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. Total acreage includes 2 acre main house lot with 6.71 acre buildable lot. Total square footage is combined main house and guest house.
For sale
$950,000
50 Southbury Road, Roxbury, CT 06783
5beds
2,000sqft
Est.:
Single Family Residence
Built in 1817
8.71 Acres Lot
$-- Zestimate®
$475/sqft
$-- HOA
What's special
Wood-burning fireplaceSpring-fed pondOriginal hand-hewn beamsMature treesLush gardensWide-plank oak floorsFormal dining room
- 141 days |
- 1,163 |
- 90 |
Zillow last checked: 8 hours ago
Listing updated: October 07, 2025 at 03:35pm
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#: 24117695
Tour with a local agent
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
- Window Unit(s)
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: 2,000
- Total interior livable area: 2,000 sqft
- Finished area above ground: 2,000
- 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: 8.71 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: $475/sqft
- Tax assessed value: $375,340
- Annual tax amount: $4,879
- Date on market: 8/7/2025
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 8/7/2025 | Listed for sale | $950,000+660%$475/sqft |
Source: | ||
| 12/30/2014 | Sold | $125,000-77.5%$63/sqft |
Source: Public Record Report a problem | ||
| 6/14/2013 | Listing removed | $555,000$278/sqft |
Source: Litchfield Hills Sotheby's International Realty #L143355 Report a problem | ||
| 7/22/2011 | Listed for sale | $555,000$278/sqft |
Source: Litchfield Hills Sotheby's International Realty #98509011 Report a problem | ||
Public tax history
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% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$5,426/mo
Principal & interest
$3684
Property taxes
$1409
Home insurance
$333
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
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