Homes with Basements for Sale in Greenfield Hill, CT

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ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
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
Home with Basement for sale in Greenfield Hill, CT:
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 Ctr, Fairfield, CT 06824

Gated community • Custom staircase • Swarovski chandelier

OPEN SUN, 2PM TO 4PM

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
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
Home with Basement for sale in Greenfield Hill, CT:
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

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
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 2180 Cross Hwy, Fairfield, CT 06824, 3 beds, 2 baths

$799,000

3 beds2 baths1,914 sq ft

2180 Cross Hwy, Fairfield, CT 06824

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 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 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 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 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 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 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 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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OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft ceilings, abundant natural light and more. The heart of this home is an eat-in chef's kitchen, replete with top-tier stainless steel appliances, which connects you to multiple other spaces for enjoyment or repose. Entertain with panache in the formal dining room, garden room, library, living room or grea

$2,799,999

5 beds6.5 baths7,269 sq ft

342 Midlock Rd, Fairfield, CT 06824

2.03 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
Custom built by the current and original owners, welcome to a rare opportunity in sought-after lower Easton. This rare and true one-of-a-kind home harmonizes a nature lover's dream with a vintage late mid-century vibe. The home spans over 3,100sqft on the main living level boasting three ensuite bedrooms at one end of the home and a private office, kitchen and den at the other end of the home. The formal dining room opens to the living room, both with soaring ceilings and original built in mid-century cabinetry anchoring the heart of the home. Enjoy an additional 2,953sqft in the finished walk out lower level offering a fourth and possible fifth bedroom, billiard room, family room, and a fl

$938,000

4 beds5 baths6,056 sq ft

100 E Common Rd, Easton, CT 06612

3.15 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
A one acre property nestled on a quiet Coleytown side street, this three bedroom, two bath home offers a neighborhood of beautiful natural surroundings, close proximity to school campuses and just a quick ride to downtown Westport! The main floor consists of a large rear facing living room, kitchen, dining room, two bedrooms that share a hall bath, and a primary bedroom with full bath. The lower level offers a family room with fireplace and backyard access. There is a 2 car garage as well as a screened porch. The full acre lot offers plenty of room for renovation, expansion or rebuilding. Property being sold As-Is.

$895,000

3 beds2.5 baths1,698 sq ft

9 Berkeley Rd, Westport, CT 06880

1 acre lot • $21 HOA • 2 garage spots

NEW CONSTRUCTION

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
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

0.55 acre lot • 2 garage spots • Pool

OPEN TODAY, 12PM TO 2PM

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
Welcome to 947 Galloping Hill Road. This true mid-century modern home was designed by the important architect Victor Civkin in 1967. This well thought out ranch has 4 bedrooms and 3 1/2 baths and is perfectly situated on a flat, private acre. Step inside the large foyer that has curved walls and a skylight. The living room is spacious with a rounded wall of floor to ceiling windows which flood the space with light. This room overlooks the professionally landscaped yard. The kitchen has white cabinets, stainless steel appliances, Subzero, granite counters, wood floor and a slider to the deck. The dining room has beautiful built-ins and a wood floor. There is also a curved wall of windows. Th

$1,299,999

4 beds3.5 baths4,024 sq ft

947 Galloping Hill Rd, Fairfield, CT 06824

1.04 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Home with Basement for sale in Greenfield Hill, CT:
Step into comfort and style at 4 Colony Road in Weston, CT. This charming home located on coveted private cul de sac, boasts 1,689 square feet of living space that's perfect for relaxed day-to-day living or entertaining friends. Walk into a bright and airy living room that flows into a cozy dining area, great for hosting or just enjoying a meal. The kitchen is ready for your culinary adventures, offering a functional and stylish space to whip up your favorite dishes. With two spacious bedrooms, each with its own bathroom, you'll find a private and peaceful escape to unwind. Natural light fills every corner of this home, creating an inviting and warm atmosphere. It's the perfect spot to enjo

$829,000

2 beds2 baths1,689 sq ft

4 Colony Rd, Weston, CT 06883

1 acre lot • 2 garage spots • Car-dependent

Property at 105 Charter Oak Rd, Fairfield, CT 06824, 4 beds, 2.5 baths

$1,500,000

4 beds2.5 baths3,900 sq ft

105 Charter Oak Rd, Fairfield, CT 06824

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 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

$750,000

3 beds2 baths1,382 sq ft

53 Hilltop Dr, Southport, CT 06890

Property at 111 & 115 Old Easton Tpke, Weston, CT 06883, 4 beds, 3 baths

$1,395,000

4 beds3 baths1,686 sq ft

111 & 115 Old Easton Tpke, Weston, CT 06883

Property at 1165 Stillson Rd, Fairfield, CT 06824, 4 beds, 2.5 baths

$1,399,000

4 beds2.5 baths2,704 sq ft

1165 Stillson Rd, Fairfield, CT 06824

Property at 4 Burr Farms Rd, Westport, CT 06880, 4 beds, 3 baths

$2,218,000

4 beds3 baths3,377 sq ft

4 Burr Farms Rd, Westport, CT 06880

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

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

Homes with Basements for Sale in Greenfield Hill

There are currently 17 homes with basements for sale in Greenfield Hill at a median listing price of $2.2M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Greenfield Hill stay on the market for 75 days. Popular neighborhoods include North End, Fairfield Beach, Black Rock, Greens Farms, and Long Island. This map is refreshed with the newest listings in Greenfield Hill every 15 minutes.

In the past month, 2 homes have been sold in Greenfield Hill. Find your dream home in Greenfield Hill using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Greenfield Hill are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Greenfield Hill. If you're looking to sell your home in the Greenfield Hill area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Greenfield Hill with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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