6 Beds /
5 Baths
/ 5354 SqFt
Waterfront.. Sachems Head – Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, …
4 Beds /
8 Baths
/ 8070 SqFt
Privately nestled high on 4+ sweeping acres, in the prestigious, yet quietly refined, Sachem’s Head enclave in Guilford, CT, this 2012 modern Mediterranean residence commands panoramic views of Long Island Sound. Grand yet classic interiors unfold in tasteful Palm Beach-insp…
3 Beds /
3 Baths
/ 2891 SqFt
Custom built with exceptional craftsmanship and attention to detail, this stunning coastal-area estate sits on one of the largest properties in the neighborhood with water views from every room, three separate deeds totaling approximately two acres, including two separate wa…
4 Beds /
5 Baths
/ 5620 SqFt
Welcome to your private coastal sanctuary in the prestigious Sachem Head area of Guilford. This 5,620 sqft estate is a masterclass in luxury living, set on 2.31 wooded waterfront acres. Come up the gated driveway and step inside to discover a home designed for ultimate leisu…
5 Beds /
6 Baths
/ 5619 SqFt
Experience exceptional luxury living in this impressive 6,700 SF stucco Colonial in The Woodlands, one of the area’s most desirable subdivisions. The remodeled kitchen features custom cabinetry, large island, Cambria quartz countertops, high-end appliances, travertine floori…
5 Beds /
9 Baths
/ 5414 SqFt
A LEGENDARY GUILFORD ESTATE-where extraordinary history, artistry, architecture, & modern luxury converge. One of New England’s most exceptional restorations, the Pitkin House is a remarkable 18th-century treasure set privately on nearly 4 acres of mature trees, stone walls,…
3 Beds /
3 Baths
/ 2969 SqFt
PRIVACY, VIEWS AND ONE LEVEL LIVING. Situated at the end of a cul-de-sac in highly desirable Sachems Head, this charming property captures breathtaking views of the marshlands and Sachems Head harbor. The home, extensively renovated by renown housewright Skip Broom, has an …
4 Beds /
4 Baths
/ 2762 SqFt
Welcome to Waystone Farm, an award-winning, energy-efficient 8+ acre mini-estate and potential horse property. Proud winner of the 2016 Highly Insulated Passive House Standard Award, this estate masterfully blends sustainability with luxury living.The main residence features…
5 Beds /
4 Baths
/ 6328 SqFt
Architecturally distinctive and beautifully sited on 2.11 private acres, this five-level contemporary offers more than 5,200 square feet of flexible living space plus a separate 862 square foot guest house. The main residence features five bedrooms, multiple gathering spaces…
3 Beds /
3 Baths
/ 3024 SqFt
The John Collins II House at 205 State Street is recognized as one of the finest colonial homes in Historic Guilford. Built in 1707, this handsome saltbox has been thoughtfully restored and updated while preserving its extraordinary historic character. Since 2005, the owners…
4 Beds /
4 Baths
/ 2966 SqFt
Discover the vibrant energy of the historic town green just outside your doorstep. The inviting sidewalk guides you to the lively center, only 600 yards away. There, you’ll find a treasure trove of quaint shops, restaurants, the recreational center, and cozy coffee spots to …
4 Beds /
5 Baths
/ 5979 SqFt
Spectacular California Contemporary nestled in a private, picturesque setting in Guilford’s desirable Fence Rock Association. Offering 5,114 square feet of above-grade living space, this distinctive four-bedroom residence showcases dramatic vaulted ceilings, skylights, expan…
4 Beds /
4 Baths
/ 3637 SqFt
A once in a lifetime opportunity to own a piece of Connecticut Shoreline history. The Black House was built in 1761 by Levi Hubbard. It was later sold to Nicholas Loyselle, of French decent, who painted it black in mourning of Louis XVI’s passing. Thus, it was dubbed, The Bl…
3 Beds /
3 Baths
/ 2920 SqFt
SO CLOSE TO TOWN! Rare opportunity to own NEW CONSTRUCTION south of Boston Post Road and close to the Guilford Center. This quality built Colonial offers a stylish from porch and is set back from the street for privacy. Professionally landscaped with dramatic hardscape featu…
6 Beds /
3 Baths
/ 3833 SqFt
Located just off the Guilford Green and across from the Guilford Community Center, this exceptional property enjoys one of Guilford’s most desirable in-town locations, with convenient access to restaurants, boutique shopping, cafes, the library, year-round community events, …
4 Beds /
4 Baths
/ 3774 SqFt
Sophisticated and elegant hip roof colonial, built in 2005, 1st floor 9+’ ceilings, 8+’ ceilings or cathedrals on 2nd floor, HW flooring and tile, all spacious rooms, oversized windows through out, classic front and back staircases, walk-up attic, cherry cabinets with granit…
4 Beds /
4 Baths
/ 3616 SqFt
Welcome to 45 Deerfield Drive, three acres of prime Guilford real estate. Situated on a desirable cul-de-sac, 45 Deerfield Drive offers a sense of space and privacy that is becoming increasingly hard to find. This beautifully 4-bedroom Colonial is uniquely positioned borderi…
4 Beds /
4 Baths
/ 2392 SqFt
Rare opportunity in Guilford! This home is currently used as a multifamily but can revert to a one family residence. Approximately 2400 sqft with the possibility of future expansion. Conveniently located close to Guilford’s Historic Green, shops, restaurants, beaches and sho…
3 Beds /
3 Baths
/ 2797 SqFt
RARE IN-TOWN GUILFORD SPRAWLING CAPE WITH WALKABLE CONVENIENCE, SHORELINE ACCESS & TIMELESS NEW ENGLAND CHARM! Enjoy privacy & space in one of Guilford’s most desirable locations, situated on over 1 acre + just steps from the historic Guilford Green, local shops, restaurants…
3 Beds /
3 Baths
/ 3056 SqFt
Welcome to 7 Laurel Ridge Road, a light and bright, well-maintained 3 bedroom, 2.5 bath Colonial situated in a quiet cul-de-sac in Guilford. Set on approximately 1.47 acres, this home offers 2,402 square feet of above-grade living space with a finished basement bonus room. E…
4 Beds /
3 Baths
/ 2426 SqFt
COMING SOON! Natural gas heat, public water, AND central air in a completely renovated 4-bedroom Colonial in Guilford? It’s here, and it’s rare in town! Step inside and fall for gleaming new hardwood floors and fresh paint from top to bottom. The renovated kitchen has been f…
4 Beds /
3 Baths
/ 2320 SqFt
Welcome to 1961 Route 80, a beautifully renovated 4 bed, 2.5 bath home offering 2,320 square feet of finished living space on 1.49 private acres. A deep, level backyard bordered by woods gives you room to relax, play and entertain with true privacy, while the location puts p…
4 Beds /
3 Baths
/ 2361 SqFt
There is a stretch of Guilford where the countryside takes over. Stone walls give way to the farmland, the road bends along the water, and the hills close in behind. This is where 811 Lake Drive sits, on nearly an acre just a short walk from Lake Quonnipaug. There’s an ease…
3 Beds /
2 Baths
/ 2238 SqFt
Imagine mornings and evenings on Guilford’s East River. This 2,238 sq ft Antique Cape sits on more than 300 feet of river frontage with the water right in your backyard. Launch a kayak, canoe, or boat from your own dock and head out to Long Island Sound. This home began as a…
3 Beds /
4 Baths
/ 2809 SqFt
Welcome to a true Guilford sanctuary. A contemporary gem tucked away on 2.2 private acres featuring a large flat yard and a babbling brook traversing the front of the property. Step inside to discover dramatic cathedral ceilings and skylights in the entry and living room tha…
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This site was last updated Nov 03 2026 9:14:13 pm.