Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. 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. This charming home blends history, potential, and natural beauty in one of Litchfield County's most coveted locations., Additional acreage available- separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. Total square footage is combined main house and guest house.
For sale
Price cut: $225K (5/26)
$725,000
50 Southbury Road, Roxbury, CT 06783
5beds
1,365sqft
Est.: Get pre-qualified
Single Family Residence
Built in 1817
2 Acres Lot
$-- Zestimate®
$531/sqft
$-- HOA
What's special
- 2 days |
- 756 |
- 39 |
Zillow last checked:
Listing updated:
Listed by:
MADONNA & PHILLIPS TEAM AT WILLIAM PITT SOTHEBY’S INTERNATIONAL REALTY,
Jeffrey Phillips (917)284-8276,
William Pitt Sotheby's Int'l 860-868-6600,
Co-Listing Agent: Mark Madonna 860-800-3344,
William Pitt Sotheby's Int'l
Source: Smart MLS,MLS#: 24178189
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Level: Main
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Other
Bedroom
- Level: Other
Living room
- Level: Main
Heating
- Baseboard, Electric
Cooling
- None
Appliances
- Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater
- Laundry: Main Level
Features
- Basement: Partial
- Attic: None
- Number of fireplaces: 1
Interior area
- Total structure area: 1,365
- Total interior livable area: 1,365 sqft
- Finished area above ground: 1,365
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Detached
- Garage spaces: 1
Features
- Patio & porch: Deck, Patio
- Exterior features: Garden, Stone Wall
- On waterfront: Yes
- Waterfront features: Waterfront, Pond, Walk to Water
Lot
- Size: 2 Acres
- Features: Few Trees, Sloped
Details
- Additional structures: Guest House
- Parcel number: 866798
- Zoning: A
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Wood Siding
- Foundation: Block, Stone
- Roof: Wood
Condition
- New construction: No
- Year built: 1817
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
HOA
- Has HOA: No
Location
- Region: Roxbury
Financial & listing details
- Price per square foot: $531/sqft
- Tax assessed value: $375,340
- Annual tax amount: $4,879
- Date on market: 5/26/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/26/2026 | Price change | $725,000-23.7%$531/sqft |
Source:  Smart MLS #24178189 Report a problem | ||
| 8/7/2025 | Listed for sale | $950,000+660%$696/sqft |
Source: Smart MLS #24117695 Report a problem | ||
| 12/30/2014 | Sold | $125,000-77.5%$92/sqft |
Source: Public Record Report a problem | ||
| 6/14/2013 | Listing removed | $555,000$407/sqft |
Source: Litchfield Hills Sotheby's International Realty #L143355 Report a problem | ||
| 7/22/2011 | Listed for sale | $555,000$407/sqft |
Source: Litchfield Hills Sotheby's International Realty #98509011 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,879 +3.2% | $375,340 |
| 2024 | $4,729 | $375,340 |
| 2023 | $4,729 +3.2% | $375,340 +24.9% |
| 2022 | $4,582 -1% | $300,470 |
| 2021 | $4,627 -2.5% | $300,470 |
| 2020 | $4,747 -0.3% | $300,470 |
| 2019 | $4,762 | $300,470 |
| 2018 | $4,762 +4% | $300,470 -6.8% |
| 2017 | $4,579 +3.6% | $322,480 |
| 2016 | $4,418 | $322,480 |
| 2015 | $4,418 +2.2% | $322,480 |
| 2014 | $4,321 +0.7% | $322,480 |
| 2013 | $4,289 +6.7% | $322,480 -2.9% |
| 2012 | $4,019 +1.7% | $332,130 |
| 2011 | $3,952 +4.4% | $332,130 |
| 2010 | $3,786 +4.6% | $332,130 |
| 2009 | $3,620 | $332,130 |
| 2008 | $3,620 -14% | $332,130 +21.5% |
| 2007 | $4,211 +1.4% | $273,470 +1.4% |
| 2006 | $4,151 | $269,570 |
| 2005 | $4,151 | $269,570 |
| 2004 | $4,151 | $269,570 |
| 2003 | $4,151 +3.6% | $269,570 +31.5% |
| 2001 | $4,006 | $205,020 |
| 2000 | $4,006 | $205,020 |
Find assessor info on the county website
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Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06783
Nearby schools
GreatSchools rating
- NABooth Free SchoolGrades: K-5Distance: 0.4 mi
- 8/10Shepaug Valley SchoolGrades: 6-12Distance: 3.3 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Litchfield County
- Roxbury
- 06783
- 50 Southbury Road
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