Home Homes for Sale Wilton, CT 305 Olmstead Hill Road

305 Olmstead Hill Road, Wilton, CT 06897

Single Family For Sale

$1,199,000
$424/sqft
305 Olmstead Hill Road, Wilton, CT
Coming Soon Open House 5/15 · 11am–2pm
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3
Bedrooms
3
Bathrooms
2,827
Sq Ft
2
Acres
1958
Year Built

About This Home

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.

Listed by Diane Millas (203) 722-8349 with William Raveis Real Estate (203) 762-8300

Listing Snapshot

Price $1,199,000 Days on Our Site 0 days
Property Tax $14,404/yr Style Modern,Other
Year Built 1958 Total Sq Ft 2,827
Lot Size 2 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 2
Total Rooms 8 Half Baths 1

Key Features

Interior
  • Auto Garage Door Opener
  • Cable - Pre-wired
  • Open Floor Plan
  • Security System
Appliances
  • Gas Range
  • Microwave
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • Deck
  • Gutters
  • Garden Area
  • Patio
Nearby
  • Lake
  • Library
  • Medical Facilities
  • Park
  • Playground/Tot Lot
  • Shopping/Mall
  • Tennis Courts

Structure & Parking

Construction Frame,Block,Concrete
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Attached Garage, Paved, Driveway
Below Grade 420 sq ft

Systems & Utilities

Heat Hot Air
Fuel Oil
Cooling Ceiling Fans, Ductless, Split System
Hot Water Electric, 40 Gallon Tank
Water Private Well
Sewer Septic

Schools

Elem Miller-Driscoll
Middle Middlebrook
High Wilton

Mortgage Calculator

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Est. Monthly Payment
Principal & Interest
Est. Property Tax $1,200/mo
Est. Home Insurance

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
May 13, 2026 Listed $1,199,000

Frequently Asked Questions

How much does 305 Olmstead Hill Road in Wilton, CT cost?
This property is listed at $1,199,000, which works out to $424 per square foot.
How many bedrooms does 305 Olmstead Hill Road have?
This home has 3 bedrooms and 3 bathrooms.
What is the square footage of 305 Olmstead Hill Road?
The home is 2,827 square feet, situated on 2 acres.
When was 305 Olmstead Hill Road in Wilton built?
This property was built in 1958.
Is 305 Olmstead Hill Road, Wilton, CT still available?
The current MLS status of this property is "Coming Soon". Contact RYZE Realty Group for the latest availability.
What school district is 305 Olmstead Hill Road, Wilton in?
This home is served by the Wilton public school system, with Miller-Driscoll as the elementary school and Wilton as the high school.
How do I schedule a tour of 305 Olmstead Hill Road, Wilton, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Diane Millas · (203) 722-8349

William Raveis Real Estate · (203) 762-8300

MLS# 24169226 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated May 13, 2026 11:30 AM UTC