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305 Olmstead Hill RoadWilton, CT 06897

For Sale

$999,000

Smart Buyer Rebate $9,990

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

·

William Raveis Real Estate

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(203) 722-8349

Last updated July 29, 2026

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Source: SmartMLS #24169226

Listing Facts

  • TypeSingle-family
  • NeighborhoodWilton
  • Bedrooms3
  • Bathrooms3
  • Days on Prevu79
  • Taxes$14,404/year
  • Size2,827 sqft
  • Price per sqft$353

Location

Mortgage Calculator

Listing History

07/27/2026
Price Decreased
$999,000
06/22/2026
Status changed to Active
$1,099,000
06/04/2026
Status changed to In Contract
$1,099,000
05/31/2026
Price Decreased
$1,099,000
05/16/2026
Status changed to Active
$1,199,000
05/15/2026
Status changed to Removed from Feed
$1,199,000
05/13/2026
Listed by William Raveis Real Estate
$1,199,000

Property Details for 305 Olmstead Hill Road

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1958
  • Year Built Details: Public Records
  • Architectural Style: Other
  • Construction Materials: Frame, Block, Concrete
  • Exterior Features: Deck, Gutters, Garden Area, Patio

Features

  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Some Wetlands, Lightly Wooded, Dry, Sloping Lot
  • Lot Size Acres: 2.00

Financial

Taxes

  • Parcel Number: 1924666
  • Tax Annual Amount: $14,404.00
  • Tax Year: 25

Interior

Features

  • Appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Fireplaces Total: 1
  • Interior Features: DROPEN, PREWIRED, OPEN, SECURESY

Measurements

  • Living Area: 2,407

Rooms

  • Basement: Partial, Heated, Interior Access, Partially Finished, Liveable Space
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 3
  • Rooms Total: 8

Parking

Parking

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

Schools

Elementary School

  • Elementary School: Miller-Driscoll

High School

  • High School: Wilton

Middle or Junior School

  • Middle Or Junior School: Middlebrook

Utilities

Equipment

  • Cooling: Ceiling Fans
  • Heating: Hot Air
  • Laundry Features: Lower Level
  • Sewer: Septic
  • Water Source: Private Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 3 bedrooms and 3 bathrooms in this single-family home at 305 Olmstead Hill Road.

What schools are nearby to 305 Olmstead Hill Road?

Nearby schools include the Miller-Driscoll Elementary School, Middlebrook Middle School, and Wilton High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 305 Olmstead Hill Road.

What are the annual taxes for 305 Olmstead Hill Road?

Annual taxes for this single-family home are estimated at $14,404.

How does 305 Olmstead Hill Road compare to other single-family homes in Wilton?

This single-family home is listed 44% below the average price for single-family homes in Wilton and has been on the market for 8 more days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,827 sqft.

305 Olmstead Hill Road is a 3-bedroom, 3-bath single-family home for sale in Wilton CT 06897. Available on Prevu for 79 days at $999,000. This includes a recent price decrease of $100,000. This home features 2,827 square feet of living space, located in Wilton. The median listing price for single-family homes in this area is $1,299,500. Nearby schools include Miller-Driscoll Elementary School, Middlebrook Middle School, and Wilton High School. Explore more single-family home listings in Fairfield County.

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.