25 Highmeadow Lane
Roxbury, Connecticut 06783
- Beds
- 4
- Baths
- 2 | 2
- SqFt
- 4,310
- Acres
- 17.31
- Year Built
- 1986
- 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
Sprawling 4-bedroom colonial as part of a peaceful and private 17-acre estate in desirable Roxbury, CT. Sighted well on open rolling lawns with sweeping sunrise/sunset views, this property offers country living with exceptional versatility. The sun-filled eat-in kitchen features has sliders that open to a jumbo 58' deck with awning and open views. Generous main-level spaces include a dramatic family room with vaulted ceilings, wood-paneled dining room, living room with fireplace, large office/den/library, laundry room, and powder room. Upstairs are four bedrooms and two baths, including a spacious primary suite with walk-in closets and dressing area. The lower level has lots to offer with another half bath, gym/workout area, lots of storage and access to the 2-car garage. Outside, the spotlight is on the Pebbletec saltwater pool that is beautiful and low maintenance. The property has an abundance of open space and open sky in all directions. Multi-stall barn with hay loft and a 930 sq ft apartment, offering flexibility for equestrian pursuits, collector storage, creative studios, wellness uses, and income potential. Plus, detached 3-bay garage and a whole-property generator. Truly perfect for those seeking a country retreat or a gentleman's farm, and only 90 minutes from NYC - near Woodbury and part of the Washington-Roxbury corridor. Welcome home to Litchfield County!
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1986
- Days on Market
- 86 days
- Beds
- 4
- Baths
- 2 full · 2 half
- Living Area
- 4,310 sq ft
- Lot Size
- 17.31 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $16,106 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
31
8 under contract
Median List Price
$1.29M
31 active listings
Median Closed Price
$1.40M
28 sales
Median Days on Market
89
31 active listings
Median $ / Sq Ft
$493
31 active listings
Sale-to-List Ratio
96.1%
28 sales
How this home compares
List Price
$1.79M
vs $1.29M median
38.6% above median
Price / Sq Ft
$416
vs $493 median
15.6% below median
Days on Market
86 days
vs 89 days median
In line with median
Based on 31 active and 28 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 29, 2026.
Location
25 Highmeadow Lane, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$9,152
- Property Taxes$1,342
- Insurance$598
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Roxbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1986
- New Construction
- No/Resale
- Living Area
- 4,310 sq ft
- Below Grade
- 500 sq ft
Schools
- Elementary
- Booth Free
- High
- Regional District 12
Interior
- Heating
- Heat Pump
- Heat Fuel
- Electric
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry Location
- Off mud room adjacent to kitchen
- Appliances
- Gas RangeWall OvenRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullPartially FinishedFull With Walk-Out
Exterior & Lot
- Lot Size
- 17.31 acres
- Zoning
- C
- Garage / Parking
- 2 garage spacesBarnAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- Clapboard
- Color
- White
- Roof
- Wood Shingle
- Foundation
- Slab
- Exterior Features
- ShedAwningsFruit TreesBarnDeckGarden AreaStablePaddock
- Lot Description
- Some WetlandsFarm LandLevel LotSloping LotOpen Lot
Listing & Financials
- Property Taxes
- $16,106 / Annually
- Days on Market
- 86
- MLS #
- 24171982
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Rick Distel
Compass Connecticut, LLC
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 10:10 AM UTC.