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$35,000,000
6 Beds ⋅ 5 Baths ⋅ 24034137 MLS
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, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House. The Main House, a testament to exceptional craftsmanship, showcases approximately 5,534 square feet of living space, with six well-appointed bedrooms and 4.1 bathrooms. Designed with the finest materials, this home seamlessly blends timeless elegance and modern conveniences, providing a harmonious living environment. Outdoor area includes a Pool, Spa & Outdoor kitchen. Guest House with 3,583 sq feet, 3 bedrooms, 3 baths, Separate 942 sq ft. 1 bedroom in-law/ staff quarters. This property shares a Common border with the main residence. The separated property which can possibly be subdivided into 2 building sites, features a Carriage House, Dock & Sandy Beach. To say there are many possibilities here would be an enormous understatement! Private residence, Family compound or High-end development. Bring your Dream here; this opportunity will not let you down. All 3 properties must be sold together unless otherwise agreed to by the current owners. Please respect the privacy of current owners. BY APPOINTMENT ONLY. Taxes represent all 3 properties.

215 Uncas Point Rd, Guilford
$7,500,000
4 Beds ⋅ 5 Baths ⋅ 24165467 MLS
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. Masterfully crafted in 2003 and transformed by the current owners with uncompromising quality, the 6,000 SF+ residence is defined by Dramatic walls of glass framing endless water views from virtually every room offering seamless indoor-outdoor living. You will be immediately wowed by the jaw dropping great room with an incredible fireplace & soaring ceiling. At the heart of the home lies a stunning Poliform kitchen, the pinnacle of modern luxury, thoughtfully appointed with premium appliances and designed to delight the most discerning chef. Oversized dining area that effortlessly steps right onto the expansive Ipe deck for additional outdoor waterfront entertaining. The all glass-enclosed family room overlooks the sound as well as the heated saltwater pool. Upstairs, a dramatic suspended gallery leads to an octagonal office and private outdoor captain's walk with endless vistas. The primary suite is a sanctuary with panoramic water views, balcony, fireplace, custom closets, and a spa-inspired bath with oversized shower and infrared sauna. A separate wing offers three en-suite bedrooms with stunning new baths and custom bunks for additional guests. Exceptional boating amenities include a permanent pier of concrete

620 Colonial Rd, Guilford
$5,950,000
6 Beds ⋅ 6 Baths ⋅ 24155090 MLS
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 Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original "porthole" windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor "flex" space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches, an expansive patio for gatherings, and the rare luxury of a private boat house. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!

39 Vineyard Pl, Guilford
$3,995,000
6 Beds ⋅ 6 Baths ⋅ 24138935 MLS ⋅ Eagleview Condominiums BLDG.
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 sunset from your private balcony, entertaining in your chef's kitchen, or exploring Guilford's vibrant coastal village, Eagleview is more than a home, it's a lifestyle. Experience 6,200 SF of refined living space (expandable to over 8,000 SF) perfectly positioned to capture the tranquil salt marshes and shimmering expanse of Long Island Sound. Each residence includes multiple private balconies that invite you to relax and savor the natural beauty that surrounds you. Unmatched craftsmanship & comfort, this community of only 11 luxury units blends architectural excellence with everyday ease. Every residence features 10-foot ceilings, custom crown moldings, and a Chef's Dream Kitchen equipped with professional-grade appliances and elegant finishes designed for both function and style. Modern conveniences include private elevators, heated 4-car garages with EV charging stations, central air, central vacuum systems, and backup generators. Flexible open floor plans allow you to create spaces that reflect your personal lifestyle and vision. Ideally situated just a 1/2 mile stroll to Jacob's Beach and the Guilford Green, Eagleview offers easy access to an array of restaurants, boutique shopping, and cafes.

405 Whitfield St Unit 2, Guilford
$3,300,000
3 Beds ⋅ 3 Baths ⋅ 24071370 MLS
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 waterfront lots, with one being the perfect site for your future docking needs. Designed for both luxury and comfort, the home features radiant heated floors on all three levels, 9-foot ceilings, extensive crown molding, custom transom windows, surround sound, intercom system, whole-house generator, and fully insulated walls throughout. The chef's kitchen is equipped with Uba Tuba granite, custom cabinetry, Viking 6-burner cooktop, full-size double Wolf ovens, dual dishwashers, and premium finishes throughout. The main-level primary suite offers tray ceilings, oversized accessible doorways, spa-like bath, walk-in closet, and private safes. Additional highlights include a heated 3-car garage, walk-out lower level with future finishing potential, multiple office/flex spaces, custom built-ins, outdoor rain shower and fire pit seating area. Enjoy nearby private beach association access at Tuttle's Beach, completing this rare luxury offering.

57 Faulkner Dr, Guilford
$2,995,000
3 Beds ⋅ 3 Baths ⋅ 24155789 MLS ⋅ The Residences At 66 High Street BLDG.
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 interior designer, contractor, and master craftspeople to conceive a truly one-of-a-kind, fully customized home. The result is an expansive and impeccably executed "double" residence in the Leete Building offering approximately 3,000 square feet of meticulously maintained, sophisticated living space designed for both grand entertaining and effortless everyday comfort. A gracious living room anchored by a gas fireplace and a mounted 150-year old half hull ship model, flows seamlessly into a dining area with access to a private balcony; creating the perfect backdrop for intimate evenings or lively gatherings. The chef's kitchen and custom millwork throughout showcase superior craftsmanship, bespoke built-ins, and curated finishes of the highest caliber. The master bedroom suite is a private sanctuary, complete with its own fireplace, a dedicated office with built-in shelves, file drawers and cabinets for remote work, private balcony, a spa-inspired bath appointed with luxury fittings and steam shower, and two walk-in closets. Two additional bedrooms and beautifully designed full baths provide comfort and flexibility for guests.

66 High St Unit 38, Guilford
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 24181939 MLS
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 leisure. The living room features a bespoke custom mural and a stunning aquarium, serving as a mesmerizing feature next to French doors leading to the patio. Entertain effortlessly in your private home theatre, escape to your sauna tucked under the stairs, cook in the gourmet Wolf kitchen, or retreat to the office, where a bookshelf conceals a secret closet. The outdoor experience is unmatched. The custom pool area, equipped with an outdoor kitchen and pizza oven, is a resort-style masterpiece, featuring two integrated hot tubs and a dramatic infinity edge that blurs the line between water and nature. A heated walkway from the first-floor bathroom leads you straight to one of the hot tubs for year-round use. This home is thoughtfully designed for pet owners, featuring a dog door, dog washing station in the garage, and wiring for an electric fence to keep your companions safe. Modern sophistication meets comfort with a 2.5-bay attached garage, a Lutron Homeworks lighting system, a Crestron audio system, and a 2025 security installation. Recent mechanical updates including a 2023 furnace and serviced air handlers, ensure peak efficiency. Experience luxury at 76 Sachem Head Road. Schedule a private showing today.

76 Sachem Head Rd, Guilford
$1,895,000
5 Beds ⋅ 9 Baths ⋅ 24159985 MLS
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 of mature trees, manicured lawns, & magical gardens. This classic revival will be celebrated by the most discerning antique home enthusiasts & home lovers alike. Modern flair has been discreetly integrated to enhance function & enjoyment. Contemporary comforts include a poured concrete foundation, geothermal system, full house generator, humidifier, CENTRAL A/C, propane gas, Pella windows, security system, CITY WATER, underground utilities, NEW SEPTIC SYSTEMS, & much more. Significant additions include attached 2-car garage, detached 2-car garage w/half bath & upper bonus room, pool & pool house w/half bath & kitchenette, tennis court, garage barn w/FULL APARTMENT, all exemplifying a harmonious fusion of old & new & completely transformed for today's living. Interiors graciously unfold over more than 5,500sf of formal, casual, & whimsical living spaces. 8 tile-lined fireplaces. Central kitchen well appointed w/large island, granite countertops, double sink, double wall ovens, extensive custom wood cabinetry, butler's pantry, & quality appliances. Sunshine flows through skylights over an eat-in dining area. A 4-story dumbwaiter makes for easy transport of items. Can be modified to be a 1-person elevator.

173 Highwoods Dr, Guilford
$960,000
3 Beds ⋅ 4 Baths ⋅ 24198089 MLS
OFFERS REQUESTED BY 8/26 at 2 pm. Enjoy life on Lake Quonnipaug! Your own private dock. Launch a kayak, drop in a line, take a swim. A gazebo on the shoreline - feel the breezes as you sit back in a rocker. This .53 acre lot includes 150 feet of lake frontage. The home's three levels open out to the lake. Everchanging water views, reflecting the weather and seasons. The main level open floor plan with the living, dining, and kitchen areas flowing to the wrap-around covered deck. The living room includes a focal point of a large stone fireplace with propane gas log. The kitchen features a Subzero, an island with gas stove and room for stools. A gas grill, attached to propane line, on the deck for easy outdoor cooking. Upstairs, 3 bedrooms and 2 full baths, with the primary bedroom and whirlpool tub facing the shoreline. The lower level 32' x 24' family room features a full bath, woodstove, and a wall of glass facing the lake. The extensive integration of wood elements throughout lends a feel of a vacation home or chalet. A whole house automatic generator is in place. A drive-by does not do this property justice! From the street, you see the three-car garage plus a barn that can accommodate another car, a workshop, studio, etc. Stepping through the front door opens up bright, sunlit spaces and panoramic views. This well-loved and well-maintained property is ready for its next caretakers. Own your own spot on the lake!

136 Quonnipaug Ln, Guilford
$649,999
3 Beds ⋅ 3 Baths ⋅ 24204560 MLS
Welcome to 245 Dunk Rock Road, a beautifully renovated 3-bedroom, 2.5-bath home offering 2,048 square feet of thoughtfully updated living space on over 5 acres of private property in Guilford. This move-in-ready home has been fully renovated with modern finishes and quality upgrades throughout. The inviting kitchen features elegant quartz countertops, brand-new stainless-steel appliances, and plenty of workspace for everyday cooking and entertaining. The bathrooms have been completely refreshed with attractive tile finishes and contemporary details. The spacious 2-car garage offers even more versatility and features professionally finished epoxy flooring, creating a clean, durable space for vehicles, storage, hobbies, or a workshop. Inside, the home offers a comfortable layout with three bedrooms, two and a half bathrooms, and plenty of room for both everyday living and entertaining. Every detail has been thoughtfully updated to provide the convenience of a modern home while maintaining the peaceful character of the property. Outside is where this property truly shines. Set on more than 5 acres, the home offers an exceptional level of privacy and tranquility. Enjoy your morning coffee, entertain guests, explore the property, or simply unwind surrounded by nature.

245 Dunk Rock Rd, Guilford
$399,900
4 Beds ⋅ 2 Baths ⋅ 24192906 MLS
Peaceful living awaits in this charming 4-bedroom, 2-bath home in shoreline, Guilford with access to Lake Quonnipaug, where the soothing sounds of the nearby creek create a relaxing setting year-round. Inside, hardwood floors flow throughout most of the home, adding warmth and timeless appeal. The living room showcases a striking stone fireplace with a reclaimed 150-year-old barn door feature, creating a truly unique focal point. The spacious primary suite offers a walk-in closet with motion-activated lighting, while the upstairs bath features a classic clawfoot soaking tub. An expansive wraparound deck provides easy access to the backyard and plenty of space for entertaining or unwinding outdoors. Recent updates include a new water heater and whole-house water filtration system for added peace of mind. Blending character, comfort, and thoughtful improvements, this one-of-a-kind home is ready for its next chapter.

3198 Durham Rd, Guilford
$399,000
2 Beds ⋅ 1 Baths ⋅ 24201790 MLS
Direct waterfront on West Lake! Enjoy exceptional year-round lake views from this charming 2-bedroom, 1-bath ranch-style home in Guilford. With 1,002 square feet of living space on a .23-acre waterfront lot, this property presents a wonderful opportunity to enjoy the beauty and lifestyle of lakeside living in one of Connecticut's desirable shoreline communities. The home's inviting living spaces are thoughtfully positioned to take full advantage of the spectacular water views, while two fireplaces add warmth and character. Outdoors, a spacious deck and patio provide the perfect setting for relaxing, dining, entertaining, or simply taking in the tranquil surroundings. A private dock offers direct access to West Lake, creating endless opportunities for boating, swimming, fishing, and enjoying time on the water. Whether envisioned as a year-round residence, weekend retreat, or private lakeside escape, this waterfront property offers a unique opportunity to enjoy the best of lake living.

14 Putzel Ave, Guilford
$340,000
2 Beds ⋅ 1 Baths ⋅ 24198433 MLS ⋅ River Colony BLDG.
Welcome to 12 River Colony Road, offering easy one-level living in a beautiful and convenient setting. This inviting home features a stunning high-end European-style kitchen with Bosch appliances, sleek cabinetry, and plenty of space for dining and entertaining. European-style windows and a new sliding door fill the home with natural light. Step outside to your private patio, perfect for entertaining, and enjoy the large courtyard and scenic marsh views that create a peaceful backdrop. Additional updates include a new roof, new washer and dryer, and a 2025 water heater. The home is serviced by public water, and additional storage is available above the garage, with garage space potentially available to rent separately. Ideally situated close to downtown, area beaches, shopping, dining, and highway access, this home combines an updated interior, beautiful outdoor space, scenic surroundings, and the convenience of one-level living. Move right in and enjoy!

12 River Colony, Unit 12, Guilford
$325,000
1 Baths ⋅ 24148563 MLS
This property would require a change-of-use from commercial to single-family for homeowners, buyer to do due diligence. Well-located antique commercial building overlooking the Guilford Mill Pond. The property features an approximately 1,200 SF ground-floor showroom with office space and restroom, currently operating as a tile showroom. Large windows provide excellent visibility and natural light. Interior stairway leads to an unfinished basement. Suitable for a variety of commercial uses including retail, gallery, or professional office - or there is potential to change to a single family as a great condo alternative. Prime location with character, flexibility, and strong visibility in the heart of Guilford. Also listed commercial MLS#: 24146465

51 Mill Rd, Guilford
$25,000
24104527 MLS ⋅ Guilford Yacht Club BLDG.
Waterfront - Guilford. Set Sail in Style and experience the charm of Guilford Yacht Club, a premier marina in one of Connecticut's most picturesque coastal towns. This 46-foot slip offers ample space and immediate access to Long Island Sound, ensuring effortless adventures on the water. Guilford is rich in history and natural beauty, making it an ideal destination for boaters. At the Guilford Yacht Club, you'll enjoy top-tier amenities, including electrical hookups, water and pump-out, and a clubhouse for members. The dock and facilities are impeccably maintained, and the club's vibrant social calendar brings together sailing and power yacht enthusiasts alike. Beyond the docks, members can take advantage of a heated pool with a pool house, tennis courts, barbecue grills, and picnic tables, perfect for relaxing and entertaining. Whether you seek a peaceful retreat or an active boating community, this slip is your gateway to the best of Guilford.

379 Whitfield St Unit CN946, Guilford
$23,500
24165818 MLS ⋅ Guilford Yacht Club BLDG.
Experience the ultimate boating lifestyle at the prestigious Guilford Yacht Club with this prime 34-foot boat slip. Nestled along the scenic River, this slip offers a front-row seat to breathtaking sunsets and immediate access to Long Island Sound. Within five minutes of leaving the channel, you'll be on your way to premier destinations like the Thimble Islands, Sag Harbor, Three Mile or Block Island. The club has been recently dredged, ensuring excellent depth and accessibility for your vessel. The docks, reconstructed in 2012, are in top-tier condition and include a large dock box for gear, with water, electricity, and cable readily available. Ownership includes a full club membership with no initiation fee, providing a resort-style experience. You'll have full use of the magnificent clubhouse, the heated pool, and professional Har-Tru tennis courts. The grounds are well maintained and there are BBQ areas perfect for social gatherings. Convenience is key with an on-site Dock House offering showers and heads, plus the option for winter boat storage. Whether you are heading out for a fishing expedition to Montauk or enjoying a quiet evening on the water, this slip represents an incredible value in a Guilford yachting community. Don't miss your chance to secure a lifestyle of luxury, recreation, and effortless nautical adventure.

379 Whitfield St Unit BN1034, Guilford
$14,900
24202298 MLS ⋅ Guilford Yacht Club BLDG.
Fantastic deal on a 46 foot slip at the beautiful Guilford Yacht Club. Motivated Seller! Gorgeous spot in a picturesque setting with stunning sunsets along the West River with immediate access to Long Island Sound. Cruise to many fun and exciting destinations such as Block Island, Mattituck, Greenport, Montauk, Sag Harbor, Newport, Martha's Vineyard and many more. The Thimble Islands are close by and GYC has a mooring designated for members use. Water and a large dock box for all your boating gear is included at the slip. Electric is available too. New docks were installed in 2012. There are amenities such as Har Tru tennis courts and heated pool and pool house with heads and showers. Dock House with heads and showers as well. There are several BBQ grills for members use, members tents for picnics and parties. Many year round activities such as Junior sailing, concerts on the lawn, Mother's Day Brunch, Friendsgiving dinners, GYC book club are scheduled throughout the year. No additional initiation fee is required. As a member the elegant clubhouse is available for your private events and parties. The Guilford Yacht Club is a short walk or drive to the Guilford Green with its charming downtown restaurants and shops and antique homes. GYC is close by the Guilford Town Marina and Jacobs Beach. Guilford is conveniently located 15 miles from New Haven and 90 miles from NYC on I95.

379 Whitfield St Unit CN1446, Guilford
$13,999
24204717 MLS ⋅ Guilford Yacht Club BLDG.
Great deal on a 38 foot slip at the Guilford Yacht Club. A great opportunity to own your own dock at the gorgeous Guilford Yacht Club. Absolutely stunning sunrises and sunsets await you. Within 5 minutes you are on your way to Long Island Sound and the many destinations of your choosing such as the Thimble Islands, Mattituck, Block Island, Newport and Martha's Vineyard. Included at your slip is a large dock box for your boating gear and water. Electricity is available. There is free pump out on the premises as well. Ownership includes membership at no extra charge. Additional amenities feature the use of the magnificent clubhouse for your private events, heated pool with heads and showers, dockhouse with heads and showers, Har Tru tennis courts and beautiful grounds. Plus there are tents and BBQ grills for member's use for your parties and barbeques.

379 Whitfield St Unit BS1738, Guilford

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