34 Hollow Road, Woodbury, CT 06798 - Photo 1

1/1

$765,000

Sold
Closed
Single Family
3 Beds
3 Full Baths
1,675 Sq. Ft.
3 Car Garage

1/1

Property Description

Welcome to one of the most charming communities in Connecticut. This darling of an antique home sits in the heart of Woodbury, CT. It is a Dutch colonial dating to circa 1700, bought in 1750 by a well-respected, wealthy local merchant/ financier, Jabez Bacon. The building became the town's first general store, known as the Red Store. After Bacon's death, the property served as a school and later as a tavern. Daniel Curtis a direct descendant of one of the founders of the town of Woodbury, bought the dwelling as part of a homestead in 1831. Since then, it has been home for only a handful of families. In January of 1934, the house was featured in an issue of American Architect for its design and modernizations. Recent updates have not spoiled the historic character of this truly charming residence. The original hand-hewn beams, stone fireplaces, wide planked floors, beautiful Dutch doors, stone floors are only a few distinctive aspects of this house. The original Tomahawk door greats guests to this treasure of a dwelling. Rock away sunny afternoons or moonlit evenings on the spacious front porch. New HVAC system and roofing in 2022. The bright, newly updated kitchen and bathrooms, spacious living and dining rooms, and cozy bedrooms are all welcoming living spaces. The property is surrounded by beautiful mature trees, shrubs and flowers. A stroll in any direction will take you to a town park, restaurants, shops and churches. Don't miss out on this unique antique

Full Property Details

Full Property Details for 34 Hollow Rd

General

Sold For: $765,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24102299
Added to Site: 219 day(s) ago

Interior

Number of Rooms: 6
Fireplace: Yes
Number of Fireplaces: 2
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 3

Bedrooms

Total Bedrooms: 3
Primary Bedroom: Primary Bedroom - Fireplace, Full Bath, Hardwood Floor, Upper
Bedroom 1: Bedroom - Hardwood Floor, Main
Bedroom 2: Bedroom - Full Bath, Hardwood Floor, Upper

Other Rooms

Living Room: Living Room - Beams, Built-Ins, Fireplace, Hardwood Floor, Main
Kitchen: Kitchen - Bay/Bow Window, Beams, Quartz Counters, Pantry, Main
Dining Room: Dining Room - Built-In Hutch, Hardwood Floor, Main

Exterior

Exterior Features: Porch

Parking

Garage: Yes
Garage Spaces: 3
Total Spaces: 4
Parking: Detached Garage, Driveway

Location

County: Litchfield
Driving Directions: Route 6 to Hollow Road

School Information

Elementary School: Mitchell
Middle School: Woodbury
High School: Nonnewaug

Heating & Cooling

Cooling Type: Central Air
Heating Type: Hot Air, Oil
Heating Fuel: Oil
Water Heater: 30 Gallon Tank

Utilities

Sewer: Septic
Water: Public Water Connected

Structural Information

Architectural Style: Colonial, Antique
Construction Status: No/Resale
Exterior Const.: Wood
Basement Desc.: Full
Roof: Asphalt Shingle
Attic: Yes
Square Feet: 1,675
Above Ground: 1,675 Sq. Ft.
Year Built: 1750

Lot Features

Lot Size (Acres): 0.41
Driveway/Sidewalk: Asphalt
Zoning: RA40
Lot Description: Level Lot

Financial Considerations

Assessment Amount: $310,520
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 936109

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Schools

Schools serving 34 Hollow Rd

School District:Regional School District 14

Name	Grades	Distance
Mitchell Elementary School 14 School Street, Woodbury, CT 06798	PK-5	0.7 mi
Bethlehem Elementary School 92 East Street, Bethlehem, CT 06751	PK-5	7 mi
Woodbury Middle School 67 Washington Avenue, Woodbury, CT 06798	6-8	0.8 mi
Nonnewaug High School 5 Minortown Road, Woodbury, CT 06798	9-12	1.6 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 34 Hollow Rd

Date

Details

Price

Change

Source

9/29/2025

Sold

$765,000

—

MLS

7/15/2025

Price Reduced

$765,000

-3.77%

MLS

6/12/2025

Listed

$795,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Condo
Active
Updated 2 days ago

2
Beds
2
Total Baths
1,432
Sq. Ft.

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Just Listed

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Updated 4 hours ago

4
Beds
3
Total Baths
2,679
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Updated 4 days ago

3
Beds
2
Total Baths
1,811
Sq. Ft.

Listed by William Raveis Real Estate

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Just Listed

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Single Family
Active
Updated 1 day ago

4
Beds
4
Total Baths
3,094
Sq. Ft.

Listed by Berkshire Hathaway NE Prop.

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Price Reduced

-$14,900 (-4.38%)

$325,000

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Condo
Active
Updated 2 days ago

2
Beds
2
Total Baths
1,432
Sq. Ft.

Listed by Century 21 Bette Real Estate

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Price Reduced

-$10,000 (-3.45%)

$279,900

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Townhouse
Active
Updated 11 hours ago

2
Beds
2
Total Baths
1,365
Sq. Ft.

Listed by Keller Williams Realty

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Townhouse
Active
Updated 11 hours ago

2
Beds
2
Total Baths
1,398
Sq. Ft.

Listed by Showcase Realty, Inc.

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Townhouse
Active
Updated 5 days ago

2
Beds
2
Total Baths
1,432
Sq. Ft.

Listed by Dave Jones Realty, LLC

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Sold

$775,000

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Single Family
Closed

4
Beds
3
Total Baths
2,600
Sq. Ft.

Listed by Drakeley Real Estate, Inc.
Sold by Drakeley Real Estate, Inc.

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Sold

$750,000

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Single Family
Closed

4
Beds
3
Total Baths
3,196
Sq. Ft.

Listed by Drakeley Real Estate, Inc.
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Sold

$722,000

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Single Family
Closed

3
Beds
2
Total Baths
2,202
Sq. Ft.

Listed by William Pitt Sotheby's Int'l
Sold by Keller Williams Realty

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Sold

$670,000

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Single Family
Closed

3
Beds
2
Total Baths
1,248
Sq. Ft.

Listed by William Raveis Real Estate
Sold by Compass Connecticut, LLC

34 Hollow Road, Woodbury, CT 06798 (MLS# 24102299) is a Single Family property that was sold at $765,000 on September 29, 2025. Want to learn more about 34 Hollow 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.

34 Hollow Rd Woodbury, CT 06798