Off market jul 2023 for $695K

$798,266

Est. refi paymentEst. refi $4,997/mo

•

3,347

sq ft

8 Reputation Dr, Chester, NY 10918

About this home

Welcome to your Private Sanctuary. Experience luxurious and resort style living. House is at the top of a private road in a beautiful setting. Featuring an amazing backyard which includes; In-ground pool w/ waterfall, Koi Pond, Deck w/ outdoor Dining area, Built in Fire Pit, & a secret reading nook all surrounded by meticulously landscaped greenery, Inside you have an open-concept living room which opens to the kitchen, perfect for entertaining. Custom Cherry Wood cabinetry & granite countertops. Private Office on First Floor. A Huge master bedroom featuring a 7 shower-head shower for an unbelievable experience. Finished full basement has CO and is included on MLS sq footage (approx. 900 sq ft) w/ Bar and Movie Theater, Recreation room. Hiking & Riding trails right in your backyard! Just Minutes to Restaurants, Night Life, Transportation & Thruway makes this home perfect for commuting. Additional Information: Amenities:Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1986Year Built

7 acresLot Size

$239Est. Price/Sq.Ft.

2 spacesParking

Listing by Junior Taveras • Legendary Realty Corp

Contact: (646) 554-4516

Bought with Jose Cruz • Douglas Elliman Real Estate

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6230029

Redfin Estimate

$798,266

$103K since sold in July 2023$15K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 18% higher than the average sale price ($677K) of 6 comparable homes.

SOLD JUL 14, 2026
$742,500
A
4 beds3.5 baths3,356 sq ft
55 Beverly Rd, Chester, NY 10918
Listing by Howard Hanna Rand Realty
SOLD SEP 16, 2026
$850,000
B
4 beds3.5 baths4,130 sq ft
102 Beverly Rd, Chester, NY 10918
Listing by Keller Williams Realty
SOLD OCT 19, 2026
$625,000
C
4 beds3 baths3,636 sq ft
10 Hidden Dr, Monroe, NY 10950
Listing by Century 21 Full Service Realty
SOLD JUL 8, 2026
$700,000
D
4 beds3.5 baths2,780 sq ft
7 Park Pl, Chester, NY 10918
Listing by Century 21 Full Service Realty
SOLD AUG 31, 2026
$647,000
E
4 beds3.5 baths2,236 sq ft
349 Mountain Ave, Monroe, NY 10950
Listing by Weichert Realtors
SOLD OCT 1, 2026
$495,000
F
4 beds3 baths1,792 sq ft
18 Southside Dr, Monroe, NY 10950
Listing by Keller Williams Realty

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Earn from this home

Sell

$228,361

Est. take-home

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Refinance

Est. cash available

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Rent

$3,905/mo

Redfin rental estimate

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Market trends in 10950, NY

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

98.2%

0.3% MoM

Median sale price

$530K

$18K MoM

Avg. days on market

55d

9 days MoM

Recently sold homes

8 MoM

New listings for sale

$945,000
4 beds2.5 baths2,777 sq ft
504 Bull Mill Rd, Chester, NY 10918
Listing by Flag Realty Group
$825,000
4 beds2.5 baths2,671 sq ft
87 Hardscrabble Rd, Blooming Grove, NY 10918
Listing by HomeSmart Homes & Estates
$880,000
5 beds2.5 baths3,600 sq ft
2 Periwinkle Ct, Chester, NY 10918
Listing by MK Realty Inc
$239,900
2 beds1 bath1,084 sq ft
2313 Whispering Hls, Chester, NY 10918
Listing by R2M Realty Inc
$1,725,000
4 beds2.5 baths3,348 sq ft
20 Goshen Rd, Chester, NY 10918
Listing by eXp Realty
See all

Provided by Redfin

Sale history for 8 Reputation Dr

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #H6230029

Jul 11, 2023

Sold

$695,000

$208/sq ft

May 12, 2023

Pending

—

Mar 9, 2023

Price Changed

$719,900

$215/sq ft

Feb 3, 2023

Listed

$749,000

$224/sq ft

Jan 31, 2023

Coming Soon

$749,000

$224/sq ft

OneKey® MLS as Distributed by MLS Grid #H6149214

Apr 1, 2022

Sold

$640,000

$191/sq ft

Dec 1, 2021

Pending

—

Oct 21, 2021

Listed

$624,999

$187/sq ft

Welcome Home to your Private Sanctuary. Situated on 7 acres of Lush Forest this Stunning Home is Nestled at the Top of a Private Road in a Beautiful Setting. Featuring an amazing backyard which includes; In-ground pool w/ waterfall, Koi Pond, Patio w/ outdoor living-room & TV, Deck w/ outdoor Dining area, Built in Fire Pit, & a secret reading nook all surrounded by meticulously landscaped greenery...,this home is sure to impress! Inside you have an open-concept living room which opens to the kitchen, perfect for entertaining. Custom Cherry Wood cabinetry & granite countertops/tables throughout. An enormous master bedroom featuring a 7 shower-head shower for an unbelievable experience! Custom stair-lift which can be easily moved and stored for later use. Finished basement w/ Bar and Movie Theater! Private Office. Hiking & Riding trails right in your backyard! Just Minutes to Restaurants, Night Life, Transportation & Thruway makes this home perfect for commuting! Come by and Take a look. Additional Information: Amenities:Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Public Records

Jul 2, 1993

Sold

$252,500

$75/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$16,781

$58,000 + $183,000

$241,000

2025

$16,781 (+4.7%)

$58,000 + $183,000

$241,000

2024

$16,028 (+3.1%)

$58,000 + $183,000

$241,000

2023

$15,550 (+1.3%)

$58,000 + $183,000

$241,000

2022

$15,349 (−1.0%)

$58,000 + $183,000

$241,000

2021

$15,499 (−0.9%)

$58,000 + $183,000

$241,000

2020

$15,640 (+1.8%)

$58,000 + $183,000

$241,000

2019

$15,360 (+10.8%)

$58,000 + $183,000

$241,000

2018

$13,868 (+4.4%)

$58,000 + $183,000

$241,000

2017

$13,289 (−4.9%)

$58,000 + $183,000

$241,000

2016

$13,968 (+9.3%)

$58,000 + $183,000

$241,000

2015

$12,782 (+0.3%)

$58,000 + $183,000

$241,000

2014

$12,747

$58,000 + $183,000

$241,000

Tax history for 8 Reputation Dr

Year

Property tax

Land + Additions

Assessment*

2026

$16,781

$58,000 + $183,000

$241,000

2025

$16,781 (+4.7%)

$58,000 + $183,000

$241,000

2024

$16,028 (+3.1%)

$58,000 + $183,000

$241,000

2023

$15,550 (+1.3%)

$58,000 + $183,000

$241,000

2022

$15,349 (−1.0%)

$58,000 + $183,000

$241,000

2021

$15,499 (−0.9%)

$58,000 + $183,000

$241,000

2020

$15,640 (+1.8%)

$58,000 + $183,000

$241,000

2019

$15,360 (+10.8%)

$58,000 + $183,000

$241,000

2018

$13,868 (+4.4%)

$58,000 + $183,000

$241,000

2017

$13,289 (−4.9%)

$58,000 + $183,000

$241,000

2016

$13,968 (+9.3%)

$58,000 + $183,000

$241,000

2015

$12,782 (+0.3%)

$58,000 + $183,000

$241,000

2014

$12,747

$58,000 + $183,000

$241,000

*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

Stories

Lot width

—

Lot depth

—

Lot size

1.8 Acres

Year renovated

—

Sq. Ft.

3,347

Year built

1986

Style

Single Family Residential

County

Orange County

APN

332289A01500000010741000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 8, 2026.

Property details

Parking

Parking Information
Parking Total: 2
Parking Features: Attached, Driveway, Garage Door Opener, Storage

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1

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

Interior Features
Interior Features: Cathedral Ceiling(s),Ceiling Fan(s),ENERGY STAR Qualified Door(s),Formal Dining,First Floor Full Bath,Marble Counters,Primary Bathroom,Open Kitchen,Walk Through Kitchen
Window Features: ENERGY STAR Qualified Windows
Appliances: Cooktop, Dishwasher, Dryer, ENERGY STAR Qualified Appliances, Refrigerator, Washer, Oil Water Heater
Flooring: Carpet, Hardwood
Levels: Three Or More
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Scuttle
Rooms Total: 9
Basement: Finished, Walk-Out Access
Additional Rooms: Dining Area,Office

Bathroom Information
Bathrooms Full: 4

Exterior

Exterior Features
Exterior Features: Basketball Hoop
Construction Materials: Advanced Framing Technique, Brick
Security Features: Security System
Waterfront YN: No

Pool Information
Pool Features: In Ground

Lot Information
Additional Parcels YN: Yes
Lot Features: Cul-De-Sac, Near Public Transit, Near Shops, Part Wooded, Views

Property Information
Stories: 3
Other Equipment: Generator, Pool Equip/Cover
Living Area Source: Other
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2022
Tax Source: Municipality
Tax Annual Amount: $15,499

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Sewer: Septic Tank
Utilities: Trash Collection Public

Location

HOA Information
Association Amenities: Park

School Information
Elementary School: Pine Tree Elementary School
Middle Or Junior School: Monroe-Woodbury High School
High School: Monroe-Woodbury High School
High School District: Monroe-Woodbury

Location Information
Directions: Gibson Hill Road to Reputation Drive. Look for Mailbox clusters. LAST HOME AT THE TOP OF THE HILL. Sentry lock box!
County Or Parish: Orange County

Community Information
Community Features: Park

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 3,347
Stories: 2.0
Lot Size: 1.8 acres
Style: Single Family Residential
Year Built: 1986
Year Renovated: —
County: Orange County
APN: 332289A01500000010741000000

Home facts updated by county records on Oct 8, 2026

Around this home

Schools

North Main Street School

Public 2-5 • Assigned • 4.3mi

5/10

Monroe Woodbury Middle School

Public 6-8 • Assigned • 6.3mi

5/10

Monroe Woodbury High School

Public 9-12 • Assigned • 6.5mi

6/10

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

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

4/10 Wind Factor

15% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Chester, NY • 10918

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 4 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$759,000 – $919,000

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Home values near 8 Reputation Dr

Data from public records.

Address	Redfin Estimate
6 Reputation Dr, Chester, NY 4 Beds \| 2.5 Baths \| 2376 Sq. Ft.	$652,088
139 Beverly Rd, Chester, NY 4 Beds \| 3.5 Baths \| 3731 Sq. Ft.	$814,380

Address	Redfin Estimate
4 Reputation Dr, Chester, NY 4 Beds \| 2.5 Baths \| 2646 Sq. Ft.	$651,564
16 Cherry Ln, Chester, NY 4 Beds \| 2.5 Baths \| 3036 Sq. Ft.	$627,835

Address	Redfin Estimate
2 Reputation Dr, Chester, NY 4 Beds \| 2.5 Baths \| 2376 Sq. Ft.	$627,135
161 Beverly Rd, Chester, NY 4 Beds \| 2.5 Baths \| 2727 Sq. Ft.	$721,570

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2023. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 10950, NY

Sale history for 8 Reputation Dr

Tax history for 8 Reputation Dr

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 10918

Home values near 8 Reputation Dr

More real estate resources