For sale

$775,000

Est. $5,644/mo —

•

2,797

sq ft

165 Hilltop Rd, Monroe, NY 10950

About this home

Welcome to this beautiful and spacious 5-bedroom, 4-bathroom home, offering 2,700+ square feet of living space and plenty of room to live, work, and entertain. Set in a desirable Monroe location, this home combines generous living spaces with the comfort and functionality today's buyers are looking for. Step inside to a warm and inviting interior featuring spacious rooms, abundant natural light, and a layout designed for both everyday living and entertaining. The generously sized bedrooms provide flexibility for a growing household, guests, a home office, or additional living space. The home's multiple bathrooms add convenience, while the expansive living areas provide plenty of opportunity to create spaces tailored to your lifestyle. Whether you're hosting family gatherings or enjoying a quiet evening at home, there is room for everyone. The outdoor space is equally impressive, featuring a breathtaking views of bear mount, beautiful paver fire pit area, perfect for relaxing evenings, entertaining friends and family, and enjoying the outdoors. A two-car garage provides convenient parking and additional storage, while the extended driveway offers ample space for recreational sports or entertaining. Conveniently located in Monroe, this home offers easy access to shopping, dining, parks, schools, major roadways, and everything the surrounding area has to offer.

Single-familyProperty Type

2011Year Built

0.34 acresLot Size

$277Price/Sq.Ft.

2 car garageParking

Listing by Jessy Daniel • KW Hudson Valley United

Contact: 845-610-6065

Listing updated: Oct 26, 2026 at 04:18pm

Redfin checked: a minute ago

•Source:OneKey® MLS as Distributed by MLS Grid #1045151

Payment calculator

$5,644 per month

Principal and interest$4,229

Property taxes

$1,311

HOA dues

Home insurance

$103

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (5)

REDFIN OPEN NOV 7, 12:30PM TO 2:30PM3D WALKTHROUGH
$750,000
4 beds3 baths2,280 sq ft
1 Sanford Ave, Chester, NY 10918
7,841 sq ft lot • 2 garage spots • Built 2014
Listing by Redfin Real Estate
OPEN NOV 8, 11AM TO 1PM
$339,000
3 beds2 baths1,518 sq ft
30 Sycamore Ct, Highland Mills, NY 10930
Garage • Built 1986 • Listed 10 days
Listing by HomeSmart Homes & Estates
OPEN NOV 8, 12PM TO 2PM3D WALKTHROUGH
$719,000
4 beds2.5 baths3,763 sq ft
28 Pewter Cir, Chester, NY 10918
0.3 acre lot • 2 garage spots • Built 1997
Listing by Century 21 Full Service Realty
OPEN NOV 8, 12PM TO 2PM
$368,000
2 beds1.5 baths1,168 sq ft
1 Nancy Ct, Monroe, NY 10950
Community pool • Built 1995 • Listed 25 days
Listing by Howard Hanna Rand Realty
OPEN NOV 8, 12PM TO 2PM
$499,999
3 beds2.5 baths1,908 sq ft
11 Chandler Dr, Chester, NY 10918
0.46 acre lot • 2 garage spots • Pool
Listing by Coldwell Banker Realty

Around this home

Schools

K - 12
Preschool & daycare

Pine Tree Elementary School

Public 2-5 • Assigned • 0.3mi

4/10

Monroe Woodbury Middle School

Public 6-8 • Assigned • 1.9mi

5/10

Monroe Woodbury High School

Public 9-12 • Assigned • 2.1mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

165 Hilltop Rd · $775,000

Strong offer

$774K and above

75% chance or better to win

Why $774K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 44 days.

SALE-TO-LIST

Most homes are selling 0% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
High ceilings
Finished basement
Pull-down attic stairs
Bi-level layout
14 total rooms

Bathrooms
3 full bathrooms
1 half bathroom

Kitchen
Gas oven
Microwave

Laundry & utility
Washer
Dryer

Heating & cooling
Forced air heating
Central air conditioning

Sale and tax history for 165 Hilltop Rd

Sale History
Tax History

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #1045151

Oct 19, 2026

Price Changed

$775,000

$277/sq ft

Sep 8, 2026

Price Changed

$799,000

$286/sq ft

Aug 31, 2026

Listed

$805,000

$288/sq ft

HGMLS #4613826

Sep 6, 2016

Sold

$410,000

$147/sq ft

Sep 6, 2016

Price Changed

$410,000

$147/sq ft

Jun 28, 2016

Contingent

—

Jun 28, 2016

Price Changed

$415,000

$148/sq ft

May 21, 2016

Price Changed

$415,000

$148/sq ft

Apr 4, 2016

Listed

$422,900

$151/sq ft

Spectacular view from this immaculate, quality-designed 2-level home with 2 decks invites comfort, and exudes modern elegance. With 4 bedrooms, 3 and a half baths, generous living space and stylish finishes, you'll enjoy a perfect setting for relaxing and entertaining. Beautiful hardwood floors and plenty of natural night flow throughout the home's open, airy layout. Other special highlights include recessed lighting and ceiling fans, washer/dryer and a 2 car garage with storage space. Enjoy gatherings in the generously-sized living/dining area graced by a charming fireplace, huge windows and glass sliding door that lead out to the upper deck. The kitchen will inspire your inner chef with its granite counters, large pantry and stainless steel appliances. Laundry is conveniently located on the main level. Lower level has the 4th bedroom, full bathroom, large family room with a walk out to the lower deck and a nice sized additional room. Monroe- Woodbury Schools This is a must see!

OneKey® MLS as Distributed by MLS Grid #H4613826

Sep 6, 2016

Sold

$410,000

$147/sq ft

Apr 4, 2016

Listed

$415,000

$148/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$15,733

$16,000 + $57,200

$73,200

2025

$15,733 (+0.1%)

$16,000 + $57,200

$73,200

2024

$15,713 (+1.1%)

$16,000 + $57,200

$73,200

2023

$15,547 (+2.0%)

$16,000 + $57,200

$73,200

2022

$15,241 (+2.1%)

$16,000 + $57,200

$73,200

2021

$14,922 (+3.2%)

$16,000 + $57,200

$73,200

2020

$14,464 (−1.9%)

$16,000 + $57,200

$73,200

2019

$14,746 (+3.0%)

$16,000 + $57,200

$73,200

2018

$14,316 (+1.6%)

$16,000 + $57,200

$73,200

2017

$14,093 (−2.0%)

$16,000 + $57,200

$73,200

2016

$14,385 (+7.3%)

$16,000 + $57,200

$73,200

2015

$13,401 (+0.3%)

$16,000 + $57,200

$73,200

2014

$13,361

$16,000 + $57,200

$73,200

Public record

Public record
Permits

Beds

Baths

3.5

Stories

Lot width

100 ft.

Lot depth

150 ft.

Lot size

0.34 Acres

Year renovated

—

Finished Sq. Ft.

2,797

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,797

Year built

2011

Style

Single Family Residential

County

Orange County

APN

334089A06400000010030000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 8, 2026.

Feb 16, 2011 • Final

Residential

Construct a two-story single-family home with a two-car built-in garage. The home includes a full unfinished basement, a lower level with a recreation room and one bedroom, and an upper level with three bedrooms and two open decks.

New construction

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Climate risks

1/10 Flood Factor

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

1/10 Fire Factor

Unlikely to be 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

16% chance of strong winds in next 30 years

2/10 Air Factor

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

Provided by First Street

Historical weather

Monroe, NY • 10950

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

90/ 100

Exceptional sunlight

Sunscore

This home receives average direct sun exposure in Monroe. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.8 hrs

5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 165 Hilltop Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $650,000 and $890,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $650K to $890K.

SOLD JUL 30, 2026
$795,000 Last sold price
4 beds3 baths3,174 sq ft
7 Maidstone Ln, Monroe, NY 10950
Listing by Keller Williams Realty
$27/sq ft
larger lot
unfinished basement
SOLD APR 30, 2026
$890,000 Last sold price
4 beds3.5 baths2,898 sq ft
86 Talbot Rd, Harriman, NY 10926
Listing by Orion Sky Realty LLC
$30/sq ft
larger lot
2 years older
SOLD MAR 30, 2026
$650,000 Last sold price
4 beds2.5 baths2,448 sq ft
120 Pine Tree Rd, Monroe, NY 10950
Listing by Keller Williams Hudson Valley
$11/sq ft
larger lot
26 years older
SOLD SEP 2, 2026
$855,000 Last sold price
4 beds3 baths4,209 sq ft
18 Windmill Ct, Monroe, NY 10950
Listing by Howard Hanna Rand Realty
$74/sq ft
larger lot
13 years older
SOLD DEC 3, 2025
$880,000 Last sold price
4 beds3.5 baths3,614 sq ft
8 Tanyas Ct, Monroe, NY 10950
Listing by HomeSmart Homes & Estates
$34/sq ft
smaller lot
SOLD MAR 26, 2026
$780,000 Last sold price
4 beds3.5 baths3,146 sq ft
5 Prestwick Dr, Monroe, NY 10950
Listing by Century 21 Realty Center
$29/sq ft
larger lot
4 years older

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