Homes with Pools for Sale in Fairfield County, CT

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NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and informal living spaces, a dramatic entry, private library, expansive kitchen, first-floor guest suite, elevator, and finished walkout lower level with golf simulator, wet bar, wellness gym, and cold plunge. Outdoor amenities include terraced landscaping, stone walls, a 20x40 pool with integrated sp

$14,495,000

7 beds10 baths14,000 sq ft

532 Round Hill Rd, Greenwich, CT 06831

Expansive kitchen • Private library • 4.01 acre lot

3D & VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Set behind gates on over four exquisitely landscaped acres in Westport's coveted Beachside enclave, 69 Beachside Avenue is a private coastal estate offering a rare blend of scale, privacy, and resort-style living just moments from the shoreline. A long, gracious approach leads to a timeless residence defined by exceptional craftsmanship and sun-filled interiors. Expansive living spaces feature soaring ceilings, seamless flow, and walls of glass that frame the estate's serene, park-like setting-ideal for both grand entertaining and everyday living. At the center of the home, a chef's kitchen opens to elegant formal and informal spaces, creating an effortless environment for hosting. Each roo

$7,350,000

6 beds6.5 baths6,585 sq ft

69 Beachside Ave, Westport, CT 06880

4 acre lot • 2 garage spots • Pool

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected open space with no immediate neighbors, the property offers a rare sense of peace and privacy-reminiscent of the Lowcountry, the Hamptons, or Nantucket, a scale and atmosphere seldom found in Westport. Beautiful in every season, the setting also offers extraordinary birdlife and nature watching. Yet

$10,500,000

7 beds6.5 baths6,215 sq ft

4 Sherwood Island Ln, Westport, CT 06880

20.85 acre lot • 2 garage spots • Pool

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Close to town from this rare in-town Greenwich gem -- a corner lot home on a quiet cul-de-sac, just steps from Greenwich Avenue's shops, restaurants, and cafés, the Greenwich Library, renowned private schools including Brunswick School and Greenwich Academy, and minutes to Metro-North Greenwich Station, with effortless access to parks, the waterfront, and all that downtown Greenwich offers. This 4-bed, 4-bath residence delivers abundant natural light and a flexible floor plan: eat-in kitchen, dining area, living room with bay windows, den/home office, and a spacious primary suite on the main level. Three additional well-proportioned bedrooms offer room for family, guests, or a second

$2,499,999

5 beds4 baths3,302 sq ft

51 Glen Rd, Greenwich, CT 06830

0.34 acre lot • Garage • Pool

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Hidden behind Shorehaven Country Club in a gated waterfront enclave, 3 Canfield Crossing offers the rare opportunity to enjoy WATERFRONT LIVING in a NATURALLY PROTECTED WATERFRONT SETTING. Thoughtfully reimagined and extensively updated, the property combines timeless coastal design with the peace of mind of significant recent improvements, including a BRAND NEW CEDAR ROOF, new windows, several new mechanical systems, a new pool heater, and an entirely new chef's kitchen with custom cabinetry and premium appliances. Designed to embrace its waterfront setting, nearly every room captures views of the ever-changing tides. A NanaWall opens the newly renovated kitchen and living areas directly t

$4,950,000

6 beds6.5 baths8,947 sq ft

3 Canfield Xing, Norwalk, CT 06855

0.32 acre lot • 3 garage spots • Pool

Property at 2a Jeanette Rd #19, Danbury, CT 06811, 1 bed, 1 bath

$255,000

1 bed1 bath741 sq ft

2a Jeanette Rd #19, Danbury, CT 06811

Property at 133 Chambers Rd, Danbury, CT 06811, 4 beds, 3.5 baths

$745,000

4 beds3.5 baths3,154 sq ft

133 Chambers Rd, Danbury, CT 06811

Property at 4800 Congress St, Fairfield, CT 06824, 7 beds, 8.5 baths

$12,000,000

7 beds8.5 baths9,129 sq ft

4800 Congress St, Fairfield, CT 06824

Property at 16 Doubling Rd, Greenwich, CT 06830, 9 beds, 11 baths

$19,950,000

9 beds11 baths16,154 sq ft

16 Doubling Rd, Greenwich, CT 06830

Property at 185 Grandview Ave, Bridgeport, CT 06606, 6 beds, 2 baths

$495,000

6 beds2 baths3,108 sq ft

185 Grandview Ave, Bridgeport, CT 06606

Property at 640 Round Hill Rd, Greenwich, CT 06831, 5 beds, 5 baths

$6,200,000

5 beds5 baths3,669 sq ft

640 Round Hill Rd, Greenwich, CT 06831

Property at 3300 Park Ave #33, Bridgeport, CT 06604, 4 beds, 3.5 baths

$699,000

4 beds3.5 baths2,474 sq ft

3300 Park Ave #33, Bridgeport, CT 06604

Property at 111 Byram Shore Rd, Greenwich, CT 06830, 5 beds, 4 baths

$10,350,000

5 beds4 baths8,223 sq ft

111 Byram Shore Rd, Greenwich, CT 06830

Property at 34 Carrington Dr, Greenwich, CT 06831, 6 beds, 7.5 baths

$8,250,000

6 beds7.5 baths9,440 sq ft

34 Carrington Dr, Greenwich, CT 06831

Property at 9 Lawson Ln #9, Ridgefield, CT 06877, 2 beds, 2.5 baths

$499,000

2 beds2.5 baths1,400 sq ft

9 Lawson Ln #9, Ridgefield, CT 06877

Property at 129 Davis Hill Rd, Weston, CT 06883, 4 beds, 4 baths

$1,695,000

4 beds4 baths3,822 sq ft

129 Davis Hill Rd, Weston, CT 06883

Property at 16 East Trl, Darien, CT 06820, 9 beds, 8.5 baths

$8,495,000

9 beds8.5 baths8,188 sq ft

16 East Trl, Darien, CT 06820

Property at 67 Stag Ln, Greenwich, CT 06831, 6 beds, 9 baths

$10,995,000

6 beds9 baths12,310 sq ft

67 Stag Ln, Greenwich, CT 06831

Property at 21 Holiday Point Rd, Sherman, CT 06784, 4 beds, 3.5 baths

$1,100,000

4 beds3.5 baths4,854 sq ft

21 Holiday Point Rd, Sherman, CT 06784

Property at 21 Lockwood Cir, Westport, CT 06880, 6 beds, 6.5 baths

$4,495,000

6 beds6.5 baths6,611 sq ft

21 Lockwood Cir, Westport, CT 06880

Property at 214 Good Hill Rd, Weston, CT 06883, 7 beds, 7 baths

$3,149,000

7 beds7 baths11,075 sq ft

214 Good Hill Rd, Weston, CT 06883

Property at 315 Navajo Ln Unit A, Stratford, CT 06614, 2 beds, 3 baths

$499,000

2 beds3 baths2,434 sq ft

315 Navajo Ln Unit A, Stratford, CT 06614

Property at 13 Algonquin Ln Unit B, Stratford, CT 06614, 1 bed, 1.5 baths

$396,000

1 bed1.5 baths1,480 sq ft

13 Algonquin Ln Unit B, Stratford, CT 06614

Property at 2 Chatham Ter, Bridgeport, CT 06606, 3 beds, 3 baths

$499,900

3 beds3 baths1,562 sq ft

2 Chatham Ter, Bridgeport, CT 06606

Property at 236 & 250 Main St, Ridgefield, CT 06877, 8 beds, 8 baths

$7,995,000

8 beds8 baths8,934 sq ft

236 & 250 Main St, Ridgefield, CT 06877

Property at 38 Partridge Hollow Rd, Greenwich, CT 06831, 5 beds, 7.5 baths

$6,995,000

5 beds7.5 baths10,981 sq ft

38 Partridge Hollow Rd, Greenwich, CT 06831

Property at 20 Laura Dr, Danbury, CT 06811, 4 beds, 3.5 baths

$975,000

4 beds3.5 baths3,668 sq ft

20 Laura Dr, Danbury, CT 06811

Property at 135 & 129 Zaccheus Mead Ln, Greenwich, CT 06831, 3 beds, 4 baths

$5,495,000

3 beds4 baths5,304 sq ft

135 & 129 Zaccheus Mead Ln, Greenwich, CT 06831

Property at 550 Round Hill Rd, Greenwich, CT 06831, 8 beds, 11 baths

$12,900,000

8 beds11 baths13,268 sq ft

550 Round Hill Rd, Greenwich, CT 06831

Property at 206 Umpawaug Rd, Redding, CT 06896, 7 beds, 10.5 baths

$7,725,000

7 beds10.5 baths13,094 sq ft

206 Umpawaug Rd, Redding, CT 06896

Property at 69 Birch Rd, Fairfield, CT 06824, 4 beds, 4.5 baths

$5,750,000

4 beds4.5 baths3,800 sq ft

69 Birch Rd, Fairfield, CT 06824

Property at 246 Brookside Rd, Darien, CT 06820, 7 beds, 8 baths

$7,900,000

7 beds8 baths8,100 sq ft

246 Brookside Rd, Darien, CT 06820

Property at 22 Pent Rd, Weston, CT 06883, 4 beds, 5.5 baths

$2,995,000

4 beds5.5 baths5,448 sq ft

22 Pent Rd, Weston, CT 06883

Property at 38 Doral Farm Rd, Stamford, CT 06902, 3 beds, 2.5 baths

$1,195,000

3 beds2.5 baths3,132 sq ft

38 Doral Farm Rd, Stamford, CT 06902

Property at 5060 Main St, Stratford, CT 06614, 3 beds, 3.5 baths

$1,699,000

3 beds3.5 baths4,643 sq ft

5060 Main St, Stratford, CT 06614

Property at 8 Loretta Ct, Westport, CT 06880, 6 beds, 7.5 baths

$6,895,000

6 beds7.5 baths9,576 sq ft

8 Loretta Ct, Westport, CT 06880

Property at 16 Shady Ln, Redding, CT 06896, 4 beds, 3 baths

$1,099,000

4 beds3 baths4,316 sq ft

16 Shady Ln, Redding, CT 06896

Property at 11 Judges Hollow Rd, Fairfield, CT 06824, 2 beds, 2 baths

$925,000

2 beds2 baths1,135 sq ft

11 Judges Hollow Rd, Fairfield, CT 06824

Property at 5 & 7 John St, Greenwich, CT 06831, 10 beds, 14 baths

$24,000,000

10 beds14 baths15,820 sq ft

5 & 7 John St, Greenwich, CT 06831

Property at 50 Glenbrook Rd Unit 5G, Stamford, CT 06902, 1 bed, 1.5 baths

$330,000

1 bed1.5 baths1,071 sq ft

50 Glenbrook Rd Unit 5G, Stamford, CT 06902

Property at 49 Great Ring Rd, Sandy Hook, CT 06482, 7 beds, 8.5 baths

$1,930,000

7 beds8.5 baths5,883 sq ft

49 Great Ring Rd, Sandy Hook, CT 06482

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Based on information submitted to the MLS GRID as of Fri Aug 28 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Fairfield County

There are currently 468 homes with pools for sale in Fairfield County at a median listing price of $719K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Fairfield County stay on the market for 45 days and receive 2 offers. This map is refreshed with the newest listings in Fairfield County every 15 minutes.

In the past month, 1094 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 875 condos, 1 townhouse, and 202 multi-family units for sale in Fairfield County last month. Find your dream home in Fairfield County 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 Fairfield County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Fairfield County. If you're looking to sell your home in the Fairfield County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Fairfield County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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