CONTINGENT

Contingent

$999,900

Est. $6,368/mo —

•

2,042

sq ft

27 Middle Quarter Rd, Woodbury, CT 06798

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!

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-familyProperty Type

1825Year Built

1.49 acresLot Size

$490Price/Sq.Ft.

4 car garageParking

Listed by Timothy Drakeley • Drakeley Real Estate, Inc.

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

Source:Smart MLS #24146826

Payment calculator

$6,368 per month

Principal and interest$5,457

Property taxes

$594

HOA dues

Home insurance

$317

Utilities

Add

5 minutes to get started. No credit impact.

Discover your buying power

Find out if this home is within budget

Down payment assistance

View down payment assistance programs for this home

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SEP 22, 4PM TO 6PM
$624,500
2 beds2.5 baths2,358 sq ft
188 Eastwood Dr #188, Seymour, CT 06483
OPEN SEP 26, 11AM TO 3PM
$799,900
4 beds2.5 baths2,896 sq ft
37 Tunnel Rd, Newtown, CT 06470
OPEN SEP 26, 11AM TO 5PM
$525,000
4 beds2.5 baths1,969 sq ft
6 Paugussett Rd, Sandy Hook, CT 06482
OPEN SEP 26, 12PM TO 2PM
$1,649,000
5 beds4.5 baths5,522 sq ft
3 Dylan Dr, Newtown, CT 06470
OPEN SEP 26, 12PM TO 2PM
$1,099,000
4 beds2.5 baths2,404 sq ft
126 Bucks Hill Rd, Southbury, CT 06488
OPEN SEP 26, 12PM TO 3PM
$769,000
5 beds3.5 baths2,682 sq ft
21 Walker Brook Dr, New Milford, CT 06776
OPEN SEP 26, 12PM TO 2PM
$745,000
3 beds2.5 baths2,750 sq ft
171 Country Club Dr #171, Oxford, CT 06478
OPEN SEP 27, 12PM TO 2PM
$574,900
3 beds2.5 baths2,360 sq ft
58 Shadduck Rd, Middlebury, CT 06762
OPEN SEP 27, 12PM TO 2PM
$355,000
2 beds2 baths1,398 sq ft
440 Heritage Vlg Unit B, Southbury, CT 06488
OPEN SEP 27, 12:30PM TO 2:30PM
$320,000
3 beds2 baths1,280 sq ft
151 Martone St, Waterbury, CT 06708

Around this home

Schools

K - 12
Preschool & daycare

Mitchell Elementary School

Public PreK-5 • Assigned • 1.6mi

5/10

Woodbury Middle School

Public 6-8 • Assigned • 1.7mi

6/10

Nonnewaug High School

Public 9-12 • Assigned • 2.4mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

27 Middle Quarter Rd · $999,900

DAYS ON MARKET

The average home goes pending in 53 days.

SALE-TO-LIST

Most homes are selling 0% below list price.

LIST PRICE

Median sale price in this area is $473,447. (53% lower than this home)

PRICE DROP

18% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Bedroom

Living

Interior features
Open floor plan
Cable available
Possible in-law apartment with detached access
Two fireplaces
Partial to full basement
Has walk-up attic

Bedrooms
3 bedrooms

Bathrooms
2 full bathrooms
1 half bathroom

Kitchen
Appliance allowance (to be provided)

Laundry & utility
Laundry on main/first level

Heating & cooling
Central air conditioning
Hot air and hot water heating
Propane-fueled heating
Above-ground fuel tank
Storm windows for energy efficiency

Sale and tax history for 27 Middle Quarter Rd

Sale History
Tax History

Date

Event

Price

Smart MLS #24146826

Jun 29, 2026

Contingent

—

Feb 28, 2026

Price Changed

$999,900

$490/sq ft

Jan 2, 2026

Listed

$1,100,000

$539/sq ft

Smart MLS #24049803

Oct 10, 2025

Listing Removed

—

Mar 12, 2025

Price Changed

$699,900

$343/sq ft

Nov 9, 2024

Listed

$1,150,000

$563/sq ft

Smart MLS #170625141

Apr 9, 2024

Sold

$320,000

$157/sq ft

Mar 12, 2024

Pending

—

Feb 16, 2024

Listed

$279,000

$137/sq ft

4 Bedroom 1.5 Bath Colonial Built in 1825 on 1.32 Acres with 2 Large Barns on the property. Interior has 4 fireplaces, eat in kitchen with walk in pantry, wide plank flooring through out. 1st floor has office and library area. 2 walk up attic areas that could be converted into additional living area. 2 large barns offer additional storage/ studio space or possible rental income. Needs some TLC but has the potential to become your home/business oasis. Walking distance to Good News Cafe or Ovens of France Bakery. Don't miss this opportunity to experience all of what Woodbury CT has to offer. THIS PROPERTY IS ELIGIBLE UNDER THE FIRST LOOK INITIATIVE WHICH EXPIRES 30 FULL DAYS ON MARKET. NO INVESTOR OFFERS UNTIL FIRST LOOK PERIOD EXPIRES. NO OFFERS REGARDLESS OF BUYER TYPE WILL NOT BE NEGOTIATED WITHIN THE FIRST 7 DAYS. FOR FINANCED OFFERS EMD TO BE 1% OR $1000 WHICHEVER IS GREATER/CASH OFFERS EMD TO BE 5% OR $5000 WHICHEVER IS GREATER. ALL OFFES SUBJECT TO OFAC CLEARENCE.

Year

Property tax

Land + Additions

Assessment*

2023

$6,542 (−0.4%)

$83,910 + $141,200

$225,110

2022

$6,566

$83,910 + $141,200

$225,110

2021

$6,566

$83,910 + $141,200

$225,110

2020

$6,566

$83,910 + $141,200

$225,110

2019

$6,566 (+0.6%)

$83,910 + $141,200

$225,110

2018

$6,525 (−2.1%)

$93,730 + $151,770

$245,500

2017

$6,668 (+3.3%)

$93,730 + $151,770

$245,500

2016

$6,454 (+2.3%)

$93,730 + $151,770

$245,500

2014

$6,307

$93,730 + $151,770

$245,500

Public record

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

1.32 Acres

Year renovated

—

Finished Sq. Ft.

2,042

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,042

Year built

1825

Style

Single Family Residential

County

Litchfield County

APN

936023

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 20, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 16 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Woodbury, CT • 06798

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

79/ 100

Good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.7 hrs

4.7 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 27 Middle Quarter Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $465,000 and $885,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $465K to $885K.

SOLD JUL 17, 2026
$465,000 Last sold price
3 beds2.5 baths2,016 sq ft
34 Transylvania Rd, Woodbury, CT 06798
$259/sq ft
larger lot
137 years newer
SOLD AUG 27, 2026
$605,000 Last sold price
3 beds3.5 baths2,479 sq ft
30 Park Rd, Woodbury, CT 06798
$246/sq ft
smaller lot
162 years newer
SOLD JUL 30, 2026
$885,000 Last sold price
4 beds3.5 baths3,784 sq ft
557 Upper Grassy Hill Rd, Woodbury, CT 06798
$256/sq ft
larger lot
174 years newer
SOLD NOV 20, 2025
$600,000 Last sold price
3 beds2.5 baths2,032 sq ft
36 Heritage Dr, Woodbury, CT 06798
$195/sq ft
143 years newer
SOLD SEP 9, 2026
$570,000 Last sold price
4 beds2.5 baths2,428 sq ft
148 Colonial Dr, Southbury, CT 06488
$255/sq ft
smaller lot
147 years newer
SOLD OCT 30, 2025
$615,000 Last sold price
3 beds2.5 baths2,124 sq ft
130 Grassy Hill Rd, Woodbury, CT 06798
$200/sq ft
larger lot
163 years newer

This home may not be allowing tours right now

The seller has already accepted an offer. You can request a tour anyway or ask an agent about submitting a backup offer.

Ask a question

Start an offer

(860) 325-4907

Nearby similar homes

NEW CONSTRUCTION

$999,900

4 beds2.5 baths3,286 sq ft

84 Lum Lot Rd, Southbury, CT 06488

$499,999

3 beds2.5 baths2,100 sq ft

110 Brushy Hill Rd, Woodbury, CT 06798

$2,995,000

4 beds5 baths5,316 sq ft

920 Main St S, Woodbury, CT 06798

3D WALKTHROUGH

$729,900

4 beds2.5 baths2,966 sq ft

16 Cedar Grove Rd, Southbury, CT 06488

$505,000

3 beds2.5 baths1,720 sq ft

40 Stony Corners Ln, Southbury, CT 06488

$1,590,000

4 beds2.5 baths2,732 sq ft

40 Ruffin Rd, Woodbury, CT 06798

New listings for sale in 06798

NEW 25 HRS AGO

$294,900

2 beds2.5 baths1,601 sq ft

3 Shagbark Ln #3, Woodbury, CT 06798

$289,000

2 beds2 baths1,112 sq ft

5 Alder Ct Unit 84A, Woodbury, CT 06798

$699,900

4 beds2.5 baths3,017 sq ft

15 Saxony Ln, Woodbury, CT 06798

$649,900

3 beds1.5 baths1,814 sq ft

10 Weekeepeemee Rd, Woodbury, CT 06798

$519,000

3 beds1.5 baths1,550 sq ft

50 Washington Rd, Woodbury, CT 06798

$209,900

2 beds1 bath913 sq ft

229 Bacon Pond Rd #313, Woodbury, CT 06798

$765,000

2 beds2 baths1,814 sq ft

31 Bethwood Ln, Woodbury, CT 06798

$1,200,000

4 beds4 baths3,968 sq ft

90 Sage Rd, Woodbury, CT 06798

Details provided by Smart MLS and may not match the public record. Learn more.

More real estate resources

Minor Civil Divisions
Neighborhoods
Cities
Zip Codes
Popular Searches

Wyckoff Township homes for sale
River Vale Township homes for sale
Mahwah Township homes for sale
West Milford Township homes for sale
Wayne Township homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

10980 homes for sale
10926 homes for sale
10930 homes for sale
10917 homes for sale
10950 homes for sale

Houses for rent in Woodbury	Agents near me	White Plains, NY homes for sale	Woodbury Housing Market
Houses for sale near me	New York, NY homes for sale	Yonkers, NY homes for sale
Land for sale near me	Manhattan, NY homes for sale	Scarsdale, NY homes for sale
Open Houses near me	Rochester, NY homes for sale	Woodbury Property Records
Condos for sale near me	Buffalo, NY homes for sale	CT New Listings

Central Valley homes for sale
Highland Mills homes for sale
Lebanon homes for sale

Ridgewood homes for sale
Tarrytown homes for sale
Beacon homes for sale