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315 Olmstead Hill Road

Wilton, Connecticut 06897

ACTIVE - NEW$899,000
Beds
3
Baths
3 | 1
SqFt
2,635
Acres
0.50
Year Built
1955
Matt Caiola

Matt Caiola

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Waterfront2-Car Garage1 Fireplace

About This Home

Charming Cape Cod home in Wilton, a desirable Mid Fairfield County community. Located along a scenic country road, yet mere minutes from the village center, top ranked Schools and popular Wilton Y campus....Not to mention commute roads; and 5 mins from Cannondale Metro North train! 315 Olmstead Hill embodies classic New England architecture paired with unbeatable convenience. This comfortably-sized Cape, with significant, quality additional space in the partially Finished Walk-Out Lower Level, offers maximum flexibility for a wide range of lifestyles and life situations. The lush half-acre Lot possesses the perfect balance of lawn/perennial beds and Nature with its gorgeous views. There are Full Bathrooms on each Level. Some Key Features and Benefits: The Living Room with Dining Area is sun-lit, and anchored by a cozy stone Fireplace--ideal for crisp New England evenings. The home's Layout is Open and Inviting, including the main level Primary, with Walk-In Closet; 2 Bright Bedrooms upstairs; the Bonus Finished Lower Level; the Mud Room/Breezeway, separating the Oversized 2 Vehicle Attached Garage from the living quarters. Seamless flow from the timelessly Updated Kitchen with newer high-end Appliances, past the Breakfast Bar, to the Dining Area and Living Room. 315 Olmstead Hill is an outstanding opportunity to acquire a Move-In Home, or to customize a Classic Home in a convenient, highly desirable Location!!

Key Facts

City/Town
Wilton
Neighborhood
North Wilton
Property / Style
Single Family · Cape Cod
Year Built
1955
Days on Market
0 days
Beds
3
Baths
3 full · 1 half
Living Area
2,635 sq ft
Lot Size
0.50 acres
Garage / Parking
2 garage
Property Taxes
$13,880 / Annually

Market Snapshot

The Wilton Market

Single Family · trailing 12 months

View area

Median Days on Market

42

27 active listings

Median $ / Sq Ft

$417

27 active listings

Sale-to-List Ratio

105.5%

215 sales

How this home compares

List Price

$899,000

vs $1.79M median

49.9% below median

Price / Sq Ft

$341

vs $417 median

18.2% below median

Days on Market

0 days

vs 42 days median

42 days fresher than median

Based on 27 active and 215 closed sales (trailing 12 mo) of single family in Wilton. Source: SmartMLS · As of September 11, 2026.

Location

315 Olmstead Hill Road, Wilton, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,126

per month

  • Principal & Interest$4,669
  • Property Taxes$1,157
  • Insurance$300
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Wilton
Neighborhood
North Wilton
County
Fairfield

Residence

Property Type
Single Family
Style
Cape Cod
Year Built
1955
New Construction
No/Resale
Living Area
2,635 sq ft
Below Grade
660 sq ft

Schools

Elementary
Cider Mill
High
Wilton

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Laundry Location
In Lower Level Bathroom.
Appliances
Electric RangeConvection OvenMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullHeatedSump PumpStorageCooledPartially FinishedFull With Walk-Out
In-Law Apartment
No
Interior Features
Auto Garage Door OpenerCable - Pre-wiredOpen Floor Plan
Additional Rooms
Mud Room

Exterior & Lot

Lot Size
0.50 acres
Zoning
R-2
Garage / Parking
2 garage spacesAttached Garage
Waterfront
Direct waterfront
Waterfront Details
BrookView
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
ShingleWood
Color
Gray
Roof
Asphalt Shingle
Foundation
BlockConcrete
Exterior Features
SidewalkPorchGuttersGarden AreaLightingStone WallPatio
Lot Description
Lightly WoodedTreedLevel LotSloping Lot

Listing & Financials

Property Taxes
$13,880 / Annually
Days on Market
0
MLS #
24205671
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Rob McCullough

(203) 803-3974

William Pitt Sotheby's Int'l

(203) 438-9531

Co-Listed By

Laurie Mortensen

William Pitt Sotheby's Int'l

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/11/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/11/2026 at 6:30 AM UTC.