27 Scratchville Road

Closed 10/8/25
Closed 10/8/25
Gallery Image 1
Last Sold Price
$380,000
2 beds1,134 sqft$335/sqft
27 Scratchville Rd, Woodbury, CT 06798

Description

This charming home has just been refreshed with recent updates, including a brand new full bathroom, reworked floor plan, fresh paint, and thoughtful touches throughout to enhance functionality and flow. It features a newer roof, beautiful cedar shingles, a generator, two separate storage sheds, and an attached 24x11 heated workshop. Don't be fooled by the square feet. There is additional living quarters in the cozy lower level family room. This walkout lower level room features wideboard flooring,...This charming home has just been refreshed with recent updates, including a brand new full bathroom, reworked floor plan, fresh paint, and thoughtful touches throughout to enhance functionality and flow. It features a newer roof, beautiful cedar shingles, a generator, two separate storage sheds, and an attached 24x11 heated workshop. Don't be fooled by the square feet. There is additional living quarters in the cozy lower level family room. This walkout lower level room features wideboard flooring, a fireplace and exposed beamed ceiling. The 325 square foot workshop connected by a breezeway, could easily be converted to full time living space. A separate barn/garage and privacy fencing add even more appeal, while a wooded hill along the side boundary provides a natural buffer and seclusion. Located on a quiet street ending at the scenic Strong Preserve and bordered by a peaceful cornfield, this property offers the best of small-town living. Set in the heart of Woodbury village, it's within walking distance to schools, the library, coffee shops, restaurants, hiking trails, parks, playgrounds, and community events including outdoor concerts and theater. Named "Best Small Town in Connecticut" by Reader's Digest and praised by The New York Times for its charm, history, and beauty, Woodbury is only 10 minutes to I-84, 30 minutes to the train, and 1.5 hours from NYC.
LISTING CLOSED: 10/08/2025 12:00 AM

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

Property Details for 27 Scratchville Road

Status
Closed
MLS #
24113223
Days on Market
24
Taxes
$3,611 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential
Year Built
1750
Lot Size
1.49 AC / 64,904 SF
County
Litchfield County
Basement Description
Full, Partially Finished, Walk-out, Liveable Space, Full With Walk-Out
Direct Waterfront
No
Expected Active Date
08-04-2025
Garages Number
2
Neighborhood
N/A
Style
Cottage
Garage Parking Info
Barn
Swimming Pool
No
Expected On Market Date
08-04-2025

Recent comparable sales

Median sold price

$335,000

Avg days on market

42

Sale-to-list ratio

95.2%

Woodbury, CT

9 comparable properties found

1

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Bedrooms
1
Bathrooms
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Square Feet
0.92
Acres

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a house with trees in front of it
2

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Bedrooms
1,340
Square Feet
0.47
Acres

142 Washington Road, Woodbury, CT 06798

$420,000 | 223 Tuttle Road, Woodbury, CT 06798
3

$420,000

Sold 11/19/25

2
Bedrooms
1,328
Square Feet
1.5
Acres

223 Tuttle Road, Woodbury, CT 06798

$250,000 | 97 Westwood Road, Woodbury, CT 06798
4

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Bedrooms
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Square Feet
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Acres

97 Westwood Road, Woodbury, CT 06798

$628,500 | 49 Jacks Bridge Road, Woodbury, CT 06798
5

$628,500

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Bedrooms
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Square Feet
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Acres

49 Jacks Bridge Road, Woodbury, CT 06798

6

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Sold 09/30/24

2
Bedrooms
1
Bathrooms
924
Square Feet
0.54
Acres

15 Atwood Road, Woodbury, CT 06798

a view of empty space with trees
7

$390,000

Sold 04/20/26

2
Bedrooms
1,421
Square Feet
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Acres

43 Hoop Pole Hill Road, Woodbury, CT 06798

8

$160,000

Sold 10/10/25

2
Bedrooms
1
Bathrooms
947
Square Feet
0.28
Acres

18 Easy Street, Woodbury, CT 06798

9

$310,000

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Bedrooms
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Bathrooms
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Square Feet
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Acres

565 Middle Rd Turnpike, Woodbury, CT 06798

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Location

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

Sold By Drakeley Real Estate, Inc., Timothy Drakeley

Add your commute

Building Information for 27 Scratchville Road

Stories-Year Built1750Building Size-Lot Size1.49 AC / 64,904 SF

Payment Calculator

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$2,232 per month

30 year fixed, 6.55% Interest

Principal and Interest

$1,931

Property Taxes

$301

HOA Dues

$0

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Property Information for 27 Scratchville Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Open the gate on the left to enter property and please close upon exiting.
  • Elementary School: Mitchell
  • High School: Nonnewaug
  • Latitude: 41.55603
  • Longitude: -73.1975
  • Middle Jr High School: Woodbury
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Playground/Tot Lot, Private School(s), Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $3,611
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Barn, Stone Wall
  • Waterfront Description: Walk to Water
Interior Features
  • Appliances Included: Oven/Range, Refrigerator
  • Attic Description: Unfinished, Access Via Hatch
  • Cooling System: Ceiling Fans, Window Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Laundry Room Info: Main Level
  • Rooms Additional: Workshop
  • Rooms Total: 6
Room 1
  • Room Entry Order: 1
  • Room Features: Ceiling Fan,Wide Board Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 2
  • Room Entry Order: 2
  • Room Features: Remodeled,Beams,Ceiling Fan,Wide Board Floor
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 3
  • Room Entry Order: 3
  • Room Features: Ceiling Fan,Wide Board Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 4
  • Room Features: Book Shelves,Fireplace,Wide Board Floor
  • Room Length: 16.0
  • Room Level: Lower
  • Room Type: Family Room
  • Room Width: 12.0
Room 5
  • Listing Key: 3A6F39473510CDC5E063E201100AFDF1
  • Room Entry Order: 5
  • Room Features: Vinyl Floor
  • Room Level: Main
  • Room Type: Kitchen
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Shingle
  • Foundation Type: Stone
  • Fuel Tank Location: In Ground
  • New Construction Type: No/Resale
  • Property Info: Horse Property
  • Roof: Asphalt Shingle
  • Year Built: 1750
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Description: main and lower level walkout
  • Sq Ft Est Heated Below Grade: 250
Lot Information
  • Lot Description: Fence - Partial, Secluded, Lightly Wooded, Level Lot
  • Parcel Number: 933113
  • Sq Ft Est Heated Above Grade: 884.0
  • Sq Ft Total: 1134.0
  • Zoning: OS60
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Propane
  • Hot Water Description: Electric, Tank Size Unknown
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 27 Scratchville Road

DateEvent & SourcePriceAppreciation
Oct 8, 2025

Closed (Public Record)

Public Record #1916528614

$380,000

+28.5% / yr

Aug 15, 2024

Closed (Public Record)

Public Record #1539333770

$285,000—
DateEvent & SourcePrice
10/08/2025

Closed (Public Record)

Public Record #1916528614

$380,000

+28.5% / yr

08/15/2024

Closed (Public Record)

Public Record #1539333770

$285,000

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

Public Records for 27 Scratchville Road

Taxable ValueLand$72,100Additions$80,780Total$152,880
Tax Record2025$3,611 ($301 / month)
Home Facts
Beds2Baths1Total Finished SqFt884 SqFtAbove Grade Finished SqFt884 SqFtUnfinished Basement SqFt238 SqFtStories1Lot Size64,904 SqFtStyleSingle Family ResidenceYear Built1979Year Renovated1984ZoningOS60CountyNAUGATUCK VALLEYAPNWOOD M:023 B:038

Schools near 27 Scratchville Road

This home is within Regional School District 14.
Rating
School
Type
Grades
Distance
Bethlehem Elementary School
Public - PK to 5
Mitchell Elementary School
Public - PK to 5
Woodbury Middle School
Public - 6 to 8
Nonnewaug High School
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.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 27 Scratchville Road, Woodbury, CT 06798
$380,000
2
1,134
64,904
21 Scratchville Road, Woodbury, CT 06798
–
1
1
720
50,094
212 Main Street North, Woodbury, CT 06798
$550,000
4
2,861
91,476
226 Main Street North, Woodbury, CT 06798
$295,000
–
–
–
204,296
284 Main Street North, Woodbury, CT 06798
$87,000
–
–
–
151,153
12 Quassuk Road, Unit 77, Woodbury, CT 06798
$163,500
2
958
–

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make 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.