PAYAM ANDALIB

27 Middle Quarter Road

Woodbury, CT
$ 999,900 Beds 3 Baths 2.5 Sq 2,042
Monthly Estimate* How much can I afford?

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! The home is under renovation and will be complete in 3 to 6 months. Buyers can still make some changes or upgrades. This MQ commercial zone provides flexibility to run businesses, add square feet for more business opportunity, or develop this parcel into a mixed use property with a commercial and residential component. Call for specifications and there is still time to make changes.

Single Family

  • Price
  • $ 999,900
  • City
  • Woodbury
  • Bedrooms
  • 3
  • Full Bathrooms
  • 2
  • County
  • Litchfield
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 1.49 Acres
  • Zip
  • 06798
  • Sqr Footage
  • 2,042
  • Year Built
  • 1825
  • Taxes
  • $ 7132
  • Style
  • MLS#
  • 24146826
Listed By: Timothy Drakeley 203-510-9184 with Drakeley Real Estate, Inc.. - (203) 263-4336
Data Source: Smart MLS

Features

General

Zoning MQ
Neighborhood Middle Quarter
County Litchfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Under Contract - Continue to Show
Acres 1.49
Directions 6 to middle quarter road or 64 to old sherman to middle quarter road
High School Nonnewaug
City Woodbury
Elementary School Mitchell
Sq Ft Total 2042
DOM 227
Year Built 1825
Style Colonial
Year Built Source Public Records
Energy Features Storm Windows

Interior Features

Cooling System Central Air
Total Rooms 9
Basement Description Partial,Full

Exterior Features

Water Source Public Water Connected
Lot Description Level Lot,Open Lot

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Mansfield Center, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
Agent Photo

Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Mitchell Elementary School
Middle School Unknown Middle School
High School Nonnewaug High School

Price History

1/2/2026 Listed $1,100,000
2/28/2026 9% - $999,900

Property vs Zip Code Average in 06798

Price
AVG $870K
$1,000K
Taxes
AVG $8,809
$7,132
Year Built
AVG 1928
1825

Areas That We Cover

27 Middle Quarter Road Woodbury, CT is a Single Family Home for sale at $999900 with 2042 sqft and a lot size of 1.49 Acres Acre(s). 27 Middle Quarter Road Woodbury has 3 bedrooms, 2 baths and was built in 1825. The property's zip code is 06798 which is in Woodbury, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

PAYAM ANDALIB

PAYAM ANDALIB

860-933-4011

By pressing Contact Me, you agree that Weichert® may contact you via phone about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our Privacy Policy