Homes with Pools for Sale in Greenfield Hill, CT

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LISTED BY REDFINVIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Greenfield Hill, CT:
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
Home with a Pool 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 a Pool for sale in Greenfield Hill, CT:
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
Home with a Pool 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 a Pool 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 Cir, Fairfield, CT 06824

Gated community • Custom staircase • Swarovski chandelier

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 2281 Redding Rd, Fairfield, CT 06824, 5 beds, 4.5 baths

$4,995,000

5 beds4.5 baths4,191 sq ft

2281 Redding 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 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 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 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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ABOUT THIS HOME
Home with a Pool for sale in Greenfield Hill, CT:
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

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Greenfield Hill, CT:
Embrace the tranquility of this exceptional equestrian estate, nestled on 4.45 acres of private beautiful land. This serene property is a haven for horse and animal lovers, featuring expansive pastures, barn, stable, shed, paddocks and sand riding ring. This one-of-a-kind property borders the Aspetuck Land Trust, offering unmatched natural beauty and privacy. The renovated and well-maintained antique farmhouse exudes charm, with many gathering spaces on the main level and a private office. The views of the property from the farmhouse are simply wonderful. There are two bedrooms and additional rooms on the upper level, allowing flexible living with excellent space. The primary suite is lovel

$1,699,000

2 beds1.5 baths2,131 sq ft

160 Cedar Rd, Southport, CT 06890

4.45 acre lot • 4 parking spots • Pool

LISTED BY REDFIN3D & VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Greenfield Hill, CT:
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
Home with a Pool for sale in Greenfield Hill, CT:
Located in one of Westport's most desirable Coleytown neighborhoods surrounded by multi-million dollar homes 24 Warnock is the 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 and 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
Home with a Pool for sale in Greenfield Hill, CT:
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

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

Custom-built home • Inviting family room • Sunlit kitchen

Property at 3 Mayflower Ln, Weston, CT 06883, 6 beds, 6 baths

$2,100,000

6 beds6 baths6,342 sq ft

3 Mayflower Ln, Weston, CT 06883

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 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 16 Burr School Rd, Westport, CT 06880, 5 beds, 4.5 baths

$3,395,000

5 beds4.5 baths5,056 sq ft

16 Burr School Rd, 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

Homes with Pools for Sale in Greenfield Hill

There are currently 13 homes with pools for sale in Greenfield Hill at a median listing price of $2.1M. 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 74 days. Popular neighborhoods include North End, West End-West Side, Fairfield Beach, Black Rock, 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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