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$1,199,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,827 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago

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Open House: 1:00 PM - 3:30 PM

Sunday 5/17 1:00 PM - 3:30 PM

305 Olmstead Hill Road,Wilton, CT 06897

305 Olmstead Hill RoadWiltonCT06897

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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.

Full Property Details for 305 Olmstead Hill Rd

General

  • Price: $1,199,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24169226
  • Updated: 5/15/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Breezeway, Foyer, Sitting Room
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Ceiling Fan, Dressing Room, Full Bath, Walk-In Closet, Upper
  • Bedroom 1: Bedroom - Full Bath, Hardwood Floor, Main
  • Bedroom 2: Bedroom - Walk-In Closet, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Balcony/Deck, Beams, Fireplace, Sliders, Hardwood Floor, Main
  • Family Room: Family Room - Sliders, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, Balcony/Deck, Quartz Counters, Dining Area, Island, , Main
  • Office: Office - Engineered Wood Floor, Lower
  • Library: Library - 9 ft+ Ceilings, Book Shelves, Built-Ins, Upper
  • Game room: Yes
  • Game Room: Rec/Play Room - Engineered Wood Floor, Lower
  • Rec Room: Engineered Wood Floor, Lower
  • Laundry: Lower Level

Exterior

  • Exterior Features: Deck, Gutters, Garden Area, Patio
  • Color: Taupe

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 10
  • Parking: Attached Garage, Paved, Driveway

Location

  • County: Fairfield
  • Neighborhood: Cannondale
  • Driving Directions: Danbury Road to Olmstead Hill Road. Pass Hulda Hill Road and house is on the left #305

School Information

  • Elementary School: Miller-Driscoll
  • Middle School: Middlebrook
  • Intermediate School: Cider Mill
  • High School: Wilton

Community

  • Community Name: Cannondale

Heating & Cooling

  • Cooling Type: Ceiling Fans, Ductless, Split System
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, 40 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Modern, Other
  • Construction Status: No/Resale
  • Exterior Const.: Vertical Siding
  • Basement Desc.: Partial, Heated, Interior Access, Partially Finished, Liveable Space
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,827
  • Above Ground: 2,407 Sq. Ft.
  • Below Ground: 420 Sq. Ft.
  • Year Built: 1958

Lot Features

  • Lot Size (Acres): 2
  • Driveway/Sidewalk: Private, Paved, Asphalt
  • Zoning: R-2
  • Lot Description: Some Wetlands, Lightly Wooded, Dry, Sloping Lot

Financial Considerations

  • Assessment Amount: $590,100
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1924666

Listed by William Raveis Real Estate, Diane Millas

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Listing agent

— 305 Olmstead Hill Rd —

  • Diane Millas

    William Raveis Real Estate

Agent Contact: (203) 722-8349 Office Contact: (203) 762-8300

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 305 Olmstead Hill Rd

School District:Wilton School District
NameGradesDistance
Cider Mill School
240 School Road, Wilton, CT 06897
3-51.2 mi
Miller-Driscoll School
217 Wolfpit Road, Wilton, CT 06897
PK-23.2 mi
Middlebrook School, Wilton, CT
131 School Road, Wilton, CT 06897
6-81.3 mi
Wilton High School
395 Danbury Road, Wilton, CT 06897
9-120.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 305 Olmstead Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/15/2026
Listed
$1,199,000
84.46%
MLS
1/31/2013
Sold
$650,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 305 Olmstead Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,404
2%
$590,100
—
2023
$14,127
13%
$590,100
38%
2023
$12,471
4%
$426,230
—
2022
$12,032
1%
$426,230
—
2021
$11,879
1%
$426,230
—
2020
$11,704
-4%
$426,230
—
2019
$12,165
4%
$426,230
3%
2018
$11,696
2%
$414,890
—
2017
$11,521
2%
$414,890
—
2016
$11,343
2%
$414,890
—
2015
$11,131
1%
$414,890
—
2014
$10,999
2%
$414,890
—
2011
$10,783
—
$414,890
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by William Raveis Real Estate, Diane Millas

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305 Olmstead Hill Road, Wilton, CT 06897 (MLS# 24169226) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 305 Olmstead Hill Road is currently listed for $1,199,000 and was received on May 15, 2026. Want to learn more about 305 Olmstead Hill Road? Do you have questions about finding other Single Family real estate for sale in Wilton? You can browse all Wilton real estate or contact a Coldwell Banker agent to request more information.

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