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For sale
    • Price cut: $100K (7/26)
    $999,000

    305 Olmstead Hill Road, Wilton, CT 06897

    3beds
    2,827sqft
    : 
    $6,875/mo
    Get pre-qualified
    Single Family Residence
    Built in 1958
    2 Acres Lot
    $-- Zestimate®
    $353/sqft
    $-- HOA

    What's special

    Wraparound deckTwo-car attached garageStriking floor-to-ceiling stone fireplaceCascading glass chandelierVaulted three-season porchDedicated prep sinkWooded grounds
    This iconic mid-century modern home offers a rare blend of architectural character and natural beauty, situated on two private acres along Olmstead Hill-one of Wilton's designated scenic roads. Designed in 1958 by architect Robert Van Summern (whose work has been featured in The New York Times) as his first family residence, the home thoughtfully integrates timeless design with its serene, wooded surroundings to create a distinctive treehouse-like feel. Original architectural elements remain beautifully intact, including a striking floor-to-ceiling stone fireplace and a dramatic wall of glass that fills the home with natural light throughout the day. The main level features an open layout that seamlessly connects the dining and living areas to a remodeled kitchen featuring custom cabinetry with seeded glass accents, a 9-foot quartz center island, and a dedicated prep sink. A brand-new powder room and freshly painted interiors add a crisp, updated feel, while the vaulted three-season porch and multiple sliding glass doors extend the living space onto the wraparound deck and wooded grounds. Upstairs, the primary suite offers cathedral ceilings, a private balcony overlooking the wooded grounds, and an oversized walk-in closet and dressing area. The en-suite bath showcases striking artisan glass vessel sinks that complement the home's mid-century modern aesthetic. The upper landing features floor-to-ceiling built-in bookcases and a cascading glass chandelier. The finished lower level adds flexible space ideal for play, exercise, or additional workspace. Outside, the home is surrounded by mature plantings and landscaping, offering a true connection to nature. A natural stone fire pit offers a great place for friends and family to gather. A two-car attached garage adds everyday convenience. New WELL water holding tank and NEW electrical panel recently installed. A tranquil setting just minutes from Wilton town center, with easy access to Route 7, Metro-North, and Wilton's top-rated public schools. An exceptional home and property in one of Wilton's most picturesque settings.
    81 days
    |
    3,288
    |
    192
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Diane Millas (203)722-8349,

    William Raveis Real Estate 203-762-8300

    Source: Smart MLS,MLS#: 24169226MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Breezeway, Sitting Room
      Primary bedroom
      • Features: High Ceilings, Ceiling Fan(s), Dressing Room, Full Bath, Walk-In Closet(s)
      • Level: Upper
      Bedroom
      • Features: Full Bath, Hardwood Floor
      • Level: Main
      Bedroom
      • Features: Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      Family room
      • Features: Sliders, Hardwood Floor
      • Level: Main
      Kitchen
      • Features: Remodeled, Balcony/Deck, Quartz Counters, Dining Area, Kitchen Island, Hardwood Floor
      • Level: Main
      Library
      • Features: High Ceilings, Bookcases, Built-in Features
      • Level: Upper
      Living room
      • Features: Balcony/Deck, Beamed Ceilings, Fireplace, Sliders, Hardwood Floor
      • Level: Main
      Office
      • Features: Engineered Wood Floor
      • Level: Lower
      Rec play room
      • Features: Engineered Wood Floor
      • Level: Lower
      Heating
      • Forced Air, Oil
      Cooling
      • Ceiling Fan(s), Ductless
      Appliances
      • Included: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater
      • Laundry: Lower Level
      Features
      • Wired for Data, Open Floorplan, Entrance Foyer, Smart Thermostat
      • Basement: Partial,Heated,Interior Entry,Partially Finished,Liveable Space
      • Attic: Storage,Pull Down Stairs
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 2,827
      • Total interior livable area: 2,827 sqft
      • Finished area above ground: 2,407
      • Finished area below ground: 420
      Video & virtual tour

      Property

      Parking
      • Total spaces: 10
      • Parking features: Attached, Paved, Driveway, Garage Door Opener, Private, Asphalt
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Deck, Patio
      • Exterior features: Rain Gutters, Garden
      Lot
      • Size: 2 Acres
      • Features: Wetlands, Few Trees, Dry, Sloped
      Details
      • Parcel number: 1924666
      • Zoning: R-2

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Modern,Other
      • Property subtype: Single Family Residence
      Materials
      • Vertical Siding
      • Foundation: Block, Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1958

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Lake, Library, Medical Facilities, Park, Playground, Shopping/Mall, Tennis Court(s)
      • Security: Security System
      • Subdivision: Cannondale
      HOA
      • Has HOA: No
      Location
      • Region: Wilton

      Financial & listing details

      • Price per square foot: $353/sqft
      • Tax assessed value: $590,100
      • Annual tax amount: $14,404
      • Date on market: 5/13/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/26/2026Price change$999,000-9.1%$353/sqft
        Source: Smart MLS #24169226 Report a problem
        5/30/2026Price change$1,099,000-8.3%$389/sqft
        Source: Smart MLS #24169226 Report a problem
        5/15/2026Listed for sale$1,199,000+84.5%$424/sqft
        Source: Smart MLS #24169226 Report a problem
        1/31/2013Sold$650,000+57.6%$230/sqft
        Source: Public Record Report a problem
        6/27/1996Sold$412,500+10%$146/sqft
        Source: Smart MLS #95007828 Report a problem
        12/8/1987Sold$375,000$133/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$14,404 +2%$590,100
        2024$14,127 +13.3%$590,100 +38.4%
        2023$12,471 +3.6%$426,230
        2022$12,032 +1.3%$426,230
        2021$11,879 +1.5%$426,230
        2020$11,704 -3.8%$426,230
        2019$12,165 +4%$426,230 +2.7%
        2018$11,696 +1.5%$414,890
        2017$11,521 +1.6%$414,890
        2016$11,343 +1.9%$414,890
        2015$11,131 +1.2%$414,890
        2014$10,999 +2%$414,890
        2013$10,783 -2.1%$414,890 -20.7%
        2012$11,010 +1%$523,040
        2011$10,905 +3.4%$523,040
        2010$10,544 +3%$523,040
        2009$10,241 +1.4%$523,040
        2008$10,100 -3.9%$523,040 +20.6%
        2007$10,507 +3.6%$433,650
        2006$10,143 +3.7%$433,650
        2005$9,779 +5%$433,650
        2004$9,315 +6.9%$433,650
        2003$8,716 +19.1%$433,650 +66.6%
        2001$7,317 +8.5%$260,300 0%
        2000$6,745 +7.6%$260,330
        1999$6,269 $260,330
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 06897

        Getting around

        5 / 100
        Car-Dependent
        4 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Miller-Driscoll
        • Middle: Middlebrook,Cider Mill
        • High: Wilton

        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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