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700 Watertown Road

Middlebury, Connecticut 06762

PENDING$590,000

Reduced from $615,000

Beds
4
Baths
3
SqFt
2,528
Acres
1.25
Year Built
1790
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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3-Car Garage2 FireplacesVirtual TourPrice Reduced

About This Home

This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates. Built-in equity! Recent appraisal values this home at $715,000. Set on 1.25 meticulously landscaped acres, this 4-bedroom, 3-bath home offers warmth, space, and versatility with a huge finished attic space. The stunning grounds feature mature plantings, classic New England stone walls, and inviting patio spaces that create a private outdoor retreat ideal for relaxing or entertaining. Easily accessed from the kitchen, the outdoor living areas offer seamless flow for gatherings, dining, and enjoying the peaceful setting. Inside, the updated eat-in kitchen features a fireplace with pellet stove insert, while the formal living room offers a second fireplace and the bright sunroom provides flexible living space. A separate outbuilding/studio expands the possibilities-perfect for an artist, home office, workshop, guest space, or easily converted into a detached in-law setup. Extensive updates include newer windows, updated plumbing, replaced well pump and pressure tank, newer oil tank, furnace burner replacement, exterior painting, new appliances, renovated studio/office, and a full first-floor bath. The main level has been updated with sheetrock replacing original plaster walls and ceilings, while the upper level retains its original plaster craftsmanship and antique character. A rare opportunity to own historic beauty, modern function, and value-without historic district restrictions

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1790
Days on Market
121 days
Beds
4
Baths
3 full
Living Area
2,528 sq ft
Lot Size
1.25 acres
Garage / Parking
3 garage
Property Taxes
$7,486 / Annually

Market Snapshot

The Middlebury Market

Single Family · trailing 12 months

Median Days on Market

45

25 active listings

Median $ / Sq Ft

$280

25 active listings

Sale-to-List Ratio

100.0%

79 sales

How this home compares

List Price

$590,000

vs $670,000 median

11.9% below median

Price / Sq Ft

$233

vs $280 median

16.8% below median

Days on Market

121 days

vs 45 days median

76 days longer than median

Based on 25 active and 79 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of October 15, 2026.

Location

700 Watertown Road, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,089

per month

  • Principal & Interest$3,268
  • Property Taxes$624
  • Insurance$197
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Middlebury
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Colonial
Year Built
1790
New Construction
No/Resale
Living Area
2,528 sq ft

Schools

Elementary
Middlebury
High
Regional District 15

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Wall Unit
Fireplaces
2
Laundry
Main Level
Appliances
Oven/RangeRefrigeratorDishwasher
Basement
PartialDirt Floor
In-Law Apartment
PossibleDetached
Interior Features
Cable - Available

Exterior & Lot

Lot Size
1.25 acres
Zoning
R40
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
ConcreteStone
Exterior Features
ShedGuttersGarden AreaLightingStone WallFrench DoorsPatio
Lot Description
Lightly WoodedLevel Lot

Listing & Financials

Property Taxes
$7,486 / Annually
Days on Market
121
MLS #
24184437
MLS Status
Under Contract - Continue to Show
Financing
FHA,VA,CHFA

Similar Properties

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Listed By

Erin Giguiere

Regall Realty, LLC

(860) 966-3804

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/15/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 10/15/2026 at 11:25 PM UTC.