Off Market Mar 2020 for $375K

$653,729

Est. refi paymentEst. refi $2,702/mo

•

2,580

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'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,

Single-familyProperty Type

1992Year Built

1.9 acresLot Size

$253Est. Price/Sq.Ft.

1 spaceParking

Listing by Megan Brenn-White • KW Hudson Valley United

Bought with Monica Schwerberg • KW Hudson Valley United

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H5111240

Redfin Estimate

$653,729

$279K since sold in March 2020$21K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1% higher than the average sale price ($648K) of 6 comparable homes.

SOLD JUL 8, 2026
$590,000
A
3 beds2.5 baths2,340 sq ft
6 Stonybrook Rd, Pine Bush, NY 12566
Listing by Curasi Realty, Inc.
SOLD NOV 6, 2025
$660,000
B
4 beds2.5 baths2,766 sq ft
3861 State Route 52, Pine Bush, NY 12566
Listing by Curasi Realty, Inc.
SOLD JAN 6, 2026
$605,000
C
4 beds2.5 baths2,299 sq ft
41 Vista Maria Rd, Cragsmoor, NY 12420
Listing by Coldwell Banker Village Green
SOLD APR 27, 2026
$750,000
D
4 beds2.5 baths2,808 sq ft
557 Oregon Trl, Pine Bush, NY 12566
Listing by Curasi Realty, Inc.
SOLD NOV 21, 2025
$420,000
E
3 beds4 baths1,760 sq ft
14 RD B, Cragsmoor, NY 12420
Listing by Rogo Realty LLC
SOLD DEC 21, 2025
$860,000
F
3 beds2.5 baths2,100 sq ft
115 Schuyler Ave, Cragsmoor, NY 12420
Listing by Rogo Realty LLC

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Earn from this home

Sell

$353,120

Est. take-home

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Refinance

Est. cash available

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Rent

$2,365/mo

Redfin rental estimate

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Market trends in 12566, NY

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.6%

+0.3% MoM

Median sale price

$450K

$5K MoM

Avg. days on market

35d

1 days MoM

Recently sold homes

9 MoM

New listings for sale

OPEN SUN, 12PM TO 3PM
$489,999
3 beds2 baths1,680 sq ft
129 Dubois St, Pine Bush, NY 12566
Listing by Keller Williams Realty
$302,000
1 bed1.5 baths1,206 sq ft
100 Boniface Dr Unit 14C, Pine Bush, NY 12566
Listing by Howard Hanna Rand Realty
$625,000
4 beds3 baths3,150 sq ft
219 Brimstone Hill Rd, Pine Bush, NY 12566
Listing by KW Hudson Valley United
$499,999
3 beds3 baths2,084 sq ft
59 Gillespie St, Pine Bush, NY 12566
Listing by Keller Williams Realty
See all

Provided by Redfin

Sale history for 285 Circle Rd

Date

Event

Price

ONEKEY #939197

Jan 26, 2026

Rental Removed

$3,500

$1/sq ft

Dec 10, 2025

Listed for Rent

$3,500

$1/sq ft

Public Records

Jun 2, 2020

Sold

$375,000

$145/sq ft

OneKey® MLS as Distributed by MLS Grid #H5111240

Mar 19, 2020

Sold

$375,000

$145/sq ft

Oct 23, 2019

Listed

$395,000

$153/sq ft

HVCRMLS #20194113

Mar 18, 2020

Sold

$375,000

$145/sq ft

Sep 23, 2019

Listed

$395,000

$153/sq ft

+24

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.

OneKey® MLS as Distributed by MLS Grid #H4711113

Jun 21, 2017

Sold

$191,000

$74/sq ft

Mar 17, 2017

Listed

$180,000

$70/sq ft

Public Records

Mar 8, 2005

Sold

$255,000

$99/sq ft

Public Records

Mar 8, 2000

Sold

$163,500

$63/sq ft

Public Records

Sep 12, 1995

Sold

$119,900

$46/sq ft

Public Records

Apr 7, 1993

Sold

$149,350

$58/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 Jul 31, 2026.

Property details

Parking

Parking Information
Parking Total: 1
Parking Features: Attached, Driveway

Interior

Fireplace Information
Fireplace Features: Wood Burning Stove

Heating & Cooling
Cooling: Central Air
Heating: Hot Water, Oil

Interior Features
Interior Features: Cathedral Ceiling(s),Ceiling Fan(s),Eat-in Kitchen,First Floor Bedroom,Master Downstairs,Primary Bathroom
Laundry Features: Inside
Appliances: Dishwasher, Dryer, Washer, Oil Water Heater
Flooring: Hardwood
Levels: Three Or More
Patio And Porch Features: Deck, Porch

Room Information
Basement YN: Yes
Attic: Scuttle
Rooms Total: 8
Basement: Finished, Full, Walk-Out Access

Bathroom Information
Bathrooms Full: 3
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Frame, Vinyl Siding
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Views

Property Information
Stories: 3
Living Area Source: Public Records
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2019
Tax Source: Municipality
Tax Annual Amount: $8,087

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Sewer: Septic Tank
Utilities: See Remarks

Location

HOA Information
Association Amenities: Park

School Information
Elementary School: Ellenville Elementary School
Middle Or Junior School: ELLENVILLE JUNIOR/SENIOR HIGH SCHOOL
High School: ELLENVILLE JUNIOR/SENIOR HIGH SCHOOL
High School District: Ellenville

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

Community Information
Community Features: Park

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 Jul 31, 2026

Around this home

Schools

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

$622,000 – $752,000

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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.	$685,594
261 Circle Rd, Pine Bush, NY 2 Beds \| 1.5 Baths \| 1120 Sq. Ft.	$286,717

Address	Redfin Estimate
267 Circle Rd, Pine Bush, NY 3 Beds \| 2.5 Baths \| 2601 Sq. Ft.	$627,620
245 Circle Rd, Pine Bush, NY 2 Beds \| 1.5 Baths \| 1116 Sq. Ft.	$413,233

Address	Redfin Estimate
292 Circle Rd, Pine Bush, NY 4 Beds \| 2.5 Baths \| 2240 Sq. Ft.	$555,669
236 Circle Rd, Pine Bush, NY 3 Beds \| 1 Baths \| 1084 Sq. Ft.	$328,699

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

Listing provided courtesy of: Compass Greater NY, LLC

Listing agent: Steven Gray (3196214840)

Based on information submitted to the MLS GRID as of Fri Sep 18 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Last Updated: 2026-01-26T21:17:21.191Z

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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 12566

Home values near 285 Circle Rd

More real estate resources