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277 Painter Hill Road, 
Roxbury, CT 06783

$2,572,500

3

Beds

3

Baths

2,559

Sq Ft

Single Family

Pending

Listed by

Stacey Matthews, (203) 671-9067

W. Raveis Lifestyles Realty, (860) 868-0511

Last updated:

December 17, 2025, 09:37 AM

MLS#

24138574

Source:

CT

About This Home

277 Painter Hill Road

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.

Home Facts

Single Family

3 Baths

3 Bedrooms

Built in 1911

Price Summary

2,572,500

$1,005 per Sq. Ft.

MLS #:

24138574

Last Updated:

December 17, 2025, 09:37 AM

Added:

2 month(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

2,559 Sq. Ft.

Structure

Structure

Architectural Style:

Colonial

Building Area:

2,559 Sq. Ft.

Year Built:

1911

Lot

Lot Size (Sq. Ft):

135,907

Finances & Disclosures

Finances

Price:

$2,572,500

Price per Sq. Ft:

$1,005 per Sq. Ft.

Source:CT
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.