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$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
$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
$1,825,000
4 Beds ⋅ 4 Baths ⋅ 24179175 MLS
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 newly refinished hardwood floors and a bright, open floor plan. A sun-filled great room flows into the chef's kitchen, complete with quartz counters, a large island, Thermador appliances, and induction cooktop. Designed for one-level living, the spacious primary suite is located on the first floor. In total, the home offers four bedrooms, three full, and one half bath. Amenities include a dedicated mudroom and laundry room equipped with an advanced ozone laundry system. Built to the highest green standards, the home utilizes geothermal heating and cooling, active solar, and energy efficient triple-pane windows. A full unfinished basement holds a large root cellar, while the three-car garage boasts an EV charging station and a walk-up attic storage area. A Generac generator ensures total peace of mind. Relax on one of the two Ipe covered front porches and take in the stunning grounds. This unique property features a passive solar greenhouse with cold frames, extensive garden bedding, a newly planted fruiting tree orchard, and sugar maples. Animal lovers will find a three-stall barn, two chicken coops, a duck coop, an enclosed dog park, and two large fenced pastures with hay fields.

51 Wimler Ln, Guilford
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 24191112 MLS
Brand NEW CONSTRUCTION. Move in Ready! This modern, luxurious 4-bedroom, 3.5-bathroom home is designed to captivate. Located only 1.5 miles from the quintessential Guilford Town Green, you'll enjoy the charm of local shops, restaurants, and a vibrant community. Plus, it's just 2.5 miles to the Guilford Marina, Guilford Yacht Club & Jacob's Beach. With quick highway access, proximity to Yale Medical nearby, this home truly delivers the best of convenience and lifestyle. Inside the home, be impressed with soaring 9' ceilings on both the main & upper floors, making the space feel open and inviting. The expansive Great Room, bathed in natural light, that features a sleek linear gas fireplace with a textured marble stone facade is perfect for cozy evenings or sophisticated entertaining. Step outside the sliders to an exquisite stone patio to enjoy in the warmer weather. The kitchen is a modern minimalist design with quartz countertops, stainless steel appliances & premium finishes. At its center is a waterfall edge island, where sleek quartz cascades down the sides for a clean, polished statement. A marble stone backsplash adds a touch of sophistication, tying in beautifully with the home's design. The home offers a tastefully designed main floor primary bedroom suite that is quiet & restful. Upstairs there is an ensuite bedroom, which is great for guests, & is tucked just steps away from the outdoor terrace- the ultimate spot to slip out & enjoy a quiet morning coffee.

539-A Boston St, Guilford
$1,349,000
4 Beds ⋅ 4 Baths ⋅ 24155372 MLS
Experience the perfect fusion of timeless distinction and modern elegance in this well-maintained home, where original architectural craftsmanship has been beautifully preserved, and recent updates have brought a fresh, stylish feel to the space. Inside, you'll discover an inviting and versatile residence with numerous unique features that make this property truly one-of-a-kind. Enjoy the warm ambiance created by wide plank wood floors, original woodwork, exposed beams, and multiple fireplaces across the family room, living room, dining area, and primary bedroom. The home features 4+ bedrooms, thoughtfully arranged across two levels for privacy and comfort. Two hall-accessed bathrooms-one with a tub and one with a shower-occupy the second floor, both easily accessible from the hallway. The updated kitchen is an entertainer's dream, featuring leathered granite counters, a Subzero refrigerator, and an LG gas stove. The four-season porch, with its well-placed windows providing a picturesque view of the backyard, offers a perfect space for relaxing, entertaining guests, or creating a media room. It is equipped with a modern-looking Rinnai heater, ensuring comfort year-round regardless of the weather Adjacent to the home is the spacious backyard, which features a fire pit, ample room for gardening or outdoor activities, and existing infrastructure ready for the easy addition of an inground pool.

147 Boston St, Guilford
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 24202711 MLS
Experience the perfect blend of elegance, privacy, and shoreline living in this Mediterranean-style Colonial, ideally located just 3 miles from downtown Guilford and up the road from a public beach. Set high above the flood plain, flood insurance is not required, offering peace of mind and a coveted coastal lifestyle. A stately brick pillar entrance welcomes you to this 4-bedroom, 3.5-bath home, set on nearly 2 professionally landscaped acres in a desirable cul-de-sac neighborhood. The private, wooded setting offers peace and natural beauty. Inside, 10-foot ceilings, columns, Palladian windows, and an open floor plan create a bright, inviting atmosphere. The foyer is flanked by formal living and dining rooms, while the impressive two-story family room with gas fireplace flows into the refreshed kitchen featuring all-new Cafe stainless steel appliances. The main level offers a primary bedroom suite, second ensuite bedroom, and laundry room, providing a convenient option for one-floor living. All bathrooms have been refreshed, adding to the home's move-in-ready appeal. Enjoy peaceful views from the expansive sunroom overlooking the private backyard. Additional highlights include city water, central air, a new roof, 3-car garage, and versatile bonus room; ideal for a home office, fitness room, playroom, or guest space. Don't miss this opportunity to enjoy privacy, flexibility, and shoreline living in a sought-after Guilford location!

122 Lower Rd, Guilford
$1,249,900
4 Beds ⋅ 5 Baths ⋅ 24165243 MLS
NEW ROOF to be installed Fall 2026! Enjoy peace of mind with a brand-new roof being installed by the sellers. Perfectly sited on 2.75 private acres overlooking a sweeping lawn, this distinguished Georgian Revival home makes an unforgettable first impression, approached by a circular driveway that creates a true sense of arrival. Newly painted interiors and enhanced landscaping complement the home's timeless elegance. Once a Connecticut Designer Showhouse, the property blends sophistication with remarkable comfort across more than 5,200 square feet. A grand foyer with dramatic staircase introduces generously scaled rooms, 10-foot ceilings, and five fireplaces. The renovated kitchen features today's most desired amenities, including a large center island and butler's pantry, ideal for effortless entertaining. Distinctive architectural details add character throughout, including a remarkable office fireplace mantel reclaimed from a Newport mansion. The spacious bedroom level offers comfort, privacy, and flexibility, highlighted by a luxurious primary suite with renovated ensuite bath and separate dressing room. The home also offers natural gas, new well equipment, and a new septic system. Minutes from the Guilford Green, boutique shopping, and renowned restaurants, this exceptional offering seamlessly combines timeless design, character, and an extraordinary setting.

625 State St, Guilford
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 24203610 MLS
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 granite counters and expansive center island and new Wolf Gas Range. Main living room open to kitchen with wall of built-in cabinets/bookcases and gas fireplace. Lower level with rear yard walk-out, 2nd full kitchen with high quality appliances, fully tiled bathroom, 2nd laundry area, exercise room or storage. Exterior expansive double deck from kitchen, paved walkways surround entire house, with beautiful stone steps and evening walkway lighting. Ring security system on all sides of house. Gently tucked into an upscale quiet community of newer homes. and added privacy at end of road with 3 houses. Oversized rear secluded yard for activities and entertainment.

9 Inwood Dr, Guilford
$1,150,000
4 Beds ⋅ 3 Baths ⋅ 24203107 MLS
Situated on a private 0.92-acre lot in a highly sought-after neighborhood, this classic four-bedroom, two-and-a-half-bath Colonial combines high-end interior updates with direct access to local nature. The main level centers around a fully renovated kitchen outfitted with the finest finishes, custom cabinetry, premium appliances, and a dedicated pantry for extra storage. Everyday living and entertaining options abound with a huge family room featuring vaulted ceilings, a cozy traditional living room with a fireplace, and a flexible main-floor room with French doors ideal as a formal dining space or dedicated home office. Upstairs, the primary bedroom suite offers a generous walk-in closet alongside an exquisitely updated full bath, joined by three additional bedrooms and a second beautifully updated full bath. Outdoor living centers on a large deck overlooking the expansive yard. Step directly from the property onto adjoining open space and scenic trail networks leading straight into the 583-acre East River Preserve. Key infrastructure updates include a newly installed high-efficiency furnace (2024) and a full roof replacement scheduled prior to closing. A full partially finished unique walk-out basement, perfectly suited for a game room, complete this home.

169 Willow Rd, Guilford
$1,125,000
4 Beds ⋅ 3 Baths ⋅ 24205158 MLS
Historic 1856 Octagon Home Just One Block from the Iconic Guilford Green. Rarely does a home of such architectural distinction and prime location become available. Crafted in 1859 by renowned local builder Edwin A. Leete, this landmark 4-bedroom, 2.5-bath octagonal residence offers a extraordinary blend of mid-19th-century character and seamless modern comfort-all just a single block from the historic Guilford Green. Inside, the distinctive eight-sided floor plan fills the home with exceptional natural light across a generous layout featuring a formal Living Room, dedicated Dining Room, and cozy Family Room. At the heart of the home is a chef-inspired, high-end custom Gulick Kitchen, beautifully appointed for both daily life and effortless entertaining. Modern infrastructure ensures year-round comfort with central air conditioning and natural gas heating. Set on a lovely, flat and fenced in .61-acre lot, the property includes a versatile detached garage providing flexible space perfect for a workshop, home studio, or bonus room. Step outside your front door to enjoy boutique shopping, fine dining, local events, and train access within minutes. A true piece of Guilford history upgraded for today's lifestyle.

84 Fair St, Guilford
$1,100,000
4 Beds ⋅ 3 Baths ⋅ 24192596 MLS
Dreaming of a new construction home without the wait? This 3,028-square-foot modern farmhouse has just been completed and offers exceptional curb appeal with a sharp white exterior and striking black windows. Inside you will experience the perfect blend of modern luxury and classic New England charm with a thoughtfully designed layout. The open-concept first floor is filled with natural light and lends itself perfectly for everyday living. The second floor has a Primary suite as well as 3 bedrooms. This home as a unique private staircase to the bonus room which is an excellent feature because it gives buyers a flexible space that feels almost like a separate wing of the home. Step outside to enjoy the private backyard, ideal for relaxing or entertaining, all while enjoying the tranquility of North Guilford's picturesque setting. Built with today's energy-efficient standards and quality craftsmanship, this home offers the peace of mind and convenience that come with brand-new construction.

450 Bluff View Dr, Guilford
$1,075,000
4 Beds ⋅ 4 Baths ⋅ 24134097 MLS
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 shoreline attractions.

51 Pearl St, Guilford
$1,075,000
4 Beds ⋅ 4 Baths ⋅ 24122847 MLS
One-of-a-Kind Opportunity in Guilford! Rarely available, this 4-unit multi-family property is ideally located on a large in-town lot in the beautiful shoreline community of Guilford. Built in 1900 and offering 2,392 sq. ft. of living space, the property features one 2-bedroom unit and three 1-bedroom units. Each unit has been thoughtfully updated and includes its own washer/dryer. Three of the four units are currently occupied, providing immediate income potential. With city water and the possibility for future expansion, this property offers both flexibility and value. Conveniently situated close to Guilford's historic Green, shops, restaurants, and shoreline attractions. A rare find you won't want to miss!

51 Pearl St, Guilford
$999,000
4 Beds ⋅ 3 Baths ⋅ 24193540 MLS
This approximately 3,000 square foot house sits on nearly 1 acre of lush, tranquil land. The property features a charming exterior with an inviting entryway, surrounded by well-maintained landscaping and greenery. The spacious lot provides ample room for outdoor living and recreation, creating a peaceful retreat from the everyday. The home's interior offers four bedrooms and two and a half bathrooms, providing ample space and privacy. The generous square footage and open floor plan with Hardwood Bamboo floors allows for a versatile living experience. The inviting entryway leads to a spacious area, setting the tone for the rest of the home. Outside, the property boasts a spacious Trex deck, and a private oasis with a soothing salt water pool, all nestled in a secluded setting. The expansive fenced yard and greenery create a serene, peaceful atmosphere, ideal for relaxation and outdoor enjoyment. Virtual tour in Added Info

67 Christopher Ln, Guilford
$949,000
4 Beds ⋅ 3 Baths ⋅ 24203783 MLS
Imagine strolling to the historic Guilford Green, with downtown shops, dining, and the train station just steps away! Situated on a level 0.68-acre lot, this turnkey 1920 Craftsman at 134 Union perfectly marries vintage soul with effortless modern living. A reclaimed wood ceiling warms the foyer, leading into an open-concept entertainer's dream. The chef's kitchen boasts sweeping quartz counters, a massive island, farmhouse sink, double ovens, and geometric tile. The dining room easily seats ten and flows into a cozy living room. Flawless red oak floors tie the 2,194 sq ft main living space together. Your main-level primary suite features a walk-in closet, reclaimed wood accent wall, and a luxurious spa bath with a marble double vanity and glass shower. A dedicated office, laundry room, and half bath complete the first floor. Upstairs, find three bright bedrooms and a full bath. Enjoy total peace of mind with extensive 2020 renovations including a new roof, upgraded electrical, and stunning kitchen/bath remodels. The home offers gas forced-air heat, central air, public water, and septic. Relax on the open porch overlooking a private yard with a storage shed. With a full walkout basement, this move-in-ready home is the ultimate lifestyle upgrade! If your wish is to live walking distance to the guilford green, here is your chance. Just turn the key, and move in!

134 Union St, Guilford
$799,000
4 Beds ⋅ 2 Baths ⋅ 24175128 MLS
Charming seasonal cottage located in the desirable Guilford Lakes community. This cozy retreat offers lake views and access to private beach rights, making it an ideal getaway for summer enjoyment. The home features a rustic interior with an open living area, kitchen, and comfortable sleeping spaces. Situated on a lightly wooded, sloping lot, the property provides a peaceful setting close to the water and community amenities. Perfect opportunity for a seasonal escape or weekend retreat.

48 Lakeside Dr, Guilford
$719,900
4 Beds ⋅ 3 Baths ⋅ 24192692 MLS
Privately set on over 2.5 beautifully maintained acres. Inside, you'll find formal living and dining rooms, a bright kitchen with newer appliances, a breakfast nook, and a large family room with a fireplace and access to the deck and backyard.The second floor features a generous primary suite with a private bath, three additional bedrooms, and a full hall bath. A finished third-floor room with new skylights and carpeting provides flexible space for a home office, playroom, or guest retreat, while the finished lower level includes a media room, laundry area, and abundant storage. Enjoy your own backyard oasis with an in-ground pool, expansive lawn, and exceptional privacy. Major updates include a new roof, skylights, and HVAC system (2023), plus a new hot water heater and kitchen appliances (2021), offering peace of mind for years to come. Ideally located just minutes from Guilford's high school, town center, beaches, marina, restaurants, and hiking trails, with convenient access to New Haven, Hartford, and New York City.

70 Stepstone Hill Rd, Guilford
$715,000
4 Beds ⋅ 3 Baths ⋅ 24196431 MLS
Well located at the end of a quiet cul-de-sac in the desirable Meadow Hills Lake community, this spacious 4-bedroom center hall Colonial offers the perfect balance of privacy, comfort, and neighborhood amenities, including private lake access and a sandy beach. Designed for both everyday living and entertaining, the main level features formal living and dining rooms, an eat-in kitchen, and an inviting family room with vaulted ceilings, a wood-burning fireplace, and sliding doors leading to an expansive deck. A versatile room just off the kitchen is ideal as a home office or playroom and opens to the welcoming front porch. Hardwood floors extend throughout the first level. Upstairs, the generous primary suite includes a walk-in closet and private bath, while three additional bedrooms share a full hall bath. The private backyard is a true retreat, highlighted by a newly rebuilt saltwater pool and plenty of space to relax or entertain. Enjoy the best of both worlds-a peaceful setting with exceptional community amenities, all just minutes from shopping, dining, and commuter routes.

98 Pond View Cir, Guilford
$650,000
4 Beds ⋅ 3 Baths ⋅ 24195110 MLS
Highest & Best due by noon, Tuesday, August 18th. The original owners are proud to present this lovingly maintained 4-bedrm, 2.5-bath Colonial! This secluded property offers peace, quiet and privacy. Best of all, ownership includes access to the beautiful Meadow Hills Lake Assoc. so you can enjoy the perfect blend of private tranquility and community recreation! The home features a traditional floor plan with hardwood flooring throughout and excellent first-floor versatility! The main level offers plenty of flexible living space, including a formal living room, an oversized family room with custom built-ins, a dedicated office with French doors, a separate den & a unique attached greenhouse for year-round gardening. A mudroom & powder room are conveniently located just off the attached Main Level 2-car garage. The spacious deck is perfect for outdoor entertaining and relaxing. During colder months, cozy up by one of the two fireplaces. Storage is abundant with double closets at both the foyer and garage entrances and 2 kitchen pantry closets. The property also features a full walk-out lower level, offering immense potential for future finished space. Outside, a massive 24'x36' detached barn equipped with electricity and a large walk-up attic offers endless possibilities for a workshop, car storage, or a studio. Featuring a wonderfully functional layout-this property offers an incredible opportunity to update, design and create your dream home.

289 S Hoop Pole Rd, Guilford
$550,000
4 Beds ⋅ 2 Baths ⋅ 24126723 MLS
MULTIPLE OFFERS-SELLER REQUESTS HIGHEST & BEST OFFERS. Submission deadline is Friday May 23rd by 8:00 PM Exceptional Investment Opportunity - Prime Guilford Location Just steps from the vibrant Guilford Green, this historic multifamily property features two spacious 2-bedroom, 1-bathroom units on a level 0.46-acre lot. (Field card Says 2 bedrooms in each apt -4 bedrooms total- In 1st floor apt. Front room was used as 2nd bedroom. Fireplace is not currently operational. Ideal for restoration, it offers potential as an owner-occupied residence with rental income or a full investment property. Located only 0.5 miles from the train station and 1 mile from Jacobs Beach, Chittenden Park, and the town marina, with easy access to shops, restaurants, the Guilford Free Library and the Guilford Fairgrounds. Priced to reflect renovation needs and offered "As Is". Inspections are for informational purposes only. Best suited for cash buyers or those using an owner-occupied rehab loan.

174 Whitfield St, 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

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