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.
For sale
Price cut: $100K (5/30)
$1,099,000
305 Olmstead Hill Road, Wilton, CT 06897
3beds
2,827sqft
Single Family Residence
Built in 1958
2 Acres Lot
$-- Zestimate®
$389/sqft
$-- HOA
What's special
- 36 days |
- 2,085 |
- 140 |
Zillow last checked:
Listing updated:
Listed by:
Diane Millas (203)722-8349,
William Raveis Real Estate 203-762-8300
Source: Smart MLS,MLS#: 24169226
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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: $389/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
| Date | Event | Price |
|---|---|---|
| 5/30/2026 | Price change | $1,099,000-8.3%$389/sqft |
Source:  Smart MLS #24169226 Report a problem | ||
| 5/15/2026 | Listed for sale | $1,199,000+84.5%$424/sqft |
Source: Smart MLS #24169226 Report a problem | ||
| 1/31/2013 | Sold | $650,000+57.6%$230/sqft |
Source: Public Record Report a problem | ||
| 6/27/1996 | Sold | $412,500+10%$146/sqft |
Source: Smart MLS #95007828 Report a problem | ||
| 12/8/1987 | Sold | $375,000$133/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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 | $260,330 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
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
Nearby schools
GreatSchools rating
- 9/10Cider Mill SchoolGrades: 3-5Distance: 1.2 mi
- 10/10Middlebrook SchoolGrades: 6-8Distance: 1.3 mi
- 10/10Wilton High SchoolGrades: 9-12Distance: 0.7 mi
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.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Fairfield County
- Wilton
- 06897
- 305 Olmstead Hill Road
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