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$499,900

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 2 Full Baths
  • 2,428 Sq. Ft.
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Welcome to this stunning Colonial, offering over 2,400 sq. ft. of living space on a rare, level 1-acre lot in one of Middlebury's most desirable locations. The first floor features an inviting eat-in kitchen with updated cabinets, new appliances, a center island, and a cozy fireplace-perfect for gathering. You'll also find a formal dining room and spacious living room, ideal for entertaining. The first-floor master suite includes its own fireplace, full bath, and walk-in closet. A convenient first-floor laundry adds to the ease of everyday living. Upstairs, you'll discover four additional bedrooms and another full bathroom, offering plenty of space for family, guests, or a home office. This home beautifully blends 18th-century charm-with wood floors and antique character-with modern updates for peace of mind, including newer vinyl replacement windows, a new driveway, new heating system, and a brand-new refrigerator. Brand new ac 18.000btu Set on a spacious, open acre, the property offers endless opportunities for outdoor enjoyment-all while being just minutes from schools, highways, and town conveniences. At asking price, the buyer will receive a brand-new roof-making this beautiful Colonial an even greater value! Don't miss your chance to own a piece of Middlebury history, offering the perfect balance of charm, comfort, and modern updates.Everything is done from roof to basement .IT like a new house and pay half of tax around 6.000 . Move in Ready. Come take a look!

Full Property Details for 281 Watertown Rd

General

  • Price: $499,900
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24130870
  • Updated: 12/22/2025
  • Added to Site: 105 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Electric Cooktop, Electric Range, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Fireplace, Full Bath, Walk-In Closet, 13 x 23, Main
  • Bedroom 1: Bedroom, 12 x 17, Upper
  • Bedroom 2: Bedroom, 15 x 15, Upper
  • Bedroom 3: Bedroom, 16 x 12, Upper
  • Bedroom 4: Bedroom, 19 x 11, Upper

Other Rooms

  • Living Room: Living Room, 18 x 15, Main
  • Kitchen: Kitchen - Remodeled, Island, 18 x 15, Main
  • Dining Room: Dining Room, 12 x 19, Main
  • Office: Office, 7 x 10, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Shed, Gutters

Parking

  • Total Spaces: 10
  • Parking: None, Paved

Location

  • County: New Haven
  • Driving Directions: Park Rd Ext to Watertown Rd.

School Information

  • Elementary School: Middlebury
  • High School: Pomperaug

Heating & Cooling

  • Cooling Type: Wall Unit
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, Domestic, Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Aluminum
  • Basement Desc.: Full
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,428
  • Above Ground: 2,428 Sq. Ft.
  • Year Built: 1780

Lot Features

  • Lot Size (Acres): 1.05
  • Zoning: R40
  • Lot Description: Level Lot, Cleared, Open Lot

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Assessment Amount: $186,800
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1192197

Listed by Coldwell Banker Realty 2000, Xin Guo

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Listing agent

— 281 Watertown Rd —

  • Xin Guo

    Coldwell Banker Realty 2000

Agent Contact: (203) 482-3932 Office Contact: (203) 706-1222

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 281 Watertown Rd

School District:Regional School District 15
NameGradesDistance
Middlebury Elementary School
550 Whittemore Road, Middlebury, CT 06762
K-51.7 mi
Memorial Middle School, Middlebury, CT
1 Memorial Drive, Middlebury, CT 06762
6-81.3 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-124.1 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 281 Watertown Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/29/2025
Price Increased
$499,900
4.15%
MLS
10/16/2025
Price Reduced
$480,000
-12.73%
MLS
10/03/2025
Listed
$550,000
151.14%
MLS
11/10/2021
Sold
$219,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 281 Watertown Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,075
—
$186,800
—
2023
$6,090
1%
$186,800
—
2023
$6,026
3%
$186,800
—
2022
$5,839
-1%
$186,800
10%
2021
$5,890
-1%
$169,100
—
2020
$5,935
5%
$169,100
—
2019
$5,648
3%
$169,100
—
2018
$5,497
3%
$169,100
—
2017
$5,325
4%
$169,100
2%
2016
$5,123
3%
$165,200
—
2015
$4,976
3%
$165,200
—
2014
$4,847
2%
$165,200
—
2011
$4,768
—
$165,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 281 Watertown Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Coldwell Banker Realty 2000, Xin Guo

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281 Watertown Road, Middlebury, CT 06762 (MLS# 24130870) is a Single Family property with 5 bedrooms and 2 full bathrooms. 281 Watertown Road is currently listed for $499,900 and was received on October 03, 2025. Want to learn more about 281 Watertown Road? Do you have questions about finding other Single Family real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.

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