509 Weekeepeemee Road
Woodbury, Connecticut 06798
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,346
- Acres
- 5.19
- Year Built
- 1747
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
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 horses, chickens, and hosting friends and extended family.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Saltbox
- Year Built
- 1747
- Days on Market
- 4 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,346 sq ft
- Lot Size
- 5.19 acres
- Garage / Parking
- 3 garage · 6 total
- Property Taxes
- $10,317 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
26
26 under contract
Median List Price
$834,450
26 active listings
Median Closed Price
$587,500
88 sales
Median Days on Market
45
26 active listings
Median $ / Sq Ft
$302
26 active listings
Sale-to-List Ratio
99.0%
88 sales
How this home compares
List Price
$1.40M
vs $834,450 median
67.2% above median
Price / Sq Ft
$595
vs $302 median
97.0% above median
Days on Market
4 days
vs 45 days median
41 days fresher than median
Based on 26 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 28, 2026.
Location
509 Weekeepeemee Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$7,113
- Property Taxes$860
- Insurance$465
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Saltbox
- Year Built
- 1747
- New Construction
- No/Resale
- Living Area
- 2,346 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Nonnewaug
Interior
- Heating
- Radiator
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Gas RangeOven/RangeRange HoodRefrigeratorDishwasherWasherElectric Dryer
- Basement
- FullUnfinishedStorageConcrete FloorFull With Walk-Out
- In-Law Apartment
- YesDetachedOver Garage
- Interior Features
- Cable - AvailableSecurity System
Exterior & Lot
- Lot Size
- 5.19 acres
- Zoning
- os100
- Garage / Parking
- 3 garage spaces6 total parking spacesDetached GarageDrivewayCircularPaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Gray Green
- Roof
- Wood Shingle
- Foundation
- Stone
- Exterior Features
- GrillShedPorchBarnGuttersGuest HouseStone WallPatio
- Lot Description
- Lightly WoodedTreedDrySloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $10,317 / Annually
- Days on Market
- 4
- MLS #
- 24192284
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 5:15 AM UTC.