Under contract

Price cut: $54K (5/20)

$995,000

286 South Street, Roxbury, CT 06783

5beds

2,804sqft

$5,953/mo

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Single Family Residence

Built in 1977

8.4 Acres Lot

$927,500 Zestimate^®

$355/sqft

$-- HOA

What's special

Comfortable layoutBright slate floored sunroomInviting heated salt poolSpacious bedroomsSerene meadowExpansive pasture area

Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen. Upstairs, you'll find four spacious bedrooms and two full bathrooms. A bright slate floored sunroom overlooks the inviting heated salt pool, perfect for relaxation and entertaining. Adding to its unique appeal is an attached 1-bedroom in law/guest house with propane heating and cooling, providing flexible space for visitors or extended family. The property boasts level land and lush grounds, including a expansive pasture area, all set against the picturesque backdrop of Pierce Brook. This Roxbury gem combines tranquility with convenience, making it an ideal retreat.

447 days

85

0

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 5
Bathrooms: 5
Full bathrooms: 3
1/2 bathrooms: 2

Rooms

Room types: Solarium, Staff Quarters

Primary bedroom

Level: Upper
Area: 200 Square Feet
Dimensions: 16 x 12.5

Bedroom

Level: Upper
Area: 156 Square Feet
Dimensions: 12 x 13

Bedroom

Level: Upper
Area: 143 Square Feet
Dimensions: 13 x 11

Bedroom

Level: Upper
Area: 110 Square Feet
Dimensions: 11 x 10

Bedroom

Level: Upper
Area: 224 Square Feet
Dimensions: 16 x 14

Dining room

Level: Main
Area: 156 Square Feet
Dimensions: 12 x 13

Kitchen

Level: Main
Area: 210 Square Feet
Dimensions: 10 x 21

Kitchen

Level: Main

Living room

Level: Main
Area: 252 Square Feet
Dimensions: 14 x 18

Living room

Level: Main

Sun room

Level: Main
Area: 143 Square Feet
Dimensions: 11 x 13

Heating

Forced Air, Oil

Cooling

Central Air

Appliances

Included: Oven/Range, Range Hood, Refrigerator, Water Heater
Laundry: Main Level

Features

Open Floorplan, Entrance Foyer, In-Law Floorplan
Basement: Crawl Space
Attic: Access Via Hatch
Number of fireplaces: 2

Interior area

Total structure area: 2,804
Total interior livable area: 2,804 sqft
Finished area above ground: 2,804

Property

Parking

Total spaces: 8
Parking features: Attached, Driveway, Garage Door Opener, Private
Attached garage spaces: 2
Has uncovered spaces: Yes

Features

Patio & porch: Porch
Exterior features: Garden
Has private pool: Yes
Pool features: Vinyl, In Ground
Has view: Yes
View description: Water
Has water view: Yes
Water view: Water
Waterfront features: Waterfront, Brook

Lot

Size: 8.4 Acres
Features: Secluded, Wetlands, Level, Open Lot

Details

Additional structures: Guest House
Parcel number: 866200
Zoning: res

Construction

Type & style

Home type: SingleFamily
Architectural style: Colonial
Property subtype: Single Family Residence

Materials

Vinyl Siding
Foundation: Block, Concrete Perimeter
Roof: Asphalt,Fiberglass

Condition

New construction: No
Year built: 1977

Utilities & green energy

Sewer: Septic Tank
Water: Well
Utilities for property: Cable Available

Community & HOA

Community

Features: Golf, Health Club, Lake, Library, Medical Facilities, Park, Private School(s), Tennis Court(s)

HOA

Has HOA: No

Location

Region: Roxbury

Financial & listing details

Price per square foot: $355/sqft
Tax assessed value: $541,240
Annual tax amount: $7,036
Date on market: 5/22/2025

Estimated market value

$927,500

$881,000 - $974,000

$5,720/mo

Price history

Date	Event	Price
7/23/2026	Pending sale	$995,000$355/sqft
Source: Smart MLS #24097497 Report a problem
5/20/2026	Price change	$995,000-5.1%$355/sqft
Source: Smart MLS #24097497 Report a problem
4/27/2026	Price change	$1,049,000-4.2%$374/sqft
Source: Smart MLS #24097497 Report a problem
11/21/2025	Price change	$1,095,000-8.4%$391/sqft
Source: Smart MLS #24097497 Report a problem
5/22/2025	Listed for sale	$1,195,000$426/sqft
Source: Smart MLS #24097497 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$7,036 +3.2%	$541,240
2024	$6,820	$541,240
2023	$6,820 +7.5%	$541,240 +30.1%
2022	$6,345 +15.7%	$416,080 +16.9%
2021	$5,484 -2.5%	$356,080
2020	$5,626 -0.3%	$356,080
2019	$5,644	$356,080
2018	$5,644 -7.2%	$356,080 -16.8%
2017	$6,079 +3.6%	$428,110
2016	$5,865 +0.4%	$428,110 +0.4%
2015	$5,843 +2.2%	$426,470
2014	$5,715 +0.8%	$426,470
2013	$5,672 +7.5%	$426,470 -2.2%
2012	$5,277 +3.5%	$436,090 +1.8%
2011	$5,099 +4.4%	$428,470
2010	$4,885 +4.6%	$428,470
2009	$4,670	$428,470
2008	$4,670 +2.5%	$428,470 +44.9%
2007	$4,555	$295,790
2006	$4,555	$295,790
2005	$4,555	$295,790
2004	$4,555	$295,790
2003	$4,555 +29.9%	$295,790 +64.9%
2001	$3,506	$179,410
2000	$3,506	$179,410