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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
$3,750,000
5 Beds ⋅ 7 Baths ⋅ 24190774 MLS
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 in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

28 Walden Hill Rd, 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
$1,995,000
3 Beds ⋅ 3 Baths ⋅ 24186090 MLS
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 impressive vaulted ceiling living room with a wood-burning fireplace, beautiful oak bookcases and opens to a spacious dining room. Both rooms have access to a large, recently updated deck, perfect for entertaining or simply taking in the expansive scenery. This level also features three bedrooms, including a primary suite with a bathroom, abundant closet space and a private balcony overlooking the view. The other two bedrooms - one currently used as a den/office - share a full family bath. An eat-in kitchen and a separate laundry room complete this level making it ideal for easy one floor living. On the lower level, a guest suite has its own living room with fireplace, a full bath, a room for overflow guests and access to an outdoor sitting area. There's also an attached two car garage with ample storage space.

473 Colonial 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
$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
$1,500,000
3 Beds ⋅ 4 Baths ⋅ 24200312 MLS ⋅ Benton's Knoll BLDG.
Beautiful single family residence in MINT turnkey condition in sought-after Benton's Knoll, Sachem's Head. Quality, high-end construction provides luxurious amenities throughout. The large light-filled LR/Dr with fireplace w/ marble surround includes Hunter Douglas shades w/ sliders to the large deck off the back of the residence. The kitchen is very well equipped with a large Sub zero refrigerator, Wolf ovens, Cove dishwasher & composite countertops. A large pantry, w/ built-ins &laundry room are conveniently located adjacent to the two car garage, providing easy access to the kitchen. The floors throughout the first and second floor are hardwood white oak. The primary bedroom, located on the main level has a custom designed bathroom adorned with beautiful marble tile & a heated floor. The total square footage of this unit is 4001 sq ft - 2942 sq ft on the first and second floor; then the finished walk out basement is 1100 sq ft which provides a family room with fpl, large office and storage area with a full bathroom. This level could work for an au pair or plenty of room for extra guests and family. Walk out directly from this level to the bluestone patio and in-ground heated Gunite pool . Enjoy the ease of ownership in this special 15 unit condo complex, but with the feel of single family residences affording privacy and fantastic location, steps away from the water. Drive 6 minutes to the Guilford Green and all it has to offer.

20 Bentons Knl, 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
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 24198331 MLS
Welcome to 212 Mulberry Point Road, a distinctive contemporary coastal retreat in a cul-de-sac neighborhood offering rare acreage in one of Guilford's most coveted shoreline areas. Beautifully landscaped, with an emphasis on privacy, the property is designed for exceptional indoor-outdoor living, with a large in-ground pool, separate all season hot tub, expansive decking, and an outdoor fireplace under a gazebo. The property is ideal for entertaining, dining, and relaxing. Inside, a sophisticated yet comfortable layout has unique architectural character throughout. The spacious primary suite features its own private loft, creating the perfect setting for a home office, reading nook, or sitting area. The finished lower level expands the living space with a generous recreation room, dedicated gym area, and wine cellar- as well as a 3-car garage. The house also boasts 3 functional fireplaces. A rare combination of land, privacy, amenities, and coastal location, this home offers a resort-like lifestyle just moments from Guilford's shoreline, village center, beaches, and all that this sought-after community provides.

212 Mulberry Point Rd, Guilford
$1,185,000
6 Beds ⋅ 3 Baths ⋅ 24181215 MLS
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, and major commuting routes, including I-95 and the Guilford Train Station. Originally constructed in 1888 by prominent Guilford builder George W. Seward, this distinguished Queen Anne Victorian offers over 3,800 square feet of living space featuring six bedrooms, four bathrooms, generous living and entertaining spaces, soaring ceilings, and original architectural details throughout. Originally designed as a single-family residence and currently utilized as a multi-family property, the flexible floor plan offers exceptional versatility for a variety of living arrangements. The seller has invested more than $300,000 in recent renovations, including the first-floor kitchen, first and third-floor bathrooms, a new roof, rebuilt front porch, driveway, updated siding, and exterior restoration. Set on approximately 0.39 acres, this is a rare opportunity to own a distinguished in-town Guilford property offering generous living space, architectural character, and an exceptional location.

33 Church 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
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 24180122 MLS
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 features, it borders the Westwood Trails. Light and bright with large windows and high ceilings. The kitchen is a Chef's delight with Wolf stove, under counter microwave, huge center island with granite counters and open to the family room. Storage galore! including a large pantry for all your needs. Open to the family room with gas Fireplace and French doors to the stone patio and private area for entertainment. Spacious front room can be used as a private office. Enormous great room offers tremendous flexibility. Formal Dining room for gracious dining. The spacious bedrooms and the spa like primary bath will soothe and delight you. A walkup attic and full basement will accommodate all your storage needs. This home has been thoughtfully and meticulously designed.

189 Three Mile Crse, 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
$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
$989,000
4 Beds ⋅ 3 Baths ⋅ 24156467 MLS
Here is your opportunity to build this beautifully designed 2,814 sq ft Cape-style home privately situated on a rear lot! This thoughtfully crafted To Be Built home blends classic New England charm with today's clean farmhouse aesthetic - board-and-batten accents, striking black windows, and timeless architectural lines. The open-concept main level is designed for today's lifestyle, featuring a spacious kitchen with center island and walk-in pantry, flowing seamlessly into the dining area and inviting family room. A first-floor primary suite option offers flexibility, complete with a walk-in closet and well-appointed bath. A private home office, mudroom, and separate laundry room complete the first floor. Upstairs, three generously sized bedrooms and a full bath create comfortable accommodations. Additionally, there is the option to expand over the garage or finish additional space in the walkout basement. The opportunity to personalize finishes make this a rare opportunity to build your dream home in a secluded yet convenient location.

Long Hill Rd, 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
$950,000
2 Beds ⋅ 3 Baths ⋅ 24194348 MLS ⋅ The Fair Street Condominium BLDG.
Experience the best of downtown Guilford at The Foundry, a 12-unit luxury condominium community tucked away on coveted Fair Street, just steps from the historic Green. Blending timeless New England charm with distinctive European-inspired architecture, this exceptional townhouse incorporated into the original brick mill building, offers a rare combination of character, privacy, and the convenience of downtown living. Inside, 10-foot high ceilings, expansive windows, exposed brick, wood beams, and rich hardwood flooring create a warm inviting atmosphere. The thoughtfully designed floor plan offers a living room with fireplace, dining room, an updated kitchen with quartz countertop, tile backsplash, BOSCH appliances, and built-in pantry. Upstairs includes the master bedroom with 2 walk-in closets and full bath, second bedroom, full bath, and laundry. A private patio provides the perfect setting for morning coffee or evening relaxation, while the attached garage, additional carport, and generous lower-level storage add everyday convenience. Surrounded by beautifully landscaped grounds, including a spacious rear lawn, this home offers a peaceful retreat in the heart of town. Enjoy an unparalleled lifestyle with boutique shopping, restaurants, the library, town marina, Beach, and the train station all just moments away. Whether you're strolling the Green, dining al fresco, or taking in a shoreline sunset, this is in-town Guilford living at its finest.

18 Fair St Unit 3, Guilford
$949,900
2 Beds ⋅ 3 Baths ⋅ 24159776 MLS ⋅ Village On State BLDG.
Welcome to 24 Village Circle! An "Under Construction" end unit in Guilford's newest luxury community, Village on State. This development features 25 - 2 bedroom townhomes, each having over 2000 square feet of living space, 2 car garages and full basements. 24 Village Circle is the Allendale model which allows for one level living with plenty of space for guests. On the main floor, there is the Primary bed/bath with a full tiled shower, a kitchen with stylish white cabinetry and Quartz counter tops, large Great room and Dining room which is perfect for entertaining, a half bath and laundry room. On the upper level you will find a spacious second bedroom with a full bath and walk in closet, a study and a large loft area. This model features 2,197 square feet of beautiful living space. Village on State is a short distance to the historic Guilford Green, shopping, restaurants, the town library and community center. These stunning townhomes will have the ultimate curb appeal. On the exterior will be black windows, black metal roof accents, a mix of siding styles and beautiful decorative stone.

24 Village Cir Unit 24, 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

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