Greenfield Hill, CT homes for sale & real estate

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LISTED BY REDFINVIDEO TOUR

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Prepare to be wowed by this extraordinary estate featuring six bedrooms and ten-and-a-half bathrooms, spanning four meticulously designed floors. Enter through a breathtaking two-story grand foyer, leading into beautifully appointed formal and informal rooms perfect for entertaining and a gourmet kitchen that any discerning chef would envy. The luxurious primary suite serves as a private retreat, complete with an expansive dressing room and a spa-like bath. The second level offers five additional spacious en-suite bedrooms, ensuring comfort and privacy. The lower walkout level is an entertainer's paradise, featuring a gym and a entertaining area. The finished third floor adds extra space fo

$5,200,000

6 beds11 baths13,979 sq ft

2959 Congress St, Fairfield, CT 06824

Rejuvenating spa • Gourmet kitchen • Spa like bath

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
Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a dramatic wall of windows. Designed for entertainment, the formal dining room features tray ceilings and bay windows that create a bright, open atmosphere. At the center of the home, the chef's kitchen boasts a professional-grade Viking range, double ovens, a central island, and a casual dining area. F

$1,695,000

6 beds4.5 baths5,325 sq ft

212 Fence Row Dr, Fairfield, CT 06824

Private acres • Gated community • Clubhouse

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Modern elegance meets estate living at 88 Merry Meet Circle, set on 3+ manicured acres in Fairfield's premier gated community, The Ridge. Perfectly positioned where Fairfield meets Westport, this gracious colonial manor offers 5+ bedrooms, 6 full and 2 half baths, and 4 beautifully finished levels-just minutes from vibrant downtowns, beaches, dining, and trains. A grand two-story foyer with a custom staircase and Swarovski chandelier sets a stunning first impression. Sunlit interiors flow effortlessly with French doors opening to expansive terraces and lush landscaping. The chef's kitchen is a true centerpiece, featuring Wolf appliances and two large islands-perfect for both casual gatherin

$2,498,000

5 beds7 baths8,136 sq ft

88 Merry Meet Cir, Fairfield, CT 06824

Gated community • Custom staircase • Swarovski chandelier

VIDEO TOUR

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate offers a rare opportunity in one of Fairfield's most coveted locations. Set on more than two acres of beautifully landscaped grounds with distant views of Long Island Sound, the property reflects timeless elegance and a sense of place that is hard to replicate today. Across from a distinguished equestrian and family compound, and abutting the Greenfield Hill Historic District without restrictions, the setting offers both distinction and privacy. Originally built in 1844 and thoughtfully expanded, restored, and renovated over the last 25 years, the residence blends irreplaceable old-world

$3,649,000

5 beds4.5 baths4,771 sq ft

2683 Bronson Rd, Fairfield, CT 06824

Formal dining room • Expansive kitchen • Root cellar

Property at 22 Brett Rd, Fairfield, CT 06824, 5 beds, 5.5 baths

$3,750,000

5 beds5.5 baths5,000 sq ft

22 Brett Rd, Fairfield, CT 06824

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 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 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 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

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NEW CONSTRUCTION

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Cast one's eyes upon this special setting and you're instantly reminded of Mark Twain's quote. .. "Buy land, they're not making it anymore!" Picture perfect, sanctuary view, expansive level lawn, located in the heart of Fairfield. Magnificent new home built by one of the towns most prominent tradesman. Architecturally stunning turreted and stone enhanced Colonial design. Gracious open floor plan incorporating the finest in craftsmanship, integrity, modern amenity and high grade building components. Special features include a Family Rm w/ FP, adjoining Den and dedicated Home Office, Chef's Kitchen w/ all the trimmings, and a luxurious Primary Bedroom Suite w/ Sitting Rm. A finished

$2,299,000

5 beds6 baths4,700 sq ft

360 Duck Farm Rd, Fairfield, CT 06824

Open floor plan • Finished attic • Expansive level lawn

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Eight minutes from downtown Westport, escape to 11 Judges Hollow-a 1930's rustic hunting cabin on 1.6 private wooded acres at the end of a long secluded driveway. A one of a kind private in holding completely surrounded by the 180 acre Brett Woods Conservation Area, this rare property offers ultimate privacy with protected open space as your permanent neighbor. Judges Hollow is nestled within Fairfield's prestigious Greenfield Hill area, known for its historic charm and upscale residential character. This tree-lined pastoral neighborhood features homes accompanied by multiple outbuildings set on generous lots, offering privacy and tranquility while remaining conveniently connected to downto

$950,000

2 beds2 baths1,135 sq ft

11 Judges Hollow Rd, Fairfield, CT 06824

Generous lots • Private wooded acres • Protected open space

LISTED BY REDFIN3D & VIDEO TOUR

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Discover a stunning custom-crafted luxury home, complete with a separate one-bedroom guest pool house, that stands as an architecturally significant estate designed to be cherished. Nestled on meticulously landscaped grounds with picturesque views of Pawtucket Valley Country Club, this grand colonial residence offers every amenity for a refined lifestyle. As you enter the soaring foyer, you are welcomed into classic, timelessly elegant interiors featuring exquisite handcrafted millwork and coffered ceilings. The home boasts five fireplaces and abundant cabinetry, with oversized French doors and large windows that fill every room with natural light. The central gourmet kitchen flows seamless

$3,999,999

5 beds8 baths11,450 sq ft

64 Old Redding Rd, Weston, CT 06883

Home theater • Guest pool house • Landscaped grounds

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Located in one of Westport's most desirable Coleytown neighborhoods surrounded by multi-million dollar homes 24 Warnock is perfect blend of style comfort & convenience This turnkey 2851sf home on 4 floors offers close proximity to Westport's top rated schools vibrant downtown & beautiful beaches-an exceptional opportunity at this price point Thoughtfully renovated & impeccably maintained this home exudes quality craftsmanship & modern elegance The chef's kitchen features granite countertops custom cabinetry & premium finishes throughout Three beautifully updated baths combine timeless design with contemporary functionality The open & sun filled main level

$1,999,000

3 beds2.5 baths2,844 sq ft

24 Warnock Dr, Westport, CT 06880

1.01 acre lot • 2 garage spots • Pool

NEW CONSTRUCTION

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
RARE OPPORTUNITY TO CUSTOMIZE NEW CONSTRUCTION BY COASTAL LUXURY HOMES. PLANS APPROVED & PERMITS IN PLACE. CONSTRUCTION CAN BEGIN IMMEDIATELY, SAVE 6+ MOS ON NEW BUILD TIMELINE. This ultra luxury modern cul-de-sac residence features stucco exterior, DaVinci Boral roof, and expansive windows up to 10ft high. Main level includes luxe chef's kitchen w/ breakfast room opening to the great room with beautiful natural light, leading to a walk-out terrace for seamless indoor/outdoor entertaining. This floor also includes dining room, modern bar/living room for entertaining, office, and mudroom servicing both pool and garage. A showstopping plaster staircase leads upstairs to a massive primar

$6,785,000

6 beds8 baths7,888 sq ft

14 Burr School Rd, Westport, CT 06880

Approved plans • Davinci boral roof • Expansive windows

NEW CONSTRUCTION

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Winner of the prestigious 2025 HOBI Award for "Best In Town Spec Home" In CT! A rare opportunity to own a showcase property in one of Connecticut's most desirable neighborhoods, on one of the most popular, quiet cul-de-sacs in Westport! 3 miles to train. Walk to Post Rd shops/restaurants, Winslow Dog Park, Main St, Library, and Levitt Pavilion! New Construction home with Pool. Traditional lay out with modern, high end finishes and filled with natural light. 6 beds/5 full baths/ 2 half baths on 4 finished floors. Gunite Pool w/ Automatic Safety Cover. Large, flat, fenced in yard. Walk Out Lower Level to pool/yard. Full House Generator. EV Charging Outlet in Garage. City Water/Sewer

$3,695,000

6 beds6 baths5,497 sq ft

2 Webb Rd, Westport, CT 06880

Full house generator • Gunite pool • Large flat yard

Property at 6 Nutcracker Ln, Westport, CT 06880, 4 beds, 3.5 baths

$2,785,000

4 beds3.5 baths5,434 sq ft

6 Nutcracker Ln, Westport, CT 06880

Property at 4 Colony Rd, Weston, CT 06883, 2 beds, 2 baths

$799,000

2 beds2 baths1,689 sq ft

4 Colony Rd, Weston, CT 06883

Property at 40 Maple Ave N, Westport, CT 06880, 3 beds, 2 baths

$1,699,900

3 beds2 baths3,171 sq ft

40 Maple Ave N, Westport, CT 06880

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

$3,550,000

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 1001 Hulls Farm Rd, Southport, CT 06890, 3 beds, 3.5 baths

$1,849,000

3 beds3.5 baths2,760 sq ft

1001 Hulls Farm Rd, Southport, CT 06890

Property at 13 Terhune Dr, Westport, CT 06880, 5 beds, 5.5 baths

$3,999,000

5 beds5.5 baths6,010 sq ft

13 Terhune Dr, Westport, CT 06880

Property at 1 Sturges Hwy Lot 1, Westport, CT 06880, 6 beds, 6 baths

$5,400,700

6 beds6 baths5,800 sq ft

1 Sturges Hwy Lot 1, Westport, CT 06880

Property at 1 Sturges Hwy #2, Westport, CT 06880, 7 beds, 7 baths

$5,472,860

7 beds7 baths6,120 sq ft

1 Sturges Hwy #2, Westport, CT 06880

Property at 844 Mill Hill Ter, Southport, CT 06890

$749,000

— beds— baths— sq ft

844 Mill Hill Ter, Southport, CT 06890

Property at Old Easton, Weston, CT 06883

$2,500,000

— beds— baths— sq ft

Old Easton, Weston, CT 06883

Property at 107 Old Rd, Westport, CT 06880, 6 beds, 6 baths

$4,985,000

6 beds6 baths6,000 sq ft

107 Old Rd, Westport, CT 06880

Property at 6 Fox Run Ln, Westport, CT 06880

$390,000

— beds— baths— sq ft

6 Fox Run Ln, Westport, CT 06880

Average home prices near Greenfield Hill, CT

Cities

Neighborhoods

Coleytown homes for sale
$1,584,000
North End homes for sale
$425,000
West Side-West End homes for sale
$439,500
West End-West Side homes for sale
$508,000
Fairfield Beach homes for sale
$2,149,000
Black Rock homes for sale
$429,900
Greens Farms homes for sale
$4,899,000
Stratfield Village homes for sale
$729,000

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)

$1,300,000

-30.4% YoY | Nov 2025

1 year
3 year
5 year

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

Location

Data

Nov 2025

Growth

% YoY

Greenfield Hill, CT

$1,300,000

-30.4%

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