27 Middle Quarter Road
Woodbury, Connecticut 06798
Reduced from $1,100,000
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,042
- Acres
- 1.49
- Year Built
- 1825
- Neighborhood
- Middle Quarter
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!
Key Facts
- City/Town
- Woodbury
- Neighborhood
- Middle Quarter
- Property / Style
- Single Family · Colonial
- Year Built
- 1825
- Days on Market
- 206 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,042 sq ft
- Lot Size
- 1.49 acres
- Garage / Parking
- 4 garage
- Property Taxes
- $6,728 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
26
26 under contract
Median List Price
$834,450
26 active listings
Median Closed Price
$587,500
88 sales
Median Days on Market
45
26 active listings
Median $ / Sq Ft
$302
26 active listings
Sale-to-List Ratio
99.0%
88 sales
How this home compares
List Price
$999,900
vs $834,450 median
19.8% above median
Price / Sq Ft
$490
vs $302 median
62.3% above median
Days on Market
206 days
vs 45 days median
161 days longer than median
Based on 26 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 28, 2026.
Location
27 Middle Quarter Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,098
- Property Taxes$561
- Insurance$333
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- Middle Quarter
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1825
- New Construction
- No/Resale
- Living Area
- 2,042 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- Hot AirHot Water
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- first
- Appliances
- Allowance
- Basement
- PartialFull
- In-Law Apartment
- PossibleDetached
- Interior Features
- Cable - AvailableOpen Floor Plan
- Additional Rooms
- Workshop
Exterior & Lot
- Lot Size
- 1.49 acres
- Zoning
- MQ
- Garage / Parking
- 4 garage spacesBarnDetached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- Underground UtilitiesBarnPatio
- Lot Description
- Level LotOpen Lot
Listing & Financials
- Property Taxes
- $6,728 / Annually
- Days on Market
- 206
- MLS #
- 24146826
- MLS Status
- Under Contract - Continue to Show
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 7/28/2026. 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 7/28/2026 at 6:55 AM UTC.