Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in one while renting the other four. Another option is to create a warm and inviting 5-cottage compound for family, friends, or a mix of the two. Imagine enjoying the Woodstock lifestyle with loved ones just a door-knock away. For a writer, artist, or home-business owner, perhaps one or more of the cottages could be used as a studio or office separate from home. Cottage 1 is a delightful two bedroom/one bath with a fireplace and Craftsman kitchen. Cottage 2 was reimagined and fully renovated in 2024. Cottage 3 is peak contemporary treehouse: a stunning two bedroom/two bath, featuring dramatic windows, balcony, and fireplace, with a spiral staircase up to the primary bedroom. Bright and airy Cottage 4 is a cheerful one bedroom/two bath that is wheelchair-accessible. The first thing you'll notice about Cottage 5 is the cool roofline with a clerestory that fills the living area with light. When not relaxing at home, there's plenty to do in the area: hiking, swimming, skiing, listening to live music, visiting art galleries and antique shops, dining and shopping in Woodstock and beyond. The bus from NYC stops near Woodstock's Village Green. Amtrak is across the Hudson in the hamlet of Rhinecliff. NYC's George Washington Bridge is about 100 miles away. The short-term rental license conveys. The 2025 cap rate with all cottages rented (either short-term or long-term) was 6, and for 2024 it was 9. Financials and rental history are available. If you're seeking an investment property, live-work dream spot, or sweet family compound in Woodstock, consider viewing this fantastic 6-acre, 5-cottage property in beautiful, famous, ever-inspiring Woodstock.
Active
$2,295,000
2465 Glasco Turnpike, Woodstock, NY 12498
7beds
7baths
4,331sqft
Multi Family
Built in 1965
-- sqft lot
$1,072,400 Zestimate®
$530/sqft
$-- HOA
What's special
Six wooded acresPeaceful forest viewsBright and airyDramatic windowsCraftsman kitchen
- 15 hours |
- 199 |
- 10 |
Zillow last checked:
Listing updated:
Listing by:
Halter Associates Realty 845-331-3110,
Lillian Kology 845-594-3477,
Gary Heckelman 845-532-1178,
Halter Associates Realty
Source: HVCRMLS,MLS#: 20262489
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 7
Heating
- Ductless, Propane Stove, Radiant Floor, Varies by Unit
Cooling
- Ductless, ENERGY STAR Qualified Equipment, Varies by Unit, See Remarks
Appliances
- Included: ENERGY STAR Qualified Appliances
- Laundry: Multiple Locations, See Remarks
Features
- Built-in Features, Ceiling Fan(s), Hot Tub, Primary Downstairs, See Remarks
- Flooring: Hardwood, Tile, Varies
- Doors: Sliding Doors
- Number of fireplaces: 2
- Fireplace features: Gas, Insert, Living Room, Metal, Stone, Wood Burning, See Remarks
Interior area
- Total structure area: 4,331
- Total interior livable area: 4,331 sqft
- Finished area above ground: 4,331
- Finished area below ground: 0
Property
Parking
- Parking features: Driveway, Additional Parking
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Accessible Approach with Ramp, Accessible Full Bath
Features
- Levels: One,Two
- Patio & porch: Covered, Deck, Patio, Porch
- Exterior features: Barbecue, Fire Pit, Private Entrance
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 6.06 Acres
- Features: Wooded
Details
- Additional structures: Shed(s), Storage
- Parcel number: 27.911
- Zoning: R3
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Cabin,Contemporary,Cottage
- Property subtype: Multi Family
Materials
- Foundation: Block, Slab
- Roof: Shingle
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1965
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Engineered Septic, Septic Tank
- Water: Well
Green energy
- Energy efficient items: Appliances, HVAC
Community & HOA
HOA
- Has HOA: No
Location
- Region: Woodstock
Financial & listing details
- Price per square foot: $530/sqft
- Tax assessed value: $606,800
- Annual tax amount: $16,659
- Date on market: 5/18/2026
- Tenant pays: Electricity, Gas, Trash Collection
- Road surface type: Gravel
Estimated market value
$1,072,400
$804,000 - $1.39M
$2,248/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/18/2026 | Listed for sale | $2,295,000-8.2%$530/sqft |
Source:  HVCRMLS #20262489 Report a problem | ||
| 11/19/2025 | Listing removed | $2,500,000$577/sqft |
Source: HVCRMLS #20250806 Report a problem | ||
| 4/4/2025 | Listed for sale | $2,500,000$577/sqft |
Source: HVCRMLS #20250806 Report a problem | ||
| 8/29/2024 | Listing removed | $2,200$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 8/22/2024 | Listed for rent | $2,200$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 10/11/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 10/4/2023 | Listed for rent | $2,200$1/sqft |
Source: Zillow Rentals Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $606,800 |
| 2024 | -- | $606,800 +0.3% |
| 2023 | -- | $605,000 |
| 2022 | -- | $605,000 |
| 2021 | -- | $605,000 |
| 2020 | -- | $605,000 |
| 2019 | -- | $605,000 |
| 2018 | -- | $605,000 |
| 2017 | $13,035 | $605,000 |
| 2016 | -- | $605,000 |
| 2015 | -- | $605,000 +1.7% |
| 2014 | -- | $595,000 +12.3% |
| 2013 | -- | $530,000 +48.9% |
| 2010 | -- | $356,000 |
| 2009 | -- | $356,000 |
| 2008 | -- | $356,000 |
| 2007 | -- | $356,000 |
| 2006 | -- | $356,000 +36% |
| 2004 | -- | $261,800 +33.6% |
| 2003 | -- | $196,000 |
| 2002 | -- | $196,000 |
| 2001 | -- | $196,000 |
| 2000 | -- | $196,000 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 12498
Nearby schools
GreatSchools rating
- 8/10Woodstock Elementary SchoolGrades: K-3Distance: 1.8 mi
- 9/10Onteora Middle SchoolGrades: 7-8Distance: 7.1 mi
- 7/10Onteora High SchoolGrades: 9-12Distance: 7.1 mi
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Ulster County
- Woodstock
- 12498
- 2465 Glasco Turnpike
Nearby cities
Nearby zip codes
Other Woodstock Topics
