3,768 houses for sale in Middlesex County, Connecticut

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

A very large home with over 2,200 square feet and 4 oversized bedrooms, this property already has a heated saltwater pool permit and all new furniture. Designer-owned and just received a brand new renovation, new natural gas connected, this exceptional North Fork retreat seamlessly blends modern sophistication with timeless coastal charm. Perfectly positioned across from pristine protected land and a scenic golf course, the home offers tranquility, privacy, and effortless access to the very best of Cutchogue living. If you love golf, you are steps to Cedars Golf Club and can play every day. Ideally located just moments from the charming Cutchogue center, enjoy a 2 minute walk to town, local shops, restaurants, North Fork Country Club, and the Hampton Jitney with direct service to Manhattan. Spend your days biking to nearby New Suffolk, renowned North Fork beaches, acclaimed vineyards, Wickham's farm stand, and waterfront dining. Just 85 miles from Manhattan, and perfect location with n

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature. Spanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise to sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level. The upper level reveals the home's most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized

Some things are worth holding onto and this one is no exception. Nestled in one of the North Fork's most coveted beachside enclaves, this authentic mid-century modern gem offers the rare combination of style, privacy and beach access to one of the best bay beaches in the region! The detached 2-car garage handles the practical side of life beautifully with owned solar panels, including backup battery, while the working vegetable garden reminds you that the good life really is grown here. There's room for a pool, room to expand, and plenty of room to exhale. Optional membership in the Fleets Neck Property Owners Association gets you access to a private bay beach on the east end of Dave Allison Beach - plus storage for two kayaks. This is the kind of property that smart buyers recognize immediately - and move on quickly. The bones are right. The location is right. The potential? Even better

Minutes from the bustle and charm of Sag Harbor Village, set on an exceedingly private and gated acre-plus flag lot with mature hedges, this immaculate 7 bedroom, 6500 square foot traditional checks all the boxes of a quintessential Hamptons summer home with a heated, gunite pool and spa, exceptional outdoor spaces, lined with hydrangeas, built-in BBQ grill kitchen, and an expansive finished lower level. Through the automated gate, a tree-lined approach leads to the handsome, white, shingled traditional with an attached 2-car garage. Adorned with shiplap, the bright, full height foyer creates a dramatic first impression. With lovely indoor and outdoor flow, the open concept floor plan offers a gourmet eat-in kitchen with an adjacent living room with fireplace and sitting area, with two sets of French door leading to the covered porch overlooking the pool area and rear grounds. A formal dining room with passthrough wet bar and wine storage serves the kitchen. A guest bedroom suite, pool

Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as

Nestled in the heart of Cutchogue along a quiet private road, this beautifully maintained four-bedroom, two-and-a-half-bath home is set on more than 3.3 picturesque acres, graced by mature trees and thoughtfully landscaped grounds. Inside, hardwood floors, three gas fireplaces, Anderson windows, and two beautifully updated full bathrooms create warm, inviting living spaces designed for both everyday comfort and entertaining. The backyard embodies the best of North Fork living, featuring a new in-ground pool, spacious patio, outdoor bar, and mature landscaping-an inviting setting for relaxing or entertaining. A detached two-and-a-half-car garage with an expansive loft above offers flexible space for a home office, studio, workshop, or additional storage, while a barn-style outbuilding and expansive grounds provide exciting possibilities for equestrian use, hobby farming, or recreation. Just minutes from beautiful Peconic Bay beaches, wineries, farm stands, and some of the North Fork's b

Sound front retreat. Designed in 1986 by architect Sanford Hanauer for his own residence and reimagined in 2011, this elegant homestead is modern luxury done the right way. Set high above the shoreline on 2.45 acres with 200 feet of direct beachfront, angled so the water is the constant-nearly every room, every day, every season. Floor-to-ceiling glass pulls in the light, while bluestone accents, wide ash plank floors, and three fireplaces keep it warm and grounded. The Eggersmann kitchen with a butler's pantry is as timeless as it is functional, ready for quiet mornings, long lunches, and the kind of dinners that start at golden hour and somehow become tradition. Outside, the 50-foot pool is set discreetly into the bluff-private, protected, yet open water views. Two additional bedrooms are positioned to work like a separate guest cottage-ideal for extended stays or flexible space for work. A loft, multiple decks, and sun-soaked patios make indoor-outdoor living feel natural-because he

Nestled in the heart of the North Fork, this beautiful 4-bedroom, 2 1/2-bath Colonial offers the perfect blend of coastal charm and everyday convenience. Ideally situated near golf courses, pristine sandy beach, acclaimed restaurants, wineries, and the vibrant downtown area, this home provides an exceptional North Fork lifestyle. Inside, you'll find spacious living areas filled with natural light, generously sized bedrooms, central ac upstairs, and a thoughtfully designed layout perfect for both entertaining and comfortable family living. Step outside to your own private retreat featuring a large patio overlooking a beautifully landscaped backyard. The tranquil koi pond, elegant arbor, and lush gardens create a peaceful setting for outdoor dining, gatherings, or simply relaxing after a day at the beach or golf course. Whether you're seeking a year-round residence or a seasonal getaway, this charming Colonial offers the best of North Fork living in a highly desirable location

Enter by way of a circular drive to this Designers own fabulous reconstruction and renovation of the Classic and Iconic Captain Cartwright House handsomely landscaped in Shelter Island. This classic. Reference: 37311 909434Key FeaturesPATIOPark ViewsDenGarage Ref: 37311-909434

Welcome to 380 Clark Road, a sun-filled North Fork escape perfectly located near the beautiful beaches of Southold. Blending comfort, charm, and endless backyard potential, this turn key home captures the easygoing lifestyle that makes the North Fork so desirable. Natural light pours throughout the home, creating bright, cheerful interiors and a warm, welcoming feel from the moment you arrive. The updated interior offers a relaxed and effortless flow, perfect for summer weekends, entertaining friends, or cozy year-round living in front of the fireplace. Additional improvements include an updated kitchen and renovated bathrooms, thoughtfully designed to combine style, comfort, and functionality. A newer roof installed just two years ago adds further peace of mind, allowing you to simply move in and enjoy. Step outside and the fun really begins. The expansive backyard offers an incredible opportunity to create your dream outdoor retreat with plenty of room for a pool, outdoor kitchen, fi

Tucked away along Terry Path, a rustic country lane within, an offshoot of the Camp Mineola Beach Association, this exceptional waterfront property is nestled in a quiet seaside enclave along the Great Peconic Bay. Opportunities to purchase within this historic neighborhood are exceptionally rare, making this a truly special offering. Set on approximately 1.4 acres with more than 110 feet of unobstructed frontage on the Great Peconic Bay, the classic Cape Cod-style residence offers timeless charm and tremendous potential. The spacious interior is centered around a striking stacked red brick wood-burning fireplace, while outside, a private sugar sand beach and full bulkhead provide an ideal setting for enjoying the waterfront. A substantial original boathouse, complemented by a newer three-car garage and expansive bonus space above, offers endless possibilities for storage, recreation, or future customization. The level, cleared grounds enjoy abundant sunlight throughout the day and pro

Welcome to 1545 Indian Neck Lane, a beautifully updated ranch set on a private 3/4 acre property in one of the North Fork’s most sought after locations. Surrounded by mature landscaping and tucked away from the road, this 3 bedroom, 3 bath home offers the perfect blend of comfort, style, and easy coastal living. Recently refreshed throughout, the home features updated kitchen w/stainless steel appliances, quartz countertops, new 48' Viking Stove, new white oak hardwood floors throughout, updated bathrooms, new Navien high efficiency boiler/water heater combo, freshly painted, and bright open living spaces filled with natural light from multiple skylights and Marvin windows. Vaulted ceilings with exposed wood beams create warmth and character, while the open concept layout offers a seamless flow for both everyday living and entertaining. The spacious kitchen opens into expansive dining and living areas overlooking the property, creating an inviting atmosphere throughout the home. The pr

Enter the Season and enjoy North Fork Serenity with the creek across the street to launch into what Southold has to offer. Discover the perfect blend of coastal charm and country tranquility at 430 Grove Road, ideally located in the heart of Southold on the beautiful North Fork of Long Island—where vineyards, farms, and waterfront serenity define the lifestyle. This inviting 3-bedroom, 1-bath ranch-style home sits just three houses from the creek, offering easy access for paddleboarding, kayaking, and peaceful waterfront strolls. The property provides a relaxed atmosphere with room to enjoy the outdoors—whether you’re savoring local wines, exploring nearby beaches, or taking in sunsets over the bay. Enjoy an amazing quality of life surrounded by nature, yet close to all the best the North Fork has to offer—boutique wineries, farm stands, marinas, and charming village shops. Perfect as a year-round residence, weekend retreat, or investment opportunity, this home captures the essence of

Price improvement! Whether year-round living or a summer getaway, do not let this one'Get Away'! Located on the much-desired Gull Pond Lane, this classic ranch-style home presents a rare opportunity to create your North Fork Dream. Architectural design plans for renovation are available to view. This home features freshly refinished hardwood floors, 3 bedrooms, 1 newly updated full bath, one primary suite half bath, a formal dining room, a spacious and inviting living room with a wood burning fireplace, large picture window and custom built-ins, a whole house standby generator and a full basement with endless possibilities. Updates also include Hot Water Tank, CAC, Electrical Service and most windows. Set on a generous-sized private lot, it is the perfect setting for quiet times or outdoor entertaining. Conveniently located, this hidden gem is near Greenport Village shops, award-winning restaurants and wineries, marinas, farm stands, Island's End Golf & Country Club, Shelter Island Fer

Welcome home to this North Fork retreat! The perfect getaway for peace and relaxation. Tucked away on a charming lane, this beautifully maintained home and features a resort-style yard centered around an in-ground pool and patio, creating the ultimate setting for entertaining. Inside this renovated home, there is plenty of room for everyone and offers a seamless flow between indoor and outdoor living. Location is everything, and this property has it all. Take a short stroll to the beach for swimming, kayaking, paddle boarding. Boating and fishing enthusiasts will appreciate being just down the road from Strong’s Marina, offering easy access to the best boating on The Peconic Bay. Whether you’re searching for a full-time residence, weekend escape, or investment opportunity, this home has it all. Close to Love Lane, shopping, restaurants, wineries, transportation and all the best Mattituck has to offer

Tucked away in the coveted waterfront hamlet of New Suffolk, this charming move-in ready ranch captures the easygoing spirit of North Fork living. Warm hardwood floors run throughout the home, where an inviting living and dining area flows effortlessly into a bright, sun-filled kitchen overlooking the backyard gardens. The layout offers two comfortable guest bedrooms, a full hall bath, and a private primary suite with its own full bath, walk-in closet, and laundry area. Outside, the property feels peaceful and established, with lush green lawns, thoughtfully maintained garden beds, and a vegetable garden tucked along the rear of the yard. Just moments from the beloved New Suffolk beach, local favorites like Minnow and Legends Restaurant, and Shagwong Marina, the location places you right in the heart of one of the North Fork’s most cherished waterfront communities. Whether envisioned as a quiet weekend escape or a year-round home, life in New Suffolk offers a timeless coastal charm tha

Welcome to 145 Baldwin Place, a spacious and inviting 5 bedroom Colonial set on two private acres in the heart of Cutchogue. A sun-filled foyer with cathedral ceilings creates an impressive first impression, leading to thoughtfully designed spacious living spaces ideal for both everyday living and entertaining. The center of the home is the expansive open concept kitchen with a seamless flow into living and dining areas. Upstairs, the private primary suite serves as a true retreat with vaulted ceilings, generous closet space and a spacious ensuite bathroom. Four additional bedrooms provide generous space and flexibility throughout the home. Set on two private acres, the property offers a beautifully landscaped setting along with plenty of open space for recreation, a pool or outdoor entertaining. Located just moments from the pristine beaches of the Peconic Bay, residents can enjoy swimming, kayaking, paddleboarding, and unforgettable sunsets. Nearby farmstands, vineyards, waterfront d

Welcome to the Heart of North Fork Wine Country! Experience the perfect blend of peace, comfort, and convenience in one of Eastern Long Island’s most sought-after destinations. Nestled on a quiet street surrounded by picturesque vineyards, this charming 3-bedroom, 1-bath home with brand-new stainless-steel appliances features a garage and full basement, offering plenty of space for everyday living and future possibilities. Enjoy the relaxed North Fork lifestyle with farm stands, local markets, and seasonal farm attractions just minutes away. Spend your summers exploring beautiful beaches on both the Long Island Sound and Peconic Bay, and visiting the area’s renowned wineries, vineyards and dining. Outdoor enthusiasts will appreciate the nearby parks featuring tennis courts, baseball fields, and recreational spaces, all within walking distance. Conveniently located with easy access to the main roads and County Road 48, you’ll enjoy both tranquility and accessibility. Don’t miss this rar

A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. Completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep. Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style and function. The open floor plan is an entertainer's dream, seamlessly connecting the living, dining, and kitchen areas. The expansive living room showcases large vaulted ceilings with a floor to ceiling doors with transoms, inviting an abundance of natural light into the space, creating a warm and welcoming atmosphere with an indoor outdoor flow. The kitchen is a culinary delight featuring high-end stainless steel appliances, modern shaker style cabinetry, a wet bar, and pantry. The design is thoughtful and efficient, making it the perfect place to prepare meals and entertain guests. The primary

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a la

Tucked away on a secluded dead-end gravel road in the heart of the North Fork, this beautifully renovated 4-bedroom, 2-bathroom home offers the perfect blend of modern comfort, craftsmanship, and East End charm. Interior updates, including the kitchen, appliances, plumbing, and electrical, were completed approximately 3 years ago, while the roof, deck, and fully equipped outdoor kitchen were added approximately 2 years ago. Radiant-heated floors run throughout the home, complemented by a handcrafted, temperature-controlled wine cellar and plumbing/electrical already in place for a future second-floor bathroom. Outside, enjoy partial water views, a premium outdoor kitchen with high-end appliances and finishes, and a welcoming fire pit ideal for entertaining or relaxing. Surrounded by vineyards, waterfront destinations, and the unique character of the North Fork, this move-in-ready property offers an exceptional opportunity to enjoy one of Long Island's most sought-after coastal communit