281 Watertown Road
Middlebury, CT, 06762 $ 499,900
Bedrooms5 Baths2.0 Sq 2,428 Monthly Estimate*
$ 3,119
for $499,900 with 5 bedrooms and 2 full baths. This 2,428 square foot home was built in 1780 on a lot size of 1.05.
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. 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!!! Circular Driveway - The home sits on about a half acre and additional half acre to the corner
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FeaturesGeneralZoning R40
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 1.05
Directions Park Rd Ext to Watertown Rd.
High School Pomperaug
City Middlebury
Elementary School Middlebury
Sq Ft Total 2428
DOM 57
Year Built 1780
Style Colonial
Year Built Source Public Records
Energy Features Thermopane Windows
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InteriorCooling System Wall Unit
Total Rooms 9
Basement Description Full
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ExteriorWater Source Private Well
Lot Description Level Lot Cleared Open Lot
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* Excluded FeaturesList ByColdwell Banker Realty 2000Broker
Affordability Calculator
- Monthly Principal & Interest
- $3,119
- Monthly Property Taxes
- $506
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Middlebury, CT
Average List Price $771,803
Percent of Sale Price 54%
About Middlebury, CT 7,671 Population
18% Since 2002
$ 105,125 Median Income
46.66 Median Age
27% Households with Children
Trends Information provided by ATTOM Data Solutions.
3041512 Elementary School
3042695 Middle School
Pomperaug High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 12/13/2025 | $499,900 | | Listed Price |