297 Painter Hill Rd

Roxbury, CT 06783

$4,495,000
Price
4
Beds
6,139 Sq. Ft.
$732 / Sq. Ft.
6,139
Sq. Ft.
$732
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Family Room into Kitchen
Family Room Bar
Sunroom
Library
Powder Room
1st Floor Primary Bedroom Ensuite...
2nd Floor Landing
Den/Office
Lower-level Gym
Lower-level Wine Cellar
Porte-Cochere w/1 BR Loft Apartment Above
Loft Apartment/Rec Room
Loft Apartment/Kitchen
Bedroom in Loft Apartment

Description

Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home...Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. 3rd floor loft. Recreation Room/Guest Apartment over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, additional bedroom, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.
  1. Listed by Peter Klemm • Klemm Real Estate Inc
    P: (917)-864-4940 C: (917)-864-4940 peterklemm@msn.com

Property Details for 297 Painter Hill Road

Basement Description
Full, Interior Access, Partially Finished, Full With Walk-Out
Direct Waterfront
Yes
Garages Number
3
Neighborhood
Painter Hill
Style
Other
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 07/20/2026 06:53 PM

Property Details for 297 Painter Hill Road

StatusActive
MLS #24192621
Days on Market1
Taxes$42,515 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1989
Lot Size14.81 AC / 645,123 SF
CountyLitchfield County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Klemm Real Estate Inc, Peter Klemm
Add your commute

Building Information for 297 Painter Hill Road

Stories-Year Built1989Building Size-Lot Size14.81 AC / 645,123 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$25,942 per month

30 year fixed, 6.36% Interest

Principal and Interest

$22,399

Property Taxes

$3,543

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 297 Painter Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: 47 S to Right on Painter Ridge to Left on Painter Hill, .5mile down on left. Long Private Driveway.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.589242
  • Longitude: -73.279091
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $42,515
Interior and Exterior Features
Exterior Features
  • Pool Description: Gunite, Heated, In Ground Pool
  • Waterfront Description: Brook
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: No
  • Fireplaces Total: 2
  • Laundry Room Info: Main Level
  • Laundry Room Location: 1 Laundry Room Main, 1 Basement
  • Rooms Additional: Foyer, Gym, Laundry Room, Wine Cellar
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Fireplace,Patio/Terrace,Hardwood Floor
  • Room Length: 28.1
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 26.9
Room 2
  • Room Entry Order: 10
  • Room Features: Vaulted Ceiling,Hardwood Floor
  • Room Length: 21.1
  • Room Level: Other
  • Room Type: Loft
  • Room Width: 22.1
Room 3
  • Room Entry Order: 11
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 25.8
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 25.1
Room 4
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 14.11
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 19.9
Room 5
  • Listing Key: 56E73612F90CC9C1E063E201100A8DF1
  • Room Entry Order: 3
  • Room Features: Beams,Wet Bar,Fireplace,Patio/Terrace,Hardwood Floor
  • Room Length: 15.4
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 27.0
Room 6
  • Room Entry Order: 4
  • Room Features: Beams,Dining Area,Double-Sink,Eating Space,Patio/Terrace,Hardwood Floor
  • Room Length: 14.7
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 22.1
Room 7
  • Room Entry Order: 5
  • Room Features: Balcony/Deck,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 15.3
  • Room Level: Main
  • Room Type: Primary BR Suite
  • Room Width: 19.7
Room 8
  • Room Entry Order: 6
  • Room Features: Book Shelves,Hardwood Floor
  • Room Length: 11.9
  • Room Level: Main
  • Room Type: Library
  • Room Width: 12.1
Room 9
  • Listing Key: 56E73612F90CC9C1E063E201100A8DF1
  • Room Entry Order: 7
  • Room Features: Ceiling Fan,Dining Area,Gas Log Fireplace,Stone Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 22.7
Room 10
  • Room Entry Order: 8
  • Room Features: Book Shelves,Full Bath,Wall/Wall Carpet
  • Room Length: 11.9
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 22.11
Room 11
  • Room Entry Order: 9
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 12.5
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 19.9
Property
Property and Assessments
  • Construction Description: Frame, Masonry
  • Exclusions: see attached
  • Exterior Siding: Shingle, Cedar, Redwood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1989
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Description: above grade
  • Living Area SQFT Per Public Records: 0
Lot Information
  • Lot Description: Secluded, Lightly Wooded, Sloping Lot, Cleared, Professionally Landscaped
  • Parcel Number: 866512
  • Sq Ft Est Heated Above Grade: 6139.0
  • Sq Ft Total: 6139.0
  • Zoning: C
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 297 Painter Hill Road

DateEvent & SourcePriceAppreciation
Nov 20, 2012

Closed (Public Record)

Public Record #343130908

$3,750,000

-3.1% / yr

Jan 19, 2010

Closed (Public Record)

Public Record #283081267

$4,100,000

+5.3% / yr

Nov 26, 1991

Closed (Public Record)

Public Record #91920245

$1,600,000—
DateEvent & SourcePrice
11/20/2012

Closed (Public Record)

Public Record #343130908

$3,750,000

-3.1% / yr

01/19/2010

Closed (Public Record)

Public Record #283081267

$4,100,000

+5.3% / yr

11/26/1991

Closed (Public Record)

Public Record #91920245

$1,600,000

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

Public Records for 297 Painter Hill Road

Taxable ValueLand$605,780Additions$2,664,620Total$3,270,400
Tax Record2024$42,515 ($3,543 / month)
Home Facts
Lot Size645,124 SqFtStyleMulti-Family Dwelling (2-4)ZoningCCountyNORTHWEST HILLSAPNRXBY M:30 L:12Fireplace TypeHas Fireplace

Schools near 297 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
Washington Primary School
Public - PK to 5
The Burnham School
Public - K to 5
Rating
School
Distance
Booth Free School
PublicK to 5

Shepaug Valley School
Public6 to 12

Washington Primary School
PublicPK to 5

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.

Similar Homes

Explore Nearby Homes

More information about 297 Painter Hill Road, Roxbury, CT 06783

297 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 Washington Primary School. 297 Painter Hill Road is a 4-bed, 7-bath, 6,139 sqft single family home built in 1989.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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 Klemm Real Estate Inc, Peter Klemm

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.