183 Hillside Road, Ashford, Connecticut

$850,000

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4

Beds

2

Baths

2,323

Square feet

4.62

Acres

About 183 Hillside Road

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.

Features of 183 Hillside Road

MLS® # 24209026
Price $850,000
Bedrooms 4
Bathrooms 2.00
Full Baths 2
Square Footage 2,323
Acres 4.62
Type Single Family For Sale
Style Cape Cod
Status Active

Community Information

Address 183 Hillside Road
Area N/A
City Ashford
County Windham
State Connecticut
Zip Code 06278

Amenities

Features Generator Ready, Programmable Thermostat, Ridge Vents, Thermopane Windows
Parking Attached Garage
# of Garages 2
Is Waterfront No
Waterfront View
Has Pool No

Interior

Interior Features Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
Appliances Oven/Range, Microwave, Refrigerator, Dishwasher
Heating Hydro Air, Propane
Cooling Ceiling Fans, Central Air
Fireplace No
Has Basement Yes
Basement Full, Unfinished, Walk-out

Exterior

Exterior Vinyl Siding
Exterior Features Covered Deck, Patio
Lot Description Lightly Wooded, Dry, Sloping Lot, Water View
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Ashford
High Region 19

Additional Information

Date Listed October 1st, 2026
Days on Market 3
Zoning RA
RE / Bank Owned No

Listing Details

OfficeHome Selling Team

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Listing information last updated on October 3rd, 2026 at 2:29pm EDT.