10,755 houses for sale in Middlesex County, Connecticut

Renovated 1910 Colonial with Open Floor Plan. Down the Road From Town Beach. Just a Short Bike Ride to Down Town Greenport and Wineries! Possibility of Selling Fully Furnished! Large Back Building Could Be Turned into a Pool House, Garage or Shed, Additional information: Appearance Diamond, Interior Features: Living Rm, Dining Area, Spacious Eat in Kitchen with Large Island, Breakfast Nook, 3 Bedrooms(Small one on First Floor, 2 On 2nd Floor), 1.5 Renovated Bathrooms. Separate hotwater heater, 2 separate driveways seller is applying for permit and variance for a inground pool, he is selling with permit only for it not install

Tucked away in a secluded waterfront setting, this charming bayside cottage offers a rare opportunity to enjoy peaceful North Fork living surrounded by natural beauty and captivating water views. Designed to embrace its exceptional location, the home features an open-concept living, dining, and kitchen area where abundant windows frame the water and fill the interior with natural light throughout the day. The seamless layout creates an inviting atmosphere for gathering with friends or simply relaxing while enjoying the tranquil waterfront setting. Offering two bedrooms and one bath, this retreat home provides the perfect escape from the everyday. Whether you're seeking a seasonal getaway or investment opportunity, the property's unique combination of privacy, water views, and North Fork charm is difficult to find

Charming 1920's farmhouse located in the heart of Greenport Village. Three blocks from Jitney/LIRR, restaurants, shops, galleries and Greenport's historic waterfront. 3 beds, 2 full baths, wide plank hardwood floors, updated kitchen, plumbing and electric. Attractive backyard with southern exposure. Ready to move right in and enjoy all Greenport and the North Fork has to offer. Close to town, beach and public transport

A rare and exceptional offering in the heart of Greenport—one of the only duplex-style properties of its kind on the North Fork—this fully turnkey property delivers a unique combination of lifestyle, flexibility, and proven income potential. Located within Greenport Village and offering approximately 3,376 square feet of living space, this back-to-back duplex features two fully independent, two-story residences, each with its own full basement, central air conditioning, and private living areas as well as two electric panels, two meters, two propane tanks and separate basements. Built approximately 7 years ago, the property offers the advantages of newer construction, including modern systems, efficient design, and low-maintenance living. The front residence offers 4 bedrooms and 2.5 baths, highlighted by a welcoming covered front porch, fireplace, and a full basement with 8-foot ceilings—ideal for expansion, recreation, or storage. The rear residence features 3 bedrooms and 2.5 baths,

Welcome to a truly exceptional property that masterfully combines the timeless allure of classic architecture with the comforts of modern living. This stunning home, built in the 1800s, showcases a wealth of character, highlighted by beautifully exposed beams that infuse warmth and charm into every room. Step inside to discover a completely updated interior that harmonizes historical elegance with contemporary style. Throughout the home, classic wide plank hardwood floors create a cohesive and inviting feel, while beautifully preserved vintage details, including salvaged tiles from past renovations, pay homage to the property's rich history. The spacious living room invites you to unwind beside the fireplace, creating a cozy atmosphere ideal for gatherings or quiet evenings. The heart of the home lies in the dining room and eat-in kitchen area, both designed with ample space to accommodate gatherings and culinary adventures. Venture outside to discover a charming mahogany deck, perfect

Discover North Fork charm at this cozy two-bedroom cottage in Cutchogue. The home features a full bath, galley kitchen, and an open living and dining area ideal for relaxed everyday living. Surrounded by mature trees, the wooded setting offers privacy and seclusion while remaining convenient to local vineyards, farm stands, shops, restaurants, and nearby Causeway Beach. An appealing opportunity to enjoy the beauty and lifestyle of the North Fork

Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, Southold, a circa-1909 farmhouse rich in warmth, character, and North Fork authenticity. This charming home, situated on a 1/2 acre, captures the essence of early-20th-century farmhouse living, offering a cozy, inviting atmosphere paired with thoughtful functionality and future potential. The residence features three bedrooms, one full bath, and one half bath, along with building plans for a potential second full bathroom on the second floor, allowing the next owner to enhance comfort while preserving the home’s original charm. Original wood flooring and original moldings combined with new windows throughout, updated kitchen featuring granite and marble countertops high end appliances and updated roof lends itself to nostalgic beauty while enjoying modern-day functionality and efficiency. The home has new I-A septic technology. The expansive 4 car garage is an excellent opportunity for car lovers.

Every once in a while, a home comes along that just makes you smile-and this is one of them. Set on just under an acre in Southold, this classic farmhouse is full of charm, character, and even its own secret garden. With 6 bedrooms and 3 bathrooms, there's plenty of room for everyone, plus multiple living spaces, cozy sitting rooms, a dining area made for gathering, an open kitchen, laundry room, and a covered porch you'll never want to leave. The backyard has room for the pool you've been dreaming about, while the gardens and outdoor space feel like your own private escape. Just minutes from Cedar Beach and Goose Creek Beach, this is the kind of home that feels like summer all year long. Whether you're looking for a forever home, a North Fork getaway, or a place to make memories for generations, this farmhouse is ready for its next chapter

The pinnacle of Luxury Living In the historic heart of Sag Harbor — a village shaped by its storied whaling past and now celebrated for its cultural sophistication — Residence A stands as a singular architectural statement along one of the most coveted stretches of waterfront. Commanding approximately 250 feet of prime frontage on the harbor, this exceptional estate is far more than a home; it is a four-level masterwork of glass, stone, and light, created for a global buyer seeking complete privacy, effortless luxury, and direct nautical access. This extraordinary property is the result of a visionary collaboration between J. Bialsky of Bialsky Premiere Design & Development and the internationally acclaimed Hollander Design Landscape Architects. Together, they have crafted a residence that exists in perfect harmony with the Peconic Bay — a seamless dialogue between architecture, landscape, and water. Every line is intentional, every perspective framed, and every material selected to en

Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious. 39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional and inviting layout featuring a comfortable living area, three nicely sized bedrooms, a full bathroom, dining room and an eat-in kitchen. The full basement provides an abundance of additional space for storage, utilities, a workshop, or the potential for future finishing. A detached garage adds even more storage and convenience. Outside, the generous. 39-acre property offers plenty of room to relax, entertain, garden, or create your ideal outdoor retreat. Conveniently located near Southold's charming village, local shops and restaurants, beaches, wineries, farm stands, and all that the North Fo

Welcome to 1175 9th Street in Greenport—a two-story, four-bedroom, three-and-a-half-bath with a full, finished basement with exterior staircase. The home is filled with natural light and hardwood floors throughout the main living spaces. The first floor offers an open living area with a wood-burning fireplace that flows into a spacious eat-in kitchen with a large island and sliding glass doors to the a secluded and private rear yard. Just off the entry, a formal dining room connects to the kitchen, and a hallway includes a conveniently placed half bath and pantry. Upstairs are four bedrooms, including a primary suite with an ensuite bath, plus a second full bathroom. In the winter months, two of the bedrooms enjoy views of the bay. The finished full basement adds flexible bonus space with a full bathroom, a dedicated laundry area with washer and dryer, and a walk-out staircase to the exterior side yard. Less than a half mile to 5th and 6th Street beach, park and dock and roughly three-

Set in the wonderful North Fork beach community of Summit Estates, this spacious 3 bedroom, 2-bath cedar shake expanded ranch is ideal with its single-story living design and large yard. Perfect for a pool and poolhouse. The Community beach, park, and dock are down an elegant private lane to a community parking lot and a magical paved trail. So handy to easily transport your beach and boat equipment from car to beach and boat! Close to Island’s End Golf Course, wineries, and the transportation hub and shopping/dining in the historic seaport Village of Greenport. A lovely North Fork retreat!

Set along one of Mattituck’s most sought-after waterfront enclaves, 2280 Deep Hole Drive offers a rare opportunity to own an exquisite waterfront residence newly built in 2022, encompassing 3,000 square feet of thoughtfully designed living space with exceptional deepwater dockage and direct access to Peconic Bay. Perfectly suited for the boating enthusiast, the property features approximately 130 feet of deepwater frontage on Deep Hole Creek and a substantial dock capable of accommodating two vessels up to 36 feet, complete with electric and water, providing protected, convenient access to the bay and beyond. The home features 9-foot ceilings on the main level, an open-concept layout filled with natural light, expansive water views, and refreshing bay breezes throughout. At the heart of the home is a custom chef’s kitchen appointed with premium, professional-grade appliances, high-end finishes, and a large center island ideal for entertaining and everyday living. The kitchen flows seam

Miami modernism meets the north fork. Set on a spacious and private. 60-acre hilltop parcel in coveted Nassau Point, this fully updated four-bedroom modernist ranch offers an unexpected departure from the ordinary. Its traditional exterior gives little indication of the sleek, light-filled interiors within—an independently conceived home with the confident glamour of Miami and the relaxed ease of Cutchogue. Individual design matters. Rather than repeating a familiar, cookie-cutter floor plan, this residence has an architectural identity all its own, expressed through gleaming white marble floors, clean lines, generously proportioned rooms and a seamless connection between indoor and outdoor living. The result feels distinctive, sophisticated and refreshingly personal. At the heart of the home is a spectacular chef’s kitchen designed for serious cooking and effortless entertaining. It opens to a private garden courtyard, creating an intimate setting for morning coffee, outdoor dining or

North Fork. Cutchogue. Create your ideal North Fork retreat in an extraordinary natural setting. This single story, four-bedroom home sits along the tranquil edge of West Creek in Cutchogue, offering the rare potential for water views and a front row seat to the area’s ever changing local wildlife. Whether you envision a thoughtful renovation or a completely new design, the property provides a canvas in one of the North Fork's desirable locations. Down the road, a 10' wide neighborhood only right-of-way leads to a 33' portion of a Bay beach. Sweeping vistas make every visit unforgettable. The New Suffolk Beach is only moments from your doorstep, and the North Fork Country Club sits just steps away, adding to the exceptional lifestyle this setting affords

Charming, private, and uniquely connected to the water, this cedar-shingled three-bedroom cottage offers a compelling combination of immediate enjoyment and future potential. Set on nearly an acre, the property includes a 50' wide section that extends to the bay, where a beachside double deck and stairs provide direct access to your private stretch of sandy beach. Inside, the living room is anchored by a beautiful fireplace and opens to a brick patio, creating an easy flow between indoor and outdoor living. Wrapped in glass, the sunroom addition serves as a cozy retreat, immersing you in the property's natural surroundings. Multiple en-suite bedrooms round out the offering. Whether enjoyed as a quintessential North Fork getaway or expanded to create a larger coastal residence, the setting is exceptional. True private bayfront at a price point that rarely exists

Set within the coveted enclave of Nassau Point, this exceptional 4,000-square-foot retreat offers privacy, timeless architecture, and an elevated North Fork lifestyle. Positioned on a shy acre with plenty of room for a pool, this beautifully designed home is crafted for effortless year-round living and entertaining. A dramatic Great Room with cathedral ceilings and wood floors anchors the residence, complemented by a chef’s kitchen, den, reading room, game room with wet bar, billiard room, wine cellar, and private second-floor primary suite with office. The home’s generous and versatile layout offers exceptional flexibility for separate guest quarters, extended living arrangements, or the potential for an owner-occupied accessory rental, subject to all applicable municipal approvals and permitting. Wraparound decks, lush gardens, a four-car garage, and full-house generator complete the property. Just moments from the Peconic Bay, residents enjoy access to private bay beaches and rights

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other fea

Beautifully Upgraded Ranch with Exceptional Garage & Setting in Mattituck Welcome to this well-maintained 3-bedroom, 2-bath Ranch-style home, set on a rise in a desirable Mattituck setting with peaceful easterly views. The home is in excellent condition and features numerous recent upgrades, offering a comfortable blend of classic Ranch-style living and modern improvements. A large deck extends the living space outdoors, providing an ideal spot for relaxing, entertaining, or enjoying the tranquil views and natural surroundings on this half acre of property, the electric is supplemented by owned solar panels offering substantial savings to electric bill. One of the property’s standout features is the oversized detached 24'x32' 4+car garage, complete with heat, electric, 768 sq. Ft. —a rare and highly versatile amenity. Whether you need substantial space for vehicles, hobbies, a workshop, storage, or recreational equipment, this garage offers tremendous flexibility. Situated on a slightl

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank