Homes with Pools for Sale in Weston, CT

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ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
Welcome to "Snowdrop Hill, " a lovingly restored gem located at 102 Eleven O'Clock Road in Weston. Surrounded by old New England stone walls and a private gate, this enchanting English stone and shingled home, originally constructed in the 1940s, has undergone a total transformation that enhances its historical charm while providing modern comforts. The home features a beautifully renovated kitchen and all new bathrooms, offering a modern touch to its timeless elegance. One of the standout features of this property is the newly built annex, which could serve as a perfect in-law, nanny or care-giver suite, offering privacy and comfort for extended family or guests or additional spa

$1,499,000

3 beds3 baths3,890 sq ft

102 Eleven O'clock Rd, Weston, CT 06883

3 acre lot • Garage • Built 1947

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ABOUT THIS HOME
Home with a Pool for sale in Weston, 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 Weston, CT:
Welcome to 8 Messex Lane, a classic Colonial perfectly positioned on a private cul-de-sac in sought-after Weston. Set on over 2 acres of beautiful, natural grounds, this 4-bedroom, 2.5-bath home offers an ideal blend of comfortable living spaces and outdoor beauty. The home's 3,208 square feet of heated living space provides generous room for everyday life and entertaining. Two cozy fireplaces add warmth and character throughout, while large windows capture abundant natural light. The thoughtful floor plan includes 9 well-proportioned rooms that flow effortlessly from one to the next. Outside, the property truly shines. A spacious deck overlooks the lovely yard and serves as the perfect van

$975,000

4 beds2.5 baths2,804 sq ft

8 Messex Ln, Weston, CT 06883

2.02 acre lot • 2 garage spots • Built 1979

ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
This exceptional stone home, blending contemporary design with natural tranquility, sits on 2 private acres in Weston. Expertly engineered & beautifully constructed, the home welcomes you through a dramatic two-story foyer into a sun-filled living room with floor-to-cathedral windows, a custom two-sided fireplace, and sweeping woodland views. Open chef's kitchen features granite countertops, custom cabinetry, granite center island, premium built-in appliances: Sub-Zero, Thermador stoves, Miele cappuccino station, warming oven, steamer. The large dining room offers perfect space for entertaining. Main level includes three bedrooms, highlighted by a spacious primary suite w sitting room

$1,199,000

5 beds4 baths3,581 sq ft

198 Steep Hill Rd, Weston, CT 06883

2 acre lot • 2 garage spots • Built 1963

ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
Discover the serenity of 335 Georgetown Road, where a grand, private approach leads you through exquisitely landscaped grounds adorned with lush foliage, natural stone, and vibrant blooms. This contemporary masterpiece is perched on 3.38 acres, featuring a professionally lit Tartan basketball court, expansive side deck and a secluded pool. The main floor primary suite has two generously sized walk in closets and a sitting room and/or gym space, also offers a private deck, with direct pool access. With soaring ceilings and expansive glass windows, the home is bathed in natural light throughout the day, while remaining comfortably shaded by strategically placed trees. The grand living room is

$1,849,000

5 beds4.5 baths4,106 sq ft

335 Georgetown Rd, Weston, CT 06883

3.38 acre lot • 2 garage spots • Pool

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 31 White Birch Rd, Weston, CT 06883, 4 beds, 2.5 baths

$1,450,000

4 beds2.5 baths3,894 sq ft

31 White Birch Rd, Weston, CT 06883

Property at 492 Newtown Tpke, Weston, CT 06883, 1 bed, 1 bath

$349,000

1 bed1 bath576 sq ft

492 Newtown Tpke, Weston, CT 06883

Property at 4 Trails End Rd, Weston, CT 06883, 5 beds, 3.5 baths

$1,495,000

5 beds3.5 baths3,888 sq ft

4 Trails End Rd, Weston, CT 06883

Property at 20 Georgetown Rd, Weston, CT 06883, 3 beds, 2 baths

$524,000

3 beds2 baths1,616 sq ft

20 Georgetown Rd, Weston, CT 06883

Property at 214 Good Hill Rd, Weston, CT 06883, 7 beds, 9 baths

$3,795,000

7 beds9 baths11,075 sq ft

214 Good Hill Rd, Weston, CT 06883

Property at 4 Good Hill Rd, Weston, CT 06883, 3 beds, 3 baths

$3,500,000

3 beds3 baths8,500 sq ft

4 Good Hill Rd, Weston, CT 06883

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 191 Steep Hill Rd, Weston, CT 06883, 5 beds, 3 baths

$999,999

5 beds3 baths2,220 sq ft

191 Steep Hill Rd, Weston, CT 06883

Property at 145 Lyons Plain Rd, Weston, CT 06883, 5 beds, 5.5 baths

$1,569,000

5 beds5.5 baths3,579 sq ft

145 Lyons Plain Rd, Weston, CT 06883

Property at 76 Lords Hwy, Weston, CT 06883, 6 beds, 9 baths

$3,900,000

6 beds9 baths10,634 sq ft

76 Lords Hwy, Weston, CT 06883

Property at 28 Old Orchard Dr, Weston, CT 06883, 5 beds, 5.5 baths

$1,779,000

5 beds5.5 baths7,611 sq ft

28 Old Orchard Dr, Weston, CT 06883

Property at 96 Georgetown Rd, Weston, CT 06883

$449,000

— beds— baths— sq ft

96 Georgetown Rd, Weston, CT 06883

Property at Old Easton, Weston, CT 06883

$2,500,000

— beds— baths— sq ft

Old Easton, Weston, CT 06883

Property at 85-95 Old Easton Tpke, Weston, CT 06883

$1,995,000

— beds— baths— sq ft

85-95 Old Easton Tpke, Weston, CT 06883

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Nearby homes that match your criteria

ABOUT THIS HOME
Home with a Pool for sale in Weston, 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

ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
Welcome to 55 Liberty St. Unparalleled modern luxury in this meticulously rebuilt 5-bedroom, 4.5-bath Wilton residence. Set on 1.8 private acres, the home delivers seamless, sun-drenched living across 4,300+ square feet, following a comprehensive 2025 renovation that saw the property rebuilt from the studs up. Step inside to discover European wire-brushed hardwood floors and an effortless, open layout. The heart of the home is a vaulted-ceiling kitchen, featuring contemporary white cabinetry and a full suite of CAFETM smart appliances. Upstairs, the spa-like primary suite is finished with Natural Marble and luxurious gold Kohler fixtures, offering a perfect sanctuary. The lower level is des

$1,775,000

5 beds4.5 baths4,504 sq ft

55 Liberty St, Wilton, CT 06897

Private acres • Natural marble • Gold kohler fixtures

ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
Welcome to this light and bright 2-bedroom, 2-bath condo that offers modern style, comfort, and convenience in one of Wilton's most sought-after communities. This desirable end unit has been completely renovated from top to bottom and is truly move-in ready. The main level features a spacious open-concept living and dining area, filled with natural light- perfect for entertaining or relaxing. The beautifully updated kitchen boasts contemporary finishes and ample cabinetry, with brand new appliances throughout. Completing the main level is a versatile main-floor bedroom and full bath, ideal for guests or a home office, or a main level bedroom! Upstairs, you'll find a private primary suite wi

$530,000

2 beds2 baths1,088 sq ft

35 Village Walk #35, Wilton, CT 06897

Main-floor bedroom • Updated kitchen • Completely renovated

OPEN SUN TO 3PM

ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
OWN A PIECE OF HISTORY Updated and fully painted Inside and Out. Historic Antique Colonial in South Wilton - 4 Beds | 2.5 Baths | 2,803 Sq Ft + Walk-Out Lower Level | 4.81 Acres. Known as the historic "James Benedict" house, this central chimney (5 fireplaces : 3 gas and 2 wood) 3-story, post and beam construction residence is one of the notable and better-preserved 18th century dwellings in town. All light fixtures have been updated with LED, Three bathrooms updated. Wide plank floors refinished , Dusk to down exterior lighting, Hot water baseboard gas heat and Mini split systems that provide high quality, low noise comfort AC and can also supply heat as an alternative energy sou

$1,249,000

4 beds2.5 baths2,803 sq ft

332 Belden Hill Rd, Wilton, CT 06897

Central chimney • 4.81 acre lot • 6 parking spots

ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
Imagine morning coffee with birdsong, and afternoons spent in your own lovely and private Backyard. If you have ever considered a move out of the city, this home offers the perfect blend of convenience, natural beauty, and sheer breathing space! Situated in coveted South Wilton, this 4 Bedroom, 3.5 Bath Classic Colonial provides both traditional New England charm and modern ambiance. The inviting main level layout is designed for everyday living and seamless entertaining; flowing effortlessly from room to room. The Heart of the Home is the gorgeous Cherry Kitchen with granite counters framing serene views of your retreat-worthy, wooded Backyard. The versatile main level Study with Full Bath

$1,299,000

4 beds3.5 baths2,698 sq ft

41 Calvin Rd, Wilton, CT 06897

Cherry kitchen • Private backyard • Lower level walkout

ABOUT THIS HOME
Home with a Pool for sale in Weston, CT:
Built by renowned master builder John Heggland, this exceptional 7,811 sq ft Georgian Colonial estate is gracefully sited on 2.45 private acres in one of Wilton's most sought-after, nature-rich locations. Known for his uncompromising craftsmanship and timeless architectural integrity, Heggland delivers a residence that blends classic elegance with the finest in modern luxury and energy-efficient design. Inside, a double-height foyer with a sweeping staircase introduces rich hardwood floors, intricate moldings, and finely paneled walls. Formal living and dining rooms open to an inviting family room centered around a fireplace. The chef's kitchen features custom cabinetry, a butler's pantry,

$3,495,000

5 beds8 baths6,990 sq ft

76 Sturges Ridge Rd, Wilton, CT 06897

Ensuite bedrooms • Spa-inspired bath • Butler's pantry

Keller Williams Prestige Prop

Property at 483 Main St, Westport, CT 06880, 3 beds, 2 baths

$1,199,000

3 beds2 baths1,450 sq ft

483 Main St, Westport, CT 06880

Property at 2190 Sturges Hwy, Westport, CT 06880, 3 beds, 3 baths

$1,100,000

3 beds3 baths3,670 sq ft

2190 Sturges Hwy, Westport, CT 06880

Property at 22 Ledgewood Rd, Redding, CT 06896, 4 beds, 3.5 baths

$979,000

4 beds3.5 baths3,578 sq ft

22 Ledgewood Rd, Redding, CT 06896

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 88 Merry Meet Cir, Fairfield, CT 06824, 5 beds, 7 baths

$2,498,000

5 beds7 baths8,136 sq ft

88 Merry Meet Cir, Fairfield, CT 06824

Property at 93 E Meadow Rd, Wilton, CT 06897, 4 beds, 3 baths

$2,149,000

4 beds3 baths3,650 sq ft

93 E Meadow Rd, Wilton, CT 06897

Property at 54 mountain rd Rd, Wilton, CT 06897, 4 beds, 2 baths

$800,000

4 beds2 baths1,026 sq ft

54 mountain rd Rd, Wilton, CT 06897

Property at 40 Hermit Ln, Westport, CT 06880, 5 beds, 5 baths

$2,849,000

5 beds5 baths4,142 sq ft

40 Hermit Ln, Westport, CT 06880

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 101 Brambley Hedge Cir, Fairfield, CT 06824, 5 beds, 5 baths

$1,695,000

5 beds5 baths5,136 sq ft

101 Brambley Hedge Cir, Fairfield, CT 06824

Property at 25 Hermit Ln, Westport, CT 06880, 6 beds, 6 baths

$3,125,000

6 beds6 baths9,454 sq ft

25 Hermit Ln, Westport, CT 06880

Property at 30 Cavalry Rd, Westport, CT 06880, 4 beds, 4 baths

$2,474,000

4 beds4 baths4,013 sq ft

30 Cavalry Rd, 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 9 Read Pl, Wilton, CT 06897, 5 beds, 3.5 baths

$1,499,000

5 beds3.5 baths4,000 sq ft

9 Read Pl, Wilton, CT 06897

Homes with Pools for Sale in Weston

There are currently 20 homes with pools for sale in Weston at a median listing price of $1.32M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Weston stay on the market for 58 days and receive 12 offers. This map is refreshed with the newest listings in Weston every 15 minutes.

In the past month, 12 homes have been sold in Weston. In addition to houses in Weston, there were also 0 condos, 0 townhouses, and 1 multi-family unit for sale in Weston last month. Find your dream home in Weston 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 Weston are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Weston. If you're looking to sell your home in the Weston area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Weston with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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