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Litchfield
277 Painter Hill Road
Listing Courtesy of: Stacey Matthews, W. Raveis Lifestyles Realty, (203) 671-9067
$2,547,500
● House - Off Market

277 Painter Hill Road

Roxbury, CT 06783
bedrooms
3 Beds
bathrooms
2 Baths, 1 Half Bath
$14,076
Est. Monthly

About This Property

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.
Unit Size
-
Days on Market
-
Land Size
-
Price per sqft
-
Property Type
House
Property Taxes
$1,444
HOA Dues
-
Year Built
1911

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Cap Rate Calculator

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Cap Rate 100% Occupancy
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What does this mean?

Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.

How much can I actually make?

Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.

How is cap rate calculated?

Cap Rate = Net Operating Income (NOI) / Property Asset Value.

When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.

Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.

Last updated: 9 months ago (Smart MLS #24138574)

Price History

Date / Event Date Event Price
Jan 30, 2026 Sold
Premium
Sold
Dec 5, 2025 In contract -
In contract
Nov 14, 2025 Listed by W. Raveis Lifestyles Realty $2,572,500
Listed by W. Raveis Lifestyles Realty
Jan 24, 2014 Sold
Premium
Sold
Nov 20, 2012 Sold
Premium
Sold

Property Highlights

Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 1911
  • Effective Year Built: 2005
  • Building Count: 2
  • Total Rooms: 7
  • Bedroom Count: 3
  • Bathroom Count: 3
  • Full Bathrooms: 2
  • Partial Bathrooms: 3
  • Building Condition: 1
  • Building Quality: 0
  • Construction Type: 6
  • Building Style: 5
  • Exterior Walls Type: 18
  • Interior Walls Type: 0
  • Roof Shape Type: 1
  • Roof Cover Type: 13
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 0
  • Basement Type: 7
  • Basement Area: 1,677
  • Garage Type: 0
  • Parking Space Count: 0
  • Patio Type: 0
  • Porch Type: 0
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 135,907
  • Total Building Area: 2,637
  • Gross Building Area: 5,383
  • Building Area: 2,637
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 13
  • Heating: 4
  • Heated Square Feet: 2,637
  • Heating Fuel Type: 6

    Utilities

  • Sewer System: 4
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000003120
  • Standard Land Use Code: 1001
  • County Land Use Code: 109

Neighborhood

  • School District Name: Regional School District 12
  • School Tax School District: REGIONAL SD 12
  • Census Tract: 268100

Zoning

  • Zoning: C

Geography

  • Account Number: 64900
  • Parcel: ROXB M:30 L:6
  • Lot: 6
  • Municipality: ROXBURY
  • Latitude: 41.5882
  • Longitude: -73.2833

    Address

  • Full Address: 277 Painter Hill Rd
  • Address - House Number: 277
  • Address - Street Name: Painter Hill
  • Address - Suffix Type: Rd
  • State: CT
  • City Name: Roxbury
  • Carrier Code: R001
  • 4-Digit Zip Code: 1207
  • Zip Code: 06783

Valuation

    Tax

  • Tax Year: 2023
  • Tax Amount: $1,378,900

    Appraisal Valuation

  • Standard Deviation: 0.2159
  • Valuation Date: Jun 28, 2023
  • Confidence Score: 70
  • Final Value: 1,761,177
  • High Value: 2,141,419
  • Low Value: 1,380,935

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $1,094,380
  • Assessed Land Value: $451,640
  • Assessed Improvements Value: $642,740

    Sales

  • Current Sale Recording Date: Jan 24, 2014
  • Current Sale Price:
    Premium
  • Current Sale Document Type: 71
  • Previous Sale Recording Date: Nov 20, 2012
  • Previous Sale Amount: $1,195,000
  • Previous Sale Document Type: 71
Data used for valuation calculations is provided by RealtyHop, and other third party sources
Request mortgage information redaction

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Litchfield

Stats & Trends

Median Asking:

$395,000

Sale Price/ft²

$242

Below Asking

0.02%

Average Days on Market

64

Average Home Size

2115 ft²

Average Home Age

73.2 years

Currently For Sale

634 Listings
Based on RH Advisors, Inc. calculations of home data from MLS and/or public records.

Similar Homes for Sale

Currently no similar homes around

Nearby Rentals

Unit for rent at 255 Woodbury Road, Washington, CT, 06793

$5,000 /mo

  • 5 Beds
  • 2 Baths
  • 2,126 ft²
255 Woodbury Road, Washington, CT, 06793 Listing by Maria Taylor

Rentals Near You

Click here to view more rentals in the neighborhood.
SMART

Listed by: Stacey Matthews
W. Raveis Lifestyles Realty
Last Updated: 9 months ago
Data Source: Smart MLS, MLS# 24138574
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.

Frequently Asked Questions

When was property at 277 Painter Hill Road built and last sold?
The property at 277 Painter Hill Road was built in 1911 and last sold on Jan 1, 1970 for $1,250,000.
How much is this home worth?
The estimated value of the home located at 277 Painter Hill Road is $0.
What are some comparable homes to 277 Painter Hill Road?
There are currently no comparable homes to 277 Painter Hill Road.
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