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
| Office | Home Selling Team |
|---|
