Guilford, CT Homes

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  $2,595,000 Open Sat 1PM - 3PM

  • 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
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  $530,000 Sold May 08, 2026

  1941 Moose Hill Rd, Guilford, CT 06437

  • 2 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $269/SF
  • 13 Days On Market

  Current Estimated Value $533,713

  Last Listing Agent Jack Hill Seabury Hill REALTORS

  1941 Moose Hill Rd, Guilford, CT 06437
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  Est $1,149,080 Not Listed For Sale

  5 Chestnut Grove, Guilford, CT 06437

  • 5 Beds
  • 6.5 Baths
  • 6,058 Sq Ft
  • Built 2005

  5 Chestnut Grove, Guilford, CT 06437

  Last Sold Summary

  • 7% Above List Price
  • $177/SF
  • 32 Days On Market

  • Last Sold Price $1,075,000
  • Jul 24, 2024

  Last Listing Agent Linda Toscano Coldwell Banker Realty
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  $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
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  $1,300,000 Sold Jun 09, 2025

  61 Cherry St, Guilford, CT 06437

  • 3 Beds
  • 3.5 Baths
  • 2,939 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Above List Price
  • $442/SF
  • 0 Days On Market

  Current Estimated Value $1,316,725

  Last Listing Agent Matt Healy Coldwell Banker Realty

  61 Cherry St, Guilford, CT 06437
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  Est $1,089,229 Not Listed For Sale

  1418 Jennifers Dr, Guilford, CT 06437

  • 4 Beds
  • 3.5 Baths
  • 4,195 Sq Ft
  • Built 2005

  1418 Jennifers Dr, Guilford, CT 06437

  Last Sold Summary

  • 1% Below List Price
  • $262/SF
  • 25 Days On Market

  • Last Sold Price $1,100,100
  • Sep 27, 2024

  Last Listing Agent Barbara Goetsch William Pitt
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  $275,000

  • 2 Beds
  • 1.5 Baths
  • 1,050 Sq Ft

  44 Mohawk Trail Unit 44, Guilford, CT 06437

  If you're looking for a serene and quiet home, you've found it at 44 Mohawk Trail. This 2-bedroom, 1.1-bath townhouse offers the perfect blend of comfort and convenience. The main level features an open floor plan connecting the kitchen, dining, and living areas. The living room is highlighted by a charming wood-burning fireplace-perfect for cozy nights. A half bathroom and in-unit washer and

  Samantha Celentano Coldwell Banker Realty

  44 Mohawk Trail Unit 44, Guilford, CT 06437
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  $750,000 Sold Oct 31, 2025

  1498 Little Meadow Rd, Guilford, CT 06437

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $288/SF
  • 54 Days On Market

  Current Estimated Value $750,727

  Last Listing Agent janet colello Century 21 AllPoints Realty

  1498 Little Meadow Rd, Guilford, CT 06437
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  Est $1,135,738 Not Listed For Sale

  1500 Jennifers Dr, Guilford, CT 06437

  • 4 Beds
  • 2.5 Baths
  • 3,864 Sq Ft
  • Built 2005

  1500 Jennifers Dr, Guilford, CT 06437

  Last Sold Summary

  • 24% Above List Price
  • $237/SF
  • 1 Day On Market

  • Last Sold Price $915,000
  • May 22, 2023

  Last Listing Agent Stephanie Dorman Coldwell Banker Realty
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  $1,350,000

  • 2 Beds
  • 2 Baths
  • 2,033 Sq Ft

  66 High St Unit 47, Guilford, CT 06437

  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.

  Laurie Trulock Compass Connecticut, LLC

  66 High St Unit 47, Guilford, CT 06437
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  $220,000 Sold Sep 26, 2025

  28 Saginaw Trail, Guilford, CT 06437

  • 1 Bed
  • 1 Bath
  • 837 Sq Ft
  • Built 1978

  Last Sold Summary

  • $263/SF
  • 50 Days On Market

  Current Estimated Value $227,247

  Last Listing Agent Paige Slocum William Raveis Real Estate

  28 Saginaw Trail, Guilford, CT 06437
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  Est $1,152,915 Not Listed For Sale

  20 Sunset Ridge Dr, Guilford, CT 06437

  • 4 Beds
  • 2.5 Baths
  • 4,414 Sq Ft
  • Built 2007

  20 Sunset Ridge Dr, Guilford, CT 06437

  Last Sold Summary

  • 10% Above List Price
  • $238/SF
  • 2 Days On Market

  • Last Sold Price $1,049,000
  • Oct 26, 2023

  Last Listing Agent Barbara Goetsch William Pitt
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  $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
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  $869,000 Sold Jul 10, 2025

  16 North St, Guilford, CT 06437

  • 3 Beds
  • 2.5 Baths
  • 2,137 Sq Ft
  • Built 1992

  Last Sold Summary

  • 9% Above List Price
  • $407/SF
  • 39 Days On Market

  Current Estimated Value $888,238

  Last Listing Agent Deborah Rowe William Raveis Real Estate

  16 North St, Guilford, CT 06437
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  Est $1,088,401 Not Listed For Sale

  4 Sunset Ridge Dr, Guilford, CT 06437

  • 3 Beds
  • 2.5 Baths
  • 3,562 Sq Ft
  • Built 2006

  4 Sunset Ridge Dr, Guilford, CT 06437

  Last Sold Summary

  • 18% Above List Price
  • $258/SF
  • 26 Days On Market

  • Last Sold Price $920,000
  • Jul 07, 2023

  Last Listing Agent Linda Toscano Coldwell Banker Realty
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  $549,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,250 Sq Ft

  25 Driveway, Guilford, CT 06437

  The Seller asks that interested parties submit Highest and Best offers by 3pm Saturday March 14th. Sweet as can be! This charming Queen Anne-style 2-family home offers several possibilities - convert it back to a single-family residence, live in one unit while renting the other, or rent out both units for strong cash flow. The inviting wraparound front porch and classic architectural lines create

  Tim Galvin William Raveis Real Estate

  25 Driveway, Guilford, CT 06437
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  $2,300,000 Sold Jul 21, 2025

  405 Whitfield St Unit 1, Guilford, CT 06437

  • 3 Beds
  • 5 Baths
  • 4,972 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $463/SF
  • 53 Days On Market

  Last Listing Agent Jennifer Leahy Compass Connecticut, LLC

  405 Whitfield St Unit 1, Guilford, CT 06437
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  Est $654,174 Not Listed For Sale

  110 Cherry St Unit 6, Guilford, CT 06437

  • 2 Beds
  • 2.5 Baths
  • 2,370 Sq Ft
  • Built 1930

  110 Cherry St Unit 6, Guilford, CT 06437

  Last Sold Summary

  • 36% Above List Price
  • $203/SF
  • 41 Days On Market

  • Last Sold Price $480,000
  • Dec 21, 2023

  Last Listing Agent Alexa Scott RE/MAX
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  /20

  $499,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  1944 Moose Hill Rd, Guilford, CT 06437

  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

  Joseph Iamunno Social & Co Realty

  1944 Moose Hill Rd, Guilford, CT 06437
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  $1,250,000 Sold Jul 09, 2025

  710 Alexander Dr, Guilford, CT 06437

  • 4 Beds
  • 5 Baths
  • 6,100 Sq Ft
  • Built 2003

  Last Sold Summary

  • $205/SF
  • 75 Days On Market

  Current Estimated Value $1,283,589

  Last Listing Agent Rose Ciardiello William Raveis Real Estate

  710 Alexander Dr, Guilford, CT 06437
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  Est $568,852 Not Listed For Sale

  110 Cherry St Unit 3, Guilford, CT 06437

  • 2 Beds
  • 2.5 Baths
  • 2,007 Sq Ft
  • Built 1930

  110 Cherry St Unit 3, Guilford, CT 06437

  Last Sold Summary

  • 19% Above List Price
  • $239/SF
  • 120 Days On Market

  • Last Sold Price $480,000
  • Feb 21, 2025

  Last Listing Agent Stephanie Jacobs Sunset Creek Realty, LLC
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  $31,000 Under Contract

  • 0.5 Baths
  • 775 Sq Ft

  379 Whitfield St Unit CN1146, Guilford, CT 06437

  This is an offering for CN1146, a 46 foot long boat slip at the amazing Guilford Yacht Club. A large dock box is included for all your boating and fishing gear needs along with water, electric hook up and winter storage on the grounds. Ownership of this slip includes a full membership to the Clubhouse which includes a heated pool, pool house, two Har Tru tennis courts and many special social

  Faith Whitehead William Raveis Real Estate

  379 Whitfield St Unit CN1146, Guilford, CT 06437
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  $380,000 Sold May 15, 2025

  235 Woodland Rd, Guilford, CT 06437

  • 3 Beds
  • 1 Bath
  • 1,288 Sq Ft
  • Built 1953

  Last Sold Summary

  • $295/SF
  • 14 Days On Market

  Current Estimated Value $406,900

  Last Listing Agent Amanda Popplewell-Sanson Coldwell Banker Realty

  235 Woodland Rd, Guilford, CT 06437
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  Est $1,212,408 Not Listed For Sale

  21 Mill Rd, Guilford, CT 06437

  • 4 Beds
  • 4.5 Baths
  • 4,346 Sq Ft
  • Built 2002

  21 Mill Rd, Guilford, CT 06437

  Last Sold Summary

  • 15% Above List Price
  • $242/SF
  • 123 Days On Market

  • Last Sold Price $1,050,000
  • Oct 31, 2023

  Last Listing Agent David Mayhew Pearce Real Estate
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  $175,000 Pending

  • Land
  • 7.09 Acres
  • $24,683 per Acre

  LOT #22 Kenneth Cir Unit MAP 77, Guilford, CT 06437

  WITH 7+ ACRES YOU CAN BUILD WHAT YOU WANT WITH THE PRIVACY YOU DESIRE !! SURVEYED, TESTED AND READY TO TURN DIRT !! SO YOU CAN GET THAT FOUNDATION IN THE GROUND AND START BUILDING YOUR DREAM HOUSE........... NOW !!!

  Tom Clancy William Pitt Sotheby's Int'l

  LOT #22 Kenneth Cir Unit MAP 77, Guilford, CT 06437
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  $595,000 Sold Jan 16, 2026

  54 Coachlamp Ln, Guilford, CT 06437

  • 4 Beds
  • 2.5 Baths
  • 2,533 Sq Ft
  • Built 1971

  Last Sold Summary

  • 15% Below List Price
  • $235/SF
  • 82 Days On Market

  Current Estimated Value $603,242

  Last Listing Agent Rose Ciardiello William Raveis Real Estate

  54 Coachlamp Ln, Guilford, CT 06437
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  Est $755,859 Not Listed For Sale

  100 Cherry St, Guilford, CT 06437

  • 3 Beds
  • 3 Baths
  • 2,343 Sq Ft
  • Built 1805

  100 Cherry St, Guilford, CT 06437

  Last Sold Summary

  • 4% Above List Price
  • $312/SF
  • 77 Days On Market

  • Last Sold Price $730,000
  • Dec 17, 2024

  Last Listing Agent Barbara Goetsch William Pitt
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  $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
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  $1,024,400 Sold Feb 19, 2026

  214 Nortontown Rd, Guilford, CT 06437

  • 5 Beds
  • 4.5 Baths
  • 4,829 Sq Ft
  • Built 1995

  Last Sold Summary

  • 18% Below List Price
  • $212/SF
  • 97 Days On Market

  Current Estimated Value $1,127,746

  Last Listing Agent Jonathan Wallace Compass Connecticut, LLC

  214 Nortontown Rd, Guilford, CT 06437
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  Est $793,255 Not Listed For Sale

  2269 Long Hill Rd, Guilford, CT 06437

  • 4 Beds
  • 3 Baths
  • 3,734 Sq Ft
  • Built 2001

  2269 Long Hill Rd, Guilford, CT 06437

  Last Sold Summary

  • 30% Above List Price
  • $163/SF
  • 125 Days On Market

  • Last Sold Price $609,900
  • Nov 01, 2023

  Last Listing Agent Gaye S. Barnett Coldwell Banker
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  $598,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  1092 Durham Rd, Guilford, CT 06437

  Opportunities like this are RARE in Guilford-a true live/work property offering exceptional flexibility, space, and income potential. Set on 1.04 acres in Guilford, this updated 4-bedroom, 2.5-bath home is complemented by a standout feature: an approximately 2,000+ sq ft warehouse with electricity, a car lift, multiple work areas, and its own separate driveway. Ideal for contractors, small

  Patsy Metcalf Compass Connecticut, LLC

  1092 Durham Rd, Guilford, CT 06437
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  $1,230,000 Sold Jul 29, 2025

  9 Bailey Dr, Guilford, CT 06437

  • 4 Beds
  • 2.5 Baths
  • 3,567 Sq Ft
  • Built 1996

  Last Sold Summary

  • 24% Above List Price
  • $345/SF
  • 41 Days On Market

  Current Estimated Value $1,230,634

  Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l

  9 Bailey Dr, Guilford, CT 06437
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  Not Listed For Sale

  1463 Little Meadow Rd, Guilford, CT 06437

  • 2 Beds
  • 2.5 Baths
  • 1,636 Sq Ft
  • Built 1950

  1463 Little Meadow Rd, Guilford, CT 06437

  Last Sold Summary

  • $373/SF
  • 37 Days On Market

  • Last Sold Price $610,000
  • Aug 12, 2024

  Last Listing Agent Linda Toscano Coldwell Banker Realty
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  $615,000 Under Contract

  • 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
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  $594,500 Sold Jul 25, 2025

  185 Meadow Hills Dr, Guilford, CT 06437

  • 4 Beds
  • 3 Baths
  • 2,216 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Above List Price
  • $268/SF
  • 22 Days On Market

  Current Estimated Value $621,546

  Last Listing Agent Kimberly Bailey William Raveis Real Estate

  185 Meadow Hills Dr, Guilford, CT 06437
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  Est $1,579,411 Not Listed For Sale

  55 Tulip Tree Dr, Guilford, CT 06437

  • 5 Beds
  • 4.5 Baths
  • 6,088 Sq Ft
  • Built 1999

  55 Tulip Tree Dr, Guilford, CT 06437

  Last Sold Summary

  • 13% Above List Price
  • $230/SF
  • 2 Days On Market

  • Last Sold Price $1,400,000
  • Jun 02, 2023

  Last Listing Agent Amy Kirst William Pitt
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  $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
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  $820,000 Sold Dec 19, 2025

  181 Denison Dr, Guilford, CT 06437

  • 3 Beds
  • 2.5 Baths
  • 1,764 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Above List Price
  • $465/SF
  • 56 Days On Market

  Current Estimated Value $817,187

  Last Listing Agent Kirsten Adams William Pitt Sotheby's Int'l

  181 Denison Dr, Guilford, CT 06437
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  Est $1,319,254 Not Listed For Sale

  144 Tulip Tree Dr, Guilford, CT 06437

  • 5 Beds
  • 5 Baths
  • 5,148 Sq Ft
  • Built 2002

  144 Tulip Tree Dr, Guilford, CT 06437

  Last Sold Summary

  • 1% Above List Price
  • $253/SF
  • 50 Days On Market

  • Last Sold Price $1,300,000
  • Jul 08, 2024

  Last Listing Agent Rose Ciardiello William Raveis Real Estate
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  /40

  $775,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,045 Sq Ft

  51 Sugar Loaf Rd, Guilford, CT 06437

  Idyllic setting in a peaceful North Guilford neighborhood, just minutes to Melissa Jones School. This beautifully maintained 4 bedroom, 3 1/2 bath Colonial offers the perfect blend of classic charm and modern updates, set on a lightly wooded, private 2-acre lot. Inside, you'll find a functional light-filled layout featuring a living room w/gas fireplace and dining area, an inviting family room

  Rose Ciardiello William Raveis Real Estate

  51 Sugar Loaf Rd, Guilford, CT 06437

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