Greenfield Hill, CT homes for sale & real estate

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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
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

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

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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

NEW CONSTRUCTION

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among notable estate properties and near Brett Woods Conservation Area (186 acres) and the Roy and Margot Larsen Wildlife Sanctuary (155 acres), with convenient access to the centers of Fairfield, Southport, and Westport and approximately 55 miles to Manhattan. Construction will begin after purchase and ex

$3,750,000

5 beds5.5 baths5,000 sq ft

22 Brett Rd, Fairfield, CT 06824

New construction • Approved for a pool • 2.65 acre lot

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

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NEW 4 HRS AGO

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to 1 Boxwood Lane, a private estate where timeless design meets a lifestyle centered on wellness, balance, & renewal. Set on a coveted quiet lane, the circular drive & stone walls introduce a sense of calm while sweeping lawns & specimen plantings create a serene, park-like environment worlds away from daily stress. Inside, sun-drenched interiors open seamlessly through French doors & expansive windows. The open layout encourages effortless living, anchored by a recently renovated custom Chef's Kitchen-perfect for nourishing gatherings & everyday enjoyment. Architectural details, intricate millwork, & graceful transitions between living & dinin

$3,500,000

5 beds7 baths7,359 sq ft

1 Boxwood Ln, Westport, CT 06880

Circular drive • Specimen plantings • Stone walls

COMING SOON

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to 84 Delaware Road, a thoughtfully expanded colonial with timeless style and modern comfort. Step on to the cozy front porch and you will know that this home is special. Enter into the 2-story foyer which is flanked by the living room and the dining room with pretty molding and Venetian chandelier. The center of the home is the chef's kitchen with 2 five ft. islands, perfect for gathering & prepping. There are stainless appliances including a 6 burner Viking range, walk-in-pantry, granite & quartz counters & a stainless farm sink. The breakfast area looks out the pretty bay window and opens directly to the family room with vaulted ceiling, stone fireplace, and hi-

$1,375,000

5 beds4.5 baths5,905 sq ft

84 Delaware Rd, Easton, CT 06612

2.06 acre lot • 3 garage spots • Built 1987

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ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Premier Long Lots Location | End-of-Cul-de-Sac | Pool! - Perfectly positioned at the end of a quiet cul-de-sac in Westport's highly sought-after Long Lots neighborhood, this bright and beautiful home offers exceptional privacy while remaining just minutes to the Parkway and Westport's Main Street shops and acclaimed restaurants. Set on a spectacular 1.05-acre property, this well-maintained residence features 5 bedrooms, 3.5 baths, a walk-up attic, and a walk-out basement. The expansive grounds are a true highlight, showcasing multiple patios, a gunite pool with spa, and generous lawn areas ideal for entertaining, play, or peaceful relaxation. Inside, refinished hardwood floors flow through

$1,900,000

5 beds3.5 baths3,228 sq ft

9 Victoria Ln, Westport, CT 06880

End-of-cul-de-sac • Multiple patios • Gunite pool with spa

COMING SOON

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Samp Mortar Lake is one of the most picturesque spots in Fairfield. As locals it's an area we appreciate passing through. At sunset it's hard not to pull over and snap a photo or sigh with joy when you see little swimmers splashing about off the beaches. Those lucky enough to own a property with deeded rights in the Lake Hills Association tend to stay for a lifetime, so you can imagine there isn't a lot of turn over making this a wonderful opportunity for the next generation. 845 Mountain Laurel has been lovingly cared for by the same family since the beginning. It is a classic Colonial that draws you in with its charm and warmth. The traditional layout includes both formal and casual rooms

$975,000

4 beds2.5 baths2,068 sq ft

845 Mountain Laurel Rd, Fairfield, CT 06824

0.55 acre lot • 2 garage spots • Built 1968

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

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

Property at 14 Burr School Rd, Westport, CT 06880, 6 beds, 8 baths

$6,785,000

6 beds8 baths7,888 sq ft

14 Burr School Rd, Westport, CT 06880

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 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 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

North End homes for sale
$425,000
West Side-West End homes for sale
$458,500
West End-West Side homes for sale
$497,650
Fairfield Beach homes for sale
$2,174,500
Black Rock homes for sale
$484,900
Greens Farms homes for sale
$4,899,000
Stratfield Village homes for sale
$699,000

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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