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.
Sold for $2,547,500
$2,547,500
277 Painter Hill Road, Roxbury, CT 06783
3beds
2,559sqft
Single Family Residence
Built in 1911
3.12 Acres Lot
$2,624,600 Zestimate®
$996/sqft
$4,843 Estimated rent
Home value
$2,624,600
$2.23M - $3.07M
$4,843/mo
Zestimate® history
Owner options
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List your homeWhat's special
Screened porchTwo-car garageScenic viewsExpansive level lawnMedia roomHeated gunite saltwater poolFormal dining room
Zillow last checked:
Listing updated:
Listed by:
Stacey Matthews (203)671-9067,
W. Raveis Lifestyles Realty 860-868-0511
Bought with:
Graham Klemm, REB.0751554
Klemm Real Estate Inc
Source: Smart MLS,MLS#: 24138574
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: $996/sqft
- Tax assessed value: $1,332,730
- Annual tax amount: $17,325
- Date on market: 11/14/2025
Price history
| Date | Event | Price |
|---|---|---|
| 1/30/2026 | Sold | $2,547,500-1%$996/sqft |
Source:  Smart MLS #24138574 Report a problem | ||
| 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 | ||
| 10/1/2008 | Sold | $1,375,000+79.7%$537/sqft |
Source: Public Record Report a problem | ||
| 6/18/2002 | Sold | $765,000$299/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $17,325 +3.2% | $1,332,730 |
| 2024 | $16,792 +21.8% | $1,332,730 +21.8% |
| 2023 | $13,789 +0.2% | $1,094,380 +21.2% |
| 2022 | $13,766 +13.4% | $902,690 +14.5% |
| 2021 | $12,136 -2.5% | $788,070 |
| 2020 | $12,452 -0.3% | $788,070 |
| 2019 | $12,491 | $788,070 |
| 2018 | $12,491 +10.9% | $788,070 -0.6% |
| 2017 | $11,260 +3.6% | $792,990 |
| 2016 | $10,864 | $792,990 |
| 2015 | $10,864 +2.2% | $792,990 |
| 2014 | $10,626 +0.7% | $792,990 |
| 2013 | $10,547 +45.1% | $792,990 +32% |
| 2012 | $7,268 +1.7% | $600,620 |
| 2011 | $7,147 +5.4% | $600,620 +1% |
| 2010 | $6,782 +4.6% | $594,910 |
| 2009 | $6,485 | $594,910 |
| 2008 | $6,485 +15.7% | $594,910 +63.5% |
| 2007 | $5,604 +3.6% | $363,870 +3.6% |
| 2006 | $5,408 | $351,190 |
| 2005 | $5,408 | $351,190 |
| 2004 | $5,408 +6.4% | $351,190 +6.4% |
| 2003 | $5,085 +14.1% | $330,190 +44.8% |
| 2001 | $4,456 | $228,020 |
| 2000 | $4,456 | $228,020 |
Find assessor info on the county website
Neighborhood: 06783
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Nearby schools
GreatSchools rating
- NABooth Free SchoolGrades: K-5Distance: 2.6 mi
- 8/10Shepaug Valley SchoolGrades: 6-12Distance: 1.5 mi
Schools provided by the listing agent
- Elementary: Booth
- Middle: Shepaug
- High: Shepaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Litchfield County
- Roxbury
- 06783
- 277 Painter Hill Road
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