$729,464Average Value$375Average Price per Sq Ft43Homes For Sale
Serene residential area in Guilford with various homes nestled among lush greenery.
A place with something for everyone
Guilford is a coastal Connecticut town that, at first glance, resembles a small town reminiscent of a 1960s-era television show. With its quaint and historic downtown sector lined with quaint local retailers, the 12-acre Guilford Town Green that is the site of various performances throughout the year and the quiet, tree-lined streets, Guilford provides an almost country feeling, like something out of a brochure for a New England bed-and-breakfast. But look a little closer and it’s also a vibrant, cosmopolitan town with a bevy of amenities, superb schools and beautiful homes, not to mention the fact that Guilford abuts Long Island Sound on its southern border, affording residents easy access to the beach and the ocean beyond. “People come here because they want waterfront and seclusion,” says local Realtor Karen Stephens of Compass, who has been representing transactions in the area for more than 20 years. “And the properties are quite amazing.” It’s that combination of qualities that leads Guilford First Selectman Matthew Hoey to describe Guilford as “a place with something for everyone.”
Out and about in Guilford
Because of its proximity to Long Island Sound, Guilford is a haven for lovers of the sea. Mariners can keep their vessels at the Guilford Marina, and members of the Guilford Yacht Club can access both slips and moorings, as well as the club’s tennis, dining and other social facilities. Jacob’s Beach is a 25-acre coastline retreat on the Sound, where kids can play on the playground and visitors of all ages can enjoy the open, sandy beach and grassy space perfect for sunbathing or a picnic. Further inland is Lake Quonnipaug, a prime spot for catching a variety of freshwater species, and also a perfect spot for swimming or relaxing on the lakeside beach. Hikers head to Timberland Preserve, a 600-acre expanse with more than 15 miles of trails, and golfers can tee off at the nine-hole Guilford Lakes Golf Course.
The centrally located Guilford Town Green is a favorite community gathering spot, serving as the site of a summer concert series, the town’s annual Halloween and holiday tree-lighting festivals, the GreenStage Guilford Live music festival and a variety of other programs throughout the year. “People come from all around for these events,” says Stephens. And don’t be too surprised if exotic animals suddenly appear on the Green, as a local anonymous artist periodically places two-dimensional (although quite lifelike) replicas of polar bears, penguins and other Arctic-dwelling animals on the Green to celebrate the season’s first snowfall. After residents have had a chance to see the art installation, the animals are auctioned off to benefit Meals and Wheels.
Serene beachside park located at Jacob's Beach in Guilford overlooking a tranquil sandy beach.
Bittner Park in Guilford features calm areas to host picnics with the family.
Serene landscape of Guilford showcasing a tranquil marsh with golden tall grass.
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Top-rated schools
The Guilford Public Schools district earns an overall grade of A from Niche, and the area’s exceptional schools include A. W. Cox Elementary, Adams Middle and Guilford High School, all of which earn an A from Niche. Students at Guilford High School have the opportunity to participate with more than 35 school-sponsored clubs, can audition for the school’s award-winning theater program and have the opportunity to play more than 15 varsity-level sports. There are also several renowned private schools in the area, including nearby Choate Rosemary Hall, ranked as the best private school in the state by Niche, which gives it an A-plus rating.
Guilford Lakes School is conveniently located on Maupas Road.
Students are proud to call Guilford High School their place for learning.
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From 18th century colonials to modern homes
Guilford has the distinction of being home to one of the largest collections of historic homes in New England, including the 1693 Henry Whitfield House, that today serves as a museum. The Whitfield House is the oldest house in Connecticut and the oldest stone dwelling built by North American settlers. And while buyers will find homes here for sale that were built as far back as the 18th century, there are plenty of options for those who prefer new construction, too. The median price in the area is $590,000, and buyers should expect to pay an average of $341 per square foot. A two-bedroom/two-bathroom ranch-style home in need of some TLC can sell for as low as $200,000, and prices can go up to nearly $6 million for a four-bedroom/three-bathroom colonial on a private waterfront peninsula with a private beach.
Picturesque Colonial style home in Guilford with a vibrant blue door and a cozy porch.
Two story home in Guilford with a neat driveway and a calm street in the foreground.
Modern home in Guilford with a manicured lawn and a calm ambiance in the background.
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Plentiful options for shopping and dining
With Big Y located in the center of town, residents don’t have to drive far for grocery shopping trips, and Bishop’s Orchards offers the opportunity for visitors to pick their own fruit in-season, typically from June through October. Walmart is located next to Big Y for any home necessities. Downtown Guilford has an array of local boutiques and shopping opportunities, and the Connecticut Post Mall – the largest mall in the state – is located in Milford, just over 20 miles away.
When dining out, Guilford Mooring is a popular destination for fresh seafood served in a waterfront setting. For a little more upscale occasion, Chapter One is well-known for exceptional service and a wide-ranging menu featuring burgers, steaks and seafood, as well as vegetarian and vegan options. And for a little grab-and-go, Cinco de Mayo Food Truck located at the north end of Guilford Town Green prepares well-known Mexican favorites for a relaxing lunch in the park.
Residents of Guilford enjoy strolling on vibrant streets featuring quaint local businesses.
Lobster Pound in Guilford is known for their incredible Hot Lobster Roll.
Charming town of Guilford as pedestrians stroll past boutique storefronts.
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Getting out of town
Commuters here have easy access to Interstate 95, which bisects the middle of Guilford, make the 16-mile trip to New Haven. Alternatively, the CTrail Shore Line East train leaves from the Guilford Station, with service to New Haven taking about 20 minutes, where riders can connect to trains going south to New York City or north to Boston.
Guilford Train Station offers residents direct access to neighboring towns and cities.
Guilford Train Station provides easy commuting for residents into New Haven.
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Photography Contributed By
Fabio Riso
Video By
Matthew Bloch
Interested in learning more about homes in this area?
Reach out to
Cathy Lynch,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Guilford, CT sell after 69 days on the market compared to the national average of 56 days. The median sale price for homes in Guilford, CT over the last 12 months is $630,375, up 8% from the median home sale price over the previous 12 months.
Own your own little oasis! Set back in the woods of guilford on 3.5 acres you have a ton of privacy with this impressive home. As you walk in, you are greeted by a spacious living room which features a new addition making this large room great for entertaining. Throughout the dining room and kitchen you see flawless finishes adding to the newly renovated kitchen with a propane gas cook top and
The Residences at 66 High Street provide a unique offering. An enclave of luxury condominiums. A private, peaceful setting overlooking the salt marsh and Long Island Sound, yet just a few blocks from the picturesque Guilford Green, the town center, and all the activity it has to offer. This immaculate first floor single level unit is in the Chittenden Building, finished in 2023. Light streams in.
Tucked away at the end of private Cedar Grove Road in the serene enclave of Tuttle's Point, this charming cedar shake classic cottage offers the kind of lifestyle most people only dream about. Perched high above the floodplain on a lush 1/3-acre lot, 59 Cedar Grove Road enjoys spectacular, million-dollar views of Long Island Sound, surrounded by mature perennial plantings in a secret garden
Own your own little oasis! Set back in the woods of guilford on 3.5 acres you have a ton of privacy with this impressive home. As you walk in, you are greeted by a spacious living room which features a new addition making this large room great for entertaining. Throughout the dining room and kitchen you see flawless finishes adding to the newly renovated kitchen with a propane gas cook top and
Charming, Meticulously Maintained Ranch on a Prime Corner Lot! Welcome to 1944 Moose Hill Road in Guilford, Connecticut-a gorgeous 1958 ranch that perfectly blends timeless character with modern updates. Nestled on a desirable corner lot, this move-in-ready home has been lovingly maintained and thoughtfully enhanced throughout. Step inside to discover beautiful oak hardwood floors that flow
First time offered in over 50 years, this ranch-style home sits on a half-acre in the heart of Indian Cove-one of Guilford's most cherished shoreline communities. With seasonal views of Long Island Sound and access to a private neighborhood beach, this property offers a rare connection to the coast and community. Originally the site of the historic Cove Store, this home carries a unique place in
The Residences at 66 High Street provide a unique offering. An enclave of luxury condominiums. A private, peaceful setting overlooking the salt marsh and Long Island Sound, yet just a few blocks from the picturesque Guilford Green, the town center, and all the activity it has to offer. This immaculate first floor single level unit is in the Chittenden Building, finished in 2023. Light streams in.
Tucked away at the end of private Cedar Grove Road in the serene enclave of Tuttle's Point, this charming cedar shake classic cottage offers the kind of lifestyle most people only dream about. Perched high above the floodplain on a lush 1/3-acre lot, 59 Cedar Grove Road enjoys spectacular, million-dollar views of Long Island Sound, surrounded by mature perennial plantings in a secret garden
Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout.
Opportunity to enjoy privacy and space in one of Guilford's convenient locations. Tucked away on a private cul-de-sac just minutes from the historic Guilford Green, this 4 bedroom, 4 full bath Colonial perched on a lightly wooded 2.16-acre lot with serene views, this home features light-filled interior spaces, a flowing floor plan with hardwood floors, crown molding, and recessed lighting
A spacious home offering 2,336 square feet of living space set on 1.3 acres. The main level features a comfortable flow between the living room, dining room, and kitchen, with a fireplace adding a central focal point. Hardwood flooring is present throughout much of the home, and a first-floor bedroom provides flexible use of space. The upper level includes the primary bedroom with a walk-in
Welcome to The Landing at Guilford, a luxury townhome community offering modern design, quality construction, and low-maintenance living in one of the shoreline's most desirable locations. This well-appointed 2-bedroom residence with flexible space for a potential third bedroom features an open-concept layout with a beautifully designed kitchen complete with Viking stainless steel appliances,
Set in the desirable North Guilford area, this expansive parcel offers a rare opportunity to create a private retreat surrounded by natural beauty. With a thoughtfully configured layout and generous frontage along Long Hill Road, the property provides both usability and a sense of seclusion. The land features a blend of open and wooded areas, allowing flexibility for a custom home, outdoor living
Experience the ultimate boating lifestyle at the prestigious Guilford Yacht Club with this prime 34-foot boat slip. Nestled along the scenic River, this slip offers a front-row seat to breathtaking sunsets and immediate access to Long Island Sound. Within five minutes of leaving the channel, you'll be on your way to premier destinations like the Thimble Islands, Sag Harbor, Three Mile or Block
Just minutes to downtown Guilford, this striking 4 bedroom contemporary offers exceptional living space & bold architectural design. A dramatic floating staircase & soaring ceilings create an unforgettable first impression the moment you enter. The expansive great room is the heart of the home, featuring a stunning floor to ceiling fireplace, walls of glass that fill the space with natural light,
Property Id: 2312572Experience impeccable craftsmanship in our elegant village of luxury apartments bordering a land preserve. The moment you enter this whimsical retreat, you'll feel an immediate sense of calm, connection, and security. Blending country soul with a contemporary edge.Beautiful views abound in our one bedroom apartment that features a beautiful spacious bedroom,
Ideally located in the heart of downtown Guilford, 26 Water Street is now officially available. This single family home currently has two floors that are identical but the second floor is will not be allowed for use so what's being rented is the first floor and the second floor will be closed off. The first floor features a renovated kitchen, open-concept living and dining area, two bedrooms, and
Clean, sunny, spacious, kitchen, dining, living, bedroom, fireplace, unfurnished or lightly furnished. Ample storage, heat included, tile flooring, off street parking, convenient location south of route 1, scenic #146, 5 minutes to beaches, marinas, grocery, banks, pharmacy, shopping, restaurants, town green where many activities occur. **Short term lease could be considered.
Available July 1st. Beautifully reimagined Classic Colonial, ideally situated just moments from the iconic Guilford Green-the vibrant centerpiece of town life, known for its seasonal festivals, farmers markets, concerts, and community events. Enjoy being within close proximity to some of Guilford's favorite restaurants, charming shops, shoreline beaches, and the nearby train station for easy
A Fresh, Fully Furnished One Year Rental Home Close to Town & Shoreline. Starting June 1st, enjoy a full year in this beautifully furnished split-level home on Guilford's sought after west side. 51 West Lake Avenue places you close to everything - the charm of the historic Village Green, the sand and sunsets of Jacobs Beach, and the boats and scenic views of the Town Marina. Inside, the main
MONTH OF AUGUST 2026 - Fully furnished beach home set up above Mulberry Point Road with AMAZING VIEWS OF LONG ISLAND SOUND, just steps from DANIEL AVENUE BEACH. 1st floor master bedroom (Queen bed) with attached bath (Includes a super deep soaking tub and a separate shower) Open floor plan with a wall of sliding glass doors out to the decks overlooking Long Island Sound- gorgeous views from every
ACADEMIC YEARLY RENTAL! Sachem's Head Association waterfront property. This is a well-designed, well-appointed, pristine history rich home. Facing Long Island Sound and backed by the tranquil South Bay, every corner of this home offers unmatched water views. Strategically situated to immerse you in the breathtaking beauty that surrounds it. The home has been updated to seamlessly provide all of
ACADEMIC RENTAL. DIRECT WATERFRONT home in beautiful Sachem Head/Vineyard Point community. Enjoy gorgeous views, a private sandy beach out your backdoor and access to tennis court right next door. Walls of glass with views of Long Island Sound from every room. An open floor plan includes a large living room with stone fireplace and dining room. A family room is also on the main floor equipped
AVAILABLE JUNE, JULY & AUGUST. DIRECT WATERFRONT home in beautiful Sachem Head/Vineyard Point community. Enjoy gorgeous views, a private sandy beach out your backdoor and access to tennis court right next door. Walls of glass with views of Long Island Sound from every room. An open floor plan includes a large living room with stone fireplace and dining room. A family room is also on the main
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
Recently converted from one family to two family. New kitchen, appliances, paint, and flooring. Includes a stack washer/ dryer. Walk to Town! Includes heat and water! Two bedroom. Second floor.
Live in the heart of downtown Guilford! This spacious 3-bedroom, 1-bath apartment sits directly across from the iconic Guilford Green, offering unbeatable walkability to shops, restaurants, cafes, and town amenities. The unit features updated finishes, central air, and the convenience of in-unit washer and dryer. Enjoy private off-street parking and low-maintenance living with cold water, sewer,
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