For Sale

Listed by Stacey Matthews and Pels Matthews from W. Raveis Lifestyles Realty

Source: SmartMLS Connecticut #24167130

220 Painter Hill Rd, Litchfield County, CT, 06783

$2,750,000

4
5
3
4570 sq. ft.
4.68 ac.

SingleFam

•

30+ days on the market

What's around 220 Painter Hill Rd

About this property

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, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & 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 ipe 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! Agent Owner.

Looking for more information on 220 Painter Hill Rd?

Explore comparables, sales history and growth for this property.
Learn more

Contact

Similar properties for sale nearby

For Sale
$1,235,000
22 East Woods Road
Litchfield County CT 06783
4
3
6
Single-Family
Listing courtesy of Compass Connecticut, LLC
For Sale
$1,295,000
77 Judds Bridge Road
Litchfield County CT 06783
4
3
3
Single-Family
Listing courtesy of Klemm Real Estate Inc
For Sale
$4,495,000
297 Painter Hill Rd
Litchfield County CT 06783
4
7
3
Single-Family
Listing courtesy of Klemm Real Estate Inc

Other properties for sale by W. Raveis Lifestyles Realty

For Sale
$2,750,000
44 Painter Ridge Road
Washington CT 06793
5
5
3
Single-Family
Listing courtesy of W. Raveis Lifestyles Realty
Under Contract
$514,900
95 Pisgah Road
New Haven County CT 06478
3
2
2
Single-Family
Listing courtesy of W. Raveis Lifestyles Realty
For Sale
$1,195,000
42 Couch Road
Washington CT 06777
3
2
1
Single-Family
Listing courtesy of W. Raveis Lifestyles Realty

Browse properties sold in nearby areas

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

© 2026 RateMyAgent