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24 Roxbury Road

Woodbury, Connecticut 06798

ACTIVE - NEW$1,149,000
Beds
3
Baths
2 | 1
SqFt
4,012
Acres
9.97
Year Built
1987
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$7,666

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Shaylene Neumann

(203) 948-4655

Houlihan Lawrence

(203) 746-6565

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.