24 Roxbury Road
Woodbury, Connecticut 06798
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 4,012
- Acres
- 9.97
- Year Built
- 1987
- Neighborhood
- Transylvania
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive Colonial-Contemporary residence offers an exceptional combination of privacy, natural beauty, and modern comfort on nearly 10 acres. Surrounded by mature trees, lush landscaping, and vibrant plantings, the property enjoys a peaceful, secluded setting with the gentle sounds of Transylvania Brook flowing just beyond the backyard. A long, paved, beautifully illuminated driveway leads to the home, where an impressive double-door entrance welcomes you into a spacious foyer featuring a unique indoor water feature. The thoughtfully designed interior offers three generously sized bedrooms, two-and-a-half beautifully renovated bathrooms with luxurious Italian marble tile, and recessed lighting throughout. The inviting lower-level family room opens through French doors to an expansive stone patio and a heated, inground Gunite swimming pool, creating an ideal setting for relaxing or entertaining. A bright four-season sunroom captures sweeping views of the surrounding landscape, while a dedicated office provides a comfortable and private work-from-home space. The spacious primary suite is a true retreat, featuring a walk-in closet, Jacuzzi tub, private balcony overlooking the pool, and a versatile bonus room that can be customized as a reading room, home gym, nursery, or additional living space. Additional fe
Key Facts
- City/Town
- Woodbury
- Neighborhood
- Transylvania
- Property / Style
- Single Family · Contemporary
- Year Built
- 1987
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 4,012 sq ft
- Lot Size
- 9.97 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $11,924 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
36
14 under contract
Median List Price
$842,450
36 active listings
Median Closed Price
$580,000
95 sales
Median Days on Market
50
36 active listings
Median $ / Sq Ft
$311
36 active listings
Sale-to-List Ratio
99.4%
95 sales
How this home compares
List Price
$1.15M
vs $842,450 median
36.4% above median
Price / Sq Ft
$286
vs $311 median
8.0% below median
Days on Market
0 days
vs 50 days median
50 days fresher than median
Based on 36 active and 95 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of October 2, 2026.
Location
24 Roxbury Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per month
- Principal & Interest$6,289
- Property Taxes$994
- Insurance$383
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- Transylvania
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1987
- New Construction
- No/Resale
- Living Area
- 4,012 sq ft
Schools
- Elementary
- Mitchell
- Middle
- Per Board of Ed
- High
- Nonnewaug
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Oven/RangeWall OvenRefrigeratorDishwasherDisposal
- Basement
- FullUnfinishedStorageConcrete Floor
- Interior Features
- Auto Garage Door OpenerCable - Available
Exterior & Lot
- Lot Size
- 9.97 acres
- Zoning
- OS80
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GarageDrivewayPrivatePaved
- Waterfront Details
- ViewAccess
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- Clapboard
- Color
- Gray
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- TerraceLightingFrench DoorsPatioBalconyShedDeckGarden AreaStone Wall
- Lot Description
- Fence - PartialSecludedInterior LotLightly WoodedLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $11,924 / Annually
- Days on Market
- 0
- MLS #
- 24209744
- MLS Status
- Active
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Co-Listed By
Joseph Kelley
Houlihan Lawrence
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/2/2026. 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 10/2/2026 at 4:05 PM UTC.