27

Guilford, CT Houses for Sale

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  • /34

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,459 Sq Ft

    4 Copper Ridge Cir, Guilford, CT 06437

    Nestled on a quiet cul-de-sac in the sought-after Copper Hill Village, this detached Cape-style condo offers the privacy of a single-family home with the effortless lifestyle of a managed community. Boasting 1,459 square feet of bright, airy living space, this 2-bedroom, 2-bathroom residence is designed for comfort and versatility.The heart of the home features a living area with a cozy

    Agent Photo

    Rob McConville

    RE/MAX Heritage

    (203) 941-7511

    4 Copper Ridge Cir, Guilford, CT 06437
  • /40

    $699,000

    • 4 Beds
    • 2 Baths
    • 2,336 Sq Ft

    9 Sparrow Bush Ln, Guilford, CT 06437

    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

    Jeremy Oliver William Raveis Real Estate

    9 Sparrow Bush Ln, Guilford, CT 06437
  • /39

    $899,900

    • 3 Beds
    • 2.5 Baths
    • 2,806 Sq Ft

    401 Three Corners Rd, Guilford, CT 06437

    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,

    Alicia Mahon William Pitt Sotheby's Int'l

    401 Three Corners Rd, Guilford, CT 06437
  • /40

    $960,000

    • 3 Beds
    • 3 Baths
    • 2,180 Sq Ft

    95 Fair St, Guilford, CT 06437

    Enjoy in-town living! This charming home is just a block and a half from the Guilford green and all the town center has to offer - including shopping, dining, library. Located in the historic district on Fair Street - one of Guilford's treasured neighborhoods of architecturally diverse antique homes. Wide board floors, custom wooden shutters. Large fireplace with stone hearth provides a family

    Laurie Trulock Compass Connecticut, LLC

    95 Fair St, Guilford, CT 06437
  • /40

    $915,000

    • 4 Beds
    • 2.5 Baths
    • 4,332 Sq Ft

    322 Willow Rd, Guilford, CT 06437

    *Multiple Offers Received***Highest and Best by 6pm April 13* Set in a picturesque neighborhood in the charming coastal town of Guilford, this classic Colonial offers over 3,300 square feet of comfortable, well-designed living space. With 4 bedrooms and 2.5 baths, the layout balances everyday functionality with effortless entertaining. A welcoming foyer opens to a spacious living room with

    Linda Toscano Coldwell Banker Realty

    322 Willow Rd, Guilford, CT 06437
  • /40

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 3,939 Sq Ft

    1800 Moose Hill Rd, Guilford, CT 06437

    Where gardens flourish and privacy surrounds you, this Moose Hill retreat offers a lifestyle rooted in beauty, nature, and quiet sophistication. Light-filled interior features oversized and bow windows, Hardie cement siding, and Marvin windows throughout. Extraordinary gardens showcase three-season blooms, perennial herbs, berry plantings, fruit trees, irrigation, and a fenced vegetable garden

    Mary Pont William Pitt Sotheby's Int'l

    1800 Moose Hill Rd, Guilford, CT 06437
  • /40

    $629,000

    • 4 Beds
    • 2 Baths
    • 2,236 Sq Ft

    148 Highwoods Dr, Guilford, CT 06437

    Welcome to 148 Highwoods Drive in Guilford-a beautifully maintained 4-bedroom, 2-bath home set on over 1.29 acres of meticulously manicured grounds. This property offers the perfect blend of comfort, space, and outdoor living. Step inside to an open-concept main level featuring hardwood floors throughout and a stunning living room with vaulted ceilings, a stunning floor to ceiling brick

    Gigi Giordano Taylor Compass Connecticut, LLC

    148 Highwoods Dr, Guilford, CT 06437
  • /40

    $1,995,000

    • 5 Beds
    • 9 Baths
    • 5,414 Sq Ft

    173 Highwoods Dr, Guilford, CT 06437

    A MAGNIFICENT REVIVAL & TIMELESS BLEND OF SOMETHING OLD & SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled & moved to its current site in 1955, the property is nestled within nearly 4 acres of mature trees, manicured lawns, & magical gardens. This classic revival will be celebrated by the most discerning antique

    Kiara Rusconi William Raveis Real Estate

    173 Highwoods Dr, Guilford, CT 06437
  • /32

    $715,000

    • 3 Beds
    • 1.5 Baths
    • 1,672 Sq Ft

    294 Church St, Guilford, CT 06437

    Mixed-use zoning (convertible to full commercial or multi unit with town permits) 2,005 sq ft total / 1,672 sq ft finished living space..30 acre lot with generous parking (10+ vehicles) Year built: 1893 with numerous modern updates. Rare to find a house in Guilford with "public water". Current layout: First Floor: Professional medical office space, 4 office space + half bath. Second Floor:

    Jason Saphire www.HomeZu.com

    294 Church St, Guilford, CT 06437
  • /40

    $5,950,000

    • 6 Beds
    • 5.5 Baths
    • 6,603 Sq Ft

    39 Vineyard Place, Guilford, CT 06437

    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

    Ana Russo William Pitt Sotheby's Int'l

    39 Vineyard Place, Guilford, CT 06437
  • /39

    $959,000

    • 2 Beds
    • 2 Baths
    • 3,140 Sq Ft

    575 Leetes Island Rd, Guilford, CT 06437

    Enjoy living in one of CT's most coveted historical treasures, the Pelatiah Leete House! Perched on a private, sweeping knoll with WATERVIEWS of Shell Beach Lagoon running into Long Island Sound, (located across the road) this Colonial Home is as close as one gets to genuine American History. Only 5 families have inhabited this 1710 English Post & Beam home that has survived Colonial Times & a

    Mary Jo McAvey William Raveis Real Estate

    575 Leetes Island Rd, Guilford, CT 06437
  • /40

    $1,295,000

    • 4 Beds
    • 5 Baths
    • 5,875 Sq Ft

    65 Ironwood Rd, Guilford, CT 06437

    Custom-Built Mediterranean Estate | Privately sited on 1.84 acres in the highly sought-after Woodlands subdivision, this stunning Country French-inspired residence combines timeless craftsmanship with architectural elegance. A grand two-story foyer with marble flooring and a sweeping spiral staircase sets the tone for the sophisticated interiors. Lovely millwork and custom built-ins are showcased

    Rose Ciardiello William Raveis Real Estate

    65 Ironwood Rd, Guilford, CT 06437
  • /32

    $1,595,000

    • 4 Beds
    • 4 Baths
    • 2,966 Sq Ft

    147 Boston St, Guilford, CT 06437

    Discover the vibrant energy of the historic town green just outside your doorstep. The inviting sidewalk guides you to the lively center, only 600 yards away. There, you'll find a treasure trove of quaint shops, restaurants, the recreational center, and cozy coffee spots to enjoy. Join in the community spirit at concerts and local events, and explore the area's rich history and character-all

    Vicky Welch William Raveis Real Estate

    147 Boston St, Guilford, CT 06437
  • /40

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft

    26 Water St, Guilford, CT 06437

    Ideally located in the heart of downtown Guilford, 26 Water Street is now officially available. Situated within the Guilford Green District, this property offers exceptional versatility with a wide range of permitted uses (see attached zoning regulations, Section 4.1). The existing use may continue as a non-conforming use if desired. The current layout is configured similarly to a multi-family

    Lauren Freedman Coldwell Banker Realty

    26 Water St, Guilford, CT 06437
  • /40

    $779,000

    • 4 Beds
    • 2 Baths
    • 2,174 Sq Ft

    402 Boston St, Guilford, CT 06437

    Antique charming house, modern quality updates with preserved antique charm and character, beautiful details, quality, character, and lovingly well-maintained. Stainless steel appliances, tiled bathrooms, bookcases galore, FENCED YARD. Upgrades include ducted central air, 4 heat zones, newer landscaping; many rooms with beautiful antique oak flooring; newer windows, roof, garage doors; vaulted

    Gloria Gibney Gibney Real Estate

    402 Boston St, Guilford, CT 06437
  • /40

    $2,595,000

    • 4 Beds
    • 4.5 Baths
    • 4,336 Sq Ft

    63 Broad St, Guilford, CT 06437

    Perfectly positioned just moments from Guilford's iconic Green, this exceptional Greek Revival residence offers a refined blend of timeless architecture and modern living. Set along historic Broad Street, the home is within easy reach of charming shops, dining, the beach, train station, and local marinas. Built in 2002, the residence showcases period-inspired design with a light-filled, open

    Michelle Wininger William Pitt Sotheby's Int'l

    63 Broad St, Guilford, CT 06437
  • /12

    $1,195,000

    • 4 Beds
    • 4 Baths
    • 2,392 Sq Ft

    51 Pearl St, Guilford, CT 06437

    Rare opportunity in Guilford! This home is currently used as a multifamily but can revert to a one family residence. Approximately 2400 sqft with the possibility of future expansion. Conveniently located close to Guilford's Historic Green, shops, restaurants, beaches and shoreline attractions.

    Philip Warner William Pitt Sotheby's Int'l

    51 Pearl St, Guilford, CT 06437
  • /39

    $945,000

    • 6 Beds
    • 4 Baths
    • 2,783 Sq Ft

    82 State St, Guilford, CT 06437

    Rare opportunity to own an in-town retreat just steps from the historic Guilford Green. This unique and well maintained two-family home offers a combination of flexibility, charm, and outdoor space that is nearly impossible to find this close to town. Whether you're seeking multi-generational living, rental income, or a lifestyle property with room to spread out, this home delivers exceptional

    Claudia Bartlett William Raveis Real Estate

    82 State St, Guilford, CT 06437
  • /40

    $5,000,000

    • 4 Beds
    • 3.5 Baths
    • 5,640 Sq Ft

    51 Andrews Rd, Guilford, CT 06437

    Exceptional Contemporary Direct Waterfront Estate. Located in Guilford, CT, on a private cove of Little Harbor, this stunning home has a private Beach, pier / dock and pool. Built in 1969 and designed by renowned architect Judith Chafee, the thoughtfully designed open-concept floor plan maximizes water views from almost every room and boundless natural light throughout. The Living Room, with

    Kirsten Adams William Pitt Sotheby's Int'l

    51 Andrews Rd, Guilford, CT 06437
  • /40

    $35,000,000

    • 6 Beds
    • 4.5 Baths
    • 5,354 Sq Ft

    215 Uncas Point Rd, Guilford, CT 06437

    Waterfront.. Sachems Head - Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House.

    Joseph Piscitelli Coldwell Banker Realty

    215 Uncas Point Rd, Guilford, CT 06437
  • /26

    $1,099,750 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    147 Blue Hills Dr, Guilford, CT 06437

    Rarely do you find such a gem as the upcoming 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

    Joseph Gregory Toledo Realty

    147 Blue Hills Dr, Guilford, CT 06437
  • /40

    $999,999 New Construction

    • 3 Beds
    • 2.5 Baths
    • 3,600 Sq Ft

    4 Jans Way, Guilford, CT 06437

    Welcome to this stunning new construction Colonial located in the heart of North Guilford, offering 2,800(Additional 900 Square feet of finished basement) square feet of living space on a private 1.9 acre lot. Situated in the sought-after Mountain View subdivision on Jans Way, this home is one of only seven exclusive parcels, providing a rare combination of privacy, space, and modern design. The

    Matthew Murchison Berkshire Hathaway NE Prop.

    4 Jans Way, Guilford, CT 06437
  • /38

    $2,595,000 New Construction

    • 4 Beds
    • 5.5 Baths
    • 4,700 Sq Ft

    23 Sheep Pasture Rd, Madison, CT 06443

    Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors, 9-foot ceilings, custom millwork, and oversized Pella windows throughout. A stunning bluestone entry leads to an elegant

    Steve Wollman Wollman Realty

    23 Sheep Pasture Rd, Madison, CT 06443
  • /40

    $790,000 Coming Soon

    • 4 Beds
    • 4 Baths
    • 3,498 Sq Ft

    11 Covey Crossing, Guilford, CT 06437

    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

    Rose Ciardiello William Raveis Real Estate

    11 Covey Crossing, Guilford, CT 06437
  • /2

    $1,000,000 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,409 Sq Ft

    59 Cedar Grove Rd, Guilford, CT 06437

    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

    Jeanne Kempton Century 21 AllPoints Realty

    59 Cedar Grove Rd, Guilford, CT 06437
  • /2

    $549,000 Coming Soon

    • 4 Beds
    • 1.5 Baths
    • 1,988 Sq Ft

    599 Durham Rd, Guilford, CT 06437

    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.

    Jane Cardarelli William Raveis Real Estate

    599 Durham Rd, Guilford, CT 06437
  • /40

    $2,650,000

    • 4 Beds
    • 4.5 Baths
    • 6,194 Sq Ft

    24 Indigo Trail, Madison, CT 06443

    Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the

    Mark McElrath William Pitt Sotheby's Int'l

    24 Indigo Trail, Madison, CT 06443

Why Live in Guilford

Guilford, Connecticut, is a coastal town that combines the charm of a historic New England village with the amenities of a modern community. Its downtown area features quaint local retailers and the 12-acre Guilford Town Green, which hosts various performances and events throughout the year. The town's proximity to Long Island Sound provides residents with easy access to waterfront activities, including the Guilford Marina and Jacob’s Beach. Inland attractions include Lake Quonnipaug for freshwater fishing and swimming, Timberland Preserve with over 15 miles of hiking trails, and the nine-hole Guilford Lakes Golf Course. The Guilford Town Green is a central gathering spot for community events such as summer concerts, holiday festivals, and the GreenStage Guilford Live music festival. Guilford Public Schools district is highly rated, with A. W. Cox Elementary, Adams Middle, and Guilford High School all earning top marks. Nearby Choate Rosemary Hall is also recognized as the best private school in the state. Housing options range from 18th-century colonials to modern constructions, with Guilford boasting one of the largest collections of historic homes in New England. Shopping and dining are convenient, with Big Y and Walmart centrally located, and Bishop’s Orchards offering seasonal fruit picking. Dining options include Guilford Mooring for seafood, Chapter One for upscale dining, and Cinco de Mayo Food Truck for casual Mexican fare. Commuters have easy access to Interstate 95 and the CTrail Shore Line East train, making the 16-mile trip to New Haven or connecting to trains for New York City and Boston.

Home Trends in Guilford, CT

Housing Trends

Median Sale Price
$632,000
Median Single Family Sale Price
$649,950
Median Townhouse Sale Price
$910,000
Median 2 Bedroom Sale Price
$975,000
Average Price Per Sq Ft
$370
Number of Homes for Sale
43
Last 12 months Home Sales
305
Months of Supply
1.70
Median List Price
$649,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
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