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.
Sold for $380,000
$380,000
27 Scratchville Road, Woodbury, CT 06798
2beds
1,134sqft
Single Family Residence
Built in 1750
1.49 Acres Lot
$389,900 Zestimate®
$335/sqft
$3,250 Estimated rent
Home value
$389,900
$328,000 - $464,000
$3,250/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: October 08, 2025 at 02:48pm
Listed by:
Timothy Drakeley 203-510-9184,
Drakeley Real Estate, Inc. 203-263-4336
Bought with:
Timothy Drakeley, REB.0791885
Drakeley Real Estate, Inc.
Source: Smart MLS,MLS#: 24113223
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Primary bedroom
- Features: Remodeled, Beamed Ceilings, Ceiling Fan(s), Wide Board Floor
- Level: Main
Bedroom
- Features: Ceiling Fan(s), Wide Board Floor
- Level: Main
Dining room
- Features: Ceiling Fan(s), Wide Board Floor
- Level: Main
Family room
- Features: Bookcases, Fireplace, Wide Board Floor
- Level: Lower
- Area: 192 Square Feet
- Dimensions: 12 x 16
Kitchen
- Features: Vinyl Floor
- Level: Main
Heating
- Hot Water, Propane
Cooling
- Ceiling Fan(s), Window Unit(s)
Appliances
- Included: Oven/Range, Refrigerator, Electric Water Heater
- Laundry: Main Level
Features
- Basement: Full,Partially Finished,Walk-Out Access,Liveable Space
- Attic: Access Via Hatch
- Number of fireplaces: 1
Interior area
- Total structure area: 1,134
- Total interior livable area: 1,134 sqft
- Finished area above ground: 884
- Finished area below ground: 250
Property
Parking
- Total spaces: 2
- Parking features: Barn
- Garage spaces: 2
Features
- Exterior features: Stone Wall
- Fencing: Partial
- Waterfront features: Walk to Water
Lot
- Size: 1.49 Acres
- Features: Secluded, Few Trees, Level
Details
- Additional structures: Shed(s), Barn(s)
- Parcel number: 933113
- Zoning: OS60
- Other equipment: Generator
- Horses can be raised: Yes
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cottage
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1750
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & neighborhood
Community
- Community features: Golf, Health Club, Lake, Library, Medical Facilities, Playground, Private School(s), Shopping/Mall
Location
- Region: Woodbury
Price history
| Date | Event | Price |
|---|---|---|
| 10/8/2025 | Sold | $380,000-5%$335/sqft |
Source:  Smart MLS #24113223 Report a problem | ||
| 9/24/2025 | Pending sale | $399,900$353/sqft |
Source: Smart MLS #24113223 Report a problem | ||
| 8/13/2025 | Price change | $399,900-3.6%$353/sqft |
Source: Smart MLS #24113223 Report a problem | ||
| 8/4/2025 | Listed for sale | $414,900+45.6%$366/sqft |
Source: Smart MLS #24113223 Report a problem | ||
| 8/16/2024 | Sold | $285,000+1.8%$251/sqft |
Source: Smart MLS #24031945 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $3,611 +1.9% | $152,880 |
| 2024 | $3,542 -4.5% | $152,880 +19.8% |
| 2023 | $3,708 -0.4% | $127,610 |
Find assessor info on the county website
Neighborhood: 06798
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 0.9 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 0.4 mi
Schools provided by the listing agent
- Elementary: Mitchell
- Middle: Woodbury
- High: Nonnewaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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$389,900
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+$7,798
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$397,698
- Connecticut
- Litchfield County
- Woodbury
- 06798
- 27 Scratchville Road