and fantastic sized dining room. This amazing abode offers plenty of large windows throughout, letting the outside in. The upstairs continues to impress with an oversized primary bedroom with 2 large walk in closets, an en suite with soaking tub and oversized walk in tile shower. One will also enjoy a walk in laundry room with plenty of space also located on the second floor. Many upgrades available including a possibility of finishing above the garage for a luxurious primary suite or 5th bedroom or bonus room/game room. Some additional standard features include granite counters, onsite finished hardwood floors throughout first floor except bathrooms, gas fireplace, decks, cabinetry color choices. The list goes on! Public sewer, public water. Foundation is in, still time to make modifications. Estimated completion is end of April 2027. No association. Sewer/water connection fee $4500.

7b Freya Ln, East Hampton

$29,900

2 Beds ⋅ 1 Baths ⋅ 24207044 MLS

Shoreline Potential at an Affordable Price! Looking for a place you can call home year round, or your own little Connecticut shoreline escape when the mood strikes? This 868 square foot, two bedroom, one bath home offers the flexibility to do both! Step inside and you'll appreciate the high ceilings, which give this cozy home a surprisingly spacious and airy feel. The practical single level layout offers comfortable living and dining areas, two bedrooms, one full bath, and plenty of opportunity to bring your own style to the space. And then there's the porch! Grab your coffee, settle in, and enjoy the marsh views and refreshing seaside air. It's the perfect place to slow down and enjoy the setting. The mechanicals have been maintained and are functional, providing a solid starting point for the buyer with a little vision. This is an opportunity for someone who isn't afraid to update and make the home their own. Similar sized updated homes in this park and surrounding parks have sold for $100,000 or more, making the potential here worth a closer look. Live here year round or make it your own affordable coastal retreat. With Clinton's town center, beaches, marinas, shopping, dining, public transportation, and local schools nearby, you'll be close to everything while still enjoying your own little slice of shoreline living. A few important details: This is an estate sale and no seller disclosures are available. The land is leased. Cash purchase preferred. Br

133 W Main St Unit LOT A23, Clinton

$1,100,000

2 Beds ⋅ 3 Baths ⋅ 24185943 MLS

Situated on historic Prospect Hill in Essex, this distinctive ranch style home is set on a .54-acre lot. Originally the Christian Science Reading Room, it was thoughtfully expanded with carefully curated additions during the 1970s, 1980s, and 1990s. Offering approximately 2,900 square feet, the home features 2 bedrooms, 3 full baths, an attached two-bay garage, and desirable one-floor living. High ceilings, wood and bluestone floors, three fireplaces, detailed paneling, moldings, and built-in bookshelves enhance much of the interior. Hand-painted marine murals throughout the home create a distinctive maritime-inspired ambience. The floor plan includes formal living and dining rooms, a comfortable library, a family room with a fireplace, and a sunroom/studio. The spacious eat-in kitchen offers banquette seating, a center island with bar seating, generous counter space, and abundant storage. A large deck spans the rear of the house and overlooks ample garden space. Filled with character and history, this unique property enjoys a convenient location close to everything Essex has to offer. This property is offered in AS-IS condition. The owner has lived here very comfortably for nearly 4 decades and this presents a superb opportunity to acquire and renovate a rare ranch style home in the Village.

27 Prospect St, Essex

$244,900

4 Beds ⋅ 1 Baths ⋅ 24205927 MLS

Set on a quiet dead-end street near Wesleyan University and downtown Middletown, 27 Fairview Ave is a classic 1934 Colonial with character, convenience, and potential. This estate property features 1,235 sq ft, 4 bedrooms, 1 full bath, (with room for a 2nd bath on the upper level) and walk-in attic space. MAJOR RECENT IMPROVEMENTS INCLUDE: NEW ROOF IN 2024 (stripped & reroofed=1 layer), NEW 200 AMP ELECTRICAL SERVICE IN 2025, a NEW OIL BOILER AND OIL TANK in 2025 as well as a NEW CEILING IN both the LIVING ROOM and ONE BEDROOM, all of which creates a strong starting point for a remodel. The traditional layout offers defined living spaces, a manageable footprint, and room to bring fresh ideas to the kitchen, bath, finishes, and overall design. Its central Middletown location provides easy access to nearby campus, downtown shops, restaurants, parks, and commuter routes. Best suited for an investor or contractor. This property will not qualify for FHA or VA financing. Cash, renovation loan or conventional financing only. This home to be sold strictly AS-IS. Seller will not make any repairs. Sale is subject to Probate Court approval.

27 Fairview Ave, Middletown

$549,900

3 Beds ⋅ 3 Baths ⋅ 24204996 MLS

Set well back from the road on 4.6 secluded acres, this beautifully maintained ranch combines generous one-level living with a bright, welcoming feel throughout. Large windows on all sides bring in abundant natural light and frame views of the expansive landscaping, lawn, and surrounding trees. The spacious remodeled kitchen anchors the home's everyday living, with beautifully crafted cabinetry, substantial granite countertops, a large custom center island, and generous workspace, complemented by expansive backyard views and seamless flow to the outdoor living space. The private bedroom wing includes a generous remodeled primary suite with hardwood floors, 3 spacious closets, and a modern private bath designed for the comfort, style, and functionality today's buyers expect. Just beyond the primary suite, a dedicated office with extensive built-ins offers flexible space for working from home, studying, meetings, or enjoying a hobby. The living and dining rooms flow together with warm hickory floors and custom millwork, while a thoughtfully designed mudroom/pantry just off the kitchen adds character and function with built-in cubbies and cabinetry. Outside, the broad, open lawn offers room to gather, play, garden, or enjoy the private setting. A Trex deck and paver patio extend the living space outdoors, creating an inviting place to relax or entertain. Meticulously cared for and truly move-in ready, this home feels spacious, comfortable, and private from the moment you arrive.

1446 Randolph Rd, Middletown

$899,000

4 Beds ⋅ 1 Baths ⋅ 24206662 MLS

Quintessential summer waterfront cottage lovingly owned by the same family for 88 years. Enjoy four bedrooms and sleeping porch option. Large Sandy beachfront. Long Island Sound views from dining room, living room, enclosed 400sf porch and upstairs bedroom. Paneling in bedrooms and hardwood floors on lower level. Also nearby access to Clinton Town Beach and Hammonasset State Park. Outlet mall and grocery stores nearby. Close public bus, commuter and Amtrak train station. Shown by appointment. Do not go on the property without permission.

105 Shore Rd, Clinton

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