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$1,100,000
5 Beds 3 Baths 24187310 MLS
Coming soon..... Historic Charm, Modern Living - On 3+ Acres in Guilford If you've been searching for something truly different, this is it. This beautifully crafted 1700s reproduction home sits on over three peaceful acres and stands alone as a property with no comparable in all of Guilford. Character abounds throughout - three fireplaces, including a stunning walk-in fireplace, give every room a sense of history and warmth. Over 3800 square foot of living space. The updated kitchen and refinished basement have been thoughtfully done, so the home is move-in ready while still feeling authentic to its roots. Three bedrooms on the second floor provide comfortable family living, and two additional finished rooms on the third floor give you the flexibility to grow, work from home, or host guests with ease. Step outside and you'll find a private retreat: a tranquil pond with a fountain, streams aligning the property, manicured gardens, and a pergola for morning coffee or evening gatherings. The large detached garage features unfinished space above - a blank canvas ready to become whatever your lifestyle calls for. Opportunities like this don't come around often. Come experience it for yourself.

1640 Little Meadow Rd, Guilford

$749,900
3 Beds 2 Baths 24186957 MLS Long Hill Farm BLDG.
Welcome to Long Hill Farm - where everyday life feels a little like a fairytale. Tucked into the serene Guilford countryside, this free-standing residence has been lovingly remodeled to deliver a lifestyle you'll adore: a rare blend of privacy, luxury, and easy, joyful living, all anchored by a private heated in-ground pool that feels like your very own slice of paradise. Step inside, where gleaming new hardwood floors flow throughout the majority of the home. The graceful open floor plan gathers the living and dining spaces around a crackling wood-burning fireplace - the kind of spot made for slow mornings and storybook evenings. The primary suite is a dreamy retreat all its own, crowned by a soaring cathedral ceiling with exposed beams, a walk-in closet, full bath, and glass sliders that invite the outdoors in. A second bedroom and full bath complete the main level, while a third bedroom charms with custom built-ins and a private balcony. Up above, a spacious loft floats over the living room, perfect for curling up with a good book. Wrapped in lush greenery and mature trees yet just minutes to Route 1, commuter rail, and the historic Guilford Green - and perfectly poised between New York City and Boston - this is shoreline-adjacent living at its most enchanting. A turn-key sanctuary you'll be proud, and delighted, to call home.

20 Long Hill Farm, Guilford

$685,000
5 Beds 2 Baths 24186474 MLS
A serene sanctuary, a historic experience. Newly restored, 50 Ledge Hill Road is a rare 1870 parsonage on a tranquil six and a half acres, yet conveniently located to Yale New Haven and the shoreline towns. Inside, the versatile layout offers five bedrooms, one-and-a-half baths (tastefully renovated), an enormous, exposed beam living room, generous family room, and mudroom. At the heart of the home, the sun-drenched eat-in kitchen invites everything from quiet morning coffees to festive gatherings. Step outside to dine in a charming stone wall courtyard, overlooking your sparkling (heated!) inground pool. The pool, flower beds, and trees have been professionally landscaped for privacy and delight. No modern comfort was spared, as HVAC was completely overhauled: new boiler, heat pump for central air and heat, and sustainable solar energy. Please see the attached list for the expansive upgrades completed by the current owners. Schedule your private tour today-50 Ledge Hill is the dream retreat that many are searching for.

50 Ledge Hill Rd, Guilford

$449,900
2 Beds 1 Baths 24185320 MLS
Ideally located between Guilford's shoreline and the Historic Green, this lovingly maintained expanded Ranch offers the ease of true one level living in one of the town's most desirable in town locations. Filled with warmth and character, the home features a spacious living room anchored by a gas fireplace with a stone surround and a huge vaulted sunroom with exposed beams that creates an inviting gathering space while overlooking the backyard and opening to a ground level deck. The flexible floor plan includes two bedrooms, a full bathroom, a den, and a private office, providing comfortable spaces for everyday living, guests, or working from home. Outside, the level yard is complemented by established gardens and offers plenty of room for outdoor enjoyment, along with a storage shed for added convenience. Recent improvements include a new roof with leaf guards, furnace, while practical amenities such as city water and an on demand whole house generator provide added comfort and peace of mind. Enjoy a highly walkable location just minutes from Guilford's historic town green with charming shops, and restaurants, walk to the marina, beach, and other beloved community amenities. A rare opportunity to enjoy a well cared for home with timeless appeal in the heart of Guilford.

32 Summer St, Guilford

$900,000
5 Beds 4 Baths 24185851 MLS
Positioned on a premier corner lot at the end of a quiet cul-de-sac with 3.19 private acres, this exceptional 5-bedroom, 3.5-bath Colonial is being reintroduced with a significant improvement package. A dramatic two-story foyer welcomes you into over 4,000 square feet of thoughtfully designed living space. Hardwood floors, abundant natural light, and a wood-burning fireplace anchor the main level. The vaulted kitchen features skylights, custom cabinetry, quartz countertops, stainless steel appliances, and a large center island perfect for entertaining. 2 bedrooms feature en-suite baths, including a luxurious primary suite with a spa-inspired marble bath and custom glass shower. Additional bedrooms are generously sized with ample closet space and natural light throughout. The finished lower level offers flexible space for recreation, fitness, media, or home office use, while the attached two-car garage provides convenience and storage. Minutes from Guilford Green, shoreline amenities, marinas, restaurants, and top-rated schools, this property has it all!

2 Greenwood Ln, Guilford

$825,000
4 Beds 3 Baths 24185800 MLS
Bluff Head Estates! Picture your perfect summer evening: pool lights glowing, a warm breeze, and friends laughing around a fire pit on a massive deck-welcome to 216 Bluff View Drive. Tucked away in Guilford's desirable North Guilford Neighborhood, this 4-bedroom, 2.5-bath open-concept Colonial delivers 3,410 square feet of pure comfort across two beautifully styled levels. The home boasts timeless Connecticut Shoreline curb appeal, situated on nearly an acre of manicured property. Step inside to find rich updated floors, two fireplaces, central air, and four bright skylights that keep the vibe light and airy. But the true showstopper is the backyard oasis. The sprawling multi-level deck wraps around an above-ground pool, built for epic daytime entertaining. When night falls, the atmosphere shifts completely as the lower lounge area comes alive with cozy string lighting and a sleek gas fire pit table. Rounded out by practical perks like a full basement, attached garage, and raised garden beds, this home is engineered for relaxation. Plus, you're just minutes from the historic Guilford Green, local coastal dining, the marina, Jacobs Beach and Lake Quonnipaug around the corner. Come experience places like Dudley Farm Market, Lakeside Feed, Bluff Head Trails, Nut Plains Farm, as well as our Guilford Green, shops, restaurants and so much more! This is Shoreline living built for how you actually want to spend your weekends. Professional pics will be coming on thursday.

216 Bluff View Dr, Guilford

$474,900
2 Beds 2 Baths 24185325 MLS
Set on a large, level lot at the end of a quiet cul-de-sac, this lovingly maintained one-owner ranch offers the ease of true one-level living in a peaceful and private setting. A welcoming double front door opens to a spacious, open floor plan designed for comfortable everyday living. The kitchen is enhanced by a skylight that fills the space with natural light, and flows seamlessly into the dining area and living rooms, where sliders flank a cozy wood stove and provide easy access to the deck overlooking the private yard. A conveniently located laundry room just off the kitchen adds to the home's practicality. Offering two bedrooms and two full bathrooms, the primary bedroom features three closets, direct access to a full bathroom, and its own access to the deck, creating a peaceful retreat. The second bedroom is generously sized and offers two closets. Additional highlights include a two-car garage, walk-out basement, central air, central vac, and an on-demand whole-house generator for added peace of mind. While some cosmetic updating may be desired, the home has been lovingly cared for over the years and offers a solid foundation for its next owner to personalize and make their own. Conveniently located just minutes from shopping, restaurants, commuter routes, and all the amenities that make Guilford so desirable, including its historic Town Green, picturesque shoreline, beaches, marinas, boutiques, & dining scene, this special property is ready to welcome its next owner.

704 Towner Swamp Rd, Guilford

$2,799,999
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

$450,000
3 Beds 2 Baths 24185256 MLS
Set in a serene Guilford location, this welcoming oneowner home has been cherished for over 50 years and offers comfort, space, and the beauty of natural surroundings. The main living areas feature an easy, functional flow ideal for gatherings, while large windows bring in soft light and views of the property. The kitchen, dining, and living spaces support both everyday routines and special occasions. Bedrooms are wellproportioned, offering privacy and versatility for guests, workfromhome, or hobbies. The property's setting provides room to explore, garden, or simply relax outdoors. After decades with the same owner, the home now needs some TLC, presenting an excellent opportunity for buyers looking to personalize and update a solid, wellloved property. Enjoy the best of shoreline living with convenient access to Guilford's historic green, shops, dining, and commuter connections. Being sold as is, where is.

1080 Hoop Pole Rd, Guilford

$700,000
3 Beds 2 Baths 24184012 MLS
Welcome to this unique home full of character, perfectly situated on a slight elevation in a private cul-de-sac. This exceptional property is bordered by protected conservation land, offering serene meadow and forest views alongside a very private yard filled with both mature and new plantings. A handsome granite and brick entry-walkway welcomes you inside to a 3-bedroom, 2-bathroom layout. This stunning home features a floor plan that allows for an easy flow and beautiful, natural light on both sides of the house, seamlessly combining historic charm and architectural details with newer, sunlit additions. Inside, you will find newly refinished hardwood floors, an impressive wood-burning fireplace, and an updated kitchen complete with quartz counters and brand-new appliances. Adding to the property's versatility is a 2-car garage featuring a heated work- or office- space above it, complete with its own separate meter-perfect for a quiet home office or studio. Location is everything, and this property puts the best of Guilford right at your fingertips. You are just 1.1 miles from the historic Guilford Green, 1.6 miles from the Guilford train station for an easy commute, and only 2.5 miles from the sandy shores of Jacobs Beach. Enjoy the perfect blend of private, peaceful living and unbeatable coastal convenience.

314 Three Mile Crse, Guilford

$800,000
4 Beds 3 Baths 24184271 MLS
Welcome to 425 Schoolside Lane, Guilford. A beautifully maintained 4-bedroom, 3-bathroom home nestled in a highly desirable neighborhood. Freshly painted throughout, this spacious residence offers the perfect blend of comfort, functionality, and outdoor living. Step inside to discover gleaming hardwood floors, granite countertops, and a warm, inviting fireplace that serves as the heart of the home. The thoughtfully designed layout includes a dedicated office space for remote work, a versatile bonus room ideal for a playroom, gym, or media room, and generous living areas perfect for everyday living and entertaining. Enjoy your morning coffee or evening gatherings in the screened-in porch overlooking the expansive, fully fenced backyard. Outdoor enthusiasts will love the above-ground swimming pool and the enormous yard, offering endless opportunities for recreation, gardening, and relaxation. Additional highlights include a spacious 2-car garage, ample storage, and a location that combines neighborhood charm with convenient access to Guilford's schools, shopping, dining, and shoreline attractions. Just around the corner from Guilford High School and mins from downtown Guilford Green, the train, and 95 make this home location perfect for any traveler. Don't miss the opportunity to make this move-in-ready home your own.

425 Schoolside Ln, 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

$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

$549,000
4 Beds 2 Baths 24181840 MLS
Multiple offers received, Sellers are requesting all offers be submitted by Tomorrow at 4pm (Sunday 7/26) Privately sited on 2.38 acres along a quiet cul-de-sac, this charming Cape offers a rare opportunity to embrace a secluded, nature-filled setting without sacrificing convenience. The property provides exceptional privacy and scenic natural surroundings, all just minutes from Guilford's vibrant town center, shoreline beaches, acclaimed restaurants, shops, and everyday amenities. Thoughtfully updated and meticulously maintained, the home welcomes you to a warm, inviting living room anchored by a fireplace, wood-burning stove and built ins. The updated eat-in kitchen features granite countertops, stainless steel appliances, and sliding doors that open to a spacious deck - an ideal setting for entertaining or simply savoring the tranquil surroundings. Recent improvements include a beautifully remodeled second-floor bathroom, newer appliances, and updated mechanicals, reflecting the care and attention invested throughout. The flexible floor plan offers two bedrooms and a full bath on the main level - perfect for guests or a home office. Upstairs, the generous primary suite is complemented by an additional well-proportioned bedroom and a stylishly updated full bath. Additional highlights include a spacious workshop-ready lower level, an attached two-car garage, whole-house generator hookup, and a large storage shed.

181 Wilderwood Dr, Guilford

$1,185,000
7 Beds 4 Baths 24182499 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

$1,185,000
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
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

$599,000
4 Beds 3 Baths 24173324 MLS
CLASSIC COLONIAL on CUL-DE-SAC! Location, Location, Location, AND 4 Bedrooms and 3 Full Baths! First time offered in 52 years! This home has been lovingly updated and maintained by the original owner. Updates include: new furnace (2025), new hot water heater (2025), new AC compressor ((2019), new patio (2021), new roof (2014). The family room features wide pine flooring, a raised-hearth fireplace, built-in bookshelves, and sliders to the inviting bluestone patio. The kitchen offers newer appliances, and there are wood floors throughout. This delightful home also offers central air conditioning, solid 6 panel doors, and a two-car garage. It is just a three minute drive to the historic and vibrant Guilford Town Green. There you will enjoy a host of wonderful restaurants and shops. As a Guilford resident, you will also have access to two beaches (Jacob's Beach and the beach at Lake Quonnipaug), several parks, and the amazing Westwoods Trails. Only 20 minutes to Yale, and Guilford is approximately halfway between NYC and Boston. Don't miss this opportunity.

29 Hungry Hill Cir, 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

$999,500
4 Beds 4 Baths 24179541 MLS
Rarely do you find such a gem as the new construction on Blue Hills Dr! Nestled in a tranquil neighborhood at the end of a cul-de-sac and surrounded by lush woods, this under construction home promises to be your dream home. No expense was spared in this perfectly done dream home. Handsome hardwood floors and recessed lighting run through this entire home, enhancing all of the other features that are thoughtfully built in. The main level features the family room, study, kitchen, dinette, dining room and guest bath. Prepare to feast your eyes on the kitchen, with striking quartz countertops, high end stainless steel appliances, tiled back splash, modern lighting and so much more! The family room features a grand fireplace to host your guests or cozy up to, which flows right out to the deck for those summer barbecues or right into the living room for all of your entertainment needs! Each bathroom leaves nothing to want for. Premium fixtures are decked thought out the home to add a luxurious feel to this palace. The upstairs hosts 4 bedrooms total, 3 full bath, a ample primary bedroom with primary bathroom and a laundry closet. The basement has walk-out access to easily accommodate a in-law apartment or finished basement! The home comes with a 1 year warranty. The grass will be seeded in the spring, pending weather. This house is under construction....purchase it now to customize it's features!!

147 Blue Hills Dr, Guilford

$489,000
2 Beds 1 Baths 24178566 MLS
Don't miss this adorable one-level home, thoughtfully updated to offer the perfect blend of charm, comfort, and flexibility. Nestled on a scenic country road, the property sits on 1.7 acres with ample room for future expansion if desired. Ideal for first-time buyers, down-sizers, or anyone seeking peaceful country living. Bright and airy throughout, the home features an open floor plan with vaulted ceilings in the living room and hardwood floors throughout most of the home. The updated kitchen is equipped with quartz countertops, stainless steel appliances, modern lighting, and a convenient breakfast bar. There is space for a small breakfast nook in the kitchen, while the expansive living room can easily accommodate a larger dining area or dining room table. Flexible layout options allow for either two bedrooms or a bedroom plus home office setup. A recently remodeled bathroom, generous bedroom closet space, central A/C, ceiling fans, shed, and even the option to relocate the washer and dryer hookups upstairs all add to this home's versatility, comfort, and convenience. A standout feature is the stunning screened-in porch with beautifully refinished wood floor - a perfect place to curl up and relax in a private outdoor setting or host gatherings with family and friends. A home at this price point with so much to offer and even more potential won't last long in Guilford. Schedule your showing today! A full list of updates is attached.

1511 Little Meadow Rd, Guilford

$929,000
3 Beds 3 Baths 24177868 MLS
Welcome to Jans Way - Where Luxury Meets Lifestyle in the Heart of North Guilford this breathtaking brand-new Colonial is the new construction opportunity you've been waiting for, offering an impressive 2,734 square feet of beautifully designed living space plus an additional 900 square feet of fully finished walk-out basement, totaling an extraordinary 3,634 square feet of move-in ready perfection. Tucked within the intimate, private Mountain View subdivision, an enclave of just seven distinguished residences, this stunning home masterfully blends privacy, luxury, and modern comfort in one of North Guilford's most sought-after settings. The sun-filled, open-concept main level is designed to impress, showcasing a gourmet kitchen and expansive great room that flow effortlessly together, ideal for entertaining and everyday living alike. A dedicated home office delivers the ultimate work-from-home retreat, while a chic powder room completes the first floor. Upstairs, your stunning primary suite awaits - a true sanctuary boasting a generous walk-in closet and spa-inspired en-suite bath featuring a deep soaking tub and oversized walk-in shower. Two additional well-appointed bedrooms, a full bath, and the incredibly convenient second-floor laundry round out the upper level, spacious additional room awaits your personal vision. The bright finished walk-out basement expands your living possibilities. Oversized two-car garage. Perfectly situated in the vibrant town of Guilford .

4 Jans Way, 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

$749,000
3 Beds 3 Baths 24177706 MLS
Welcome to this inviting 3-bedroom, 2.5-bath home on one of the most scenic roads in Guilford. The spacious primary suite is a true highlight of this home -- a retreat featuring a fireplace, private office or sitting area, en-suite bath, expansive closet space, and newly installed hardwood floors. Hardwood and tile flooring flow throughout much of the home, filled with abundant natural light. The kitchen offers granite countertops, stainless steel appliances, and ample cabinetry, flowing seamlessly into the living room with a cozy second fireplace. Additional features include central air, vinyl siding, a 2-car garage, screened porch, deck, and a private level yard with mature garden beds ready for summer harvest. As a bonus, this home even has an outdoor shower, perfect for a rinse after a day of yard-work. Situated just a short distance from Guilford's beloved "Little Augusta" golf course and Guilford Lakes Elementary School, this home offers the perfect opportunity to enjoy comfort, convenience, and access to some of the very best amenities Guilford has to offer. *Highest/Best due 6/8 by 5PM. No Escalation Clauses, please.

941 Nut Plains Rd, Guilford

$1,200,000
5 Beds 6 Baths 24153131 MLS
43 Chestnut Grove.. offering approx. 6,700 sq ft with a prime location on a cul-de-sac street w/ 1.78 acres features a beautiful 2-story covered front entry featuring an arched opening, columns & woodwork/moldings throughout along with beautiful inlaid hardwood floors. At the heart of the home, the expansive great room features a gas fireplace & an impressive entertainment space complete with a wet bar. This area is open to the 2nd-floor balcony, creating a bright & airy atmosphere. Just off the great room is a sun-filled bonus room surrounded by windows with direct access to the backyard. The main entertaining space flows effortlessly into the dining area & open-concept kitchen. The kitchen is equipped with high-end appliances, including Viking/Thermador, along with custom cabinetry, granite countertops, a walk-in pantry & a large center island with seating. Completing the main level, the home wraps back toward the front, where French doors lead to a dedicated home office, and also your sitting room and or formal dining room or formal living room. The 2nd floor offers a spacious laundry room with cabinetry & sink. The primary suite features cathedral ceilings, a walk-in closet & en-suite bath with dual sinks, a soaking tub & walk-in shower. Another bedroom includes its own en-suite bath & walk-in closet, with hallway access. 2 more bedrooms share a Jack-and-Jill bathroom, while a 2nd primary suite offers yet another en-suite bath with dual sinks & a walk-in closet. A walk-up

43 Chestnut Grv, Guilford

$1,299,900
4 Beds 5 Baths 24165243 MLS
Perfectly sited on 2.75 private acres overlooking a sweeping lawn, this distinguished Georgian Revival estate makes an unforgettable first impression, approached by a circular driveway that creates a true sense of arrival. Recently refreshed with newly painted interiors and enhanced landscaping, the property presents beautifully from the moment you enter. Once a Connecticut Designer Showhouse, the home blends timeless elegance with remarkable comfort and sophistication. A grand foyer with a dramatic staircase introduces more than 5,200 square feet of thoughtfully designed living space, where 10 foot ceilings, generously scaled rooms, and five fireplaces create warmth and sophistication throughout. At the heart of the home is a renovated kitchen thoughtfully designed with today's most desired amenities, featuring a large center island and butler's pantry that seamlessly blend style and functionality for effortless entertaining. Distinctive architectural details and one of a kind features add character throughout, including the remarkable office fireplace mantel reclaimed from a Newport mansion. The spacious bedroom level offers comfort, privacy, and flexibility, including a luxurious primary suite with a renovated ensuite bath and separate dressing room. Conveniently located minutes from the Guilford Green, boutique shopping, and renowned restaurants, this is a truly special offering that seamlessly combines timeless design, character, and an exceptional setting.

625 State St, Guilford

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