Greenfield Hill Homes

• 

  $998,000 Sold Jul 21, 2025

  • 4,406 Sq Ft
  • $227/SF
  • 55 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  85 Whiting Pond Rd, Fairfield, CT 06824

  Welcome to your private retreat in the heart of Greenfield Hill. Set on two lush, landscaped acres at the end of a peaceful cul-de-sac, this classic 4-bedroom Colonial boasts the charm, space, and setting that are becoming increasingly rare. Framed by stone walls and blooming gardens, it offers privacy and natural beauty in every direction. The backyard is made for living-sprawl out on the

  Laura Kottler Compass Connecticut, LLC

  85 Whiting Pond Rd, Fairfield, CT 06824
• 

  Est $1,830,406 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,140 Sq Ft

  440 Redding Rd, Fairfield, CT 06824

  440 Redding Rd, Fairfield, CT 06824
• 

  

  

  /37

  $1,350,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,525 Sq Ft

  225 Dunham Rd, Fairfield, CT 06824

  Escape to space and tranquility! Beautifully updated home nestled in the heart of Greenfield Hill, ideally situated on 3 private acres. Classic and inviting layout, which flows effortlessly. Enjoy lovely views of the property from the bright and spacious renovated kitchen featuring granite counters, stainless appliances & breakfast area. The adjacent study is a cozy retreat with custom built-ins.

  Katie O'Grady Compass Connecticut, LLC

  225 Dunham Rd, Fairfield, CT 06824
• 

  $1,575,000 Sold Jul 18, 2025

  • 3,226 Sq Ft
  • $488/SF
  • 11 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1961

  362 Joan Dr, Fairfield, CT 06824

  **H&B offer submission deadline please by Mon 6/23 5PM** Stunning 4BR Colonial with thoughtful open floor plan, sited in the highly desirable neighborhood of lower Greenfield Hill. This exquisite home has been beautifully renovated from top to bottom with high-end finishes - Designer lighting, custom cabinetry, shiplap, and grasscloth wall coverings, to name just a few. The sprawling, fully

  Carol Langeland William Pitt Sotheby's Int'l

  362 Joan Dr, Fairfield, CT 06824
• 

  Est $2,251,115 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 6,332 Sq Ft

  148 Quarter Horse Ln, Fairfield, CT 06824

  148 Quarter Horse Ln, Fairfield, CT 06824
• 

  /2

  $1,161,400 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 4,340 Sq Ft

  2425 Merwins Ln, Fairfield, CT 06824

  Welcome to an exceptional investment opportunity! This large Colonial-style residence exudes timeless charm and potential. Featuring four spacious bedrooms and three-and-a-half bathrooms, this two-story home sits on approximately 2.19 acres, offering ample space for outdoor activities and privacy. Enjoy the cozy ambiance of two fireplaces, perfect for chilly New England evenings. The property

  Christopher Rose Realhome Services & Solutions

  2425 Merwins Ln, Fairfield, CT 06824
• 

  $1,400,000 Sold Jul 16, 2025

  • 4,138 Sq Ft
  • $338/SF
  • 12 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1993

  181 Lakewood Dr, Fairfield, CT 06824

  HIGHEST & BEST BY 5/14 @ NOON. Nestled at the end of a quiet cul-de-sac, this enchanting residence offers the perfect blend of privacy, elegance, and everyday comfort-complete with a private path leading to a serene pond retreat. From the inviting front porch swing to the spacious rear deck and sun-drenched sunroom, this home is designed for both peaceful living and effortless entertaining. Step

  Denise Walsh William Raveis Real Estate

  181 Lakewood Dr, Fairfield, CT 06824
• 

  Est $1,990,864 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,856 Sq Ft

  39 Quarter Horse Ln, Fairfield, CT 06824

  39 Quarter Horse Ln, Fairfield, CT 06824
• 

  $925,000 Sold Jul 02, 2025

  • 3,022 Sq Ft
  • $306/SF
  • 97 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1964

  203 Wildflower Ln, Fairfield, CT 06824

  Tucked at the end of a cul-de-sac in Greenfield Hill, this sprawling ranch offers an incredible opportunity to create your dream home. A welcoming front porch leads into a living room with hardwood floors & fireplace. Continue to the heart of the home, the bright and expansive open concept kitchen, dining area & family room under soaring vaulted ceilings. Walls of windows, skylights, and sliders

  Sarah Pritchard William Raveis Real Estate

  203 Wildflower Ln, Fairfield, CT 06824
• 

  Est $2,422,301 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 7,732 Sq Ft

  1066 Merwins Ln, Fairfield, CT 06824

  1066 Merwins Ln, Fairfield, CT 06824
• 

  $2,022,000 Sold Jul 01, 2025

  • 4,258 Sq Ft
  • $475/SF
  • 125 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  478 Hollydale Rd, Fairfield, CT 06824

  Home currently under construction will be completed by July. High quality new construction. Custom kitchen cabinets, Sub Zero refrigerator/freezer, Sharp microwave drawer, 48" Wolf gas range, wine chiller, large center island, tile splash, pantry. Large mudroom with bench and cubbies, large family room open to kitchen with 9' ceiling, fireplace, Dining room open to kitchen with 9' ceiling and

  Robert Richter Coldwell Banker Realty

  478 Hollydale Rd, Fairfield, CT 06824
• 

  Est $2,304,866 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 8,126 Sq Ft

  280 Fair Oak Dr, Fairfield, CT 06824

  280 Fair Oak Dr, Fairfield, CT 06824
• 

  $2,500,000 Sold Jun 30, 2025

  • 5,449 Sq Ft
  • $459/SF
  • 83 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1970

  1700 Hillside Rd, Fairfield, CT 06824

  Welcome to an exceptional estate in Greenfield Hill, where classic allure meets contemporary luxury. This 2-acre sanctuary boasts manicured gardens, a private pool, a charming pool house, and ample parking with a 4-car garage. Inside, high ceilings and natural light accentuate the spacious, elegant rooms. Five cozy fireplaces enrich the ambiance. The formal living room and wood-paneled dining

  Cindy Raney Coldwell Banker Realty

  1700 Hillside Rd, Fairfield, CT 06824
• 

  Est $1,425,353 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,729 Sq Ft

  1220 Redding Rd, Fairfield, CT 06824

  1220 Redding Rd, Fairfield, CT 06824
• 

  $1,025,000 Sold Jun 30, 2025

  • 3,494 Sq Ft
  • $293/SF
  • 23 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1987

  4665 Black Rock Turnpike, Fairfield, CT 06824

  Welcome to 4665 Black Rock Turnpike. A beautifully designed and well-maintained 4-bedroom, 3.5-bathroom Colonial home offering nearly 3,500 square feet of elegant living space in one of Fairfield's most convenient locations. Privately set back from the roadway, this home is surrounded by natural beauty, with a stream running through the property and beautifully landscaped grounds providing a

  Michael Mastronardi Keller Williams Realty

  4665 Black Rock Turnpike, Fairfield, CT 06824
• 

  Est $1,323,223 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,624 Sq Ft

  1992 Redding Rd, Fairfield, CT 06824

  1992 Redding Rd, Fairfield, CT 06824
• 

  $1,600,000 Sold Jun 30, 2025

  • 3,504 Sq Ft
  • $457/SF
  • 13 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1973

  499 Hollydale Rd, Fairfield, CT 06824

  Welcome to a lifestyle of comfort & elegance in this meticulously maintained home, set back off the road on a lush acre lot in the sought-after Rock Ridge and Lake Hills community.Step inside to the fabulous open floor plan designed for effortless living and inspired entertaining.The family room is a showstopper, with vaulted ceiling and gas fp w shiplap surround, perfect for gatherings all year.

  Tracie Rigione William Raveis Real Estate

  499 Hollydale Rd, Fairfield, CT 06824
• 

  Est $1,209,689 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,939 Sq Ft

  120 Riders Ln, Fairfield, CT 06824

  120 Riders Ln, Fairfield, CT 06824
• 

  $2,402,000 Sold Jun 30, 2025

  • 7,000 Sq Ft
  • $343/SF
  • 25 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1980

  3010 Redding Rd, Fairfield, CT 06824

  Perched at the end of a private, tree-lined drive, this grand 5/6 bedroom, 5 full and 1 half bathroom, Georgian-style home seamlessly blends form and function. Designed to highlight the property's exquisite natural beauty, each room looks out onto lush, professionally landscaped lawns, gardens, & mature trees. Sunrises and sunsets are stunning. In every room, out every window are the most

  Terry Keegan Fairfield County Real Estate

  3010 Redding Rd, Fairfield, CT 06824
• 

  Est $1,857,995 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,635 Sq Ft

  2030 Merwins Ln, Fairfield, CT 06824

  2030 Merwins Ln, Fairfield, CT 06824
• 

  $1,400,000 Sold Jun 20, 2025

  • 2,808 Sq Ft
  • $499/SF
  • 9 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1969

  503 Mountain Laurel Rd, Fairfield, CT 06824

  Quintessential Connecticut colonial perched upon a gentle hill overlooking a babbling brook and abutting protected open space in premiere lower Greenfield Hill location is drawing the neighborhood's attention. This home has been loved for more than fifty years by the same family and now leveled up with a complete renovation with every surface touched by award winning builder. High design for the

  Susan Vanech Compass Connecticut, LLC

  503 Mountain Laurel Rd, Fairfield, CT 06824
• 

  Est $1,643,283 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,478 Sq Ft

  120 Catamount Rd, Fairfield, CT 06824

  120 Catamount Rd, Fairfield, CT 06824
• 

  $2,500,000 Sold Jun 17, 2025

  • 4,396 Sq Ft
  • $569/SF
  • 19 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1941

  43 Hickory Ln, Fairfield, CT 06824

  Timeless Charm Meets Modern Living in Prestigious Greenfield Hill. Thoughtfully designed for both luxurious living and everyday comfort, this residence offers serenity, privacy, gardens and stunning natural beauty at every turn. Nestled on a beautifully landscaped 3-acre property in the heart of Fairfield's coveted Greenfield Hill, this 1941 Classic Colonial offers the perfect blend of

  Lynn Dolan William Pitt Sotheby's Int'l

  43 Hickory Ln, Fairfield, CT 06824
• 

  Est $1,495,341 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  54 Catamount Rd, Fairfield, CT 06824

  54 Catamount Rd, Fairfield, CT 06824
• 

  $1,049,000 Sold Jun 16, 2025

  • 3,518 Sq Ft
  • $298/SF
  • 50 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1978

  4680 Black Rock Turnpike, Fairfield, CT 06824

  Welcome to 4680 Black Rock Tpk.This expansive 3,600 sq. ft. colonial is set back from the road, with large picture windows that fill the home with natural light and frame the beauty of every season. Ideally located near the Merritt Parkway and shopping, it offers both convenience and privacy in a sought-after area with top-rated schools. The inviting foyer opens to an airy main level, where the

  Stacy Varvaro Coldwell Banker Realty

  4680 Black Rock Turnpike, Fairfield, CT 06824
• 

  Est $2,016,571 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,482 Sq Ft

  81 Coventry Ln, Fairfield, CT 06824

  81 Coventry Ln, Fairfield, CT 06824
• 

  $1,810,000 Sold Jun 11, 2025

  • 3,673 Sq Ft
  • $493/SF
  • 25 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1962

  2101 Burr St, Fairfield, CT 06824

  We have multiple offers and are asking for all offers by 5:00 Sunday March 30th. Welcome to your dream home in Greenfield Hill! This exquisitely renovated Colonial is much more than meets the eye. Thoughtfully enlarged & transformed, blending timeless elegance with modern comfort. A traditional & balanced floor plan includes a sun drenched Living Room with fireplace, a sophisticated Dining Room

  Lis Reed Berkshire Hathaway NE Prop.

  2101 Burr St, Fairfield, CT 06824
• 

  Est $2,454,645 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 5,200 Sq Ft

  212 Coventry Ln, Fairfield, CT 06824

  212 Coventry Ln, Fairfield, CT 06824
• 

  $1,475,000 Sold Jun 04, 2025

  • 2,844 Sq Ft
  • $519/SF
  • 31 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1904

  351 Hillside Rd, Fairfield, CT 06824

  351 Hillside Rd is located in Lower Greenfield Hill, on one of the most scenic & desirable roads in Fairfield CT! This darling 2 acre Farmhouse boasts Great Room leading to Sunroom, Home Office, Primary Suite, 3 add'l Bedrooms, partially finished Walk out Lower Level including Full Bath & Sauna plus Patio-Terrace. Irresistible 2 Story PARTY BARN features Kitchen, Full Bath, Common Space & Loft

  Mary Jo McAvey William Raveis Real Estate

  351 Hillside Rd, Fairfield, CT 06824
• 

  

  /27

  Est $1,128,000 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,188 Sq Ft

  3737 North St, Fairfield, CT 06824

  3737 North St, Fairfield, CT 06824
• 

  $2,270,000 Sold May 29, 2025

  • 5,291 Sq Ft
  • $429/SF
  • 102 Days On Market

  • 7 Beds
  • 6 Baths
  • Built 1810

  2031 Redding Rd, Fairfield, CT 06824

  Wonderful lifestyle opportunity to own a curated estate property nestled on over two picturesque acres in scenic Greenfield Hill. This beautifully restored antique home boasts spacious rooms with original, meticulously restored wide plank wood floors. A standout feature is the spectacular room with brick flooring and an oversized fireplace, leading to a working climatized greenhouse. The property

  Katie O'Grady Compass Connecticut, LLC

  2031 Redding Rd, Fairfield, CT 06824
• 

  Est $1,694,980 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  63 Leslie Ln, Fairfield, CT 06824

  63 Leslie Ln, Fairfield, CT 06824
• 

  $1,343,500 Sold May 29, 2025

  • 3,482 Sq Ft
  • $386/SF
  • 61 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1967

  885 Duck Farm Rd, Fairfield, CT 06824

  Not one but two. Renowned architect, Jack Franzen and builder, Frank Dooley, applied their respective talents to design and build this consummate colonial on just over two acres at various times in its' history. The result is a home that is both openly warm and noticeably refined. Anchored by beautiful hardwood flooring and custom millwork throughout, every space and room feels like an invitation

  Gabrielle DiBianco Higgins Group Bedford Square

  885 Duck Farm Rd, Fairfield, CT 06824
• 

  Est $1,159,746 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,360 Sq Ft

  50 Judges Hollow Rd, Fairfield, CT 06824

  50 Judges Hollow Rd, Fairfield, CT 06824
• 

  $2,070,000 Sold May 20, 2025

  • 5,169 Sq Ft
  • $400/SF
  • 8 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1980

  410 Redding Rd, Fairfield, CT 06824

  Breathtaking Colonial situated on one of Greenfield Hill's most picturesque and sought after streets. Welcome to 410 Redding Road. Set on two acres of manicured and professionally landscaped level grounds, ideal for entertaining or relaxing. This five bedroom home seamlessly blends elegance with modern comfort. Upon entering you are greeted to a welcoming and spacious foyer. Showcasing an open

  Lisa Mancini William Raveis Real Estate

  410 Redding Rd, Fairfield, CT 06824
• 

  Est $2,606,090 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 6,035 Sq Ft

  580 Hillside Rd, Fairfield, CT 06824

  580 Hillside Rd, Fairfield, CT 06824
• 

  $1,165,000 Sold May 13, 2025

  • 3,617 Sq Ft
  • $322/SF
  • 20 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1995

  57 Franklin Ln, Fairfield, CT 06824

  Move right in to this beautiful colonial style home set on a premier lot in the center of the cul-de-sac with a private level yard and woodland views. The spacious layout includes a formal living and dining room, a kitchen open to the family room with a fireplace, soaring ceilings and walls of windows which overlook the deck and pretty yard. The magnificent primary suite features a full bath with

  Marlene Fischer William Raveis Real Estate

  57 Franklin Ln, Fairfield, CT 06824
• 

  Est $3,023,571 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 6,773 Sq Ft

  456 Hillside Rd, Fairfield, CT 06824

  456 Hillside Rd, Fairfield, CT 06824
• 

  $1,790,000 Sold May 01, 2025

  • 5,730 Sq Ft
  • $312/SF
  • 40 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 1859

  658 Hoydens Hill Rd, Fairfield, CT 06824

  OPEN 2/23 from 1-3! The property is withdrawn from the market this week - we are back on Sunday 2/23. Antique lover's dream...If you love authentic features and appreciate excellent craftsmanship, this house is the one! The home features wide board floors, plaster walls, hand-blown glass-paned windows, latched doors, nine fireplaces, and antique charm; truly a piece of history. Two stunning

  Mary Phelps William Pitt Sotheby's Int'l

  658 Hoydens Hill Rd, Fairfield, CT 06824
• 

  Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,176 Sq Ft

  1081 Hillside Rd, Fairfield, CT 06824

  1081 Hillside Rd, Fairfield, CT 06824

Showing Results 81 - 120, Page 3 of 18