315 Olmstead Hill Road
Wilton, Connecticut 06897
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 2,635
- Acres
- 0.50
- Year Built
- 1955
- Neighborhood
- North Wilton
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
27
19 under contract
Median List Price
$1.79M
27 active listings
Median Closed Price
$1.41M
215 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per 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
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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.