Homes with Pools for Sale in New Canaan, CT

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FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Hidden away at the end of a coveted West Side cul-de-sac, 48 Driftway Lane is a private estate tucked among the winding back roads of New Canaan. Perched atop 1.62 beautifully landscaped acres and surrounded by nature, the setting offers a rare sense of peace and privacy, yet remains just minutes from downtown New Canaan and approximately one hour from New York City. Newly constructed from the ground up in 2017 and offering over 10,000 square feet of thoughtfully curated living space, the home unfolds through a series of light-filled rooms where architectural detail, craftsmanship, and connection take center stage. A grand central foyer showcases a statement staircase framed by glass railin

$5,999,500

5 beds6 baths10,655 sq ft

48 Driftway Ln, New Canaan, CT 06840

Designer kitchen • Landscaped acres • Soaring ceilings

OPEN NOV 3, 12PM TO 2PM

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
A private world of its own. Newly built and set behind a gated entrance on 2.25 landscaped acres, this Scandinavian-inspired contemporary estate pairs thoughtful architecture and exceptional craftsmanship with custom-stained Accoya siding, a pool and spa, attached pool house and full guest house-all remarkably close to the heart of New Canaan. Inside, generous rooms, seven fireplaces and an elevator set the stage for interiors rich in detail. Limewashed walls, designer lighting, custom millwork and distinctive architectural elements give each room its own personality, while natural light and views of the grounds are a constant. Control4 home automation, whole-home audio and California Close

$8,740,000

7 beds9.5 baths14,216 sq ft

259 Frogtown Rd, New Canaan, CT 06840

Landscaped acres • Elevator • Gated entrance

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Masterfully reimagined in 2026 through a complete renovation and expansion by GreenDay Co. , this 6,529SF modern estate spans 2.43 scenic acres, incorporating refined architecture in an extraordinary natural sanctuary. Historic stone walls, walking trails, mature specimen plantings and a tranquil pond frame the private grounds once home to George Valchar, author of the book "My Connecticut Garden. " Inside, an organic-modern aesthetic unfolds with wide-plank white oak flooring, bespoke limewash finishes, seamless flush baseboards and expansive glass windows filling the interior with natural light. The chef's kitchen features custom white oak millwork, Dolce Vita stone surfaces, a

$4,295,000

6 beds7.5 baths6,529 sq ft

311 S Bald Hill Rd, New Canaan, CT 06840

Complete renovation • Spa-inspired bath • Butler's pantry

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Hidden behind gates and surrounded by 5.5 acres of pristine, rolling lawns, this extraordinary stone manor estate is a masterclass in old-world craftsmanship and cutting-edge modern innovation. Anchored by a separately deeded 2 acre lot with a guest house, the property presents rare flexibility and long-term value, perfectly suited for multi-generational living, guests, or future expansion. Originally constructed in 1927, the residence has been comprehensively reimagined and renovated from the inside out, preserving its architectural integrity while delivering a fully modernized, high-tech smart home experience. With all new systems, infrastructure, and finishes including new HVAC, electric

$9,250,000

7 beds7 baths9,573 sq ft

78 & 92 Pastures Ln, New Canaan, CT 06840

High-tech smart home • New hvac • Guest house

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Set high above West Road on nearly five sunlit acres, the Leuthold House embraces south and west light and looks out over its own spring-fed pond from every room. Allan Gelbin, the Frank Lloyd Wright apprentice who supervised the building of Tirranna, designed it in 1966 with an unlimited budget and considered it his finest work. Offered for the first time in 29 years. A long curve of glass, white plaster and mahogany follows the land beneath deep overhangs and two planted green roofs. Life flows easily inside and out. The generous living room, with clerestory windows, fireplace and wet bar, opens through walls of glass to the terrace and a pool that traces the curve of the house. The dinin

$6,200,000

6 beds4.5 baths5,657 sq ft

631 West Rd, New Canaan, CT 06840

Private terrace • Covered carport • Spring fed pond

Property at 34 Sherwood Ln, New Canaan, CT 06840, 6 beds, 6.5 baths

$3,695,000

6 beds6.5 baths7,102 sq ft

34 Sherwood Ln, New Canaan, CT 06840

Property at 321 Oenoke Rdg, New Canaan, CT 06840, 3 beds, 3.5 baths

$2,975,000

3 beds3.5 baths3,040 sq ft

321 Oenoke Rdg, New Canaan, CT 06840

Property at 51 Briscoe Rd, New Canaan, CT 06840, 5 beds, 6 baths

$3,995,000

5 beds6 baths8,243 sq ft

51 Briscoe Rd, New Canaan, CT 06840

Property at 250 Dans Hwy, New Canaan, CT 06840, 4 beds, 3.5 baths

$2,895,000

4 beds3.5 baths4,180 sq ft

250 Dans Hwy, New Canaan, CT 06840

Property at 179 South Ave #9, New Canaan, CT 06840, 3 beds, 2.5 baths

$1,399,000

3 beds2.5 baths1,955 sq ft

179 South Ave #9, New Canaan, CT 06840

Property at 125 West Rd, New Canaan, CT 06840, 6 beds, 6.5 baths

$4,595,000

6 beds6.5 baths6,246 sq ft

125 West Rd, New Canaan, CT 06840

Property at 192 Cross Ridge Rd, New Canaan, CT 06840, 3 beds, 3 baths

$3,000,000

3 beds3 baths3,096 sq ft

192 Cross Ridge Rd, New Canaan, CT 06840

Property at 537 Oenoke Rdg, New Canaan, CT 06840, 5 beds, 6 baths

$4,595,000

5 beds6 baths6,823 sq ft

537 Oenoke Rdg, New Canaan, CT 06840

Property at 190 Brookwood Ln, New Canaan, CT 06840, 6 beds, 7 baths

$8,250,000

6 beds7 baths10,495 sq ft

190 Brookwood Ln, New Canaan, CT 06840

Property at 104 Dans Hwy, New Canaan, CT 06840, 9 beds, 12 baths

$25,500,000

9 beds12 baths14,266 sq ft

104 Dans Hwy, New Canaan, CT 06840

Property at Undisclosed address, New Canaan, CT 06840, 6 beds, 7.5 baths

$6,495,000

6 beds7.5 baths11,607 sq ft

Undisclosed address, New Canaan, CT 06840

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COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Tucked away in a beautiful, secluded setting, this tastefully updated residence is designed for both easy everyday living and effortless entertaining. With an inviting pool, expansive lawn stretching down to the Five Mile River, and wonderful indoor and outdoor gathering spaces, this property offers the perfect balance of comfort, style, and natural beauty. Bright and welcoming throughout, the thoughtfully designed interior features tasteful updates, convenient one-level living, and move-in-ready spaces. The finished walk-out lower level adds an entirely new dimension to entertaining, with direct access to the patio and in-ground pool. Whether hosting summer pool parties, gathering with fri

$1,475,000

4 beds3.5 baths3,283 sq ft

232 W Norwalk Rd, Norwalk, CT 06850

In-ground pool • Expansive lawn • Inviting pool

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
FOR SALE OR LEASE. ALSO AVAILABLE FOR RENT AT $15,000/MONTH. Tucked away on a private cul-de-sac in Wilton's sought-after Keelers Ridge neighborhood, this exceptionally maintained estate spans 2.28 acres of professionally landscaped grounds. Offering over 9,100+ sq. ft. of total finished space across the main residence and heated/cooled pool house, the property enjoys complete privacy and ideal positioning for both morning sunrises and evening sunsets. 9,100+ Sq Ft. .. Main House 6,115 sq. ft. Lower Level is finished with 1,995 sq. ft. and Pool House 1031 sq. ft. The main residence features 5 bedrooms, 4 full and 3 half baths, including a convenient main-level bedroom suite. The finished lo

$3,795,000

5 beds5.5 baths6,115 sq ft

39 Keelers Ridge Rd, Wilton, CT 06897

Private cul-de-sac • Finished lower level • Outdoor kitchen

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Not a drive by! Welcome to this bright, spacious 4-5 bedroom, 4.5-bathroom home offering endless possibilities on 1.11 private acres in the highly desirable Newfield area. Featuring hardwood floors throughout, the main level boasts a stunning gourmet granite eat-in kitchen complete with a gas stove, double ovens, and an extra-large center island with seating-perfect for entertaining. The open-concept flow leads through sliders to a spacious deck overlooking a beautiful, private backyard and a sparkling in-ground pool. The expansive dining room is built for grand entertaining, while the living room features a cozy fireplace and its own deck access. A private main-level bedroom with an en-sui

$1,340,000

4 beds3 baths3,406 sq ft

11 Joan Rd, Stamford, CT 06905

In-ground pool • Inlaw apartment • Walkout lower level

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Welcome to this beautiful, traditional Colonial offering an exceptional blend of timeless charm, spacious interiors, and outstanding indoor-outdoor living. Set on a beautifully landscaped, private and peaceful property, this inviting home offers generous room to gather, entertain, and enjoy everyday life. Hardwood floors run throughout the home, complementing its spacious rooms and warm, welcoming character. At the heart of the home is an impressive chef's kitchen featuring premium Wolf and Sub-Zero appliances, a six-burner range, double ovens, a pantry, and an extraordinary 5-by-10-foot center island-perfect for meal preparation, casual dining, and gathering with family and friends. The ex

$2,195,000

4 beds4 baths4,376 sq ft

429 Eden Rd, Stamford, CT 06907

Six-burner range • Renovated bathrooms • Expansive great room

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
Welcome to Ledgebrook, one of Norwalk's most picturesque condominium communities! This beautifully updated home offers a wonderful combination of modern improvements, comfortable living and a peaceful setting. Recent renovations include two updated bathrooms, new flooring and new carpeting in the entrance and stairway. Enjoy relaxing or entertaining on your private deck overlooking the beautifully landscaped grounds. Ledgebrook offers a resort-like atmosphere with a swimming pool, clubhouse, scenic walking paths and a lovely pond with fountain. Conveniently located near shopping, restaurants, Oak Hills Park Golf Course, Norwalk Hospital and major commuting routes. An exceptional opportunity

$505,226

2 beds2 baths1,662 sq ft

5 Ledgebrook Dr #5, Norwalk, CT 06850

Private deck • Clubhouse • Landscaped grounds

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Home with a Pool for sale in New Canaan, CT:
SELLER WILL PAY UP TO 3% CLOSING COST & PREPAIDS ACCDEPTED OFFER! POOL, FENCED YARD, SCREENED PORCH & FIREPLACE - WELCOME TO 51 MAHER DRIVE! This inviting 3-bedroom, 1-1.5bath split-level offers the perfect combination of indoor comfort, outdoor enjoyment and convenient Norwalk living. Situated on a . 20-acre lot, the home features 6 rooms with a versatile split-level layout, a warm and inviting living area with fireplace, 3 bedrooms above with a possible 4th converting family room by placing a door at stairs, 1 full 1 Half baths and a one-car garage. Step outside and enjoy your own backyard retreat! The fenced-in yard provides privacy and plenty of room for entertaining, recrea

$699,900

3 beds1.5 baths1,076 sq ft

51 Maher Dr, Norwalk, CT 06850

Fenced yard • Convenient access • Screened porch

Property at 225 Lakeside Dr, South Salem, NY 10590, 1 bath

$349,000

Studio1 bath986 sq ft

225 Lakeside Dr, South Salem, NY 10590

Listing by Redfin Real Estate

Property at 292 Smith Ridge Rd, South Salem, NY 10590, 4 beds, 4.5 baths

$1,899,000

4 beds4.5 baths5,666 sq ft

292 Smith Ridge Rd, South Salem, NY 10590

Listing by William Raveis-New York LLC

Property at 451 Mansfield Ave, Darien, CT 06820, 7 beds, 10 baths

$6,985,000

7 beds10 baths9,058 sq ft

451 Mansfield Ave, Darien, CT 06820

Property at 21 School Rd, Wilton, CT 06897, 6 beds, 6 baths

$3,999,999

6 beds6 baths7,793 sq ft

21 School Rd, Wilton, CT 06897

Property at 140 Vista Rd, Wilton, CT 06897, 1 bed, 2 baths

$1,050,000

1 bed2 baths2,560 sq ft

140 Vista Rd, Wilton, CT 06897

Property at 64 Huckleberry Holw, Stamford, CT 06903, 5 beds, 4.5 baths

$2,395,000

5 beds4.5 baths6,440 sq ft

64 Huckleberry Holw, Stamford, CT 06903

Property at 100 Gillies Ln #100, Norwalk, CT 06854, 3 beds, 2 baths

$689,000

3 beds2 baths1,806 sq ft

100 Gillies Ln #100, Norwalk, CT 06854

Property at 121 Parry Rd, Stamford, CT 06907, 5 beds, 3.5 baths

$1,399,000

5 beds3.5 baths4,177 sq ft

121 Parry Rd, Stamford, CT 06907

Property at 100 Glen SIDE #100, Wilton, CT 06897, 2 beds, 2.5 baths

$579,000

2 beds2.5 baths1,555 sq ft

100 Glen SIDE #100, Wilton, CT 06897

Property at 474 Brookside Rd, New Canaan, CT 06840, 6 beds, 4.5 baths

$5,895,000

6 beds4.5 baths7,723 sq ft

474 Brookside Rd, New Canaan, CT 06840

Property at 68 Parry Rd, Stamford, CT 06907, 3 beds, 2.5 baths

$1,350,000

3 beds2.5 baths2,790 sq ft

68 Parry Rd, Stamford, CT 06907

Property at 29 Bender Way, Pound Ridge, NY 10576, 4 beds, 3.5 baths

$2,250,000

4 beds3.5 baths4,170 sq ft

29 Bender Way, Pound Ridge, NY 10576

Listing by Ginnel Real Estate

Property at 24 Graenest Ridge Rd, Wilton, CT 06897, 3 beds, 3.5 baths

$3,800,000

3 beds3.5 baths4,386 sq ft

24 Graenest Ridge Rd, Wilton, CT 06897

Property at 72 Old Mill River Rd, Pound Ridge, NY 10576, 3 beds, 3.5 baths

$1,850,000

3 beds3.5 baths3,435 sq ft

72 Old Mill River Rd, Pound Ridge, NY 10576

Listing by Ginnel Real Estate

Homes with Pools for Sale in New Canaan

There are currently 16 homes with pools for sale in New Canaan at a median listing price of $2.5M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in New Canaan stay on the market for 44 days and receive 1 offers. This map is refreshed with the newest listings in New Canaan every 15 minutes.

In the past month, 23 homes have been sold in New Canaan. In addition to houses in New Canaan, there were also 31 condos, 0 townhouses, and 4 multi-family units for sale in New Canaan last month. Find your dream home in New Canaan 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 New Canaan are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in New Canaan. If you're looking to sell your home in the New Canaan area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in New Canaan with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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