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Colonial Homes for Sale in Guilford, CT

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  • /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

    $1,395,000

    • 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
  • /39

    $2,175,000

    • 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

    $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
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    $1,650,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 5,659 Sq Ft

    350 Squaw Ln, Guilford, CT 06437

    Set on over four park-like acres in sought-after Guilford, this stately custom built colonial blends exceptional craftsmanship with refined modern living. Thoughtfully enhanced by the current owner, the home features integrated smart home technology paired with curated, high-end upgrades, creating a seamless balance of innovation and timeless design. A dramatic two-story foyer with marble floors

    Linda Toscano Coldwell Banker Realty

    350 Squaw Ln, Guilford, CT 06437
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    $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
  • /40

    $1,395,000 Coming Soon

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

    7 Timber Ln, Guilford, CT 06437

    Tucked within a double cul-de-sac in the coveted Woodlands neighborhood, this renovated Colonial offers the perfect blend of luxury and comfort. Imagine morning walks on nearby Eastwoods trails, afternoons spent outdoors, and evenings gathered in a home designed for both everyday living and effortless entertaining. This sunlit home feels refined yet welcoming, with hardwood floors, custom

    Rose Ciardiello William Raveis Real Estate

    7 Timber Ln, Guilford, CT 06437
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    $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
  • /40

    $950,000

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    2 Greenwood Ln, Guilford, CT 06437

    Set at the end of a quiet cul-de-sac, this beautifully renovated 5-bedroom, 3.5-bath colonial delivers the space, privacy, and finishes today's buyers are searching for - all on 3.19 private acres. Step through the dramatic two-story foyer with a chandelier and sidelights into a home thoughtfully updated from top to bottom. The main level flows seamlessly from the formal living room - anchored by

    Mustafa Muaremi Coldwell Banker Realty

    2 Greenwood Ln, Guilford, CT 06437
  • /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

    $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
  • /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
  • /40

    $1,200,000 Open Sat 12PM - 2PM

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

    94 Cooks Ln, Guilford, CT 06437

    Privately set on 3.6 picturesque acres, this exceptional equestrian estate offers the perfect balance of luxury living, resort-style amenities, and a true horse property lifestyle. Built in 2004 and recently refreshed, the home features 4 bedrooms, 4 full baths, and beautifully designed spaces that blend comfort, sophistication, and effortless functionality. A dramatic two-story foyer opens to a

    Linda Toscano Coldwell Banker Realty

    94 Cooks Ln, Guilford, CT 06437
  • /2

    $1,050,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 5 Baths
    • 4,891 Sq Ft

    65 Little Meadow Rd, Guilford, CT 06437

    Tucked off a private road in one of Guilford's most desirable neighborhoods, this distinguished 5 bedroom Colonial offers exceptional space, flexibility, and peace of mind with extensive recent improvements already completed for the next owner. Updates include a new roof and exterior painted in 2025, two new A/C units, a newer furnace, new double wall ovens, and a newer gas cooktop. The main

    Linda Toscano Coldwell Banker Realty

    65 Little Meadow 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
  • /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

    $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
  • /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
  • /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

    $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

Home Trends in Guilford, CT

Housing Trends

Median Sale Price
$630,750
Median Single Family Sale Price
$640,000
Median Townhouse Sale Price
$928,015
Median 2 Bedroom Sale Price
$1,250,000
Average Price Per Sq Ft
$370
Number of Homes for Sale
53
Last 12 months Home Sales
297
Months of Supply
2.10
Median List Price
$650,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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