Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an open-concept floor plan enhanced by timeless architectural details and modern upgrades. Sun-drenched living spaces on the main level include a gourmet kitchen, formal living room, dining area, family room, office, and a versatile pool cabana or fitness room-all seamlessly opening to an expansive patio for effortless indoor-outdoor living. Two first-floor ensuite bedrooms provide flexible accommodations. Upstairs, the luxurious primary offers a private retreat, complemented by a large playroom, laundry room, and two additional bedrooms with a shared bath-creating a versatile layout. The resort-style outdoor setting is equally impressive, featuring a gunite pool with spa, pergola, fire pit, outdoor grill area, vegetable garden, and a fully integrated lighting and sound system. Mature, century-old trees, curated specimen plantings, and extensive stonework create a private, park-like oasis. For the buyer seeking privacy while being near all the amenities that Westport has to offer, this extraordinary property combines classic elegance, modern amenities, and an unbeatable location.
Sold for $3,600,000
$3,600,000
10 Winding Lane, Westport, CT 06880
5beds
4,602sqft
Single Family Residence
Built in 2003
1 Acres Lot
$3,609,700 Zestimate®
$782/sqft
$7,505 Estimated rent
Home value
$3,609,700
$3.28M - $3.97M
$7,505/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Sue Lieberman and Justine Fink Team,
Susan Lieberman (203)858-9411,
The Riverside Realty Group 203-226-8300,
Co-Listing Agent: Justine Fink 203-246-1906,
The Riverside Realty Group
Bought with:
Katie Benson, RES.0810366
Houlihan Lawrence
Source: Smart MLS,MLS#: 24163168
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Laundry
Primary bedroom
- Features: Vaulted Ceiling(s), Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Main
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Main
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Dining room
- Features: French Doors, Hardwood Floor
- Level: Main
Family room
- Features: Fireplace, French Doors, Hardwood Floor
- Level: Main
Kitchen
- Features: Skylight, Vaulted Ceiling(s), Kitchen Island, Pantry, Hardwood Floor
- Level: Main
Living room
- Features: Fireplace, French Doors, Hardwood Floor
- Level: Main
Office
- Features: French Doors, Hardwood Floor
- Level: Main
Rec play room
- Features: French Doors, Hardwood Floor
- Level: Main
Rec play room
- Features: Vaulted Ceiling(s), Hardwood Floor
- Level: Upper
Heating
- Hot Water, Oil, Propane
Cooling
- Central Air, Zoned
Appliances
- Included: Cooktop, Oven, Microwave, Refrigerator, Freezer, Dishwasher, Disposal, Washer, Dryer, Water Heater
- Laundry: Mud Room
Features
- Sound System
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Crawl Space
- Number of fireplaces: 2
Interior area
- Total structure area: 4,602
- Total interior livable area: 4,602 sqft
- Finished area above ground: 4,602
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Patio & porch: Patio
- Exterior features: Rain Gutters, Garden, Lighting, Stone Wall
- Has private pool: Yes
- Pool features: Gunite, Heated, Pool/Spa Combo, In Ground
- Fencing: Full
- Waterfront features: Water Community, Access
Lot
- Size: 1 Acres
- Features: Level
Details
- Additional structures: Shed(s)
- Parcel number: 413860
- Zoning: AA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod,Colonial
- Property subtype: Single Family Residence
Materials
- Shingle Siding, Stone, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2003
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Green energy
- Energy efficient items: Thermostat, Windows
Community & HOA
Community
- Features: Golf, Health Club, Library, Park, Shopping/Mall, Tennis Court(s)
- Security: Security System
- Subdivision: Old Hill
HOA
- Has HOA: No
Location
- Region: Westport
Financial & listing details
- Price per square foot: $782/sqft
- Tax assessed value: $1,360,200
- Annual tax amount: $25,653
- Date on market: 3/31/2026
- Exclusions: wall mounted tv's, gas grill
Price history
| Date | Event | Price |
|---|---|---|
| 6/8/2026 | Sold | $3,600,000+1.4%$782/sqft |
Source:  Smart MLS #24163168 Report a problem | ||
| 4/14/2026 | Pending sale | $3,550,000$771/sqft |
Source: Smart MLS #24163168 Report a problem | ||
| 4/2/2026 | Listed for sale | $3,550,000+65.1%$771/sqft |
Source: Smart MLS #24163168 Report a problem | ||
| 5/15/2017 | Sold | $2,150,000-6%$467/sqft |
Source: Smart MLS #99173540 Report a problem | ||
| 12/7/2007 | Sold | $2,287,500+4%$497/sqft |
Source: Smart MLS #98350029 Report a problem | ||
| 2/27/2006 | Sold | $2,200,000-6.9%$478/sqft |
Source: Public Record Report a problem | ||
| 11/17/2005 | Sold | $2,362,500+329.5%$513/sqft |
Source: Public Record Report a problem | ||
| 11/1/1995 | Sold | $550,000$120/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $25,653 +1.3% | $1,360,200 |
| 2024 | $25,327 +1.5% | $1,360,200 |
| 2023 | $24,960 +1.6% | $1,360,200 |
| 2022 | $24,579 | $1,360,200 |
| 2021 | $24,579 -0.6% | $1,360,200 -8.1% |
| 2020 | $24,736 -0.9% | $1,480,300 |
| 2019 | $24,958 | $1,480,300 |
| 2018 | $24,958 | $1,480,300 |
| 2017 | $24,958 | $1,480,300 |
| 2016 | $24,958 | $1,480,300 |
Find assessor info on the county website
Neighborhood: Old Hill
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Nearby schools
GreatSchools rating
- 9/10King's Highway Elementary SchoolGrades: K-5Distance: 0.7 mi
- 9/10Coleytown Middle SchoolGrades: 6-8Distance: 2.6 mi
- 10/10Staples High SchoolGrades: 9-12Distance: 2.5 mi
Schools provided by the listing agent
- Elementary: Kings Hwy
- Middle: Coleytown
- High: Staples
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Fairfield County
- Westport
- 06880
- Old Hill
- 10 Winding Lane
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