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35 Schoolhouse Road

Roxbury, Connecticut 06783

COMING SOON - NEW$3,495,000
Beds
4
Baths
4 | 1
SqFt
4,456
Acres
10.00
Year Built
1951
Matt Caiola

Matt Caiola

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WaterfrontGuest HousePool2-Car Garage1 Fireplace

About This Home

Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

Key Facts

City/Town
Roxbury
Neighborhood
N/A
Property / Style
Single Family · Cottage
Year Built
1951
Days on Market
1 day
Beds
4
Baths
4 full · 1 half
Living Area
4,456 sq ft
Lot Size
10.00 acres
Garage / Parking
2 garage · 5 total
Property Taxes
$11,461 / Annually

Market Snapshot

The Roxbury Market

Single Family · trailing 12 months

Median Days on Market

105

31 active listings

Median $ / Sq Ft

$478

31 active listings

Sale-to-List Ratio

93.6%

31 sales

How this home compares

List Price

$3.50M

vs $1.27M median

2.8× the median

Price / Sq Ft

$784

vs $478 median

64.0% above median

Days on Market

1 day

vs 105 days median

104 days fresher than median

Based on 31 active and 31 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of August 22, 2026.

Location

35 Schoolhouse Road, Roxbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$20,069

per month

  • Principal & Interest$17,949
  • Property Taxes$955
  • Insurance$1,165
  • 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
Cottage
Year Built
1951
New Construction
No/Resale
Living Area
4,456 sq ft
Below Grade
1,341 sq ft

Schools

Elementary
Booth Free
Middle
Regional District 12
High
Regional District 12

Interior

Heating
Hydro AirRadiant
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Laundry
Lower LevelMain Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullHeatedCooledPartially FinishedLiveable SpaceConcrete FloorFull With Walk-Out
In-Law Apartment
YesDetachedOver Garage
Interior Features
Audio SystemAuto Garage Door OpenerOpen Floor PlanSecurity System

Exterior & Lot

Lot Size
10.00 acres
Zoning
C
Garage / Parking
2 garage spaces5 total parking spacesDetached GaragePavedDrivewayPrivateAsphalt
Waterfront
Direct waterfront
Waterfront Details
Pond
Water Source
Private Well
Sewer
Septic
Pool
GuniteHeatedIn Ground Pool
Construction
Vertical Siding
Color
Red
Roof
Metal
Foundation
Concrete
Exterior Features
BalconyDeckGuttersGuest HouseFrench DoorsPatio
Lot Description
Lightly WoodedLevel LotClearedProfessionally LandscapedRollingWater View

Listing & Financials

Property Taxes
$11,461 / Annually
Days on Market
1
MLS #
24201025
MLS Status
Coming Soon

Similar Properties

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

Listed By

Pels Matthews

(203) 671-5432

W. Raveis Lifestyles Realty

(860) 868-0511

Co-Listed By

Rebecca Doh

W. Raveis Lifestyles Realty

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/22/2026. 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 8/22/2026 at 1:41 AM UTC.