Greenfield Hill, CT homes for sale & real estate

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ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's kitchen opens to elegant dining and living areas, with French doors to a bluestone terrace designed for candlelit dinners under the stars. A first-floor guest suite with a full bath provides flexibility and privacy, while upstairs, four additional bedrooms-including a serene primary suite-offer ref

$4,995,000

5 beds4.5 baths4,191 sq ft

2281 Redding Rd, Fairfield, CT 06824

5.03 acre lot • 4 garage spots • Pool

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury homes on manicured grounds. This sun-drenched five-bedroom, six-bathroom home has been freshly painted inside and out and features extensive millwork, gleaming hardwood floors, and floor-to-ceiling windows that flood the home with natural light. The open-concept layout is ideal for entertaining, centere

$1,695,000

5 beds5 baths5,136 sq ft

101 Brambley Hedge Cir, Fairfield, CT 06824

Pickle ball • Manicured grounds • Heated pool

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Crafted by noted custom builder Garrett Wilson and meticulously enhanced with recent upgrades, this Greenfield Hill home is as impressive as it is inviting. Finished to the highest standard, the residence is set on just over two private acres with a tennis court and expansive open space offering room for a pool and pool house. At the heart of the home, the chef's kitchen is filled with natural light and outfitted with Wolf and Sub-Zero appliances, two farmhouse sinks, two dishwashers, two wine refrigerators and a beautifully refinished wood island. Upstairs, you will find 5 bedrooms, all en-suite with walk-in closets and a spacious laundry room. The primary suite provides a serene retreat w

$2,499,999

5 beds7 baths5,978 sq ft

2775 North St, Fairfield, CT 06824

Two dishwashers • Two farmhouse sinks • Chef's kitchen

3D WALKTHROUGH

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to 480 Riders Lane, a timeless mid-century contemporary residence situated at the end of a charming cul-de-sac in the desirable Greenfield Hill neighborhood. This home features 4 to 5 bedrooms and 4 updated bathrooms, offering over 5,000 square feet of carefully crafted living space on a beautiful 2-acre lot, complete with a peaceful pond and fountain. Upon arrival, you'll be welcomed by a long circular driveway that leads to a roomy 4-car attached garage. Inside, the living and formal dining areas showcase impressive ceilings over 9 feet high, enhanced by a series of windows that bathe the rooms in natural light. The remodeled kitchen includes a walk-in pantry and an adjacent sunli

$1,149,000

4 beds3.5 baths5,081 sq ft

480 Riders Ln, Fairfield, CT 06824

Remodeled kitchen • Cul-de-sac • Peaceful pond

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
There are houses you tour, and then there are estates that capture your imagination. This extraordinary Greenfield Hill Colonial is the latter-a 9,700+ sq. ft. residence set on a pristine 2-acre corner lot in one of Fairfield's most prestigious neighborhoods. A paver-stone drive winds past manicured gardens to a grand two-story entry with a sweeping staircase, setting the tone for elegant living. Meticulously landscaped grounds, fountain, serene stone pathways, and a tranquil koi pond create a private oasis for quiet reflection or outdoor enjoyment. Inside, elegant formal living and dining rooms provide a perfect backdrop for entertaining, while the sun-filled family room, with vaulted ceil

$3,250,000

6 beds7.5 baths14,110 sq ft

21 Queens Grant Dr, Fairfield, CT 06824

2 acre lot • 3 garage spots • Pool

Property at 158 Coventry Ln, Fairfield, CT 06824, 4 beds, 3.5 baths

$2,199,000

4 beds3.5 baths4,255 sq ft

158 Coventry Ln, Fairfield, CT 06824

Property at 2683 Bronson Rd, Fairfield, CT 06824, 5 beds, 4.5 baths

$3,649,000

5 beds4.5 baths4,771 sq ft

2683 Bronson Rd, Fairfield, CT 06824

Property at 212 Fence Row Dr, Fairfield, CT 06824, 6 beds, 4.5 baths

$1,795,000

6 beds4.5 baths5,325 sq ft

212 Fence Row Dr, Fairfield, CT 06824

Property at 2180 Cross Hwy, Fairfield, CT 06824, 3 beds, 2 baths

$950,000

3 beds2 baths1,914 sq ft

2180 Cross Hwy, Fairfield, CT 06824

Property at 2015 Redding Rd, Fairfield, CT 06824, 5 beds, 5.5 baths

$2,995,000

5 beds5.5 baths5,965 sq ft

2015 Redding Rd, Fairfield, CT 06824

Property at 1084 Sturges Hwy, Westport, CT 06880, 6 beds, 8.5 baths

$4,250,000

6 beds8.5 baths6,897 sq ft

1084 Sturges Hwy, Westport, CT 06880

Property at 688 Hulls Farm Rd, Southport, CT 06890, 7 beds, 9 baths

$9,995,000

7 beds9 baths10,800 sq ft

688 Hulls Farm Rd, Southport, CT 06890

Property at 4800 Congress St, Fairfield, CT 06824, 7 beds, 8.5 baths

$15,000,000

7 beds8.5 baths9,129 sq ft

4800 Congress St, Fairfield, CT 06824

Property at 3853 Congress St, Fairfield, CT 06824, 4 beds, 5.5 baths

$1,395,000

4 beds5.5 baths4,906 sq ft

3853 Congress St, Fairfield, CT 06824

Property at 180 Catamount Rd, Fairfield, CT 06824, 4 beds, 3.5 baths

$2,199,000

4 beds3.5 baths3,700 sq ft

180 Catamount Rd, Fairfield, CT 06824

Property at 22 Brett Rd, Fairfield, CT 06824

$1,300,000

— beds— baths— sq ft

22 Brett Rd, Fairfield, CT 06824

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COMING SOON

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to 300 Winnepoge, a beautifully appointed home in Fairfield's desirable Lake Hills community. Set on a sun-filled corner lot with a large flat yard, this property combines classic charm with thoughtful updates and private association amenities. Step inside to find a spacious kitchen anchored by a 9' center island, granite countertops, and abundant skylights that flood the space with natural light. Hardwood floors with a decorative feature strip border enhance the main level, while the adjoining mudroom with a stone floor provides convenience right off the expansive wrap-around porch. A versatile first-floor flex room with an adjacent full bath offers the perfect space for guests, an

$1,250,000

4 beds3 baths3,131 sq ft

300 Winnepoge Dr, Fairfield, CT 06825

0.48 acre lot • $21 HOA • 2 garage spots

NEW 7 HRS AGO

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
254 Sherwood Farm Road, tucked away at the end of a cul-de-sac in the desirable lower Greenfield Hill section of Fairfield, this stately brick Colonial blends timeless curb appeal with a flexible floor plan and rare amenities. Mature plantings, stone walkways, and professional landscape lighting frame the home with elegance from the moment you arrive. Inside, the first level offers remarkable versatility with an en-suite bedroom featuring a walk-in closet, a dedicated office, a large chef's kitchen with an impressive Wolf and Sub-Zero appliance package, and dining and living rooms that soar with elevated ceiling heights, bringing light and luxury to the main living spaces. Upstairs, the wel

$1,899,000

4 beds4.5 baths4,515 sq ft

254 Sherwood Farm Rd, Fairfield, CT 06824

1 acre lot • 3 garage spots • Pool

COMING SOON

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Absolutely GORGEOUS new construction, elegantly crafted, that blends modern sophistication with coastal charm in this 5-BDR, 5 Full Bath home. The main level offers a balance of open-concept living and defined spaces, featuring 9' ceilings, white oak floors, custom millwork, and curated designer fixtures. The gourmet kitchen is a showstopper, featuring Thermador Pro appliances, quartz countertops, and a custom white oak island, flowing seamlessly into a sun-drenched family room with a statement custom designed fireplace and 8' sliding doors leading to a private patio and landscaped yard-spacious enough to accommodate a pool. A home office on the main floor offers functionality and flexibili

$1,925,000

5 beds5 baths4,440 sq ft

93 Millspaugh Dr, Fairfield, CT 06825

0.23 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered for sale. Passed down through generations, this classic colonial has been a cornerstone of one family's legacy for over a century - and now it's ready for its next chapter. Set on nearly a half-acre in the heart of Southport, this property offers tranquil water views, timeless charm, and unmatched potential. Originally a four-bedroom single-family home, a thoughtfully designed in-law suite with its own private entrance, separate mechanicals, and utilities was added in 1991 - ideal for multi-generational living, guests, or a private ho

$950,000

4 beds2.5 baths2,644 sq ft

647 Bronson Rd, Southport, CT 06890

0.41 acre lot • 2 garage spots • Car-dependent

COMING SOON

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to this exquisitely designed and completely rebuilt Colonial, crafted by one of Fairfield's premier builders. From the moment you arrive, the home's exceptional curb appeal and timeless architecture set the tone for what's inside. The bright and open floorplan is perfect for both everyday living and entertaining. The spacious Family Room features a cozy fireplace, custom built-ins, and a stylish entertainment bar complete with cabinetry and a wine cooler. The heart of the home is the beautifully appointed Kitchen, showcasing a large island, high-end finishes and appliances, and a seamless flow into the generous Dining Area. Also on the main level, you'll find a private Office, a wal

$1,699,000

4 beds4.5 baths3,200 sq ft

34 Ridgedale Rd, Fairfield, CT 06824

9,583 sq ft lot • Garage • Car-dependent

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to the University Area of Fairfiled, CT! This well-maintained three-bedroom, two-bath Colonial is perfectly situated in one of the most sought-after neighborhoods in town. Step inside to find a spacious front-to-back living room, dining room, and updated kitchen with quartz countertops, solid wood cabinets and stainless steel appliances. The large primary bedroom offers ample comfort, while two additional bedrooms provide plenty of space for family, guests, or a home office. Full, unfinished basement with plenty of headway, sets up an easy transformation to a lower level playroom. Recent updates include two-year-old siding, newer central air system, irrigation system (front and back

$829,000

3 beds2 baths1,440 sq ft

46 Middlebrook Dr, Fairfield, CT 06824

0.24 acre lot • Car-dependent

Property at 66 Morehouse Rd, Easton, CT 06612, 3 beds, 2.5 baths

$979,000

3 beds2.5 baths2,617 sq ft

66 Morehouse Rd, Easton, CT 06612

Property at 4 Highland Rd, Westport, CT 06880, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,556 sq ft

4 Highland Rd, Westport, CT 06880

Property at 276 Carroll Rd, Fairfield, CT 06824, 3 beds, 1.5 baths

$750,000

3 beds1.5 baths2,488 sq ft

276 Carroll Rd, Fairfield, CT 06824

Property at 52 Glover St, Fairfield, CT 06824, 3 beds, 2 baths

$850,000

3 beds2 baths1,344 sq ft

52 Glover St, Fairfield, CT 06824

Property at 1207 Stillson Rd, Fairfield, CT 06824, 5 beds, 4.5 baths

$1,539,000

5 beds4.5 baths4,073 sq ft

1207 Stillson Rd, Fairfield, CT 06824

Property at 1 Coastal Ct, Westport, CT 06880, 5 beds, 6 baths

$4,995,000

5 beds6 baths5,550 sq ft

1 Coastal Ct, Westport, CT 06880

Property at 111 Sturges Hwy, Westport, CT 06880, 5 beds, 7 baths

$3,750,000

5 beds7 baths7,359 sq ft

111 Sturges Hwy, Westport, CT 06880

Property at 17 Clover Ln, Westport, CT 06880, 5 beds, 3.5 baths

$2,195,000

5 beds3.5 baths3,000 sq ft

17 Clover Ln, Westport, CT 06880

Property at 214 Henry St, Fairfield, CT 06824, 3 beds, 3 baths

$975,000

3 beds3 baths2,141 sq ft

214 Henry St, Fairfield, CT 06824

Property at 37 Lamplighter Ln, Fairfield, CT 06825, 5 beds, 4.5 baths

$1,325,000

5 beds4.5 baths3,556 sq ft

37 Lamplighter Ln, Fairfield, CT 06825

Property at 1135 Mill Hill Rd, Southport, CT 06890, 2 beds, 1.5 baths

$1,289,000

2 beds1.5 baths1,424 sq ft

1135 Mill Hill Rd, Southport, CT 06890

Property at 245 Unquowa Rd Apt 64, Fairfield, CT 06824, 3 beds, 2 baths

$625,000

3 beds2 baths1,650 sq ft

245 Unquowa Rd Apt 64, Fairfield, CT 06824

Property at 251 Winnepoge Dr, Fairfield, CT 06825, 4 beds, 3 baths

$1,495,000

4 beds3 baths3,883 sq ft

251 Winnepoge Dr, Fairfield, CT 06825

Property at 64 Old Redding Rd, Weston, CT 06883, 5 beds, 8 baths

$3,999,999

5 beds8 baths11,450 sq ft

64 Old Redding Rd, Weston, CT 06883

Average home prices near Greenfield Hill, CT

Cities

Neighborhoods

Coleytown homes for sale
$2,032,000
North End homes for sale
$460,000
West Side-West End homes for sale
$429,950
West End-West Side homes for sale
$565,000
Fairfield Beach homes for sale
$2,247,500
Black Rock homes for sale
$649,950
Greens Farms homes for sale
$4,697,500
Old Hill homes for sale
$2,795,000
Stratfield Village homes for sale
$787,000

Greenfield Hill, CT real estate trends

All Home Types trends in Greenfield Hill, CT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,842,500

+8.1% YoY | Aug 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2025

Growth

% YoY

Greenfield Hill, CT

$1,842,500

+8.1%

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