Greenfield Hill, CT homes for sale & real estate

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ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to Pepperidge Acres - a unique enclave of four homes tucked away on a private cul-de-sac ideally located on the Westport line. Conveniently to both Westport & Fairfield town amenities, this classic home sits peacefully on two level acres, offering a serene and picturesque setting. Step into the grand living room featuring a vaulted ceiling and a dramatic floor-to-ceiling, double-sided fireplace. Flowing into the state-of-the-art kitchen featuring custom cabinetry, stainless steel appliances, granite countertops, and an oversized island that opens to a cozy sitting area. Off the living areas enter to the primary bedroom en-suite, additional bedroom and updated full hall bath. C

$1,100,000

3 beds3 baths3,670 sq ft

2190 Sturges Hwy, Westport, CT 06880

2.01 acre lot • 2 garage spots • Pool

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
Discover the ease of one-level living at 2180 Cross Highway, perfectly situated in a convenient Fairfield location on the Westport border, with a full home Generac Generator and sprinkler system. This home offers a fantastic opportunity to bring your vision to life, ready for your cosmetic updates and improvements. Many expansion possibilities. Surrounded by mature plantings that provide natural beauty and privacy, the property offers a welcoming setting with plenty of potential. Whether you're looking to downsize, invest, or create your dream home, this is a rare chance to make a well-located Fairfield property your own.

$799,000

3 beds2 baths1,914 sq ft

2180 Cross Hwy, Fairfield, CT 06824

Privacy • One-level living • Mature plantings

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

$2,250,000

5 beds7 baths5,978 sq ft

2775 North St, Fairfield, CT 06824

Two dishwashers • Two farmhouse sinks • Chef's kitchen

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

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

$2,065,000

4 beds3.5 baths4,255 sq ft

158 Coventry Ln, Fairfield, CT 06824

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

$1,695,000

6 beds4.5 baths5,325 sq ft

212 Fence Row Dr, 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 480 Riders Ln, Fairfield, CT 06824, 4 beds, 3.5 baths

$1,149,000

4 beds3.5 baths5,081 sq ft

480 Riders Ln, Fairfield, CT 06824

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 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 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 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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ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Location, lifestyle, and luxury converge in this beautifully updated Transitional Colonial in Fairfield's sought-after University area. Just minutes from downtown & Black Rock shopping, this chic residence offers designer interiors, quality finishes, and a private, manicured backyard. The classic layout is open and airy, with a gracious foyer accented by shiplap, an entertaining-sized dining room, and a flexible layout that offers a main level office with built-ins and window seat plus a LR or 2nd office w/ French doors. A custom kitchen with large center island, stone counters and Viking, Monogram & Bosch appliances flows into the vaulted ceiling family room with a sleek, moder

$1,599,000

4 beds2.5 baths3,867 sq ft

338 Orchard Hill Ln, Fairfield, CT 06824

0.57 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Ideally located in the heart of the University Area, this charming colonial sits on a quiet cul-de-sac just minutes from downtown Fairfield. Step through the front door into a welcoming foyer that opens to a sun-filled living room and a spacious dining room, perfect for entertaining family and friends. The kitchen features generous counter space and flows seamlessly into the breakfast area and family room, offering access to the deck for easy indoor-outdoor living. The family room impresses with soaring ceilings and a cozy wood-burning fireplace. Upstairs, the primary suite includes a full bath and a walk-in closet. A second bedroom, home office, hallway laundry, and a second full bath comp

$899,900

2 beds2.5 baths1,900 sq ft

44 Deer Run Rd, Fairfield, CT 06824

0.43 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Welcome to 2107 North Benson, a rare Fairfield gem offering a perfect blend of versatility, space, and comfort. The property features a three bedroom main residence plus a spacious 1,300 sq. ft. one-bedroom in-law/ au pair suite, ideal for multi-generational living, guests, or supplemental income. Inside the main home, a bright eat-in kitchen with granite countertops opens to the dining area and flows seamlessly into an expansive living room with hardwood floors and a cozy fireplace-perfect for gatherings and everyday relaxation. The four-season sunroom brings the outdoors in, leading to a large deck overlooking a private yard and in-ground pool, creating the ultimate entertaining retreat.

$1,000,000

4 beds4 baths3,957 sq ft

2107 N Benson Rd, Fairfield, CT 06824

0.6 acre lot • 2 garage spots • Pool

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Tucked away on a picturesque property with a peaceful pond and complete privacy, this custom-built home is truly exceptional. From the moment you step onto the welcoming front porch, you'll feel the warmth and quality throughout. The sunlit kitchen is beautifully appointed with top-of-the-line appliances and a built-in banquette by the cozy fireplace, opening seamlessly to the inviting family room with a stunning fireplace & French doors to the patio. Entertain effortlessly in the elegant dining room w/ butler's pantry & spacious living room. A first-floor office w/ pocket doors offers a quiet retreat for work or study. Upstairs, the primary suite is a sanctuary w/ vaulted ceili

$3,950,000

5 beds6 baths5,771 sq ft

116 Roseville Rd, Westport, CT 06880

2.55 acre lot • 3 garage spots • Pool

OPEN TODAY, 11AM TO 2PM

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
Refreshed and gorgeous, 3 Mayflower Lane offers a perfect blend of modern sophistication and timeless charm. This beautiful home is set on over two idyllic acres, overlooking the Aspetuck Valley Country Club Golf Course. It has been meticulously maintained and upgraded, offering a fresh, contemporary feel while retaining its classic charm. Upon entering the grand foyer with double-height ceilings and a spiral staircase, you are immediately struck by the abundant light and spaciousness. The chef's kitchen has been designed for both functionality and beauty, featuring top-of-the-line appliances, custom cabinetry, a large center island, and granite countertops. The primary suite, located on th

$2,100,000

6 beds6 baths6,342 sq ft

3 Mayflower Ln, Weston, CT 06883

2.24 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Greenfield Hill, CT Homes for Sale
An incredible opportunity has become available to purchase a much-loved, solid home on excellent property in a sought-after location. One of the most exciting new listings to hit the Westport market in months- a scenic, usable 1.25 acres on a beautiful street of high-value homes is the setting for this spacious Colonial. This timeless floor plan offers gracious rooms, hardwood floors in many areas and upgraded thermopane windows. The large front-to-back living room has a fireplace, and an oversized dining room. The kitchen overlooks a gorgeous backyard & flows through to a large family room/alternative dining room w/ vaulted ceiling & access to a deck. A main level play/rec room

$1,250,000

4 beds3 baths3,446 sq ft

26 Cob Dr, Westport, CT 06880

1.25 acre lot • 2 garage spots • Car-dependent

Property at 33 Middlebrook Pl, Fairfield, CT 06824, 4 beds, 5.5 baths

$2,099,900

4 beds5.5 baths5,256 sq ft

33 Middlebrook Pl, Fairfield, CT 06824

Property at 80 Gilbert Hwy, Fairfield, CT 06824, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths1,664 sq ft

80 Gilbert Hwy, Fairfield, CT 06824

Property at 342 Midlock Rd, Fairfield, CT 06824, 5 beds, 6.5 baths

$2,799,999

5 beds6.5 baths7,269 sq ft

342 Midlock Rd, Fairfield, CT 06824

Property at 2 Webb Rd, Westport, CT 06880, 6 beds, 6 baths

$3,695,000

6 beds6 baths5,497 sq ft

2 Webb 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

$829,000

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 125 Old Rd, Westport, CT 06880, 6 beds, 7.5 baths

$5,200,000

6 beds7.5 baths8,545 sq ft

125 Old Rd, Westport, CT 06880

Property at 10 Debra Ln, Westport, CT 06880, 6 beds, 7.5 baths

$5,500,000

6 beds7.5 baths9,601 sq ft

10 Debra Ln, Westport, CT 06880

Property at 53 Hilltop Dr, Southport, CT 06890, 3 beds, 2 baths

$699,999

3 beds2 baths1,382 sq ft

53 Hilltop Dr, Southport, CT 06890

Property at 118 Roseville Rd, Westport, CT 06880, 3 beds, 2.5 baths

$3,100,000

3 beds2.5 baths4,243 sq ft

118 Roseville Rd, Westport, CT 06880

Property at 254 Sherwood Farm Rd, Fairfield, CT 06824, 4 beds, 4.5 baths

$1,899,000

4 beds4.5 baths4,515 sq ft

254 Sherwood Farm Rd, 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

Average home prices near Greenfield Hill, CT

Cities

Neighborhoods

North End homes for sale
$427,500
West Side-West End homes for sale
$429,900
West End-West Side homes for sale
$499,900
Fairfield Beach homes for sale
$2,297,000
Black Rock homes for sale
$529,900
Greens Farms homes for sale
$4,797,500
Old Hill homes for sale
$2,527,000

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)

$1,787,500

-5.5% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Greenfield Hill, CT

$1,787,500

-5.5%

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