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Good morning. Welcome to 281 Watertown Road, Middlebury, CT

$499,900
5
Beds
2.00
Baths
2,428
SqFt
1.05
Acres

Pricing Insight: Originally listed for $550,000, the price was last adjusted to $499,900 on February 1, 2026, a –$50,100 (9.1%) change, approximately 0 days ago. This property has been on the market for approximately 121 days.

281 Watertown Road, Middlebury, CT is a 5-bed, 2-bath, 2,428 square foot home built in 1780 , featuring colonial architecture.

This home is within the Middlebury school district. Local, with nearby schools including Middlebury.

MLS #: 24130870

Offered Price: $499,900

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 2,428 Sq. Ft.

Lot Size: 1.05 Acres

Neighborhood: N/A

County: New Haven

Year Built: 1780

Design & Construction: Frame

Heating: Hot Water

Cooling: Wall Unit

Garage Spaces: 0

Price per Sq Ft as listed: $206

Estimated Tax: $6,075

Days on Market: 106

$200,000
0 Beds · 0 Baths · 0 Sq Ft
288 Watertown Road, Middlebury

Home Automation: Not specified

Energy Features: Thermopane Windows

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Water

Fuel Tank Location: In Basement

Cooling System: Wall Unit

Hot Water System: Electric, Domestic, Tank Size Unknown

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $206 / Sq. Ft.

Tax assessed value: $186,800

Estimated Tax: $6,075

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1780

Living Area: 2,428 Sq. Ft.

Lot Size: 1.05 Acres

Fuel: Oil

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AUTOMATED VALUATION ESTIMATE

Powered by Realtors Property Resource® (RPR)

Note: Computer-generated estimate, not an appraisal.

Understanding This Valuation

The RPR AVM considers:

  • Recent sales of comparable properties
  • Property characteristics and location
  • Market trends in Middlebury
  • Statistical modeling algorithms
Local Market Context
Active Listings: 26
Average Price: $519,052
Average DOM: 106 days

Complimentary CMAs, no obligation

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!

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Flood Risk Assessment

Location Analysis:
Inland Middlebury location
Water Proximity:
No direct water access
Topography:
Standard terrain • 1.1 acres
Recommendations:
  • Consult FEMA Flood Maps for accurate zone info
  • Consider flood insurance based on professional assessment
  • Evaluate property drainage during inspection
  • Review local flood history with town officials
Risk Level: Low

Minimal flood risk indicators. Verify with FEMA flood maps.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

  • Dining & Café Access: Low to Moderate
  • Daily Services: Limited
  • Recreational Space: Limited Nearby
How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

  • Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
  • Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

26

Homes For Sale

$519,052

Average List Price

Mechanicals & Utilities: Hot Water • Oil • Wall Unit • Private Well water • 2 fireplaces

Exterior Features

Exterior Construction: Aluminum

Roof Type: Asphalt Shingle

Foundation: Masonry

Garage: Paved

Parking: 10 Total

Patio/Deck: Shed,Gutters

Utilities: Water: Private Well

Outbuildings: Shed,Gutters

Only motif connects you to a certified
"Local Market Expert"

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Steve Simos
Real Estate Advisor
Middlebury • Connecticut Shoreline
Licensed Real Estate Agent – Connecticut
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 Verified Motif Advisor
Good morning Steve, I'm interested in
281 Watertown Road, Middlebury, Connecticut
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Steve Simos
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800-555-0003
Presented by motif • Source: MLS • Listed by: Xin Guo • Coldwell Banker Realty 2000 • MLS# 24130870