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, …
1 Beds /
8 Baths
/ 8378 SqFt
A truly unforgettable and exceptionally rare offering-Rogers Island presents an exciting opportunity to own a private island paired with a mainland residence, delivering the perfect balance of seclusion and convenience. The mainland property includes its own dock, parking, a…
4 Beds /
5 Baths
/ 5475 SqFt
This is not simply waterfront living. This is a waterfront lifestyle unlike any other. Tucked within the coveted enclave of Sachem’s Head, this extraordinary estate commands direct Long Island Sound frontage with unobstructed harbor views and breathtaking sunsets. Masterfull…
6 Beds /
7 Baths
/ 7945 SqFt
This magical light-filled New England 7,945 s.f. "cottage" takes full advantage of its private waterfront location overlooking LIS and a wildlife estuary. Sited in a private community on 1.27 acres with 300′ of water frontage provides panoramic water views of sunri…
6 Beds /
6 Baths
/ 6603 SqFt
Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem’s Head community. Boasting breathtaking, panoramic views of Long Isl…
4 Beds /
4 Baths
/ 3871 SqFt
Discover the extraordinary: a one-of-a-kind private island nestled in the legendary Thimble Islands, just seconds from the charming village of Stony Creek. While easily accessible by private boat or hourly water taxi, the island offers a variety of outdoor spaces that highli…
6 Beds /
6 Baths
/ 6216 SqFt
Eagleview at Guilford – Where Luxury Meets Lifestyle. Discover Guilford’s newest luxury coastal condominium community, where superior craftsmanship, modern design, and breathtaking views of Long Island Sound redefine Connecticut shoreline living. Whether you’re enjoying a su…
5 Beds /
7 Baths
/ 5185 SqFt
A true once in a lifetime opportunity! As you wind through picturesque Sachem’s Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points i…
4 Beds /
4 Baths
/ 4017 SqFt
Welcome to one of Connecticut’s most desirable waterfront communities. Pine Orchard blends waterfront recreation, country club access, historic coastal character and a relaxed luxury lifestyle. For generations, families have been drawn to this unique shoreline community for …
5 Beds /
6 Baths
/ 5657 SqFt
Exceptionally located less than a tenth of a mile from both the town green and beaches – with your own private beach access – this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materi…
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…
3 Beds /
4 Baths
/ 3143 SqFt
DIRECT WATERFRONT within the private enclave of homes in Johnson’s Point. This is the one you hoped would come on the market. Originally built circa 1915, and now completely rebuilt from the foundation up. The architect and builder have collaborated to create a masterpiece, …
3 Beds /
3 Baths
/ 2983 SqFt
Exquisitely reimagined with uncompromising attention to detail, this exceptional upper-level residence at The Residences at 66 High Street presents refined luxury in a premier in-town setting. Originally created by seamlessly merging two units, the owner collaborated with an…
3 Beds /
3 Baths
/ 3348 SqFt
Welcome to a truly exceptional living experience at The Residences at 66 High Street! This stunning three-bedroom, two-and-a-half-bathroom condo presents a rare opportunity for those seeking luxury and convenience in one of Guilford’s most desirable locations. Spanning an im…
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…
4 Beds /
5 Baths
/ 6194 SqFt
Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gentl…
4 Beds /
6 Baths
/ 4700 SqFt
Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors…
5 Beds /
5 Baths
/ 4143 SqFt
Less than one mile from downtown Madison, this new construction home offers refined living with white oak floors, custom millwork, coffered ceilings, and abundant natural light throughout. The main level features 9-foot ceilings, a dramatic floor-to-ceiling gas stone firepla…
5 Beds /
3 Baths
/ 3172 SqFt
COME EXPERIENCE THIS ONE-OF-A-KIND, FULLY RENOVATED MADISON HOME ON A RARE DOUBLE LOT WITH PRIVATE BEACH RIGHTS! Just 300 feet from the sandy shoreline, this exceptional home has been completely reimagined from a traditional raised ranch into a stunning elevated ranch with …
4 Beds /
2 Baths
/ 2251 SqFt
Rare opportunity to own a Nantucket-style coastal retreat on coveted Middle Beach Road in Madison. Just moments from East Wharf Beach and downtown, this distinctive property offers timeless shoreline charm, a huge porch, breathtaking tidal marsh views, and glimpses of Long I…
Beds /
Baths
/ SqFt
Multi-family development lot that will allow up to 55 residential units. 9.75 acres. Lot area per unit is 7,620 SF, which can conceivably allow 55 units i.e. (Lot area of 424,710 SF/7,620).
4 Beds /
4 Baths
/ 2850 SqFt
Modern luxury in a premier location. Set on over two private acres in a highly desirable neighborhood, this brand-new contemporary home offers an open, light filled floor plan designed for both comfort and style. The chef’s kitchen is a standout, featuring a Subzero refriger…
4 Beds /
2 Baths
/ 3882 SqFt
Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in th…
3 Beds /
4 Baths
/ 2160 SqFt
Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison’s charming Seafields Association. Thoughtfully designed with designer details throughout, the home provides elevated shoreline living with glimpses of Long Island…
5 Beds /
9 Baths
/ 5414 SqFt
A MAGNIFICENT REVIVAL & TIMELESS BLEND OF SOMETHING OLD & SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled & moved to its current site in 1955, the property is nestled within nearly 4 acres o…
The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
This site was last updated Jul 29 2026 9:42:20 pm.