28 School Street
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,708
- Acres
- 1.41
- Year Built
- 1728
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1728
- Days on Market
- 123 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 2,708 sq ft
- Lot Size
- 1.41 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $11,185 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
30
14 under contract
Median List Price
$797,000
30 active listings
Median Closed Price
$580,000
93 sales
Median Days on Market
61
30 active listings
Median $ / Sq Ft
$331
30 active listings
Sale-to-List Ratio
99.2%
93 sales
How this home compares
List Price
$775,000
vs $797,000 median
In line with median
Price / Sq Ft
$286
vs $331 median
13.6% below median
Days on Market
123 days
vs 61 days median
62 days longer than median
Based on 30 active and 93 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of September 16, 2026.
Location
28 School Street, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$4,025
- Property Taxes$932
- Insurance$258
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Antique
- Year Built
- 1728
- New Construction
- No/Resale
- Living Area
- 2,708 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Nonnewaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Appliances
- Refrigerator
- Basement
- FullFull With Hatchway
Exterior & Lot
- Lot Size
- 1.41 acres
- Zoning
- R40
- Garage / Parking
- 2 garage spacesBarn
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Clapboard
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- ShedBarnDeckGarden Area
- Lot Description
- Corner LotLevel Lot
Listing & Financials
- Property Taxes
- $11,185 / Annually
- Days on Market
- 123
- MLS #
- 24138386
- MLS Status
- Active
Similar Properties
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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 9/16/2026. 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 9/16/2026 at 10:10 PM UTC.