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$2,895,000
New Listing

220 Painter Hill Road
Roxbury, CT 06783

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
3,870
SqFt
$748
/SqFt
2007
Built
County:
Litchfield
Listing courtesy of Stacey Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-9067
Call Now: 203-641-3233
Is this the listing for you? We can help make it yours.
203-641-3233
220 Painter Hill Road220 Painter Hill Road220 Painter Hill Road220 Painter Hill Road
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Mortgage Calculator

Monthly Payment (Est.)

$13,208
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, the home features 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & a dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive mahogany deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County!

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Listing Snapshot
Price 
$2,895,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
3,870 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
4.68 Acres
Year Built 
2007
MLS® Number 
24167130
Status 
Active
Property Tax 
$10,164
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
2 hours agoListing updated with changes from the MLS®
2 hours agoListing first seen on site
General Features
Acres 
4.68
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
3
Parking 
Garage Door OpenerCarportAttached
Property Sub Type 
Single Family Residence
Security 
Security System
Sewer 
Septic Tank
SqFt Total 
4570
Style 
Colonial
Utilities 
Underground Utilities
Water Source 
Well
Zoning 
C
Interior Features
Appliances 
DishwasherDryerGas RangeMicrowaveWasherElectric Water HeaterRange HoodWine Cooler
Basement 
FullPartially Finished
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
1
Heating 
ElectricOilPropaneHeat PumpForced AirZoned
Interior 
ElevatorEntrance FoyerOpen Floorplan
Laundry Features 
Main LevelLaundry Room
Bedroom 
Level - UpperFeatures - Walk-In Closet(s)
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Exterior Features
Construction Details 
FrameHardiPlank TypeClapboard
Exterior 
Garden
Lot Features 
Cleared
Patio And Porch 
DeckPatioPorchScreened
Pool Features 
GuniteHeatedOutdoor PoolSalt WaterLapIn Ground
Roof 
AsphaltMetal
Windows/Doors 
French Doors
Community Features
Accessibility Features 
Accessible Hallway(s)
Community Features 
GolfTennis Court(s)
Schools
School District
Unknown
Elementary School
Booth Free
Middle School
Unknown
High School
Regional District 12
Listing courtesy of Stacey Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-9067



The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
Last checked: 2026-04-16 01:12 AM UTC.

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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