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$1,100,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,042 Sq. Ft.
  • 4 Car Garage
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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!

Full Property Details for 27 Middle Quarter Rd

General

  • Price: $1,100,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24146826
  • Updated: 1/2/2026
  • Added to Site: 15 day(s) ago

Interior

  • Number of Rooms: 9
  • Rooms/Areas: Workshop
  • Interior Features: Cable - Available, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Allowance

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Cathedral Ceiling, Bedroom Suite, Full Bath, Walk-In Closet, Upper
  • Bedroom 1: Bedroom - Wide Board Floor, Main
  • Bedroom 2: Bedroom - Wide Board Floor, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Wide Board Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Cathedral Ceiling, Beams, Main
  • Dining Room: Dining Room - Fireplace, Wide Board Floor, Main
  • Library: Library - Wide Board Floor, Upper
  • Laundry: Main Level

Exterior

  • Exterior Features: Underground Utilities, Barn, Patio

Parking

  • Garage: Yes
  • Garage Spaces: 4
  • Parking: Barn, Detached Garage

Location

  • County: Litchfield
  • Neighborhood: Middle Quarter
  • Driving Directions: 6 to middle quarter road or 64 to old sherman to middle quarter road

School Information

  • Elementary School: Mitchell
  • High School: Nonnewaug

Community

  • Community Name: Middle Quarter

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Hot Water, Propane
  • Heating Fuel: Propane
  • Water Heater: Other

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Description/Design: Horse Property
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Partial, Full
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,042
  • Above Ground: 2,042 Sq. Ft.
  • Year Built: 1825

Lot Features

  • Lot Size (Acres): 1.49
  • Zoning: MQ
  • Lot Description: Level Lot, Open Lot

Horse Property

  • Horse Property: Yes

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Brook

Green Features

  • Energy Features: Storm Windows

Financial Considerations

  • Assessment Amount: $284,830
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 936023

Listed by Drakeley Real Estate, Inc., Timothy Drakeley

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Listing agent

— 27 Middle Quarter Rd —

  • Timothy Drakeley

    Drakeley Real Estate, Inc.

Agent Contact: (203) 510-9184 Office Contact: (203) 263-4336

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 27 Middle Quarter Rd

School District:Regional School District 14
NameGradesDistance
Mitchell Elementary School
14 School Street, Woodbury, CT 06798
PK-51.6 mi
Woodbury Middle School
67 Washington Avenue, Woodbury, CT 06798
6-81.8 mi
Nonnewaug High School
5 Minortown Road, Woodbury, CT 06798
9-122.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Middle Quarter Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/02/2026
Listed
$1,100,000
243.75%
MLS
3/19/2024
Sold
$320,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 27 Middle Quarter Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,728
2%
$284,830
—
2023
$6,600
1%
$284,830
27%
2023
$6,542
—
$225,110
—
2022
$6,566
—
$225,110
—
2021
$6,566
—
$225,110
—
2020
$6,566
—
$225,110
—
2019
$6,566
1%
$225,110
-8%
2018
$6,525
-2%
$245,500
—
2017
$6,668
3%
$245,500
—
2016
$6,454
1%
$245,500
—
2015
$6,400
1%
$245,500
—
2014
$6,307
9%
$245,500
—
2011
$5,766
—
$246,410
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 27 Middle Quarter Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Home Warranty : Included

Listed by Drakeley Real Estate, Inc., Timothy Drakeley

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27 Middle Quarter Road, Woodbury, CT 06798 (MLS# 24146826) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 27 Middle Quarter Road is currently listed for $1,100,000 and was received on January 02, 2026. Want to learn more about 27 Middle Quarter Road? Do you have questions about finding other Single Family real estate for sale in Woodbury? You can browse all Woodbury real estate or contact a Coldwell Banker agent to request more information.

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