27 Middle Quarter Rd

$1,100,000
Price
3
Beds
2,042 Sq. Ft.
$539 / Sq. Ft.
2,042
Sq. Ft.
$539
per Sq. Ft.

Description

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....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!
  1. Listed by Timothy Drakeley • Drakeley Real Estate, Inc.
    P: (203)-510-9184 C: (203)-510-9184 tim@drakeley.com

Property Details for 27 Middle Quarter Road

Basement Description
Partial, Full
Direct Waterfront
Yes
Garages Number
4
Neighborhood
Middle Quarter
Style
Colonial
Garage Parking Info
Barn, Detached Garage
Swimming Pool
No
LISTING UPDATED: 01/02/2026 07:05 PM

Property Details for 27 Middle Quarter Road

StatusActive
MLS #24146826
Days on MarketListed Today
Taxes$6,728 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1825
Lot Size1.49 AC / 64,904 SF
CountyLitchfield County

Location

Listing Courtesy of Drakeley Real Estate, Inc., Timothy Drakeley
Add your commute

Building Information for 27 Middle Quarter Road

Stories-Year Built1825Building Size-Lot Size1.49 AC / 64,904 SF

Payment Calculator

$5,996 per month

30 year fixed, 6.28% Interest

Principal and Interest

$5,435

Property Taxes

$561

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 27 Middle Quarter Road

Summary
Property and Location
  • Acres Source: Owner
  • Directions: 6 to middle quarter road or 64 to old sherman to middle quarter road
  • Elementary School: Mitchell
  • Flood Zone: No
  • High School: Nonnewaug
  • Latitude: 41.525665
  • Longitude: -73.20143
  • Neighborhood Amenities: Basketball Court, Golf Course, Private School(s)
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $6,728
Interior and Exterior Features
Exterior Features
  • Exterior Features: Underground Utilities, Barn, Patio
  • Waterfront Description: Brook
Interior Features
  • Appliances Included: Allowance
  • Attic Description: Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air, Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Cable - Available, Open Floor Plan
  • Laundry Room Info: Main Level
  • Laundry Room Location: first
  • Rooms Additional: Workshop
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Wide Board Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Fireplace,Wide Board Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Cathedral Ceiling,Bedroom Suite,Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Features: Wide Board Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Listing Key: 476C5CF4417B2EAAE063E201100A5F9F
  • Room Entry Order: 5
  • Room Features: Wide Board Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Features: Cathedral Ceiling,Beams
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 7
  • Room Entry Order: 7
  • Room Features: Wide Board Floor
  • Room Level: Upper
  • Room Type: Library
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete, Stone
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Property Info: Horse Property
  • Roof: Asphalt Shingle
  • Year Built: 1825
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Detached
  • In Law Apartment: Possible
  • Living Area SQFT Per Public Records: 2042
Lot Information
  • Lot Description: Level Lot, Open Lot
  • Parcel Number: 936023
  • Sq Ft Est Heated Above Grade: 2042.0
  • Sq Ft Total: 2042.0
  • Zoning: MQ
Utilities
  • Energy Features: Storm Windows
  • Heat Fuel Type: Propane
  • Hot Water Description: Other
  • Radon Mitigation Air: Unknown
  • Radon Mitigation Water: Unknown
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 27 Middle Quarter Road

DateEvent & SourcePriceAppreciation
Jan 2, 2026

Listed (Active)

SMARTMLS #24146826

$1,100,000—
Mar 19, 2024

Closed (Public Record)

Public Record #1530087624

$320,000—
DateEvent & SourcePrice
01/02/2026

Listed (Active)

SMARTMLS #24146826

$1,100,000
03/19/2024

Closed (Public Record)

Public Record #1530087624

$320,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 27 Middle Quarter Road

Taxable ValueLand$83,930Additions$200,900Total$284,830
Tax Record2024$6,728 ($561 / month)
Home Facts
Beds4Baths1.5Total Finished SqFt2,042 SqFtAbove Grade Finished SqFt2,042 SqFtUnfinished Basement SqFt806 SqFtStories2Lot Size57,499 SqFtStyleSingle Family ResidenceYear Built1825Year Renovated1987ZoningMQCountyLITCHFIELDAPNWOOD M:102 B:041Fireplace TypeHas Fireplace

Schools near 27 Middle Quarter Road

This home is within Regional School District 14.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Bethlehem Elementary School
PublicPK to 5

Mitchell Elementary School
PublicPK to 5

Woodbury Middle School
Public6 to 8

Nonnewaug High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

27 Middle Quarter Road is a single family home for sale in Woodbury, CT 06798. This listing's school district is Regional School District 14. Nearby schools include Bethlehem Elementary School, Mitchell Elementary School and Woodbury Middle School. 27 Middle Quarter Road is a 3-bed, 3-bath, 2,042 sqft single family home built in 1825.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Drakeley Real Estate, Inc., Timothy Drakeley

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.