About 509 Weekeepeemee Road
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.
Features of 509 Weekeepeemee Road
| MLS® # | 24192284 |
|---|---|
| Price | $1,395,000 |
| Bedrooms | 3 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,346 |
| Acres | 5.19 |
| Type | Single Family For Sale |
| Style | Saltbox |
| Status | Active |
Community Information
| Address | 509 Weekeepeemee Road |
|---|---|
| Area | N/A |
| City | Woodbury |
| County | Litchfield |
| State | Connecticut |
| Zip Code | 06798 |
Amenities
| Parking Spaces | 6 |
|---|---|
| Parking | Detached Garage, Driveway |
| # of Garages | 3 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | No |
Interior
| Interior Features | Cable - Available, Security System |
|---|---|
| Appliances | Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer |
| Heating | Radiator, Oil |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 2 |
| Has Basement | Yes |
| Basement | Full, Unfinished, Storage, Concrete Floor, Full With Walk-Out |
Exterior
| Exterior | Clapboard |
|---|---|
| Exterior Features | Grill, Shed, Porch, Barn, Gutters, Guest House, Stone Wall, Patio |
| Lot Description | Lightly Wooded, Treed, Dry, Sloping Lot, Professionally Landscaped |
| Roof | Wood Shingle |
| Foundation | Stone |
School Information
| Elementary | Per Board of Ed |
|---|---|
| Middle | Woodbury |
| High | Nonnewaug |
Additional Information
| Date Listed | July 24th, 2026 |
|---|---|
| Days on Market | 64 |
| Zoning | os100 |
| RE / Bank Owned | No |
Listing Details
| Office | William Pitt Sotheby's Int'l |
|---|