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28 Walden Hill Rd, 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

66 High St Unit 38, 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

66 High St Unit 17, Guilford
$2,990,000
3 Beds ⋅ 3 Baths ⋅ 24167886 MLS ⋅ The Residences At 66 High Street BLDG.
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 impressive 3,148 square feet, this custom single-level home offers elegant design and modern amenities, ensuring comfort and style at every turn. Step inside to discover an exquisite open floor plan highlighted by two-inch marble and black walnut countertops, complemented by high-end finishes from Waterworks and custom built-ins throughout. Enjoy the culinary delight of a gourmet kitchen equipped with Subzero appliances, a 48" Wolf range, and two spacious walk-in pantries. The inviting living area features a gas fireplace for cozy evenings and a state-of-the-art Full Swing sports simulator that also serves as a perfect media room. This smart home boasts temperature-controlled fresh air and is easily managed via iPad. Step outside to your covered private terrace and be captivated by stunning marsh and Long Island Sound views, accompanied by refreshing salty breezes. The vibrant community offers a heated pool, fitness center, fire pit, dog park, and more, making it an ideal setting for relaxation and recreation. With easy access to the marina, beach, dining, shopping, and cultural experiences in downtown Guilford, this property epitomizes Connecticut shoreline living at its finest.

66 High St Unit 17, Guilford

539-A Boston St, 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

3 Caleb Ct, Guilford
$1,400,000
5 Beds ⋅ 5 Baths ⋅ 24208684 MLS
A distinguished Colonial with a sophisticated twist, this exceptional 5-bedroom, 4.5-bath residence beautifully blends timeless elegance with remarkable versatility. Privately nestled on nearly 2 professionally manicured acres at the end of a coveted cul-de-sac, the home welcomes you with a dramatic two-story foyer, gracious living room & banquet-sized dining room accented by exquisite millwork. At the heart of the home, an expansive chef's kitchen showcases custom-crafted cabinetry, an oversized island, breakfast bar & inviting dining area, all opening to a spectacular deck & beautifully appointed patio. The adjoining family room is a showstopper, with soaring cathedral ceilings & a wall of windows capturing views of the lush gardens and breathtaking grounds. A thoughtfully designed main-level guest or in-law suite offers a private bedroom, elegant full bath and generous living space. An amazing mudroom just off the 3 car garage. A second staircase leads to an impressive bonus room, full bath, laundry and spacious home office. Three generously proportioned bedrooms and 2 full baths provide exceptional comfort. In addition, the extraordinary primary suite serves as a private sanctuary, complete with an expansive dressing room, luxurious bath & romantic private patio, an idyllic setting for morning coffee. Offering an exceptional combination of refined living, flexible accommodations and serene outdoor beauty, this remarkable property is in a phenomenal neighborhood. Min to 95

3 Caleb Ct, Guilford

122 N Fair St Unit 3, Guilford
$1,250,000
3 Beds ⋅ 4 Baths ⋅ 24206814 MLS ⋅ Guilford Commons BLDG.
Experience luxury living in the heart of downtown Guilford! Offering approximately 3,500 sq ft across 3 beautifully designed levels, this exceptional condominium perfectly combines space, privacy & convenience. A private elevator provides effortless access to every floor. The impressive main level features an open floor plan filled with natural light from expansive windows. At the heart of the home is a stunning custom kitchen w/gas cooking, beautiful tile backsplash & an oversized center island, all overlooking the formal dining room-perfect for everyday living & entertaining. The inviting sitting room features a fireplace & overlooks the private terrace. The spacious living room & guest half bath complete this thoughtfully designed level. The second floor is highlighted by an expansive primary suite featuring a sitting area, walk-in closet, full bathroom with jacuzzi tub & oversized tile shower & private deck overlooking the beautifully landscaped gardens. A generously sized 2nd bedroom offers its own full bathroom, walk-in closet & charming overlook. The versatile 3rd level features a 3rd bedroom complete with a full bathroom & multiple walk-in closets. Outside, enjoy your own private terrace w/a granite patio overlooking gorgeous, professionally landscaped gardens. Additional highlights include an oversized 2-car garage & a basement for extra storage. Privately positioned within an exclusive community w/just a 1/2 mile from the Guilford Green & Guilford Train Station

122 N Fair St Unit 3, Guilford

66 High St Unit 4, Guilford
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 24212233 MLS ⋅ The Residences At 66 High Street BLDG.
Just steps from Guilford's historic town green, vibrant boutiques, and gourmet dining-and a short stroll to the town marina and train station-The Residences at 66 High Street offers an extraordinary blend of historic character & cosmopolitan luxury in the award-winning complex. Step inside this stunning two-bedroom unit, once honored as the coveted HOBI (Home Building Industry) Project of the Year. The open-concept main level showcases original exposed brick, seamlessly connecting a living area anchored by a sleek gas fireplace to a gourmet kitchen outfitted with a Wolf range, Sub-Zero refrigerator, quartz countertops, and an entertaining island w seating. Designed for effortless living, the first floor features a convenient guest suite w a connecting full bath, first-floor laundry, & heated bathroom floors. A dramatic wood-and-metal staircase leads to a second-floor loft w a built-in workspace & custom shelving. Retreat to the private primary suite, boasting dramatic 12-foot ceilings, a generous walk-in closet, & a spa-inspired bath. The crown jewel of the home is your very own secret rooftop deck crafted from teak & shaded by a pergola-an outdoor sanctuary offering expansive town views. This unit includes a detached oversized private garage w storage plus an assigned parking space just steps from your door. Residents enjoy an exceptional lifestyle enriched by community amenities, including an in-ground pool, gas fire pit lounge, garden beds, state of the art fitness center

66 High St Unit 4, Guilford

212 Mulberry Point Rd, Guilford
$1,150,000
3 Beds ⋅ 4 Baths ⋅ 24198331 MLS
PLEASE NOTE: Roof being replaced in October 2026. Welcome to 212 Mulberry Point Road, a private coastal luxury retreat tucked away on a peaceful cul-de-sac in one of Guilford's most coveted shoreline settings. Set on rare acreage and surrounded by beautifully landscaped grounds, this distinctive contemporary residence offers effortless indoor-outdoor living. At the heart of the property is a resort-inspired outdoor oasis, featuring a large in-ground pool, separate all-season hot tub, expansive decking, and an inviting outdoor fireplace beneath a gazebo. Whether hosting summer gatherings, dining under the stars, or simply unwinding in complete serenity, the setting is perfect. Inside, sophisticated yet comfortable living spaces are complemented by distinctive architectural details and three functional fireplaces. The spacious primary suite features a private loft-an ideal setting for a home office, reading nook, or intimate sitting area. The finished lower level provides even more space to relax and entertain, with a generous recreation room, dedicated gym, and wine cellar. A three-car garage adds to the home's impressive list of amenities. Offering a rare combination of acreage, privacy, resort-style amenities, and an exceptional coastal location, this home captures the essence of relaxed shoreline luxury-just moments from Guilford's beaches, village center, and everything that makes this sought-after community so special.

212 Mulberry Point Rd, Guilford

450 Bluff View Dr, 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

136 Quonnipaug Ln, 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

18 Fair St Unit 3, 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

134 Union St, 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

12 Village Cir Unit 12, Guilford
$909,900
2 Beds ⋅ 3 Baths ⋅ 24161578 MLS ⋅ Village On State BLDG.
Welcome to 12 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. 18 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.

12 Village Cir Unit 12, Guilford

33 Village Cir Unit 33, Guilford
$879,900
2 Beds ⋅ 3 Baths ⋅ 24139166 MLS ⋅ Village On State BLDG.
Welcome to 33 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. 18 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.

33 Village Cir Unit 33, Guilford

4 Chasse Dr, Guilford
$875,000
3 Beds ⋅ 3 Baths ⋅ 24205909 MLS
A nature lover's paradise on 2.15 private acres, 4 Chasse Drive pairs total seclusion with close proximity to everything the shoreline has to offer. One mile to the Guilford Green, minutes to the beaches, hiking trails, and easy highway and train access, the property is still screened from the road by mature plantings and a private drive that feels like a retreat the moment you turn in. An English garden greets you at the top of the driveway, and the back of the property cascades with trees, creating a natural setting for gatherings or a quiet night by the fire pit. Inside, just under 3,000 square feet unfolds across a modern, light-filled floor plan with hardwood floors throughout. An oversized, sun-filled entryway offers a view of the grounds through the front door. A generous sitting room sits just to the left of the entry, flowing into a formal dining room with wainscoting, which continues into the bright eat-in kitchen. French doors off the kitchen lead to the expansive deck attached to the screened-in porch, and sliders from the porch open into the family room. A study attached to the family room completes the circuit back to the front entry, ideal as a home office. Upstairs, an oversized, bright landing leads to a clean laundry closet. The primary suite, a genuine retreat, features its own private deck overlooking the backyard, two closets including a walk-in, and a newly remodeled spa-like bathroom with a glass-door walk-in shower, soaking tub, & dbl sink vanity.

4 Chasse Dr, Guilford

44 Coventry Way, Guilford
$799,000
3 Beds ⋅ 3 Baths ⋅ 24208812 MLS
Beautifully updated Guilford Lakes Colonial offering nearly 2,800 square feet of spacious, comfortable living. Inside, the bright and welcoming floor plan features hardwood flooring, generously sized rooms and plenty of space for both everyday living and entertaining. The eat-in kitchen with center island opens to an impressive family room with vaulted ceilings, a fireplace and French doors leading to the expansive deck and patio-perfect for indoor-outdoor living. Formal living and dining rooms provide additional space for entertaining, while the oversized bonus/media room offers incredible flexibility as a home office, playroom, gym or second family room. Upstairs, you'll find three spacious bedrooms with newly added hardwood flooring, including a generous primary suite featuring two walk-in closets and a private bath with soaking tub and separate shower. Additional highlights include new central air conditioning, fresh interior paint, main-level laundry, a walk-up attic, full basement and attached two-car garage. With its spacious floor plan, thoughtful updates and serene setting, 44 Coventry Way offers a picturesque lot accented by classic stone walls and inviting outdoor spaces, this home offers the perfect combination of privacy, space and convenience.

44 Coventry Way, Guilford

137 Flat Meadow Rd, Guilford
$789,000
3 Beds ⋅ 2 Baths ⋅ 24205448 MLS
Nestled behind original stacked stone walls and lush greenery, this New England saltbox home has been lovingly reimagined by its current owners. The front entry welcomes you with a gorgeous, vaulted ceiling spanning two stories featuring lovely natural wood detailing. The light-filled living and dining room greets you with lovely views of the surrounding landscape and a cozy wood burning fireplace, perfect for enjoying dinners by the fire and hosting intimate winter gatherings. Inside the newly renovated kitchen are beautifully designed custom cabinets, stainless steel appliances and gas range along with a pantry featuring antique glass-paneled French wood doors. The family room opens to vaulted ceilings featuring original wood beams and tons of natural light and a pass-through to the bright and airy mudroom / laundry room. On the main floor you'll also find a cozy bedroom which can also be used as a private office, the first full bath and beautiful three-season screened porch overlooking the lawns and mature cedar trees. On the second floor is the primary bedroom featuring vaulted ceilings, wood beams and tall windows overlooking the landscape below. Across the hall is your third bedroom with a spiral staircase leading to a third-floor loft, perfect for a reading nook, meditation space, art studio, teen hang-out, play space or office. Rounding out the second floor is the second full bath, walk-in linen closet and a fully lined cedar closet.

137 Flat Meadow Rd, Guilford

98 Pond View Cir, 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

150 Mulberry Point Rd, Guilford
$650,000
3 Beds ⋅ 3 Baths ⋅ 24199038 MLS
HIGHEST AND BEST OFFERS DUE SATURDAY, AUG 29TH BY 6 PM. Perfectly remodeled and move-in ready, this inviting Guilford home offers an ideal blend of comfort, style, and an unbeatable shoreline location. Just 1.5 miles to the beautiful and historic Guilford Town Green, you'll enjoy easy access to charming shops, restaurants, cafes, and community events. Chaffinch Island Park, recognized as one of Connecticut's top spots, is less than a mile away, as is beloved Jacobs Beach and the sparkling waters of Long Island Sound. Thoughtfully renovated from top to bottom, this home features a flexible open floor plan with three bedrooms and two and a half beautifully updated baths. The bright living and dining areas flow into a bright updated kitchen with a huge central island, creating a wonderful space for everyday living and entertaining. Sliding glass doors open to a spacious composite deck that is perfect for summer gatherings and relaxing outdoors. The primary bedroom offers a stylish ensuite bath, while two additional bedrooms share a renovated family bath. The lower-level family room with wood-burning fireplace provides additional living space and could easily serve as a home office or retreat. Recent improvements include a septic system (2021), a Viessmann combination boiler, central air, and numerous quality upgrades. Nothing to do but move in and enjoy all that the beautiful town of Guilford and the Connecticut shoreline have to offer!

150 Mulberry Point Rd, Guilford

952 Maple Hill Rd, Guilford
$639,999
3 Beds ⋅ 3 Baths ⋅ 24205121 MLS
Welcome to your own private oasis. Set on a quiet, partly wooded lot, this property has been meticulously renovated and thoughtfully reimagined, offering the rare combination of high-end finishes, modern amenities, and effortless indoor/outdoor living. The stunning kitchen is open to the dining and living areas, and is designed to impress, with granite countertops, center island, Viking appliances, Bosch dishwasher, and farmhouse sink. Luxury additions such as heated bathroom floors, and integrated indoor/outdoor surround sound allows the music to continue wherever the day takes you. The lower level family room allows for an additional 600 sq. ft. of living space and features a fireplace, and sliders leading directly out to the patio. The outdoor space offers a propane-heated in-ground pool surrounded by an expansive patio. The outdoor kitchen is exceptional, with granite countertops, grill, and pizza oven. The beautiful Azek deck, fire pit, and multiple outdoor spaces provide plenty of room to dine and unwind. A new driveway leads to the spacious two-car garage, and allows for plenty of additional parking for guests. Whether hosting a crowd or enjoying a quiet evening by the fire, this home was designed to make every day feel like a getaway.

952 Maple Hill Rd, Guilford

1431 Long Hill Rd, Guilford
$639,000
3 Beds ⋅ 3 Baths ⋅ 24202376 MLS
This inviting home welcomes you with bright, open living spaces highlighted by a large skylight that fills the main areas with natural light. The well-equipped gourmet kitchen features high-end appliances, custom cabinetry, and a movable island beneath a vaulted ceiling-perfect for cooking and gathering. The finished lower level includes a cozy fireplace and offers direct access to the pool area, making it ideal for entertaining or relaxing. Step out from the enclosed porch onto the spacious deck, which, along with the outdoor spaces, expands the living area beyond the home's walls. Solar panels provide energy efficiency and modern convenience. The primary suite offers a comfortable retreat with its own bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. This home brings together comfort, thoughtful details, and versatile spaces-ready for your everyday enjoyment.

1431 Long Hill Rd, Guilford

289 S Hoop Pole Rd, Guilford
$635,000
4 Beds ⋅ 3 Baths ⋅ 24195110 MLS
The original owners of 53 years are proud to present this lovely 4-bedrm, 2.5-bath Colonial tucked away on 1.53 acres. Ownership includes deeded rights and access to beautiful Meadow Hills Lake & Beach. Offered AS-IS at a newly reduced price reflecting needed repairs, this property invites you to bring your vision and create a truly personalized forever home. A massive 24' x 36' detached barn with electricity offers endless possibilities for hobbyists, car enthusiasts, or storage seekers. Inside, hardwood floors run throughout. Versatile living spaces include a formal living room with pocket doors, an oversized family room with custom built-ins, a dedicated office and a dining room both with French doors, and an attached greenhouse for year-round gardening. The spacious deck provides an ideal setting for entertaining, while 2 fireplaces add warmth. Upstairs, the primary bedroom features a walk-in closet and ensuite bath. You will find exceptional storage throughout the home, from double foyer closets, an oversized mudroom closet off the garage and a kitchen pantry closet. Even the secondary bedroom features a private walk-in closet. The attached 2-car garage adds convenience, while the full WALK-OUT lower level offers immense potential for future finished space. Offering wonderful lake access for a blend of quiet privacy and active community recreation, a massive barn, & a fresh price adjustment, those ready to add their personal touch & investment will be richly rewarded.

289 S Hoop Pole Rd, Guilford

962 Moose Hill Rd, Guilford
$629,900
4 Beds ⋅ 2 Baths ⋅ 24206807 MLS
Quietly nestled on a magnificent 3.5+ acre lot, additionally bordered by Land Trust property and Westwoods hiking trails, this striking four-bedroom, two-full-bath home offers exceptional privacy, endless natural beauty, and a sophisticated contemporary flair. The inviting living room features a cathedral ceiling, skylight, & wood-burning stove, flowing seamlessly into the stunning remodeled kitchen with abundant cabinetry, gorgeous granite counters, and an oversized breakfast bar where an enormous picture window captures sweeping views. An incredible home office with built-ins-also ideal as a dining room-opens to a stone patio. The first floor includes a bedroom, updated full bath, and an expansive deck. Upstairs, the primary bedroom features a loft, along with two additional bedrooms, and a newly remodeled full bath with skylight. The completely renovated walkout lower level offers a gym, a bonus room with sliders out to a patio with a fire-pit! Spacious storage areas, and huge laundry room. Additional features include oil heat with three zones and an incredible oversized shed. Professionally landscaped grounds are simply perfection, with manicured lawns, multiple patios, and total privacy surrounded by nature. Yet, this peaceful retreat is just minutes from the highway, shopping, Guilford Green, beaches, and the in-town train station.

962 Moose Hill Rd, Guilford

221 Water St, Guilford
$600,000
2 Beds ⋅ 2 Baths ⋅ 24200641 MLS
Live the lifestyle-a fantastic condo alternative with zero HOA fees! This completely renovated with unique touches, 1916 Cape Cod offers water views AND a truly prime location just ONE HALF MILE from Guilford Green's charming shopping, fine dining of all types, and historic churches with scenic views of the West River and surrounding salt meadows. Inside light-filled spaces showcase the bright painted interiors and rich hardwood floors throughout. The expansive chef's kitchen features Soho gray quartz countertops, a double stainless steel farmer's sink and all stainless steel appliances. Relax in the sun-drenched four-seasoned sun room offering views south towards Long Island Sound. Both bathrooms have been exquisitely updated: the main-level bath boasts quartz counters, a vessel sink, and a custom finger tiled shower, while the upper-level bath features marble flooring, crisp subway tiles as well as a luxurious marble rain shower! Out back, enjoy a private firepit area, a very useable storage outbuilding and convenient rear parking. Major updates provide complete peace of mind, including a 6 month old state-of-the-art hot water furnace, three high-efficiency ductless mini-splits, connected city water, a clean open full basement and mostly new siding, roofs and gutters. This property has an excellent Airbnb record as an option but better yet move right in and enjoy turnkey coastal Connecticut living! An opportunity like this doesn't happen very often so don't wait.

221 Water St, Guilford

1054 Boston Post Rd, Guilford
$600,000
5 Baths ⋅ 24165156 MLS
RARE OPPORTUNITY TO OWN A BUILDINGS ON RTE. 1 IN GUILFORD ~ Unlock the potential of this prime commercial property on the bustling Boston Post Road, just one block from Guilford's historic town Green. Within the PV zone (Post Road Village Zone District) with dedicated parking; an ideal setup for businesses seeking a prestigious location with convenience & visibility. Step inside to find multiple private offices, a spacious reception area, and convenient bathroom access on the main level; perfect for professional or medical offices. The second floor boasts four additional offices and a walk-up attic, offering flexible workspace options and storage. Behind the main building, three additional private offices each feature separate exterior entrances beneath a covered porch deck, along with interior access to two adjoining offices and two half baths. The property features hardwood floors throughout most rooms, many updated windows, vinyl siding, and modern comforts including central A/C in the main building and wall units in the rear offices. With high visibility, easy accessibility, and a prime downtown location, this is an exceptional investment opportunity for owner-occupiers or investors looking to expand their portfolio. Buyers looking to convert or use as residential to perform their own due diligence. Don't miss your chance to own a piece of Guilford's thriving commercial district

1054 Boston Post Rd, Guilford

91 Stone Boat Rd, Guilford
$599,000
3 Beds ⋅ 3 Baths ⋅ 24099708 MLS
First time on the market in decades, this traditional center hall colonial style home in lovely Northwoods Subdivision has been lovingly maintained by the same family for generations. Located in the coastal town of Guilford with its award winning school system and historic town green and center just miles away, this home offers a spacious eat-in style kitchen with ceramic tile flooring, lovely formal living room and dining room with hardwood floors and family room with gas log fireplace and wide board pine wood flooring. Upper level boasts a generous sized master bedroom, complete with full bath and walk-in closet. Two other bedrooms are bright and nice sized and entire second level has hardwood floors throughout. Additional bonuses are newer furnace and hot water heater. Deck in rear of home is accessed by both kitchen and sliders from the family room. This home sits on a beautiful, parklike 1.66 acre lot complete with babbling brook and is awaiting its next owner. Come see the potential this home has to offer. Subdivision is located close to Route 80 and 77, making it easy for commuters.

91 Stone Boat Rd, Guilford

96 Glenwood Dr, Guilford
$550,000
3 Beds ⋅ 3 Baths ⋅ 24212684 MLS
Beautifully Remodeled Ranch welcomes you the moment you step inside. The open layout creates a comfortable flow between the kitchen, dining, and living areas - perfect for gathering with loved ones or enjoying quiet everyday moments. The kitchen offers generous workspace with new cabinets, quartz countertops, and all new appliances. The living room's Picture Window fills the home with soft natural morning sunlight. Nearby, you'll find a large Study with its own private entrance. Complete with Laundry & Full Bath for added convenience, this space offers comfort and privacy for family or guests. On the other side of the home, you will find 3 Additional Bedrooms all with gorgeous, redone & exposed hardwood floors with a fresh "Special Walnut" stain. Step out onto the back deck, accessible off Dining Area, to enjoy the quiet acre of lightly wooded & private rear yard. This quiet Neighborhood is the perfect setting for a 1,548 square foot Ranch offering One Floor Living with Full House Generator and Updated........ well, Just About Everything !!

96 Glenwood Dr, Guilford

83 Crestwood Dr, Guilford
$549,000
3 Beds ⋅ 3 Baths ⋅ 24203336 MLS
Set on over an acre, this 3 bedroom, 2 1/2 bath Colonial offers a wonderful floor plan with spacious rooms and wonderful indoor and outdoor living space. The kitchen offers granite countertops, a center island, and pantry, and is open to the family room and dining area with built-in storage and a convenient serving bar. A front-to-back living room offers additional flexibility, with ample space for both living and dining. The spacious family room features a wood-burning fireplace with brick surround, a bay window overlooking the front yard, and access to the screened-in porch. Enjoy views of the mature gardens and an in-ground pool, creating an inviting setting for relaxing and entertaining. All three bedrooms are located on the second floor and have hardwood flooring. The master bedroom offers a walk-in closet and private full bath with shower, while a second full bath with tub/shower serves the additional bedrooms. The fenced backyard area provides privacy and space surrounding the in-ground pool, complete with a hot/cold outdoor shower and room to lounge and sunbathe. Additional features include a second driveway to the right of the home for extra parking, a shed, 2-car garage with one smaller bay, partially finished basement with additional storage space, and generator transfer switch. Conveniently located less than 10 minutes from the center of town, with an easy commute to New Haven and convenient access to major commuter routes.

83 Crestwood Dr, Guilford

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