35 Schoolhouse Road
Roxbury, Connecticut 06783
Reduced from $3,495,000
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 4,456
- Acres
- 10.00
- Year Built
- 1951
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
- 63 days
- 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
Active Listings
25
1 under contract
Median List Price
$1.29M
25 active listings
Median Closed Price
$960,000
31 sales
Median Days on Market
95
25 active listings
Median $ / Sq Ft
$485
25 active listings
Sale-to-List Ratio
96.8%
31 sales
How this home compares
List Price
$3.25M
vs $1.29M median
2.5× the median
Price / Sq Ft
$729
vs $485 median
50.3% above median
Days on Market
63 days
vs 95 days median
32 days fresher than median
Based on 25 active and 31 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of October 24, 2026.
Location
35 Schoolhouse Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$17,860
- Property Taxes$955
- Insurance$1,083
- 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
- 63
- MLS #
- 24201025
- MLS Status
- Active
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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 10/24/2026. 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 10/24/2026 at 12:01 AM UTC.