50 Southbury Rd

Roxbury, CT 06783

$950,000
Price
5
Beds
2,000 Sq. Ft.
$475 / Sq. Ft.
2,000
Sq. Ft.
$475
per Sq. Ft.

Description

Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning...Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks the spring-fed pond and includes a generous living room, two bedrooms, and a full bath-serviced by its own septic. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and gently rolling lawn. Whether you envision building a bespoke estate or simply enjoying the charm and privacy of the existing homes, this rare offering blends history, potential, and natural beauty in one of Litchfield County's most coveted locations.
  1. Listed by Jeffrey Phillips • William Pitt Sotheby's Int'l
    P: (917)-284-8276 C: (917)-284-8276 jrphillips@wpsir.com
  2. Listed by Mark Madonna • William Pitt Sotheby's Int'l
    P: (860)-868-6600 C: (860)-800-3344 mmadonna@wpsir.com

Property Details for 50 Southbury Road

Basement Description
Partial
Direct Waterfront
Yes
Garages Number
1
Neighborhood
N/A
Style
Cape Cod
Garage Parking Info
Detached Garage
Swimming Pool
No
LISTING UPDATED: 10/07/2025 10:35 PM

Property Details for 50 Southbury Road

StatusActive
MLS #24117695
Days on Market138
Taxes$4,879 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1817
Lot Size8.71 AC / 379,407 SF
CountyLitchfield County

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Jeffrey Phillips; William Pitt Sotheby's Int'l, Mark Madonna
Add your commute

Building Information for 50 Southbury Road

Stories-Year Built1817Building Size-Lot Size8.71 AC / 379,407 SF

Payment Calculator

$5,101 per month

30 year fixed, 6.28% Interest

Principal and Interest

$4,694

Property Taxes

$407

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 50 Southbury Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Southbury Rd house on the left from Roxbury
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.553471
  • Longitude: -73.300054
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $4,879
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Garden Area, Guest House, Stone Wall, Patio
  • Waterfront Description: Pond, Walk to Water
Interior Features
  • Appliances Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer
  • Cooling System: Window Unit
  • Heat Type: Baseboard
  • Attic YN: No
  • Fireplaces Total: 1
  • Laundry Room Info: Main Level
  • Laundry Room Location: laundry in guest house
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 3
  • Room Entry Order: 3
  • Room Level: Upper
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Listing Key: 3BC577163ABF6377E0631A01100A43D4
  • Room Entry Order: 5
  • Room Level: Other
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Other
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Wood
  • Foundation Type: Block, Stone
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1817
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Detached
  • In Law Apartment: Possible
  • Sq Ft Description: 3 bedroom cape plus 2 bedroom guest house
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 0
Lot Information
  • Lot Description: Lightly Wooded, Sloping Lot
  • Parcel Number: 866798
  • Sq Ft Est Heated Above Grade: 2000.0
  • Sq Ft Total: 2000.0
  • Zoning: A
Utilities
  • Heat Fuel Type: Electric
  • Hot Water Description: Electric, Upright Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 50 Southbury Road

DateEvent & SourcePriceAppreciation
Dec 30, 2014

Closed (Public Record)

Public Record #486697522

$125,000—
DateEvent & SourcePrice
12/30/2014

Closed (Public Record)

Public Record #486697522

$125,000

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

Public Records for 50 Southbury Road

Taxable ValueLand$130,410Additions$244,930Total$375,340
Tax Record2024$4,879 ($407 / month)
Home Facts
Beds0Lot Size87,120 SqFtStyleSingle Family ResidenceZoningACountyLITCHFIELDAPNRXBY M:18 L:107Fireplace TypeHas Fireplace

Schools near 50 Southbury 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 50 Southbury Road, Roxbury, CT 06783

50 Southbury Road is a single family home for sale in Roxbury, CT 06783. This property was listed for sale on August 7, 2025 by William Pitt Sotheby's Int'l, it's currently listed at $950,000. It has been on the market for a total of 138 days and was last sold on December 30, 2014. This listing's school district is Regional School District 12. Nearby schools include Booth Free School, Shepaug Valley School and The Burnham School. 50 Southbury Road is a 5-bed, 3-bath, 2,000 sqft single family home built in 1817.

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 makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Jeffrey Phillips; William Pitt Sotheby's Int'l, Mark Madonna

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.