305 Olmstead Hill Rd

Wilton, CT 06897

$1,099,000
Price
3
Beds
2,827 Sq. Ft.
$389 / Sq. Ft.
2,827
Sq. Ft.
$389
per Sq. Ft.
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Virtual Tour
Slider doors lead to screened porch. Full bath and private study located in this room
Main Floor
2nd floor landing
2nd floor
2nd floor
Primary bedroom
Artisan glass vessel sinks
2nd floor
Lower Level
Lower Level
FIRST FLOOR
SECOND FLOOR
LOWER LEVEL floor plan (Laundry located in Utility Room)

Description

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...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.
  1. Listed by Diane Millas • William Raveis Real Estate
    P: (203)-722-8349 C: (203)-722-8349 diane@dianemillas.com

Property Details for 305 Olmstead Hill Road

Basement Description
Partial, Heated, Interior Access, Partially Finished, Liveable Space
Direct Waterfront
No
Expected Active Date
05-15-2026
Garages Number
2
Neighborhood
Cannondale
Style
Modern, Other
Garage Parking Info
Attached Garage, Paved, Driveway
Swimming Pool
No
LISTING UPDATED: 06/14/2026 02:06 PM

Property Details for 305 Olmstead Hill Road

StatusActive
MLS #24169226
Days on Market31
Taxes$14,404 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1958
Lot Size2.00 AC / 87,120 SF
CountyFairfield County
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Location

Listing Courtesy of William Raveis Real Estate, Diane Millas
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Building Information for 305 Olmstead Hill Road

Stories-Year Built1958Building Size-Lot Size2.00 AC / 87,120 SF

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$6,677 per month

30 year fixed, 6.36% Interest

Principal and Interest

$5,476

Property Taxes

$1,200

HOA Dues

$0

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Property Information for 305 Olmstead Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Danbury Road to Olmstead Hill Road. Pass Hulda Hill Road and house is on the left #305
  • Elementary School: Miller-Driscoll
  • Flood Zone: No
  • High School: Wilton
  • Intermediate School: Cider Mill
  • Latitude: 41.221502
  • Longitude: -73.437918
  • Middle Jr High School: Middlebrook
  • Neighborhood Amenities: Lake, Library, Medical Facilities, Park, Playground/Tot Lot, Shopping/Mall, Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 10
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $14,404
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Gutters, Garden Area, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Cooling System: Ceiling Fans, Ductless, Split System
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Home Automation: Thermostat(s)
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
  • Laundry Room Info: Lower Level
  • Rooms Additional: Breezeway, Foyer, Sitting Room
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Balcony/Deck,Beams,Fireplace,Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Remodeled,Balcony/Deck,Quartz Counters,Dining Area,Island,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 3
  • Room Entry Order: 3
  • Room Features: Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 4
  • Room Entry Order: 4
  • Room Features: Full Bath,Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 5
  • Listing Key: 50058AFDEF795D62E063E201100A5A64
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Ceiling Fan,Dressing Room,Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 6
  • Room Entry Order: 6
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: Engineered Wood Floor
  • Room Level: Lower
  • Room Type: Rec/Play Room
Room 8
  • Room Entry Order: 8
  • Room Features: Engineered Wood Floor
  • Room Level: Lower
  • Room Type: Office
Room 9
  • Listing Key: 50058AFDEF795D62E063E201100A5A64
  • Room Entry Order: 9
  • Room Features: 9 ft+ Ceilings,Book Shelves,Built-Ins
  • Room Level: Upper
  • Room Type: Library
Property
Property and Assessments
  • Color: Taupe
  • Construction Description: Frame, Block, Concrete
  • Driveway Type: Private, Paved, Asphalt
  • Exterior Siding: Vertical Siding
  • Foundation Type: Block, Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1958
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Est Heated Below Grade: 420
  • Living Area SQFT Per Public Records: 2407
Lot Information
  • Lot Description: Some Wetlands, Lightly Wooded, Dry, Sloping Lot
  • Parcel Number: 1924666
  • Sq Ft Est Heated Above Grade: 2407.0
  • Sq Ft Total: 2827.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Electric, 40 Gallon Tank
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 305 Olmstead Hill Road

DateEvent & SourcePriceAppreciation
Jan 31, 2013

Closed (Public Record)

Public Record #347749477

$650,000

+2.8% / yr

Jun 27, 1996

Closed (Public Record)

Public Record #91322474

$412,500—
DateEvent & SourcePrice
01/31/2013

Closed (Public Record)

Public Record #347749477

$650,000

+2.8% / yr

06/27/1996

Closed (Public Record)

Public Record #91322474

$412,500

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 305 Olmstead Hill Road

Taxable ValueLand$306,110Additions$283,990Total$590,100
Tax Record2024$14,404 ($1,200 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt2,407 SqFtAbove Grade Finished SqFt2,407 SqFtUnfinished Basement SqFt660 SqFtStories3Lot Size87,120 SqFtStyleSingle Family ResidenceYear Built1958ZoningR-2CountyWESTERN CONNECTICUTAPNWILT M:0048 B:008 L:00Fireplace TypeHas Fireplace

Schools near 305 Olmstead Hill Road

This home is within Wilton School District.
Rating
School
Type
Grades
Distance
Miller-Driscoll School
Public - PK to 2
Cider Mill School
Public - 3 to 5
Middlebrook School
Public - 6 to 8
Wilton High School
Public - 9 to 12
Rating
School
Distance
Miller-Driscoll School
PublicPK to 2

Cider Mill School
Public3 to 5

Middlebrook School
Public6 to 8

Wilton High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Wilton
Wilton
Indulge in away-from-it-all serenity. Once a small farming town, today's Wilton is a charming residential community spanning 27 square miles in Fairfield County, north of Merritt Parkway. Here, 18,500 residents enjoy a peaceful, community-focused lifestyle alongside bountiful outdoor space and the...
Wilton Guide

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More information about 305 Olmstead Hill Road, Wilton, CT 06897

305 Olmstead Hill Road is a single family home for sale in Wilton, CT 06897. This property was listed for sale on May 13, 2026 by William Raveis Real Estate, it's currently listed at $1,099,000. It has been on the market for a total of 31 days and was last sold on January 31, 2013. This listing's school district is Wilton School District. Nearby schools include Miller-Driscoll School, Cider Mill School and Middlebrook School. 305 Olmstead Hill Road is a 3-bed, 3-bath, 2,827 sqft single family home built in 1958.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Diane Millas

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.