Fairfield, CT Homes

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  /35

  $1,289,000

  • 4 Beds
  • 3.5 Baths
  • 2,166 Sq Ft

  20 Whetstone Hill Ct, Fairfield, CT 06824

  Some homes simply grow with you - and this is one of them. Nestled on a quiet cul-de-sac in a sought-after beach neighborhood, this inviting home has been the backdrop for years of cherished memories. Designed with both comfort and flexibility in mind, its thoughtful layout easily adapts to changing lifestyles. A legal studio - with a private entrance, full bathroom and kitchenette - offers

  Alina Rodescu-Pitchon William Raveis Real Estate

  20 Whetstone Hill Ct, Fairfield, CT 06824
• 

  $2,600,000

  Sold Apr 01, 2026

  154 Gorham Rd, Fairfield, CT 06824

  • 5 Beds
  • 4.5 Baths
  • 4,478 Sq Ft
  • Built 2025

  Last Sold Summary

  • $581/SF
  • 218 Days On Market

  Current Estimated Value $2,259,970

  Last Listing Agent Bette Gigliotti William Raveis Real Estate

  154 Gorham Rd, Fairfield, CT 06824
• 

  Est $1,751,312

  Not Listed For Sale

  380 Pine Creek Ave, Fairfield, CT 06824

  • 2 Beds
  • 1 Bath
  • 976 Sq Ft
  • Built 1978

  380 Pine Creek Ave, Fairfield, CT 06824

  Last Sold Summary

  • 117 Days On Market

  Last Listing Agent Katie O'Grady Compass Connecticut, LLC
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  /9

  $599,000

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  11 Redfield Rd, Fairfield, CT 06824

  Located on a cul-de-sac, walking distance to Fairfield's desirable downtown which offers great shopping, restaurants & easy access to the Metro North Train Station that brings you into Grand Central Station, the heart of NYC, in @ 70 minutes! Walk to the Town Gazebo which hosts Sunday Farmer's Market & live music in the summer! A Short bike ride to the Fairfield coastline with beautiful beaches

  Heidi Cinder William Raveis Real Estate

  11 Redfield Rd, Fairfield, CT 06824
• 

  $3,800,000

  Sold Oct 06, 2025

  1241 Hulls Hwy, Southport, CT 06890

  • 5 Beds
  • 8 Baths
  • 8,299 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Above List Price
  • $458/SF
  • 56 Days On Market

  Current Estimated Value $3,979,647

  Last Listing Agent Libby Tritschler William Raveis Real Estate

  1241 Hulls Hwy, Southport, CT 06890
• 

  Est $4,520,244

  Not Listed For Sale

  420 Pine Creek Ave, Fairfield, CT 06824

  • 5 Beds
  • 6 Baths
  • 4,568 Sq Ft
  • Built 2008

  420 Pine Creek Ave, Fairfield, CT 06824

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Denise Walsh William Raveis Real Estate
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  /27

  $1,995,000

  • 3 Beds
  • 3.5 Baths
  • 3,328 Sq Ft

  2 Elmwood Dr Unit 2, Southport, CT 06890

  Enjoy the privacy of a stand-alone home with the effortless convenience of condominium living in coveted Southport Green. One of only two detached residences in this desirable 24-home community, the three-level property offers three bedrooms, three renovated full baths, a powder room, and an attached two-car garage. A private patio-an uncommon amenity within the enclave-provides a peaceful

  Wendy Ryan Brown Harris Stevens

  2 Elmwood Dr Unit 2, Southport, CT 06890
• 

  $710,000

  Sold Oct 29, 2025

  5 Random Rd, Fairfield, CT 06825

  • 4 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $328/SF
  • 52 Days On Market

  Current Estimated Value $770,086

  Last Listing Agent Gaetano Marra BHGRE Gaetano Marra Homes

  5 Random Rd, Fairfield, CT 06825
• 

  Est $3,093,856

  Not Listed For Sale

  459 Pine Creek Ave, Fairfield, CT 06824

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • Built 2019

  459 Pine Creek Ave, Fairfield, CT 06824

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Denise Walsh William Raveis Real Estate
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  /40

  $729,900

  $20K PRICE DROP Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,998 Sq Ft

  312 Bennett St, Fairfield, CT 06825

  Brick Cape on quiet Stratfield cul de sac! Enjoy refinished hardwood floors throughout. Living room with fireplace opens to 3 season porch, formal Dining room, sunny white eat in Kitchen, main level bedroom and powder room on main floor. Upper level has 2 Bedrooms - both with generous closets/ storage - and tile Bath. Lower level heated Playroom with new floor, summer Kitchen and wine cellar.

  Jeff Craw William Raveis Real Estate

  312 Bennett St, Fairfield, CT 06825
• 

  $2,070,000

  Sold Jul 13, 2026

  187 Catherine Terrace, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 3,126 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $662/SF
  • 19 Days On Market

  Current Estimated Value $2,154,482

  Last Listing Agent Denise Walsh William Raveis Real Estate

  187 Catherine Terrace, Fairfield, CT 06824
• 

  Est $2,059,515

  Not Listed For Sale

  160 Old Dam Rd, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 3,446 Sq Ft
  • Built 2015

  160 Old Dam Rd, Fairfield, CT 06824

  Last Sold Summary

  • 77 Days On Market

  Last Listing Agent Nancy Thorne Berkshire Hathaway NE Prop.
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  /27

  $1,399,000

  Pending

  • 5 Beds
  • 6.5 Baths
  • 3,856 Sq Ft

  148 Szost Dr, Fairfield, CT 06824

  Completely reimagined from top to bottom, 148 Szost Drive offers the rare opportunity to own a move-in ready home on one of Fairfield's most sought-after neighborhoods. Thoughtfully renovated with today's lifestyle in mind, this 5-bedroom, 5.5-bath residence spans over 3,800 square feet on nearly a quarter-acre, blending timeless design with exceptional functionality. Designed for the way people

  Clyde Wauchope Coldwell Banker Realty

  148 Szost Dr, Fairfield, CT 06824
• 

  $1,005,000

  Sold Mar 11, 2026

  25 Helen St, Fairfield, CT 06824

  • 3 Beds
  • 2.5 Baths
  • 1,747 Sq Ft
  • Built 1920

  Last Sold Summary

  • 14% Above List Price
  • $575/SF
  • 8 Days On Market

  Current Estimated Value $1,033,670

  Last Listing Agent Clyde Wauchope Coldwell Banker Realty

  25 Helen St, Fairfield, CT 06824
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  Est $2,503,009

  Not Listed For Sale

  1810 Fairfield Beach Rd, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,412 Sq Ft
  • Built 2005

  1810 Fairfield Beach Rd, Fairfield, CT 06824

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Amanda Thaw The Riverside Realty Group
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  /39

  $749,900

  $20K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,569 Sq Ft

  166 Glengarry Rd, Fairfield, CT 06825

  Welcome to 166 Glengarry Road, a beautifully maintained end-unit townhouse in Fairfield's sought-after Woodfield Village community. Offering 3 bedrooms, 3 full baths, 1 half bath,and a versatile floor plan, this move-in-ready home combines comfort, space, and convenience. Freshly painted throughout and featuring refinished hardwood floors, the home is filled with natural light. The spacious

  Myles Simon MBA Realty, LLC

  166 Glengarry Rd, Fairfield, CT 06825
• 

  $900,000

  Sold Nov 12, 2025

  28 Primrose Ln, Fairfield, CT 06825

  • 4 Beds
  • 4 Baths
  • 2,521 Sq Ft
  • Built 1976

  Last Sold Summary

  • 2% Above List Price
  • $357/SF
  • 21 Days On Market

  Current Estimated Value $978,115

  Last Listing Agent Debra Carson William Raveis Real Estate

  28 Primrose Ln, Fairfield, CT 06825
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  Est $3,239,636

  Not Listed For Sale

  1522 Fairfield Beach Rd, Fairfield, CT 06824

  • 4 Beds
  • 4.5 Baths
  • 3,884 Sq Ft
  • Built 1910

  1522 Fairfield Beach Rd, Fairfield, CT 06824

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Merry Hampton William Raveis Real Estate
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  /40

  $5,499,000

  • 5 Beds
  • 5.5 Baths
  • 4,000 Sq Ft

  2268 Fairfield Beach Rd, Fairfield, CT 06824

  Experience the pinnacle of coastal luxury at this extraordinary waterfront builder's own residence on prestigious Fairfield Beach Road. Designed with uncompromising craftsmanship and impeccable attention to detail, this one-of-a-kind modern masterpiece offers the ultimate waterfront lifestyle with a private sandy beach and your own private dock. Showcasing over-the-top custom finishes throughout,

  Sara Santos Coldwell Banker Realty

  2268 Fairfield Beach Rd, Fairfield, CT 06824
• 

  $1,156,000

  Sold Jul 01, 2026

  2032 N Benson Rd, Fairfield, CT 06824

  • 4 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • Built 1941

  Last Sold Summary

  • 32% Above List Price
  • $670/SF
  • 12 Days On Market

  Current Estimated Value $907,540

  Last Listing Agent Ryan Sullivan Berkshire Hathaway NE Prop.

  2032 N Benson Rd, Fairfield, CT 06824
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  Est $4,378,636

  Not Listed For Sale

  2115 Fairfield Beach Rd, Fairfield, CT 06824

  • 4 Beds
  • 5.5 Baths
  • 3,709 Sq Ft
  • Built 2018

  2115 Fairfield Beach Rd, Fairfield, CT 06824

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Jackie Davis William Raveis Real Estate
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  /33

  $950,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,812 Sq Ft

  600 Cedar Rd, Southport, CT 06890

  Nestled on approximately 1.1 acres in Southport, this classic 1941 Colonial offers a rare opportunity to create something truly special. Set in a picturesque, lightly wooded setting, the property combines privacy with a beautiful natural backdrop. The gently sloping lot opens to a spacious backyard, providing plenty of room to enjoy the outdoors. Inside, you'll find three bedrooms and one full

  Pat Conroy Higgins Group Bedford Square

  600 Cedar Rd, Southport, CT 06890
• 

  $790,000

  Sold Jul 02, 2026

  644 Melville Ave, Fairfield, CT 06825

  • 3 Beds
  • 3 Baths
  • 1,635 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Below List Price
  • $483/SF
  • 76 Days On Market

  Current Estimated Value $820,498

  Last Listing Agent John Shea William Raveis Real Estate

  644 Melville Ave, Fairfield, CT 06825
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  Est $2,484,931

  Not Listed For Sale

  2087 Fairfield Beach Rd, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,748 Sq Ft
  • Built 1983

  2087 Fairfield Beach Rd, Fairfield, CT 06824

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Helen Cusa Brown Harris Stevens
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  /34

  $970,000

  Open Sun 11AM - 1PM Under Contract

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  134 Shoreham Village Dr, Fairfield, CT 06824

  Water Views! Unforgettable sunsets and a front-row seat to Fairfield's Fourth of July fireworks-this is the Fairfield Beach community lifestyle! Designed for everyday living and effortless entertaining, this move-in-ready two-bedroom home offers an inviting flow from the living and dining rooms to the newly renovated sunroom and spacious, newly refurbished AZEK deck. Whether hosting summer

  John Harvey Compass Connecticut, LLC

  134 Shoreham Village Dr, Fairfield, CT 06824
• 

  $1,753,000

  Sold May 18, 2026

  3810 Congress St, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 4,051 Sq Ft
  • Built 1890

  Last Sold Summary

  • 15% Above List Price
  • $433/SF
  • 5 Days On Market

  Current Estimated Value $1,714,645

  Last Listing Agent Mar Jennings Higgins Group Bedford Square

  3810 Congress St, Fairfield, CT 06824
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  Est $2,141,163

  Not Listed For Sale

  1895 Fairfield Beach Rd, Fairfield, CT 06824

  • 3 Beds
  • 1.5 Baths
  • 1,572 Sq Ft
  • Built 1917

  1895 Fairfield Beach Rd, Fairfield, CT 06824

  Last Sold Summary

  • 178 Days On Market

  Last Listing Agent Helen Cusa Brown Harris Stevens
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  /15

  $1,179,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1646 Jennings Rd, Fairfield, CT 06824

  Completely renovated from top to bottom, this stunning 4-bedroom, 2-bath home blends modern luxury with timeless charm in Fairfield's desirable University area. Offering 1,814 sq ft of finished living space plus an 884 sq ft unfinished basement, this move-in-ready home delivers style, comfort, and future potential. The open-concept layout centers on a designer kitchen with custom cabinetry, an

  Nijat Binnatov Realty ONE Group Connect

  1646 Jennings Rd, Fairfield, CT 06824
• 

  $736,000

  Sold Sep 25, 2025

  1134 Valley Rd, Fairfield, CT 06825

  • 3 Beds
  • 1.5 Baths
  • 1,687 Sq Ft
  • Built 1928

  Last Sold Summary

  • 6% Above List Price
  • $436/SF
  • 21 Days On Market

  Current Estimated Value $782,836

  Last Listing Agent Elise Larrabure Coldwell Banker Realty

  1134 Valley Rd, Fairfield, CT 06825
• 

  Est $6,152,417

  Not Listed For Sale

  665 Sasco Hill Rd, Fairfield, CT 06824

  • 6 Beds
  • 5.5 Baths
  • 6,073 Sq Ft
  • Built 1924

  665 Sasco Hill Rd, Fairfield, CT 06824

  Last Sold Summary

  • 112 Days On Market

  Last Listing Agent Libby Tritschler William Raveis Real Estate
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  /39

  $1,495,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,163 Sq Ft

  26 Spruce St, Southport, CT 06890

  SOUTHPORT VILLAGE ITALIANATE VICTORIAN - The Legrand Sherwood | William Northrop House - Circa 1872. Ideally located in Southport Village, this exceptional 3,163 square foot, four bedroom Italianate Victorian has been thoughtfully restored and sensitively updated, blending exceptional architectural elements with beautiful interiors. Designer finishes (marble, tiles, fixtures and hardware),

  Victoria Fingelly Higgins Group Real Estate

  26 Spruce St, Southport, CT 06890
• 

  $1,525,000

  Sold Jul 27, 2026

  12 Sconset Dr, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 2,399 Sq Ft
  • Built 1940

  Last Sold Summary

  • 17% Above List Price
  • $636/SF
  • 65 Days On Market

  Current Estimated Value $1,291,587

  Last Listing Agent Jackie Davis William Raveis Real Estate

  12 Sconset Dr, Fairfield, CT 06824
• 

  Est $3,036,788

  Not Listed For Sale

  753 Sasco Hill Rd, Fairfield, CT 06824

  • 7 Beds
  • 5.5 Baths
  • 5,967 Sq Ft
  • Built 1925

  753 Sasco Hill Rd, Fairfield, CT 06824

  Last Sold Summary

  • 194 Days On Market

  Last Listing Agent Victoria Fingelly Higgins Group Real Estate
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  /40

  $2,850,000

  $145K PRICE DROP Pending

  • 6 Beds
  • 5.5 Baths
  • 4,322 Sq Ft

  598 S Benson Rd, Fairfield, CT 06824

  Rare Beach Property~ Steps to Sandcastle Playground, Jennings Beach and South Benson Marina - this striking Colonial delivers a unique blend of luxurious beach living and exceptional build quality. Homes of this caliber seldom become available along the shoreline. ~ EXPANSIVE FIRST FLOOR ~ The house features a sprawling first floor Great Room and show stopping Chef's Kitchen which combine in a

  Julie Vanderblue Higgins Group Real Estate

  598 S Benson Rd, Fairfield, CT 06824
• 

  $2,150,000

  Sold Aug 18, 2025

  347 Lalley Blvd, Fairfield, CT 06824

  • 4 Beds
  • 5 Baths
  • 3,031 Sq Ft
  • Built 2013

  Last Sold Summary

  • 6% Below List Price
  • $709/SF
  • 96 Days On Market

  Current Estimated Value $2,364,118

  Last Listing Agent Carrie Sakey Coldwell Banker Realty

  347 Lalley Blvd, Fairfield, CT 06824
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  Est $1,060,844

  Not Listed For Sale

  150 Flora Blvd, Fairfield, CT 06824

  • 3 Beds
  • 2 Baths
  • 1,229 Sq Ft
  • Built 1948

  150 Flora Blvd, Fairfield, CT 06824

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Craig Oshrin RE/MAX Heritage
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  /39

  $2,699,000

  • 5 Beds
  • 5.5 Baths
  • 5,014 Sq Ft

  1123 Round Hill Rd, Fairfield, CT 06824

  There's a certain kind of iconic home that settles over you the moment you step inside, because the craftsmanship was never meant to be temporary. Nine-foot ceilings in the living & dining rooms, 3 wood-burning fireplaces, solid proportions & large windows & glass doors that still frame the light the way they were designed to nearly a century ago. The kind of quiet authority that newer

  Veronica Monahan Compass Connecticut, LLC

  1123 Round Hill Rd, Fairfield, CT 06824
• 

  $2,425,000

  Sold Jul 13, 2026

  57 Beaumont Place, Fairfield, CT 06824

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $485/SF
  • 65 Days On Market

  Current Estimated Value $2,376,689

  Last Listing Agent Anthony Fabrizio Coldwell Banker Realty

  57 Beaumont Place, Fairfield, CT 06824
• 

  Est $1,178,132

  Not Listed For Sale

  114 Flora Blvd, Fairfield, CT 06824

  • 3 Beds
  • 3 Baths
  • 1,586 Sq Ft
  • Built 1948

  114 Flora Blvd, Fairfield, CT 06824

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Mary Beth Grasso Keller Williams Realty
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  /40

  $1,199,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,773 Sq Ft

  41 Pepperbush Ln, Fairfield, CT 06824

  Welcome home to this fully renovated Colonial in one of Fairfield's most desirable neighborhoods! Comprehensively updated with high-quality finishes throughout, this 3-bedroom, 2.5-bath home offers move-in ready living w/ nothing left to do but unpack. Brand-new open concept kitchen over looks dining room & features modern shaker-style cabinetry, quartz countertops, & all-new st/st appliances,

  Max Dober Keller Williams Prestige Prop.

  41 Pepperbush Ln, Fairfield, CT 06824

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