For sale by owner

Price cut: $49K (4/7)

$450,000

281 Watertown Rd, Middlebury, CT 06762

5beds

2,428sqft

Est.:

SingleFamily

Built in 1780

1.05 Acres Lot

$-- Zestimate^®

$185/sqft

$-- HOA

What's special

Circular drivewayNew drivewayNew furnaceNew windowsNew bathroom floorBrand new appliancesNew kitchen floor

This 2428 square foot single family home has 5 bedrooms and 2.0 bathrooms. This home is located at 281 Watertown Rd, Middlebury, CT 06762.

40 days

1,486

38

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 5
Bathrooms: 2
Full bathrooms: 2

Heating

Baseboard, Other, Oil

Cooling

None

Appliances

Included: Dishwasher, Range / Oven, Refrigerator
Laundry: In Unit

Features

Flooring: Tile, Hardwood, Laminate
Basement: Unfinished
Has fireplace: Yes

Interior area

Total interior livable area: 2,428 sqft

Property

Parking

Parking features: Off-street

Features

Exterior features: Other, Vinyl, Cement / Concrete

Lot

Size: 1.05 Acres

Details

Parcel number: MIDDM510L050

Construction

Type & style

Home type: SingleFamily
Architectural style: Conventional

Materials

Roof: Asphalt

Condition

New construction: No
Year built: 1780

Community & HOA

Location

Region: Middlebury

Financial & listing details

Price per square foot: $185/sqft
Tax assessed value: $186,800
Annual tax amount: $6,075
Date on market: 3/2/2026

Estimated market value

Not available

Estimated sales range

Not available

$4,630/mo

Price history

Date	Event	Price
4/7/2026	Price change	$450,000-9.8%$185/sqft
Source: Owner Report a problem
3/21/2026	Price change	$499,000-33.5%$206/sqft
Source: Owner Report a problem
3/19/2026	Price change	$750,000+51.5%$309/sqft
Source: Owner Report a problem
3/2/2026	Listed for sale	$495,000-1%$204/sqft
Source: Owner Report a problem
2/17/2026	Listing removed	$499,900$206/sqft
Source: Smart MLS #24130870 Report a problem
12/13/2025	Listed for sale	$499,900$206/sqft
Source: Smart MLS #24130870 Report a problem
11/29/2025	Listing removed	$499,900$206/sqft
Source: Smart MLS #24130870 Report a problem
10/29/2025	Price change	$499,900+4.1%$206/sqft
Source: Smart MLS #24130870 Report a problem
10/16/2025	Price change	$480,000-12.7%$198/sqft
Source: Smart MLS #24130870 Report a problem
10/3/2025	Listed for sale	$550,000+151.1%$227/sqft
Source: Smart MLS #24130870 Report a problem
12/2/2023	Listing removed	--
Source: Zillow Rentals Report a problem
10/30/2023	Listed for rent	$2,500-7.4%$1/sqft
Source: Zillow Rentals Report a problem
9/21/2023	Listing removed	--
Source: Zillow Rentals Report a problem
9/14/2023	Listed for rent	$2,700$1/sqft
Source: Zillow Rentals Report a problem
8/31/2023	Listing removed	--
Source: Zillow Rentals Report a problem
8/9/2023	Listed for rent	$2,700+8%$1/sqft
Source: Zillow Rentals Report a problem
7/2/2022	Listing removed	--
Source: Zillow Rental Manager Report a problem
6/19/2022	Price change	$2,500-16.7%$1/sqft
Source: Zillow Rental Manager Report a problem
6/9/2022	Price change	$3,000-9.1%$1/sqft
Source: Zillow Rental Manager Report a problem
5/27/2022	Listed for rent	$3,300$1/sqft
Source: Zillow Rental Manager Report a problem
11/10/2021	Sold	$219,000-12.4%$90/sqft
Source: Smart MLS #170427025 Report a problem
9/6/2021	Pending sale	$249,900$103/sqft
Source: Real Living Real Estate #170427025 Report a problem
8/12/2021	Contingent	$249,900$103/sqft
Source: Smart MLS #170427025 Report a problem
8/6/2021	Listed for sale	$249,900$103/sqft
Source: Smart MLS #170427025 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$6,075 -0.2%	$186,800
2024	$6,090 +1.1%	$186,800
2023	$6,026 +3.2%	$186,800
2022	$5,839 -0.9%	$186,800 +10.5%
2021	$5,890 -0.8%	$169,100
2020	$5,935 +5.1%	$169,100
2019	$5,648 +2.7%	$169,100
2018	$5,497 +3.2%	$169,100
2017	$5,325 +7%	$169,100 +2.4%
2015	$4,976 +2.7%	$165,200
2014	$4,847 +1.7%	$165,200
2013	$4,768 +2.8%	$165,200
2012	$4,637 -14.1%	$165,200 -27.2%
2011	$5,396 +0.7%	$226,800
2009	$5,359 +1.8%	$226,800
2008	$5,264 +6%	$226,800
2007	$4,967 +10.6%	$226,800 +54.2%
2005	$4,492 -0.9%	$147,050
2004	$4,532 +8.2%	$147,050 0%
2003	$4,189 -2.4%	$147,100 +9.8%
2000	$4,293	$133,960