Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
5 Beds
4 Baths
2,467 sqft

$779,000

500 Route 169, Woodstock CT, 06281

Price per sqft$315.77
Built in1800
Property size2,467 sqft
Property typeResidential

Overview

Active

Listed Sep 24, 2026

Updated 5 days ago

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals.

$5,183/mo

Est. mortgage payment based on a $779,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
24209434

Interior Features

Bedrooms
5
Bathrooms
4
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.3 Acres

Other Property Details

Taxes
$6,200
Tax Frequency
Annually
Garage
Yes
MLS provider logo

Listed by June Cazeault with Hope Real Estate Group, Inc. (860) 377-2044

The IDX display contains information sourced from SmartMLS, Inc. as of 10/5/2026. This information is for personal, non-commercial use only and may not be used for any purpose other than identifying properties the viewer may be interested in purchasing. MLS data is generally considered reliable but is not guaranteed accurate by the MLS. Buyers are responsible for verifying all information and should conduct their own investigation or consult a professional. Some MLS data may have been provided by sources other than the listing agent. Unless stated in writing, the Broker/Agent has not verified information obtained from outside sources. The Broker/Agent may or may not have been the listing and/or selling agent, and cannot guarantee the accuracy of any property location shown on a map. Any offer of compensation is made only to participants of the MLS where the listing is filed.

©2026 SmartMLS, Inc. All rights reserved.

Data last updated on 10/5/2026 at 3:55 AM UTC.

Powered by Luxury Presence