Under contract

$2,572,500

277 Painter Hill Road, Roxbury, CT 06783

3beds

2,559sqft

Est.:

Single Family Residence

Built in 1911

3.12 Acres Lot

$-- Zestimate^®

$1,005/sqft

$-- HOA

What's special

Screened porchTwo-car garageScenic viewsExpansive level lawnMedia roomHeated gunite saltwater poolFormal dining room

This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered porch with outdoor fireplace overlooking the heated gunite saltwater pool, scenic views, and expansive level lawn. The property features a two-car garage and borders a major estates and conserved land, ensuring privacy and beauty in an exceptional setting. Just minutes to the Mayflower Inn/Spa and chic shopping/dining in Washington and Woodbury.

42 days

448

25

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 3
Full bathrooms: 2
1/2 bathrooms: 1

Primary bedroom

Level: Upper

Bedroom

Level: Main

Bedroom

Level: Upper

Dining room

Level: Main

Living room

Level: Main

Media room

Level: Main

Heating

Forced Air, Oil, Propane

Cooling

Central Air

Appliances

Included: Cooktop, Dishwasher, Freezer, Microwave, Oven/Range, Refrigerator, Subzero, Water Heater
Laundry: Main Level

Features

In-Law Floorplan
Basement: Full,Unfinished
Attic: Pull Down Stairs
Number of fireplaces: 3

Interior area

Total structure area: 2,559
Total interior livable area: 2,559 sqft
Finished area above ground: 2,559
Finished area below ground: 0

Property

Parking

Total spaces: 10
Parking features: Detached, Driveway, Gravel
Garage spaces: 2
Has uncovered spaces: Yes

Features

Patio & porch: Covered
Exterior features: Lighting
Has private pool: Yes
Pool features: In Ground

Lot

Size: 3.12 Acres
Features: Borders Open Space, Level, Cleared, Landscaped, Open Lot

Details

Additional structures: Cabana, Guest House
Parcel number: 866630
Zoning: C
Other equipment: Generator

Construction

Type & style

Home type: SingleFamily
Architectural style: Colonial
Property subtype: Single Family Residence

Materials

Clapboard, Wood Siding
Foundation: Concrete Perimeter, Stone
Roof: Wood,Metal

Condition

New construction: No
Year built: 1911

Utilities & green energy

Sewer: Septic Tank
Water: Well
Utilities for property: Cable Available

Community & HOA

Community

Features: Library, Park, Playground, Private School(s), Stables/Riding, Tennis Court(s)

HOA

Has HOA: No

Location

Region: Roxbury

Financial & listing details

Price per square foot: $1,005/sqft
Tax assessed value: $1,332,730
Annual tax amount: $17,325
Date on market: 11/14/2025

Estimated market value

Not available

Estimated sales range

Not available

Price history

Date	Event	Price
12/12/2025	Pending sale	$2,572,500$1,005/sqft
Source: Smart MLS #24138574 Report a problem
11/14/2025	Listed for sale	$2,572,500+105.8%$1,005/sqft
Source: Smart MLS #24138574 Report a problem
1/23/2014	Sold	$1,250,000-10.4%$488/sqft
Source: Smart MLS #99043745 Report a problem
10/8/2013	Listed for sale	$1,395,000+16.7%$545/sqft
Source: William Raveis Real Estate #99043745 Report a problem
11/19/2012	Sold	$1,195,000-13.1%$467/sqft
Source: Smart MLS #L143435 Report a problem