10 Winding Lane, Old HillWestport, CT 06880MLS Number 24163168

  • Price: $3,550,000
  • Est. Mortgage of $/month
  • 10 Days on Market
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Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
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  • 5Bedrooms
  • 1Acreage
  • 5Bathrooms
  • 2003Year Built

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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.
Listed by Susan Lieberman of The Riverside Realty Group ((203) 858-9411)

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More Info

Basic Information

  • MLS Number24163168
  • StatusACT
  • List Price$3,550,000
  • Square Feet4,602
  • Property TypeSingle Family For Sale
  • ColistofficenameThe Riverside Realty Group
  • Co-List TeamSue Lieberman and Justine Fink Team
  • List TeamSue Lieberman and Justine Fink Team

Property

  • Acreage1
  • Lot DescriptionFence - Full, Level Lot
  • Parking Spaces
  • SwimmingpoolYes
  • Pool descriptionGunite, Heated, Spa, In Ground Pool

Utilities

  • Waters ourcePublic Water Connected
  • Cooling SystemCentral Air, Zoned
  • Hot water descriptionOther
  • Heating FuelOil, Propane
  • Fuel tank locationAbove Ground
  • Heat SystemHot Water
  • Sewage systemSeptic

Other

  • Appliances Included
    • Cook Top
    • Dishwasher
    • Disposal
    • Dryer
    • Freezer
    • Microwave
    • Refrigerator
    • Wall Oven
    • Washer
  • Original listprice$3,550,000
  • Exclusionswall mounted tv's, gas grill
  • Date Listed03/31/2026

Tax Information

  • Assessed value$1,360,200
  • Milrate total17
  • Tax YearJuly 2025-June 2026
  • Taxes$25,653

Location

  • StateCT
  • Zip06880
  • CountyFairfield
  • NeighborhoodOld Hill
  • Middle Junior High SchoolColeytown

Interior

  • Rooms12
  • Rooms additionalLaundry Room, Mud Room
  • Interior featuresAudio System, Security System
  • RoofAsphalt Shingle

Exterior

  • ColorSage
  • Exterior features
    • French Doors
    • Garden Area
    • Gutters
    • Lighting
    • Patio
    • Shed
    • Stone Wall
  • Exterior sidingShingle, Stone, Wood

Amenities

  • Amenities
    • Golf Course
    • Health Club
    • Library
    • Park
    • Shopping/Mall
    • Tennis Courts
  • Other Amenities
    • Basement
    • Fireplace
    • Garden
    • Golf
    • Pool
    • Tennis
    • Waterfront

School Information

  • Elementary SchoolKings Hwy
  • High SchoolStaples

Rooms

  • Laundry room location2nd Floor

Building

  • Full Bath4
  • Half Baths1
  • BasementCrawl Space
  • Attic descriptionWalk-In
  • AtticYes
  • Garage Spaces2
  • Bedrooms5
  • Bathroom5
  • Year Built2003
  • Property StyleCape Cod, Colonial
  • Energy FeaturesProgrammable Thermostat, Thermopane Windows
  • Fireplaces2
  • FoundationConcrete
  • Garage Parking InfoAttached Garage
  • New construction typeNo/Resale

Water Body

  • Waterfront DescriptionWater Community, Access
Sotheby's International Realty | William Pitt
Sotheby's International Realty | William Pitt
Office: 203-796-7700
112 Federal Road
Danbury, CT 06811

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