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$779,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,467 Sq. Ft.
  • 2 Car Garage
  • Updated 5 days ago
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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.

Full Property Details for 500 Route 169

General

  • Price: $779,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24209434
  • Updated: 9/30/2026
  • Added to Site: 13 day(s) ago

Interior

  • Number of Rooms: 11
  • Rooms/Areas: Laundry Room
  • Interior Features: Cable - Available
  • Appliances: Electric Range, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Full Bath: Main
  • Partial Bath: Remodeled, Built-Ins, Hardwood Floor, Main

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, Main
  • Bedroom 2: Bedroom - Hardwood Floor, Main
  • Bedroom 3: Bedroom - Hardwood Floor, Upper
  • Bedroom 4: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Eating Space, Tile Floor, Main
  • Dining Room: Dining Room - Combination Liv/Din Rm, Hardwood Floor, Main
  • Laundry: Main Level
  • Other Room 1: Other, Main

Exterior

  • Exterior Features: Sidewalk, Shed, Porch, Garden Area
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 10
  • Parking: Detached Garage, Off Street Parking, Unpaved

Location

  • County: Windham
  • Neighborhood: South Woodstock
  • Driving Directions: GPS

School Information

  • Elementary School: Woodstock
  • Middle School: Woodstock
  • Intermediate School: Per Board of Ed
  • High School: Woodstock Academy

Community

  • Community Name: South Woodstock

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Baseboard, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Upright Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Antique
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Full, Unfinished, Interior Access, Concrete Floor
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,467
  • Above Ground: 2,467 Sq. Ft.
  • Year Built: 1800

Lot Features

  • Lot Size (Acres): 1.3
  • Zoning: CD
  • Lot Description: Level Lot, Sloping Lot, Cleared, Professionally Landscaped, Historic District

Green Features

  • Energy Features: Storm Windows

Financial Considerations

  • Assessment Amount: $306,800
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Exclusions: Some personal property.
  • Property ID: 1738416

Listed by Hope Real Estate Group, Inc., June Cazeault

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Listing agent

— 500 Route 169 —

  • June Cazeault

    Hope Real Estate Group, Inc.

Agent Contact: (860) 377-2044 Office Contact: (508) 943-4333

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 500 Route 169

School District:Woodstock Public Schools
NameGradesDistance
Woodstock Elementary School
24 Frog Pond Road, Woodstock, CT 06281
PK-40.5 mi
Woodstock Middle School
147 B-Route 169, Woodstock, CT 06281
5-81.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 500 Route 169 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/30/2026
Listed
$779,000
73.11%
MLS
9/30/2025
Sold
$450,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 500 Route 169

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,829
6%
$238,800
—
2023
$5,502
3%
$238,800
—
2023
$5,352
7%
$238,800
—
2022
$4,979
-3%
$238,800
19%
2021
$5,108
15%
$200,300
11%
2020
$4,435
100%
$181,000
—
2019
-100%
$181,000
—
2018
$4,435
1%
$181,000
—
2017
$4,398
7%
$181,000
6%
2016
$4,123
3%
$171,500
—
2015
$4,006
1%
$171,500
—
2014
$3,962
4%
$171,500
—
2011
$3,821
—
$171,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 500 Route 169

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Hope Real Estate Group, Inc., June Cazeault

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500 Route 169, Woodstock Valley, CT 06281 (MLS# 24209434) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 500 Route 169 is currently listed for $779,000 and was received on September 24, 2026. Want to learn more about 500 Route 169? Do you have questions about finding other Single Family real estate for sale in Woodstock Valley? You can browse all Woodstock Valley real estate or contact a Coldwell Banker agent to request more information.

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