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$2,895,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,570 Sq. Ft.
  • 3 Car Garage
  • Updated 12 hours ago
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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!

Full Property Details for 220 Painter Hill Rd

General

  • Price: $2,895,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24167130
  • Updated: 4/15/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 12
  • Rooms/Areas: Foyer, Laundry Room, Mud Room, Sitting Room, Wine Cellar
  • Interior Features: Auto Garage Door Opener, Elevator, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: 9 ft+ Ceilings, Dressing Room, Walk-In Closet, Wall/W, Upper
  • Bedroom 1: Bedroom - 9 ft+ Ceilings, Full Bath, Hardwood Floor, Walk-In Closet, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom - Full Bath, Hardwood Floor, Walk-In Closet, Upper

Other Rooms

  • Laundry: Main Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Salt Water, Lap Pool, In Ground Pool

Exterior

  • Exterior Features: Porch-Screened, Underground Utilities, Porch, Deck, Garden Area, Stone Wall, French Doors, Underground Sprinkler, Patio
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Carport, Attached Garage

Location

  • County: Litchfield
  • Neighborhood: Painter Hill
  • Driving Directions: Painter Ridge to Right on Painter Hill

School Information

  • Elementary School: Booth Free
  • Intermediate School: Regional District 12
  • High School: Regional District 12

Community

  • Community Name: Painter Hill

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Heat Pump, Hot Air, Zoned, Electric, Oil, Propane
  • Heating Fuel: Electric, Oil, Propane
  • Water Heater: Electric, Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Hardie Board
  • Basement Desc.: Full, Partially Finished
  • Roof: Asphalt Shingle, Metal
  • Attic: Yes
  • Disability Access: Hallways 36+ Inches Wide
  • Square Feet: 4,570
  • Above Ground: 3,870 Sq. Ft.
  • Below Ground: 700 Sq. Ft.
  • Year Built: 2007

Lot Features

  • Lot Size (Acres): 4.68
  • Zoning: C
  • Lot Description: Fence - Stone, Lightly Wooded, Cleared, Professionally Landscaped, Open Lot

Green Features

  • Energy Features: Generator, Humidistat, Programmable Thermostat, Ridge Vents, Thermopane Windows

Financial Considerations

  • Assessment Amount: $781,830
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 867195

Listed by W. Raveis Lifestyles Realty, Stacey Matthews

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Listing agent

— 220 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

Price & Sales History for 220 Painter Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/15/2026
Listed
$2,895,000
313.57%
MLS
5/19/2021
Sold
$700,000
—
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 220 Painter Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,164
3%
$781,830
—
2023
$9,851
—
$781,830
—
2023
$9,872
15%
$783,510
39%
2022
$8,597
—
$563,750
2%
2021
$8,597
-31%
$553,880
-30%
2020
$12,450
—
$787,960
—
2019
$12,489
—
$787,960
—
2018
$12,489
—
$787,960
-10%
2017
$12,451
4%
$876,810
—
2016
$12,012
—
$876,810
—
2015
$12,012
2%
$876,810
—
2014
$11,749
1%
$876,810
—
2012
$11,662
—
$876,810
—
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 220 Painter Hill Rd

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

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with our affiliated lender
NMLS#: 1598647

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Listed by W. Raveis Lifestyles Realty, Stacey Matthews

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220 Painter Hill Road, Roxbury, CT 06783 (MLS# 24167130) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 220 Painter Hill Road is currently listed for $2,895,000 and was received on April 15, 2026. Want to learn more about 220 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.

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