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$2,547,500

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,559 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 277 Painter Hill Rd

General

  • Sold For: $2,547,500
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24138574
  • Added to Site: 109 day(s) ago

Interior

  • Number of Rooms: 7
  • Interior Features: Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Cook Top, Dishwasher, Freezer, Microwave, Oven/Range, Refrigerator, Subzero

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Dining Room: Dining Room, Main
  • Theater/Media: Media Room, Main
  • Laundry: Main Level
  • In-Law/Au Pair Suite: Yes

Additional Information

  • Pool: Yes
  • Pool Description: In Ground Pool

Exterior

  • Exterior Features: Cabana, Lighting, Guest House, Covered Deck
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 10
  • Parking: Detached Garage, Driveway

Location

  • County: Litchfield
  • Driving Directions: painter ridge to painter hill road

School Information

  • Elementary School: Booth
  • Intermediate School: Shepaug
  • High School: Shepaug

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil, Propane
  • Heating Fuel: Oil, Propane
  • Water Heater: Other, Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Wood
  • Basement Desc.: Full, Unfinished
  • Roof: Wood Shingle, Metal
  • Attic: Yes
  • Square Feet: 2,559
  • Above Ground: 2,559 Sq. Ft.
  • Year Built: 1911

Lot Features

  • Lot Size (Acres): 3.12
  • Driveway/Sidewalk: Gravel
  • Zoning: C
  • Lot Description: Borders Open Space, Level Lot, Cleared, Professionally Landscaped, Open Lot

Green Features

  • Energy Features: Generator

Financial Considerations

  • Assessment Amount: $1,332,730
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 866630

Listed by W. Raveis Lifestyles Realty, Stacey Matthews
Sold by Klemm Real Estate Inc, Graham Klemm

Listing agent

— 277 Painter Hill Rd —

  • Stacey Matthews

    W. Raveis Lifestyles Realty

Agent Contact: (203) 671-9067 Office Contact: (860) 868-0511

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 277 Painter Hill Rd

School District:Regional School District 12
NameGradesDistance
Shepaug Valley School
159 South Street, Washington, CT 06793
6-121.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 277 Painter Hill Rd

Date
Details
Price
Change
Source
1/30/2026
Sold
$2,547,500
-0.97%
MLS
11/14/2025
Listed
$2,572,500
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by W. Raveis Lifestyles Realty, Stacey Matthews
Sold by Klemm Real Estate Inc, Graham Klemm

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277 Painter Hill Road, Roxbury, CT 06783 (MLS# 24138574) is a Single Family property that was sold at $2,547,500 on January 30, 2026. Want to learn more about 277 Painter Hill Road? Do you have questions about finding other Single Family real estate for sale in Roxbury? You can browse all Roxbury real estate or contact a Coldwell Banker agent to request more information.