Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,572,500

  • For Sale
  • Under Contract
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,559 Sq. Ft.
  • 2 Car Garage
See This Home
Save This Home
See This Home
Save This Home
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

  • Price: $2,572,500
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24138574
  • Updated: 12/12/2025
  • Added to Site: 63 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

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/14/2025
Listed
$2,572,500
87.09%
MLS
10/01/2008
Sold
$1,375,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 277 Painter Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$17,325
3%
$1,332,730
—
2023
$16,792
22%
$1,332,730
22%
2023
$13,789
—
$1,094,380
21%
2022
$13,766
13%
$902,690
15%
2021
$12,136
-3%
$788,070
—
2020
$12,452
—
$788,070
—
2019
$12,491
—
$788,070
—
2018
$12,491
11%
$788,070
-1%
2017
$11,260
4%
$792,990
—
2016
$10,864
—
$792,990
—
2015
$10,864
2%
$792,990
—
2014
$10,626
1%
$792,990
—
2012
$10,547
—
$792,990
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 277 Painter Hill Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by W. Raveis Lifestyles Realty, Stacey Matthews

Similar Properties near 277 Painter Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1030 Washington-Woodbury Rd, Roxbury, CT 06783 - Photo 1
$2,475,000

1030 Washington-Woodbury Rd  Roxbury, CT 06783

  • Single Family
  • Active
  • Updated 10 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 4,874
    Sq. Ft.
Listed by Klemm Real Estate Inc
96 Kinney Hill Rd, Washington, CT 06777 - Photo 1 Just Listed
$2,650,000

96 Kinney Hill Rd  Washington, CT 06777

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 5
    Total Baths
  • 4,832
    Sq. Ft.
Listed by W. Raveis Lifestyles Realty
370 Northrop St, Bridgewater, CT 06752 - Photo 1
$2,595,000

370 Northrop St  Bridgewater, CT 06752

  • Single Family
  • Active
  • 3
    Beds
  • 6
    Total Baths
  • 4,531
    Sq. Ft.
Listed by Klemm Real Estate Inc
88 Rucum Rd, Roxbury, CT 06783 - Photo 1
$2,195,000

88 Rucum Rd  Roxbury, CT 06783

  • Single Family
  • Active
  • 5
    Beds
  • 6
    Total Baths
  • 5,113
    Sq. Ft.
Listed by W. Raveis Lifestyles Realty

Just Listed near 277 Painter Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

148 Flanders Rd, Woodbury, CT 06798 - Photo 1 Just Listed
$849,000

148 Flanders Rd  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 23 hours ago
  • 3
    Beds
  • 4
    Total Baths
  • 3,082
    Sq. Ft.
Listed by William Raveis Real Estate
13 Park Ln, Woodbury, CT 06798 - Photo 1 Just Listed
$649,900
Open House

13 Park Ln  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 8 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,264
    Sq. Ft.
Listed by RE/MAX Right Choice
96 Kinney Hill Rd, Washington, CT 06777 - Photo 1 Just Listed
$2,650,000

96 Kinney Hill Rd  Washington, CT 06777

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 5
    Total Baths
  • 4,832
    Sq. Ft.
Listed by W. Raveis Lifestyles Realty
30 Saddle Ridge Rd, New Milford, CT 06776 - Photo 1 Just Listed
$899,000
Open House

30 Saddle Ridge Rd  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 5
    Total Baths
  • 4,814
    Sq. Ft.
Listed by Chris LaCava (860) 354-4111 x39

Price Reduced near 277 Painter Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

126 Sherman Hill Rd, Woodbury, CT 06798 - Photo 1 Price Reduced
-$10,000 (-4.44%)
$215,000

126 Sherman Hill Rd  #APT B12  Woodbury, CT 06798

  • Apartment
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,150
    Sq. Ft.
Listed by RE/MAX Right Choice
74 Middle Quarter Rd, Woodbury, CT 06798 - Photo 1 Price Reduced
-$15,000 (-2.07%)
$710,000
Open House

74 Middle Quarter Rd  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,874
    Sq. Ft.
Listed by Re/Max Rise
31 Cedar Hill Rd, New Milford, CT 06755 - Photo 1 Price Reduced
-$25,000 (-2.94%)
$825,000

31 Cedar Hill Rd  New Milford, CT 06755

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 3,334
    Sq. Ft.
Listed by Ray Poppe (203) 790-9500 x242
7 Candace Ct, New Milford, CT 06776 - Photo 1 Price Reduced
-$20,000 (-8%)
$230,000

7 Candace Ct  New Milford, CT 06776

  • Land Residential
  • Active
  • Updated 1 day ago
  • 2.11
    Acres
Listed by Hegarty & Co Real Estate

Recent Sales near 277 Painter Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

[Address not provided], Roxbury, CT 06783 - Photo 1 Sold
$2,700,000

[Address not provided]  Roxbury, CT 06783

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 5,455
    Sq. Ft.
Listed and Sold by W. Raveis Lifestyles Realty
225 Roxbury Rd, Washington, CT 06793 - Photo 1 Sold
$2,370,000

225 Roxbury Rd  Washington, CT 06793

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,149
    Sq. Ft.
Listed by Klemm Real Estate Inc
Sold by W. Raveis Lifestyles Realty
9 Mallory Brook Rd, Washington, CT 06793 - Photo 1 Sold
$2,190,000

9 Mallory Brook Rd  Washington, CT 06793

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 3,743
    Sq. Ft.
Listed by Klemm Real Estate Inc
Sold by Klemm Real Estate Inc
18 Mallory Rd, Roxbury, CT 06783 - Photo 1 Sold
$2,575,000

18 Mallory Rd  Roxbury, CT 06783

  • Single Family
  • Closed
  • 3
    Beds
  • 4
    Total Baths
  • 3,384
    Sq. Ft.
Listed and Sold by Klemm Real Estate Inc

277 Painter Hill Road, Roxbury, CT 06783 (MLS# 24138574) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 277 Painter Hill Road is currently listed for $2,572,500 and was received on November 14, 2025. 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.

Tour this property