220 Painter Hill Rd

Roxbury, CT 06783

$2,895,000
Price
4
Beds
4,570 Sq. Ft.
$633 / Sq. Ft.
4,570
Sq. Ft.
$633
per Sq. Ft.
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Foyer
New Kitchen, custom cerused Oak cabinets
2 dishwashers, Sub Zero side by side with glass door, walk in pantry
Family Room. Fireplace can be wood burning or gas
Family Room
Dining Nook/Game Table in Family Room
Bar/Breakfast Nook
Screened Porch
Bar
Sitting Room
Dining Room
Powder Room
Main Level Guest Room with En-suite Bath
Foyer
Upstairs Landing
Primary Bedroom
Primary Bath, also includes Walk In shawer and Toto toilet
2nd Upstairs Bedroom En-suite Bath Walk In Closet
3rd Upstairs Bedroom, En-suite Bath Walk In Closet
Office/5th Bedroom, shared En-suite Bath.
3000 Bottle Climate-Controlled Wine Cellar
Game Room - Walk out.
Media Room
Firepit area with floating stone steps
New Gunite Heated Pool with wifi controls, lounging ledge and swim lane
50 foot long pool
View over neighboring fields, back of house
View from Sunset Porch
Sunsets from Pool Area

Description

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...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!
  1. Listed by Stacey Matthews • W. Raveis Lifestyles Realty
    P: (203)-671-9067 C: (203)-671-9067 stacey.matthews@raveis.com

Property Details for 220 Painter Hill Road

Basement Description
Full, Partially Finished
Direct Waterfront
No
Garages Number
3
Neighborhood
Painter Hill
Style
Colonial
Garage Parking Info
Carport, Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 04/15/2026 10:57 PM

Property Details for 220 Painter Hill Road

StatusActive
MLS #24167130
Days on Market1
Taxes$10,164 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built2007
Lot Size4.68 AC / 203,860 SF
CountyLitchfield County
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Location

Listing Courtesy of W. Raveis Lifestyles Realty, Stacey Matthews
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Building Information for 220 Painter Hill Road

Stories-Year Built2007Building Size-Lot Size4.68 AC / 203,860 SF

Payment Calculator

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$15,425 per month

30 year fixed, 6.46% Interest

Principal and Interest

$14,578

Property Taxes

$847

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 220 Painter Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Painter Ridge to Right on Painter Hill
  • Elementary School: Booth Free
  • High School: Regional District 12
  • Intermediate School: Regional District 12
  • Latitude: 41.586357
  • Longitude: -73.29256
  • Neighborhood Amenities: Golf Course, Health Club, Library, Park, Playground/Tot Lot, Private School(s), Stables/Riding, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $10,164
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Screened, Underground Utilities, Porch, Deck, Garden Area, Stone Wall, French Doors, Underground Sprinkler, Patio
  • Pool Description: Gunite, Heated, Salt Water, Lap Pool, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Heat Pump, Hot Air, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Home Automation: Lighting, Security System
  • Interior Features: Auto Garage Door Opener, Elevator, Open Floor Plan, Security System
  • Laundry Room Info: Main Level
  • Laundry Room Location: Main level
  • Rooms Additional: Foyer, Laundry Room, Mud Room, Sitting Room, Wine Cellar
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Dressing Room,Walk-In Closet,Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 2
  • Room Entry Order: 2
  • Room Features: Full Bath,Hardwood Floor,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Full Bath,Hardwood Floor,Walk-In Closet
  • Room Level: Main
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Clapboard, Hardie Board
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • Handicap Features: Hallways 36+ Inches Wide
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Metal
  • Year Built: 2007
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: Possible
  • Sq Ft Est Heated Below Grade: 700
  • Living Area SQFT Per Public Records: 3870
Lot Information
  • Lot Description: Fence - Stone, Lightly Wooded, Cleared, Professionally Landscaped, Open Lot
  • Parcel Number: 867195
  • Sq Ft Est Heated Above Grade: 3870.0
  • Sq Ft Total: 4570.0
  • Zoning: C
Utilities
  • Energy Features: Generator, Humidistat, Programmable Thermostat, Ridge Vents, Thermopane Windows
  • Heat Fuel Type: Electric, Oil, Propane
  • Hot Water Description: Electric, Tank Size Unknown
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 220 Painter Hill Road

DateEvent & SourcePriceAppreciation
May 19, 2021

Closed (Public Record)

Public Record #1462854343

$700,000—
May 19, 2021

Closed (Public Record)

Public Record #1554992435

$700,000

+10.8% / yr

Aug 27, 2020

Closed (Public Record)

Public Record #677540246

$650,000—
DateEvent & SourcePrice
05/19/2021

Closed (Public Record)

Public Record #1462854343

$700,000
05/19/2021

Closed (Public Record)

Public Record #1554992435

$700,000

+10.8% / yr

08/27/2020

Closed (Public Record)

Public Record #677540246

$650,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 220 Painter Hill Road

Taxable ValueLand$257,740Additions$524,090Total$781,830
Tax Record2024$10,164 ($847 / month)
Home Facts
Beds4Baths4.5Total Finished SqFt3,870 SqFtAbove Grade Finished SqFt3,870 SqFtUnfinished Basement SqFt1,324 SqFtStories2Lot Size203,861 SqFtStyleSingle Family ResidenceYear Built2007Year Renovated2014ZoningCCountyLITCHFIELDAPNRXBY M:30 L:48Fireplace TypeHas Fireplace

Schools near 220 Painter Hill Road

This home is within Regional School District 12.
Rating
School
Type
Grades
Distance
Booth Free School
Public - K to 5
Shepaug Valley School
Public - 6 to 12
The Burnham School
Public - K to 5
Rating
School
Distance
Booth Free School
PublicK to 5

Shepaug Valley School
Public6 to 12

The Burnham School
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 220 Painter Hill Road, Roxbury, CT 06783

220 Painter Hill Road is a single family home for sale in Roxbury, CT 06783. This listing's school district is Regional School District 12. Nearby schools include Booth Free School, Shepaug Valley School and The Burnham School. 220 Painter Hill Road is a 4-bed, 5-bath, 4,570 sqft single family home built in 2007.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of W. Raveis Lifestyles Realty, Stacey Matthews

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.