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27 Middle Quarter Road, Woodbury, CT 06798

Single Family For Sale

$999,900
$490/sqft
27 Middle Quarter Road, Woodbury, CT
Active
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3
Bedrooms
3
Bathrooms
2,042
Sq Ft
1.49
Acres
1825
Year Built

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!

Listed by Timothy Drakeley (203) 510-9184 with Drakeley Real Estate, Inc. (203) 263-4336

Listing Snapshot

Price $999,900 Days on Our Site 90 days
Property Tax $6,728/yr Style Colonial
Year Built 1825 Total Sq Ft 2,042
Lot Size 1.49 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 2
Total Rooms 9 Half Baths 1

Key Features

Interior
  • Cable - Available
  • Open Floor Plan
Appliances
  • Allowance
Outdoor
  • Underground Utilities
  • Barn
  • Patio
  • Brook
Nearby
  • Basketball Court
  • Golf Course
  • Private School(s)

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 4
Garage Type Barn, Detached Garage

Systems & Utilities

Heat Hot Air, Hot Water
Fuel Propane
Cooling Central Air
Hot Water Other
Water Public Water Connected
Sewer Septic

Schools

Elem Mitchell
High Nonnewaug

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $561/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Feb 28, 2026 Price Reduced $999,900
Jan 2, 2026 Listed $1,100,000

Frequently Asked Questions

How much does 27 Middle Quarter Road in Woodbury, CT cost?
This property is listed at $999,900, which works out to $490 per square foot.
How many bedrooms does 27 Middle Quarter Road have?
This home has 3 bedrooms and 3 bathrooms.
What is the square footage of 27 Middle Quarter Road?
The home is 2,042 square feet, situated on 1.49 acres.
When was 27 Middle Quarter Road in Woodbury built?
This property was built in 1825.
Is 27 Middle Quarter Road, Woodbury, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 27 Middle Quarter Road, Woodbury in?
This home is served by the Woodbury public school system, with Mitchell as the elementary school and Nonnewaug as the high school.
How do I schedule a tour of 27 Middle Quarter Road, Woodbury, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Timothy Drakeley · (203) 510-9184

Drakeley Real Estate, Inc. · (203) 263-4336

MLS# 24146826 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Feb 28, 2026 4:48 PM UTC