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25 Highmeadow Lane

Roxbury, Connecticut 06783

ACTIVE$1,795,000
Beds
4
Baths
2 | 2
SqFt
4,310
Acres
17.31
Year Built
1986
Matt Caiola

Matt Caiola

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Pool2-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,092

per 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.

Listed By

William Bolls

(646) 285-8197

Compass Connecticut, LLC

(203) 293-9715

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.