OFF MARKET

Off market mar 2020 for $375K

$696,994

Est. refi paymentEst. refi $2,674/mo

•

2,080

sq ft

285 Circle Rd, Pine Bush, NY 12566

About this home

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.

Single-familyProperty Type

1992Year Built

1.9 acresLot Size

$335Est. Price/Sq.Ft.

1 car garageParking

Listing by Megan Brenn-White • Compass Greater NY, LLC

Bought with Monica Schwerberg • Keller Williams Realty HV Nort

Redfin checked: a minute ago

•Source:HVCRMLS #20194113

Redfin Estimate

$696,994

$322K since sold in March 2020$4,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.3% higher than the average sale price ($615K) of 6 comparable homes.

SOLD OCT 5, 2026
$530,000
A
3 beds3 baths1,502 sq ft
340 Marl Rd, Pine Bush, NY 12566
Listing by Howard Hanna Rand Realty
SOLD SEP 11, 2026
$710,000
B
4 beds2.5 baths2,266 sq ft
95 Weeds Rd, Pine Bush, NY 12566
Listing by Quinn Realty Group Inc.
SOLD SEP 23, 2026
$475,000
C
4 beds3 baths1,905 sq ft
1036 Benjamin Van Keuren Dr, Pine Bush, NY 12566
Listing by Century 21 Hudson Valley Rlty.
SOLD OCT 5, 2026
$595,000
D
4 beds2.5 baths2,184 sq ft
508 Walker Valley Rd, Pine Bush, NY 12566
Listing by Real Broker NY LLC
SOLD SEP 11, 2026
$675,000
E
4 beds2.5 baths2,923 sq ft
19 Pirog Rd, Pine Bush, NY 12566
Listing by Howard Hanna Rand Realty
SOLD SEP 23, 2026
$705,000
F
4 beds3 baths2,400 sq ft
267 Shawanga Lodge Rd, Bloomingburg, NY 12721
Listing by Keller Williams Realty

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Earn from this home

Sell

$394,902

Est. take-home

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Refinance

Est. cash available

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Rent

$2,470/mo

Redfin rental estimate

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Market trends in 12566, NY

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

101.0%

0.6% MoM

Median sale price

$472K

$22K MoM

Avg. days on market

42d

7 days MoM

Recently sold homes

12 MoM

New listings for sale

COMING SOON
$875,000
6 beds3.5 baths2,958 sq ft
5 Dellenbaugh Road, Cragsmoor, NY 12420
Listing by KW Hudson Valley North
$420,000
2 beds2 baths1,848 sq ft
9 Gross St, Pine Bush, NY 12566
Listing by KW Hudson Valley United
$2,099,000
3 beds2 baths2,119 sq ft
248 Brimstone Hill Rd, Pine Bush, NY 12566
Listing by Prospes Real Estate Corp
$349,000
2 beds1 bath1,107 sq ft
3 Edward Dr, Pine Bush, NY 12566
Listing by Cronin & Company Real Estate
$625,000
3 beds2.5 baths1,909 sq ft
5200 Searsville Rd, Pine Bush, NY 12566
Listing by ReAttached
$379,900
3 beds1.5 baths1,529 sq ft
795 Burlingham Rd, Pine Bush, NY 12566
Listing by Curasi Realty, Inc.
$725,000
3 beds2.5 baths1,927 sq ft
474 Oregon Trl, Pine Bush, NY 12566
Listing by Howard Hanna Rand Realty
$599,000
3 beds2.5 baths2,654 sq ft
165 Burlingham Rd, Pine Bush, NY 12566
Listing by KW MidHudson
See all

Provided by Redfin

Sale history for 285 Circle Rd

Date

Event

Price

ONEKEY #939197

Jan 26, 2026

Rental Removed

$3,500

$2/sq ft

Dec 10, 2025

Listed for Rent

$3,500

$2/sq ft

Public Records

Jun 2, 2020

Sold

$375,000

$180/sq ft

OneKey® MLS as Distributed by MLS Grid #H5111240

Mar 19, 2020

Sold

$375,000

$180/sq ft

Oct 23, 2019

Listed

$395,000

$190/sq ft

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've entered 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!) with the smart layout of bedrooms, bathrooms, and "bonus spaces", including a finished walk-out basement. The owners have made significant improvements, including an eat-in kitchen, new oak hardwood floors, new roof, freshly painted interior and exterior, and new gravel drive. Under 80 miles to NYC, Cragsmoor is a 19th century artist colony that maintains a strong sense of community, allowing you to tuck away in your own home or 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. The owners have also had success with Airbnb. Additional Information: Amenities:Guest Quarters,HeatingFuel:Oil Below Ground,ParkingFeatures:1 Car Attached,

HVCRMLS #20194113

Mar 18, 2020

Sold

$375,000

$180/sq ft

Sep 23, 2019

Listed

$395,000

$190/sq ft

OneKey® MLS as Distributed by MLS Grid #H4711113

Jun 21, 2017

Sold

$191,000

$92/sq ft

Mar 17, 2017

Listed

$180,000

$87/sq ft

Public Records

Mar 8, 2005

Sold

$255,000

$123/sq ft

Public Records

Mar 8, 2000

Sold

$163,500

$79/sq ft

Public Records

Sep 12, 1995

Sold

$119,900

$58/sq ft

Public Records

Apr 7, 1993

Sold

$149,350

$72/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$8,945 (+4.8%)

$61,300 + $176,900

$238,200

2024

$8,539 (+2.5%)

$61,300 + $176,900

$238,200

2023

$8,327 (+2.6%)

$61,300 + $176,900

$238,200

2022

$8,117 (−1.1%)

$61,300 + $176,900

$238,200

2021

$8,203 (−0.2%)

$61,300 + $176,900

$238,200

2020

$8,217 (+1.5%)

$61,300 + $176,900

$238,200

2019

$8,097 (−25.9%)

$61,300 + $176,900

$238,200

2018

$10,934 (+2.1%)

$61,300 + $176,900

$238,200

2017

$10,705 (+37.5%)

$61,300 + $176,900

$238,200

2016

$7,784 (+1.6%)

$61,300 + $176,900

$238,200

2015

$7,659 (+17.5%)

$61,300 + $176,900

$238,200

2014

$6,520

$61,300 + $176,900

$238,200

Tax history for 285 Circle Rd

Year

Property tax

Land + Additions

Assessment*

2025

$8,945 (+4.8%)

$61,300 + $176,900

$238,200

2024

$8,539 (+2.5%)

$61,300 + $176,900

$238,200

2023

$8,327 (+2.6%)

$61,300 + $176,900

$238,200

2022

$8,117 (−1.1%)

$61,300 + $176,900

$238,200

2021

$8,203 (−0.2%)

$61,300 + $176,900

$238,200

2020

$8,217 (+1.5%)

$61,300 + $176,900

$238,200

2019

$8,097 (−25.9%)

$61,300 + $176,900

$238,200

2018

$10,934 (+2.1%)

$61,300 + $176,900

$238,200

2017

$10,705 (+37.5%)

$61,300 + $176,900

$238,200

2016

$7,784 (+1.6%)

$61,300 + $176,900

$238,200

2015

$7,659 (+17.5%)

$61,300 + $176,900

$238,200

2014

$6,520

$61,300 + $176,900

$238,200

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1.9 Acres

Year renovated

1995

Sq. Ft.

2,580

Year built

1992

Style

Single Family Residential

County

Ulster County

APN

515689A09800100040010000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 21, 2026.

Property details

Parking

Parking/Garage Information
# of Garage Spaces: 1
Parking Features: Other

Interior

Bathroom Information
# of Full Bathrooms: 3

Heating & Cooling
Has Cooling
Cooling: Central Air, Ceiling Fan(s)
Has Heating
Heating: Hot Water, Oil, Wood

Interior Features
Interior Features: Eat-in Kitchen, High Ceilings, High Speed Internet
Appliances: Dryer, Dishwasher, Other, Range, Washer, Water Heater
Flooring: Ceramic Tile, Hardwood
Fireplace Features: Living Room, Other, See Remarks

Room Information
Has Basement
Basement Details: Finished, Full, Walk-Out Access

Exterior

Exterior Features
Door Features: Sliding Doors
Roof: Asphalt, Shingle

Building Information
Sq. Ft.: 2080.0
Construction Materials: Frame, Vinyl Siding

Property Information
Property Type: Residential
Property Sub Type: Single Family Residence
Raw Mls Property Sub Type: Single Family Residence

Lot Information
Lot Features: Sloped, Gentle Sloping, Private
Road Surface Type: Gravel
Road Responsibility: Private Maintained Road
Lot Size : 1.9
Lot Size Dimensions: 80 x 400
Lot Size Area: 1.9
Lot Size Units: Acres
Lot Size Acres: 1.9
Zoning: Res1

Financial

Tax Information
Tax Annual Amount: $8,087

Utilities

Utility Information
Water Source: Private, Well
Sewer: Septic Tank

Location

Schools Information
High School District: Ellenville Central

Location Information
Directions: Driving up from Ellenville on 52, take a left on Cragsmoor Road, a left on Dellenbaugh, a left on Circle and the property will be on your left.

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 2,580
Stories: 2.0
Lot Size: 1.9 acres
Style: Single Family Residential
Year Built: 1992
Year Renovated: 1995
County: Ulster County
APN: 515689A09800100040010000000

Home facts updated by county records on Oct 21, 2026

Around this home

Schools

K - 12
Preschool & daycare

Ellenville Elementary School

Public PreK-6 • Assigned • 3.5mi

7/10

Ellenville High School

Public 7-12 • Assigned • 3.5mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

4/10 Fire Factor

1% chance of being in a wildfire in next 30 years

1/10 Heat Factor

6 days above 94° expected this year, 12 days in 30 years

3/10 Wind Factor

6% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Pine Bush, NY • 12566

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 3.6 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$663,000 – $802,000

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Listing by KW Hudson Valley North

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Listing by KW Hudson Valley United

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Listing by Prospes Real Estate Corp

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Listing by Curasi Realty, Inc.

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Home values near 285 Circle Rd

Data from public records.

Address	Redfin Estimate
277 Circle Rd, Pine Bush, NY 3 Beds \| 2 Baths \| 1576 Sq. Ft.	$719,259
261 Circle Rd, Pine Bush, NY 2 Beds \| 1.5 Baths \| 1120 Sq. Ft.	$301,169
296 Circle Rd, Pine Bush, NY 3 Beds \| 2 Baths \| 1572 Sq. Ft.	$471,861
270 Circle Rd, Pine Bush, NY 3 Beds \| 2.5 Baths \| 2576 Sq. Ft.	$591,733
277 Circle Rd, Cragsmoor, NY 3 Beds \| 3 Baths \| 1576 Sq. Ft.	$848,585
95 Inn Rd, Pine Bush, NY 5 Beds \| 2 Baths \| 2460 Sq. Ft.	$490,861

Address	Redfin Estimate
267 Circle Rd, Pine Bush, NY 3 Beds \| 2.5 Baths \| 2601 Sq. Ft.	$624,434
245 Circle Rd, Pine Bush, NY 2 Beds \| 1.5 Baths \| 1116 Sq. Ft.	$417,076
291 Circle Rd, Pine Bush, NY 3 Beds \| 2.5 Baths \| 2080 Sq. Ft.	$544,399
278 Circle Rd, Pine Bush, NY 3 Beds \| 2.5 Baths \| 1848 Sq. Ft.	$643,454
292 Circle Rd, Cragsmoor, NY 4 Beds \| 2.5 Baths \| 2240 Sq. Ft.	$606,937
36 Inn Rd, Pine Bush, NY 2 Beds \| 2 Baths \| 1104 Sq. Ft.	$480,113

Address	Redfin Estimate
292 Circle Rd, Pine Bush, NY 4 Beds \| 2.5 Baths \| 2240 Sq. Ft.	$542,947
236 Circle Rd, Pine Bush, NY 3 Beds \| 1 Baths \| 1084 Sq. Ft.	$335,178
282 Circle Rd, Pine Bush, NY 3 Beds \| 2 Baths \| 1404 Sq. Ft.	$439,447
273 Circle Rd, Pine Bush, NY 2 Beds \| 2 Baths \| 2348 Sq. Ft.	$682,675
296 Circle Rd, Cragsmoor, NY 3 Beds \| 2 Baths \| 2000 Sq. Ft.	$442,697
292 Circle Road Rd, Cragsmoor, NY 4 Beds \| 2.5 Baths \| 2068 Sq. Ft.	$582,812

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2026. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 12566, NY

Sale history for 285 Circle Rd

Tax history for 285 Circle Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12420

Home values near 285 Circle Rd

More real estate resources