281 Watertown Rd

Middlebury, CT 06762

$499,900
Price
5
Beds
2,428 Sq. Ft.
$206 / Sq. Ft.
2,428
Sq. Ft.
$206
per Sq. Ft.
Living room
Formal Dining room
Formal dining room
First floor master suite with fireplace
Master Suite Bath
Upstairs bedroom

Description

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...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!
  1. Listed by Xin M Guo • Coldwell Banker Realty 2000
    P: (203)-482-3932 C: (203)-482-3932 xinguo808@gmail.com

Property Details for 281 Watertown Road

Basement Description
Full
Direct Waterfront
No
Garages Number
0
Neighborhood
N/A
Style
Colonial
Garage Parking Info
None, Paved
Swimming Pool
No
LISTING UPDATED: 12/22/2025 01:11 PM

Property Details for 281 Watertown Road

StatusActive
MLS #24130870
Days on Market68
Taxes$6,075 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1780
Lot Size1.05 AC / 45,738 SF
CountyNew Haven County

Location

Listing Courtesy of Coldwell Banker Realty 2000, Xin M Guo
Add your commute

Building Information for 281 Watertown Road

Stories-Year Built1780Building Size-Lot Size1.05 AC / 45,738 SF

Payment Calculator

$2,976 per month

30 year fixed, 6.28% Interest

Principal and Interest

$2,470

Property Taxes

$506

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 281 Watertown Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Park Rd Ext to Watertown Rd.
  • Elementary School: Middlebury
  • Flood Zone: No
  • High School: Pomperaug
  • Latitude: 41.549759
  • Longitude: -73.116689
  • State: Connecticut
Parking
  • Parking Total Spaces: 10
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $6,075
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Gutters
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Electric Cooktop, Electric Range, Refrigerator, Dishwasher
  • Attic Description: Storage Space, Pull-Down Stairs
  • Cooling System: Wall Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Cable - Available
  • Laundry Room Info: Main Level
  • Laundry Room Location: First floor
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 15.0
Room 2
  • Room Entry Order: 2
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 19.0
Room 3
  • Room Entry Order: 3
  • Room Features: Fireplace,Full Bath,Walk-In Closet
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 23.0
Room 4
  • Room Entry Order: 4
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 17.0
Room 5
  • Listing Key: 402E6CE6185DF10DE063E201100AF82C
  • Room Entry Order: 5
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Room 6
  • Room Entry Order: 6
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 7
  • Room Entry Order: 7
  • Room Features: Remodeled,Island
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 15.0
Room 8
  • Room Entry Order: 8
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 9
  • Listing Key: 402E6CE6185DF10DE063E201100AF82C
  • Room Entry Order: 9
  • Room Length: 7.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 10.0
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Aluminum
  • Foundation Type: Masonry
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1780
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Living Area SQFT Per Public Records: 2428
Lot Information
  • Lot Description: Level Lot, Cleared, Open Lot
  • Parcel Number: 1192197
  • Sq Ft Est Heated Above Grade: 2428.0
  • Sq Ft Total: 2428.0
  • Zoning: R40
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Electric, Domestic, Tank Size Unknown
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 281 Watertown Road

DateEvent & SourcePriceAppreciation
Nov 10, 2021

Closed (Public Record)

Public Record #1476627435

$219,000

+193.1% / yr

Jun 4, 2010

Closed (Public Record)

Public Record #327145178

$1—
DateEvent & SourcePrice
11/10/2021

Closed (Public Record)

Public Record #1476627435

$219,000

+193.1% / yr

06/04/2010

Closed (Public Record)

Public Record #327145178

$1

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 281 Watertown Road

Taxable ValueLand$66,800Additions$120,000Total$186,800
Tax Record2024$6,075 ($506 / month)
Home Facts
Beds4Baths2Total Finished SqFt2,428 SqFtAbove Grade Finished SqFt2,428 SqFtStories2Lot Size45,738 SqFtStyleSingle Family ResidenceYear Built1981ZoningR40CountyNEW HAVENAPNMDBY M:5-10 L:050Fireplace TypeHas Fireplace

Schools near 281 Watertown Road

This home is within Regional School District 15.
Rating
School
Type
Grades
Distance
Middlebury Elementary School
Public - K to 5
Memorial Middle School
Public - 6 to 8
Pomperaug Regional High School
Public - 9 to 12
Rating
School
Distance
Middlebury Elementary School
PublicK to 5

Memorial Middle School
Public6 to 8

Pomperaug Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 281 Watertown Road, Middlebury, CT 06762

281 Watertown Road is a single family home for sale in Middlebury, CT 06762. This property was listed for sale on October 3, 2025 by Coldwell Banker Realty 2000, it's currently listed at $499,900. It has been on the market for a total of 68 days and was last sold on November 10, 2021. This listing's school district is Regional School District 15. Nearby schools include Middlebury Elementary School, Memorial Middle School and Pomperaug Regional High School. 281 Watertown Road is a 5-bed, 2-bath, 2,428 sqft single family home built in 1780.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Realty 2000, Xin M Guo

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.