183 Hillside Road
Ashford, Connecticut 06278
- Beds
- 4
- Baths
- 2
- SqFt
- 2,323
- Acres
- 4.62
- Year Built
- 2010
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Set high above the road at approximately 900 feet in elevation, this beautifully maintained home combines privacy, natural light and a versatile floor plan in a picturesque setting. Southwestern exposure fills the home with sunlight, while the two-story entry and catwalk overlooking the dramatic living room create an impressive sense of space. The living room features a woodstove and direct access to the covered back deck, creating an inviting connection to the outdoors. A charming three-season sunroom at the front of the home provides another bright and comfortable space to enjoy the surrounding setting. The main level offers convenient one-floor living with two bedrooms, a full bath and a laundry room with both exterior and garage access. There is no carpet in the home-hardwood and tile run throughout. Upstairs, the private primary bedroom suite is joined by an additional bedroom and a flexible office/library/den. An unfinished walk-out basement provides excellent storage and plenty of potential for future finished space or possible in-law accommodations. Well insulated with 12-inch foundation walls, a dry basement, good drainage and excellent well water. Enjoy the privacy of the property while being just down the road from the approximately 8,000-acre Yale-Myers Forest with miles of trails and outdoor recreation. Conveniently located only 1 mile to I-84, with easy access to Hartford and approximately one hour to Boston and two hours to New York City.
Key Facts
- City/Town
- Ashford
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 2010
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 2,323 sq ft
- Lot Size
- 4.62 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $10,526 / Annually
Market Snapshot
The Ashford Market
Single Family · trailing 12 months
Active Listings
19
6 under contract
Median List Price
$499,900
19 active listings
Median Closed Price
$425,000
40 sales
Median Days on Market
37
19 active listings
Median $ / Sq Ft
$264
19 active listings
Sale-to-List Ratio
100.0%
40 sales
How this home compares
List Price
$850,000
vs $499,900 median
70.0% above median
Price / Sq Ft
$366
vs $264 median
38.6% above median
Days on Market
0 days
vs 37 days median
37 days fresher than median
Based on 19 active and 40 closed sales (trailing 12 mo) of single family in Ashford. Source: SmartMLS · As of October 1, 2026.
Location
183 Hillside Road, Ashford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$4,538
- Property Taxes$877
- Insurance$283
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Ashford
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 2010
- New Construction
- No/Resale
- Living Area
- 2,323 sq ft
Schools
- Elementary
- Ashford
- High
- Region 19
Interior
- Heating
- Hydro Air
- Heat Fuel
- Propane
- Cooling
- Ceiling FansCentral Air
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasher
- Basement
- FullUnfinishedWalk-out
- In-Law Apartment
- PossibleLower LevelFirst Floor
- Interior Features
- Auto Garage Door OpenerCable - Pre-wiredOpen Floor Plan
Exterior & Lot
- Lot Size
- 4.62 acres
- Zoning
- RA
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- View
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Covered DeckPatio
- Lot Description
- Lightly WoodedDrySloping LotWater View
Listing & Financials
- Property Taxes
- $10,526 / Annually
- Days on Market
- 0
- MLS #
- 24209026
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/1/2026. 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 10/1/2026 at 5:05 PM UTC.