700 Watertown Road
Middlebury, Connecticut 06762
Reduced from $615,000
- Beds
- 4
- Baths
- 3
- SqFt
- 2,528
- Acres
- 1.25
- Year Built
- 1790
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
25
20 under contract
Median List Price
$670,000
25 active listings
Median Closed Price
$574,900
79 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per 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
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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.