500 Route 169
Woodstock, CT 06281
5
Bed
4
Bath
2,467Sqft
1.30Acres(Lot)
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 Acade
Property Details
Open House
- 10/04 12 PM-2 PM
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 5Bathroom Information
Total Baths: 4 Full Baths: 3 Half Baths: 1Room Information
Rooms Total: 11 Has Basement: Yes Basement: Full, Unfinished, Concrete -
Roofing Information
Asphalt -
Interior Features
Roof: Asphalt Appliances: Dryer, Electric Range, Washer Laundry Features: Main Level, Laundry Room Window Features: Storm Window(s) -
Heating & Cooling
Has Heating: Yes Heating: Oil, Baseboard Cooling: None
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Building Information
Year Built: 1800 Building Area Total: 2467 Construction Materials: Wood Siding, Frame Patio And Porch Features: Porch Private Pool: No -
Exterior Features
Exterior Features: Garden
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Lot Information
Lot Size Acres: 1.3 Lot Description: Cleared, Level, Sloped
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Listing Price Information
Listing Price: $779000
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Tax Information
Parcel Number: 1738416 Annual Tax: $6200
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Parking Information
Parking Total: 10 Off Street, UnpavedGarage Information
Has Garage: Yes Garage Space: 2
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School Information
Elementary School: WoodstockJunior High School: WoodstockSenior High School: Woodstock Academy -
Location Information
Direction: GPS WaterSource: Well
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 8-2 Tayler Trail, Woodstock, CT, 06281 | $499,900 | 3 | 3 | 1,912 | 0.96 Acre |
| 48 Grey Fox Landing, Woodstock, CT, 06281 | $875,000 | 4 | 5 | 3,429 | 2.12 Acres |
| 555 Senexet Road, Woodstock, CT, 06281 | $799,000 | 4 | 2 | 3,794 | 9 Acres |
| 155 Paine Road, Woodstock, CT, 06281 | $1,650,000 | 4 | 6 | 4,873 | 3.29 Acres |
| 20 Loyola Road, Woodstock, CT, 06281 | $698,900 | 2 | 3 | 2,216 | 0.40 Acre |
| 101 Child Hill Road, Woodstock, CT, 06281 | $520,000 | 4 | 3 | 2,150 | 0.90 Acre |
| 122 Child Hill Road, Woodstock, CT, 06281 | $679,000 | 4 | 3 | 3,865 | 8.50 Acres |
| 158 W Quasset Road, Woodstock, CT, 06281 | $1,995,000 | 4 | 4 | 3,723 | 5.50 Acres |
| 25 Rte 197 Route, Woodstock, CT, 06281 | $74,999 | 2 | 1 | 450 | 0.05 Acre |
| Rr 197 Road, Woodstock, CT, 06281 | $597,000 | 4 | 3 | 2,212 | 2.70 Acres |
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
ByOwner last updated this listing 09/30/2026 @ 20:23
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