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183 Hillside Road

Ashford, Connecticut 06278

ACTIVE - NEW$850,000
Beds
4
Baths
2
SqFt
2,323
Acres
4.62
Year Built
2010
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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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

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

Property + 7 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,698

per 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

Similar Properties

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

Listed By

Noah King

Home Selling Team

(860) 456-7653

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.