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Guilford, CT Houses for Sale

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  • /40

    $1,149,900

    • 4 Beds
    • 5 Baths
    • 3,220 Sq Ft

    1607 Great Hill Rd, Guilford, CT 06437

    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

    Agent Photo

    Alex Rodrigues

    RE/MAX RISE

    (475) 244-8651

    1607 Great Hill Rd, Guilford, CT 06437
  • /32

    $1,399,000

    • 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

    $1,000,000

    • 4 Beds
    • 3.5 Baths
    • 3,402 Sq Ft

    48 State St, Guilford, CT 06437

    The Nathaniel Hall House (c. 1770) offers the perfect canvas for restoration to a prestigious single-family residence while also offering multi-generational potential. Situated ONLY 6 HOUSES from the quintessential Guilford Green and rich in architectural evolution, the main home started in the late colonial era with a significant 1810 addition introducing the elegant Federal-style details that

    Lisa Rollins Team Compass Connecticut, LLC

    48 State St, Guilford, CT 06437
  • /40

    $1,395,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,877 Sq Ft

    4 Benton's Knoll Unit 2, Guilford, CT 06437

    Why build new when you can own this incredible home? Located at the doorway to Sachem's Head, this 3,000 sq ft custom-built in 2022 with no expense spared. With 4 bedrooms, 3.5 baths, a first-floor office, an attached two-car garage, and a basement ready to be finished, it checks all the boxes. The dramatic great room has double-height ceilings, a striking wall of windows, and a showpiece gas

    Jack Hill Seabury Hill REALTORS

    4 Benton's Knoll Unit 2, 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
  • /40

    $974,999 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
  • /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
  • /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
  • /39

    $639,000

    • 4 Beds
    • 2 Baths
    • 1,906 Sq Ft

    170 Weatherly Trail, Guilford, CT 06437

    This 4-bedroom Cape Cod offers a nice sense of privacy, set back on a quiet cul-de-sac street. Sitting on 1.21 acres, there is plenty of outdoor space to enjoy, including a brand-new deck that's perfect for grilling or relaxing. The interior is light and bright with hardwood floors throughout, updated kitchen and bathrooms. It's a great opportunity for anyone looking for a comfortable home with a

    Rob McConville RE/MAX Heritage

    170 Weatherly Trail, Guilford, CT 06437
  • /38

    $2,595,000 Open House 5/16

    • 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
  • /32

    $712,000

    • 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

    $619,000

    • 4 Beds
    • 2.5 Baths
    • 2,126 Sq Ft

    64 Dohm Ave, Guilford, CT 06437

    This well-maintained ranch offers easy single-level living with a layout designed for comfort and convenience. Expanded and renovated to the studs in 2008, the home now features a new 1,500-gallon septic tank for a potential 5th bedroom and a radon-in-air mitigation system. Hardwood floors run throughout a bright, open floor plan with central air, while the spacious primary suite includes dual

    Linda Toscano Coldwell Banker Realty

    64 Dohm Ave, Guilford, CT 06437
  • /39

    $899,000

    • 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

    $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
  • /38

    $649,000 Open Sat 11AM - 1PM

    • 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
  • /40

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,442 Sq Ft

    15 Copper Hill Dr Unit 15, Guilford, CT 06437

    Welcome to this stunning, fully renovated, free standing, 2-bedroom, 2-bath townhouse (with an additional, very large 3rd space that can be used as an office or work-out space!), where modern design meets everyday comfort, perfectly positioned with peaceful, scenic views. From the moment you enter, natural sunlight blends seamlessly with recessed lighting, creating a bright, warm, and inviting

    David Lemel Coldwell Banker Realty

    15 Copper Hill Dr Unit 15, Guilford, CT 06437
  • /37

    $699,000

    • 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

    $600,000 Open Sat 11:30AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,453 Sq Ft

    41 Preble Dr, Guilford, CT 06437

    ONE FLOOR LIVING ranch style home in the desirable Rolf Gardens neighborhood, just a short stroll to the Guilford Green. This 3-bedroom, 2 full bath residence offers the ease of one level living paired with an exceptional in town lifestyle. Step inside to find a thoughtfully designed layout featuring a dining room with gas fireplace that flows seamlessly into a step-down living room. The

    Rose Ciardiello William Raveis Real Estate

    41 Preble Dr, 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
  • /39

    $2,175,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,754 Sq Ft

    200 Whitfield St, Guilford, CT 06437

    Possibly the most admired of the historic homes closeby to the storied Guilford Town Green and Jacobs Beach, the Captain Joel Stone House, c.1853 is now seeking a new owner. This remarkable grand Italianate Villa offers quite a pedigree having been built by a wealthy steamship owner, Joel Stone, son of the second lighthouse keeper of beloved Faulkner's Island. The quality of this gracious home

    Margaret Muir William Pitt Sotheby's Int'l

    200 Whitfield St, 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
  • /40

    $675,000

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft

    441 Water St, Guilford, CT 06437

    Just one mile from the historic Guilford Green, this like-new Contemporary Farmhouse offers a rare blend of modern comfort, coastal charm, and beautiful natural views. Set on one acre with views of the marsh and West River, the home is designed to feel both private and connected to one of Guilford's most desirable village settings. The open floor plan is ideal for everyday living and

    Willard Finkle Coldwell Banker Realty

    441 Water St, Guilford, CT 06437
  • /40

    $549,000

    • 3 Beds
    • 1.5 Baths
    • 1,344 Sq Ft

    737 Leetes Island Rd, Guilford, CT 06437

    Welcome to 737 Leetes Island Road, a stone's throw from Shell Beach, one of Guilford's most desirable shoreline areas! With some TLC, the potential for this property is endless! Situated on beautiful grounds, 737 embraces all the natural elements of this area...salt water breeze coupled with lightly wooded, open space. This property was known as the "Marilyn House", as it was said that Marilyn

    Carissa Mastriano GRL & Realtors, LLC

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

    $539,000 Open Sat 12PM - 2PM

    • 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
  • /39

    $529,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,630 Sq Ft

    94 Quonnipaug Hill Rd, Guilford, CT 06437

    "Vermont in Guilford": Extraordinary hilltop privacy surrounded by woods and fields in North Guilford. This well-maintained 3-bedroom, 1.5-bath home with attached 2-car garage is ideally sited atop a hill in a desirable setting. Recent updates include mini-splits, a new roof, fresh interior paint, and gleaming hardwood floors. The main level features an open living area with wood stove, offering

    Tim Galvin William Raveis Real Estate

    94 Quonnipaug Hill Rd, Guilford, CT 06437
  • /38

    $699,000

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    507 Little Meadow Rd, Guilford, CT 06437

    Serene Living at 507 Little Meadow Road Discover the perfect blend of coastal charm and modern comfort in this beautifully inviting 4-bedroom, 2-bathroom expanded Raised Ranch. Nestled on over an acre of level, lightly wooded land, this home offers a private sanctuary on one of Guilford's most scenic roads. The heart of the residence is a stunning vaulted-ceiling sunroom, complete with skylights,

    Jaider Osorno Alpha Capital Realty, LLC

    507 Little Meadow Rd, Guilford, CT 06437
  • /20

    $696,000

    • 4 Beds
    • 1.5 Baths
    • 2,060 Sq Ft

    60 Three Mile Course, Guilford, CT 06437

    Live, Love, Laugh and Play a short walk to Guilford Center, Library, Public Transportation, Dining and Shopping! The expanded Cape offers a newer Great Room addition offering the perfect space to entertain in style with doors to yard and future patio. The adjacent kitchen was updated 6yrs ago when addition was added and boast granite counters, SS appliances and adjacent original dining room for

    Diane Beckwith Popolizio William Raveis Real Estate

    60 Three Mile Course, Guilford, CT 06437
  • /40

    $1,700,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,284 Sq Ft

    539A Boston St, Guilford, CT 06437

    Brand NEW CONSTRUCTION. Move in Ready! This modern, luxurious 3284sf, 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

    Anne Marie Straka Compass Connecticut, LLC

    539A Boston St, Guilford, CT 06437
  • /40

    $1,500,000

    • 5 Beds
    • 5 Baths
    • 5,310 Sq Ft

    7 Caleb Ct, Guilford, CT 06437

    Absolutely stunning 5+ bedroom light-filled home offers the perfect blend of elegance & modern updates. A dramatic 2-story foyer with a striking contemporary fixture sets the tone. The living room with glass French doors offers flexibility as a first-floor office. The oversized family room features a soaring ceiling, custom built-ins & stone fireplace, flowing seamlessly into the remodeled

    Susan Santoro William Pitt Sotheby's Int'l

    7 Caleb Ct, Guilford, CT 06437
  • /28

    $365,000

    • 4 Beds
    • 2 Baths
    • 1,236 Sq Ft

    409 Boston St, Guilford, CT 06437

    Rare opportunity in desirable Guilford. This 9 room, 3-bedroom, 2-bath Raised Ranch sits on .46 acres with marshland and wooded views behind the home, creating a peaceful backdrop with abundant birdlife. Hardwood floors, dining room, large rear three season porch and a light-filled layout provide a solid starting point. The unfinished lower level offers expansion potential. Detached

    Steven Rivkin Planet Realty, LLC

    409 Boston St, 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
$631,375
Median Single Family Sale Price
$637,000
Median Townhouse Sale Price
$921,031
Median 2 Bedroom Sale Price
$1,250,000
Average Price Per Sq Ft
$371
Number of Homes for Sale
45
Last 12 months Home Sales
300
Months of Supply
1.80
Median List Price
$649,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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