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:
UNDER CONSTRUCTION - Photos are architectural renderings and are intended to illustrate the home's anticipated finished appearance. Actual finishes, materials, features, and landscaping may vary. Be the first to own this exceptional new luxury home in one of Weston's most desirable locations. Situated on approximately 2 private acres, this custom-designed 5,600 SF residence offers 4 bedrooms, 4 full bathrooms, 1 half bath, and a 3-car garage. Designed with luxury and comfort in mind, the home features soaring cathedral ceilings, an open-concept floor plan, a fireplace, a gourmet kitchen with premium appliances, a finished lower level, heat pump with central air, private well and septic, and

$2,299,000

4 beds5.5 baths5,600 sq ft

15 Cannondale Rd, Weston, CT 06883

Private acres • Gourmet kitchen • Custom designed

OPEN SAT, 1PM TO 4PM

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Well-maintained 3-bedroom townhouse in the desirable Villages at Rivington! This inviting home features an open-concept floor plan with a seamless flow between the living room, highlighted by a custom accent wall, the dining area, and the spacious kitchen with a center island overlooking the breakfast area. Sliding glass doors lead to a private patio, creating the perfect space for outdoor dining and entertaining. Upstairs, the primary suite boasts a vaulted ceiling, a walk-in closet, and a private full bath. Two additional bedrooms share a full bath and are conveniently located near the second-floor laundry closet. The lower level offers a practical mudroom that leads to the tandem two-car

$659,900

3 beds2.5 baths1,776 sq ft

42 Moorland Dr #42, Danbury, CT 06810

Custom accent wall • Walk-in closet • Primary suite

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
If you've been searching for the perfect 55+ townhome in Newtown, the search ends at 23 Woods Lane. Tucked in the sought-after Newtown Woods community, this beautifully maintained 2-bedroom, 2.5-bathroom townhome offers just over 2,000 square feet of thoughtfully designed living space, and it truly shows. Soaring vaulted ceilings and an open-concept layout create an immediate wow factor from the moment you walk in. The living and dining areas flow effortlessly together, anchored by a cozy gas fireplace and flooded with natural light from large windows. Sliding glass doors open to a private deck overlooking peaceful, wooded surroundings, the kind of backdrop that makes every season beautiful

$600,000

2 beds2.5 baths2,073 sq ft

23 Woods Ln #23, Newtown, CT 06470

Private deck • Cozy gas fireplace • Spa like en suite

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance. Designed by Hunt & Hunt Architects and completed in 1914 for inventor Thomas Robins, the main residence has been thoughtfully renovated and modernized throughout, including new electrical and plumbing systems, an expanded eat-in chef's kitchen, and beautifully reimagined open living and dining spaces designed for both grand entertaining and everyday

$12,100,000

5 beds5.5 baths5,560 sq ft

123 Saddle Rock Rd, Stamford, CT 06902

Private balcony • Waterfront compound • Private peninsula

ABOUT THIS HOME
Home with a Pool for sale in Fairfield County, CT:
Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal architecture, exceptional craftsmanship, and modern construction. Thoughtfully designed for both grand entertaining and everyday living, the residence balances expansive gathering spaces with private retreats, all oriented toward the water. A cedar shake exterior, stone detailing, and sunrise to sun

$14,500,000

6 beds7 baths8,738 sq ft

379 Ocean Dr W, Stamford, CT 06902

Primary suite • Cedar shake exterior • Waterfront residence

Property at 98 Gillies Ln #98, Norwalk, CT 06854, 2 beds, 2 baths

$499,000

2 beds2 baths1,662 sq ft

98 Gillies Ln #98, Norwalk, CT 06854

Property at 91 Strawberry Hill Ave #533, Stamford, CT 06902, 2 beds, 1 bath

$315,000

2 beds1 bath875 sq ft

91 Strawberry Hill Ave #533, Stamford, CT 06902

Property at 76 Maple Tree Ave #3, Stamford, CT 06906, 2 beds, 1 bath

$545,000

2 beds1 bath1,058 sq ft

76 Maple Tree Ave #3, Stamford, CT 06906

Property at 125 Battery Park Dr, Bridgeport, CT 06605, 3 beds, 2.5 baths

$1,999,900

3 beds2.5 baths2,381 sq ft

125 Battery Park Dr, Bridgeport, CT 06605

Property at 106 Gillies Ln #106, Norwalk, CT 06854, 3 beds, 2 baths

$499,500

3 beds2 baths1,806 sq ft

106 Gillies Ln #106, Norwalk, CT 06854

Property at 96 Allencrest Dr, Stratford, CT 06614, 4 beds, 2 baths

$550,000

4 beds2 baths1,884 sq ft

96 Allencrest Dr, Stratford, CT 06614

Property at 260 Pilgrim Ln, Stratford, CT 06614, 4 beds, 3 baths

$749,900

4 beds3 baths2,304 sq ft

260 Pilgrim Ln, Stratford, CT 06614

Property at 6 Elizabeth St, Newtown, CT 06470, 4 beds, 2.5 baths

$950,000

4 beds2.5 baths3,362 sq ft

6 Elizabeth St, Newtown, CT 06470

Property at 5 Deer Run #5, Bethel, CT 06801, 2 beds, 1.5 baths

$340,000

2 beds1.5 baths1,312 sq ft

5 Deer Run #5, Bethel, CT 06801

Property at 203 Wildflower Ln, Fairfield, CT 06824, 5 beds, 5 baths

$1,995,000

5 beds5 baths6,136 sq ft

203 Wildflower Ln, Fairfield, CT 06824

Property at 222 Brookside Rd, Darien, CT 06820, 5 beds, 5.5 baths

$3,900,000

5 beds5.5 baths10,000 sq ft

222 Brookside Rd, Darien, CT 06820

Property at 109 Woodland Rd #1009, Danbury, CT 06810, 2 beds, 2 baths

$510,000

2 beds2 baths1,215 sq ft

109 Woodland Rd #1009, Danbury, CT 06810

Property at 110 Woodland Rd #1010, Danbury, CT 06810, 2 beds, 2 baths

$567,000

2 beds2 baths1,277 sq ft

110 Woodland Rd #1010, Danbury, CT 06810

Property at 13 Edgemarth Hill Rd, Westport, CT 06880, 7 beds, 7.5 baths

$5,999,999

7 beds7.5 baths8,700 sq ft

13 Edgemarth Hill Rd, Westport, CT 06880

Property at 95 Old Saugatuck Rd, Norwalk, CT 06855, 5 beds, 6.5 baths

$4,200,000

5 beds6.5 baths8,294 sq ft

95 Old Saugatuck Rd, Norwalk, CT 06855

Property at 2625 Park Ave Unit 10H, Bridgeport, CT 06604, 1 bath

$149,000

— beds1 bath571 sq ft

2625 Park Ave Unit 10H, Bridgeport, CT 06604

Property at 83 Chestnut St Unit D, Bethel, CT 06801, 1 bed, 1 bath

$239,900

1 bed1 bath764 sq ft

83 Chestnut St Unit D, Bethel, CT 06801

Property at 49 Middle River Rd, Danbury, CT 06811, 4 beds, 4.5 baths

$2,180,000

4 beds4.5 baths8,274 sq ft

49 Middle River Rd, Danbury, CT 06811

Property at 351 Wilton Rd W, Ridgefield, CT 06877, 5 beds, 6 baths

$2,600,000

5 beds6 baths5,410 sq ft

351 Wilton Rd W, Ridgefield, CT 06877

Property at 736 Lake Ave, Greenwich, CT 06830, 6 beds, 7 baths

$7,450,000

6 beds7 baths6,972 sq ft

736 Lake Ave, Greenwich, CT 06830

Property at 1076 Westover Rd, Stamford, CT 06902, 4 beds, 4.5 baths

$2,399,000

4 beds4.5 baths4,531 sq ft

1076 Westover Rd, Stamford, CT 06902

Marr Caruso Realty Group

Property at 77 Havemeyer Ln #310, Stamford, CT 06902, 3 beds, 2 baths

$1,100,000

3 beds2 baths1,400 sq ft

77 Havemeyer Ln #310, Stamford, CT 06902

Property at 2289 Bedford St Unit G2, Stamford, CT 06905, 2 beds, 2 baths

$599,000

2 beds2 baths1,199 sq ft

2289 Bedford St Unit G2, Stamford, CT 06905

Property at 32 Silver Ridge Cmn, Weston, CT 06883, 4 beds, 4 baths

$1,750,000

4 beds4 baths4,234 sq ft

32 Silver Ridge Cmn, Weston, CT 06883

Property at 6 Rolling Ridge Rd #6, Monroe, CT 06468, 2 beds, 1.5 baths

$409,900

2 beds1.5 baths1,444 sq ft

6 Rolling Ridge Rd #6, Monroe, CT 06468

Property at 96 Ledgebrook Dr #96, Norwalk, CT 06854, 2 beds, 1 bath

$465,000

2 beds1 bath1,095 sq ft

96 Ledgebrook Dr #96, Norwalk, CT 06854

Property at 91 Strawberry Hill Ave #425, Stamford, CT 06902, 1 bed, 1 bath

$255,000

1 bed1 bath725 sq ft

91 Strawberry Hill Ave #425, Stamford, CT 06902

Property at 25 Forest St Unit 4F, Stamford, CT 06901, 1 bed, 1 bath

$465,000

1 bed1 bath875 sq ft

25 Forest St Unit 4F, Stamford, CT 06901

Property at 156 Morningside Ct #156, Shelton, CT 06484, 3 beds, 2.5 baths

$579,900

3 beds2.5 baths2,385 sq ft

156 Morningside Ct #156, Shelton, CT 06484

Property at 279 Saugatuck Ave, Westport, CT 06880, 5 beds, 7.5 baths

$14,900,000

5 beds7.5 baths9,546 sq ft

279 Saugatuck Ave, Westport, CT 06880

Property at 835 Thorme St, Bridgeport, CT 06606, 4 beds, 2 baths

$490,000

4 beds2 baths1,665 sq ft

835 Thorme St, Bridgeport, CT 06606

Property at 8 Live Oak Rd, Norwalk, CT 06851, 4 beds, 2.5 baths

$1,325,000

4 beds2.5 baths2,505 sq ft

8 Live Oak Rd, Norwalk, CT 06851

Property at 135 Mayfield Dr #135, Trumbull, CT 06611, 2 beds, 2 baths

$539,900

2 beds2 baths1,767 sq ft

135 Mayfield Dr #135, Trumbull, CT 06611

Property at 51 Faith Ln #51, Danbury, CT 06810, 2 beds, 2.5 baths

$475,000

2 beds2.5 baths2,202 sq ft

51 Faith Ln #51, Danbury, CT 06810

Property at 38 Prospect Rd, Westport, CT 06880, 6 beds, 7.5 baths

$9,200,000

6 beds7.5 baths8,623 sq ft

38 Prospect Rd, Westport, CT 06880

Property at 293 Sturges Ridge Rd, Wilton, CT 06897, 5 beds, 3.5 baths

$1,799,000

5 beds3.5 baths4,347 sq ft

293 Sturges Ridge Rd, Wilton, CT 06897

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Based on information submitted to the MLS GRID as of Thu Aug 27 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 469 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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