285 Circle Rd
Pine Bush, NY 12566
Cragsmoor
4 Beds
3 Baths
2,080 sqft (on 1.90 acres)
4 Beds
3 Baths
2,080 sqft
(on 1.90 acres)
Local Information
- Map ViewExplore the area around 285 Circle Rd.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1992
Lot Size
1.9 acres
Living Area
2,080 sqft
Price/Sqft
$280
Parking
Garage
Description
Stepping into the double-height, south-facing living room and glimpsing the deck that stretches the full length of this house gives you the first inkling that you're entering something truly special! With a wood stove in the living room, you'll be ready to enjoy every season - and have the space to host guests (or a home office or gym or whatever you need!) with the smart layout of bedrooms, bathrooms, and "bonus spaces" spread across three floors, including a finished walk-out basement. This is the rare property that ticks all the boxes for a relaxing weekend getaway or fully functional full-time home. The current owners have made significant improvements, including a modern, eat-in kitchen opening to the deck; new oak hardwood floors, a new roof, freshly painted interior and exterior, and new gravel on the driveway. Located under 80 miles to NYC, Cragsmoor is what everyone dreams of for an historic upstate community: a 19th century mountaintop artist colony that maintains a strong sense of community OR allows you to simply tuck away in your own home and enjoy being able to walk to the Bear Hill Preserve hiking with its spectacular views or events at the library, Cragsmoor Association, Historical Society, or Stone Church. Note: the owners have been enjoying this home for their own family getaway but have also had success renting it out on Airbnb.
285 Circle Rd, Pine Bush, NY 12566 is a 4 bedroom, 3 bathroom, 2,080 sqft single-family home in Cragsmoor, built in 1992. It last sold for $375,000 on Jun 2, 2020. More recently, it was listed as a rental in December 2025 with an asking price of $3,500 per month. That rental listing was removed on January 26, 2026. It is currently off market. The Trulia Estimate is $583,300, with a rent estimate of $4,776/month.
Home Details for 285 Circle Rd
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Interior Details BasementNumber of Rooms: 8Types of Rooms: Walk In ClosetCeiling Fan |
Heating & Cooling Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood |
Appliances & Utilities Cable ReadyDishwasherDryerWasher |
Fireplace & Spa Fireplace |
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Year Built Year Built: 1992Year Updated: 1995 |
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary |
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Exterior Home Features Exterior: Other |
Parking & Garage GarageParking Space: 1Parking: Garage Detached |
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Units in Building: 1 |
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Lot Area: 1.90 acres |
Price History for 285 Circle Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 01/26/2026 | $3,500 | ListingRemoved | OneKey® MLS as distributed by MLS GRID #939197 |
| 12/08/2025 | $3,500 | Listed For Rent | OneKey® MLS as distributed by MLS GRID #939197 |
| 06/02/2020 | $375,000 | Sold | N/A |
| 03/18/2020 | $375,000 | Sold | HVCRMLS #20194113 |
| 01/13/2020 | $395,000 | Pending | Agent Provided |
| 09/23/2019 | $395,000 | Listed For Sale | Agent Provided |
| 07/05/2019 | $349,900 | ListingRemoved | Agent Provided |
| 07/02/2019 | $349,900 | Listed For Sale | Agent Provided |
| 06/21/2017 | $191,000 | Sold | OneKey® MLS as distributed by MLS GRID #H4711113 |
| 04/24/2017 | $180,000 | Pending | Agent Provided |
| 04/04/2017 | $178,928 | Sold | N/A |
| 03/17/2017 | $180,000 | Listed For Sale | Agent Provided |
| 03/19/2014 | $254,500 | ListingRemoved | Agent Provided |
| 02/28/2014 | $254,500 | PriceChange | Agent Provided |
| 11/26/2013 | $274,500 | Listed For Sale | Agent Provided |
| 09/11/2013 | $284,500 | ListingRemoved | Agent Provided |
| 08/26/2013 | $284,500 | PriceChange | Agent Provided |
| 08/05/2013 | $294,500 | Listed For Sale | Agent Provided |
| 03/08/2005 | $255,000 | Sold | N/A |
| 03/08/2000 | $163,500 | Sold | N/A |
| 09/12/1995 | $119,900 | Sold | N/A |
Market trends in Pine Bush
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
60
9MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $397,000 |
Home facts updated by county records
Comparable Sales for 285 Circle Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.33 | Single-Family Home | $579,900 | 09/18/25 | 4 | 3 | 2,400 | |
0.26 | Single-Family Home | $698,000 | 03/18/26 | 4 | 2 | 2,094 | |
0.26 | Single-Family Home | $698,000 | 03/12/26 | 4 | 2 | 2,094 | |
0.53 | Single-Family Home | $420,000 | 11/21/25 | 3 | 2.5 | 1,760 | |
0.64 | Single-Family Home | $520,000 | 12/30/25 | 3 | 2.5 | 1,700 | |
0.72 | Single-Family Home | $860,000 | 12/21/25 | 3 | 2.5 | 2,100 | |
1.05 | Single-Family Home | $605,000 | 01/06/26 | 4 | 2.5 | 2,299 | |
1.05 | Single-Family Home | $605,000 | 01/06/26 | 4 | 2.5 | 2,299 | |
1.33 | Single-Family Home | $555,000 | 12/09/25 | 3 | 3 | 2,200 | |
1.32 | Single-Family Home | $575,000 | 08/13/25 | 3 | 2 | 1,560 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETKeller Williams Realty HV Nort, Closed
SOLDMAR 12, 2026Compass Greater NY, LLC, Closed
OFF MARKETCompass Greater NY, LLC
OFF MARKETHoward Hanna Rand Realty
OFF MARKETRMA Realty & Associates Ltd
OFF MARKETCentury 21 Stoeckeler R.E., Closed
OFF MARKETKeller Williams Realty HV Nort, Closed
Assigned Schools
These are the assigned schools for 285 Circle Rd.
- Ellenville Elementary School
- PK-6
- Public
- 728 Students
7/10GreatSchools RatingParent Rating AverageHay racismo mucho discrimen no hay comunicacion no trabajan con los caso no entienden a los niños no dejan que se expresen.Parent Review8mo ago - Ellenville High School
- 7-12
- Public
- 698 Students
4/10GreatSchools RatingParent Rating AverageOverall, it’s okay. My child wants to finish out here and graduate from Ellenville. Comparing this school to my high school and even others in the area... this school does NOT offer many interesting electives (only language is Spanish) and they subscribe to ‘common core’ which is annoying. One of the “path to graduation” options the kids are required to follow does NOT include a science path, but art is a path??? Odd. Science is WAY more useful than art.Parent Review6y ago 
Check out schools near 285 Circle Rd.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Cragsmoor
At least 1 Trulia users voted on each feature.
100 % Say it's dog friendly
100 % Say there are community events
100 % Say they plan to stay for at least 5 years
100 % Say car is needed
100 % Say yards are well-kept
100 % Say kids play outside
80 % Say it's quiet
71 % Say neighbors are friendly
50 % Say parking is easy
50 % Say there's wildlife
33 % Say there's holiday spirit
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near 285 Circle Rd
1 ACREListing by: Century 21 Stoeckeler RE
34.4 ACRESListing by: KW Hudson Valley North
34.4 ACRESListing by: Keller Williams Realty HV Nort, Active
2.6 ACRESListing by: Howard Hanna Rand Realty, Active
NEW CONSTRUCTION5.04 ACRESListing by: Taft Street Realty, Inc., Active
NEW - 2 DAYS AGO24.2 ACRESListing by: Curasi Realty, Inc.
See more homes for sale inPine Bush
Off Market Homes Near 285 Circle Rd
SOLDJUL 10, 2026RE/MAX Benchmark Realty Group
SOLDJUL 8, 2026Century 21 Stoeckeler R.E., Closed
SOLDJUL 8, 2026Curasi Realty, Inc.
SOLDJUN 26, 2026
SOLDJUN 26, 2026Keller Williams Realty
SOLDJUN 23, 2026The Machree Group, LLC, Closed
SOLDJUN 11, 2026- SOLDJUN 10, 2026
SOLDJUN 1, 2026eXp Realty, LLC, Closed- See more homes for sale inPine Bush
