OFF MARKET

Off market oct 2023 for $775K

$954,382

Est. refi paymentEst. refi $5,847/mo

•

6,971

sq ft

101 Rolling Hills Rd, Stroudsburg, PA 18360

About this home

PROPERTY IS UNDER CONTRACT- CONSIDERING BACK-UP OFFERS ONLY AT THIS TIME. This 7,000 sq ft. home is situated on over 2 acres of alluring views, which includes an overlook of Water Gap Golf Course. Once you step inside you will be charmed by 6 bdrms, and 6.5 baths of luxury which includes an au pair suite, stunning hardwood floors, fabulous kitchen with 2 sinks and 2 dishwashers, heated master bath floor, executive office, wet bar finished basement and pool table, padded children's area with puppet theater, swing, and barn, among countless other once in a lifetime features. Outside you will find landscape lighting, 3 car garage, waterfall landscape feature, koi pond, driveway alarm, security camera system, sprinkler system

Single-familyProperty Type

2006Year Built

2.17 acresLot Size

$137Est. Price/Sq.Ft.

3 car garageParking

Listed by Kaitlyn Poje • Poconos Properties Real Estate, Inc.

Bought with Benjamin, Associate Broker, Stephanie Benjamin • Classic Properties - Mountainhome

Redfin checked: a few seconds ago

•Source:PMAR #PM-102285

Redfin Estimate

$954,382

$179K since sold in October 2023$25K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 82.4% higher than the average sale price ($523K) of 6 comparable homes.

SOLD JUL 30, 2026
$401,000
A
5 beds3 baths2,238 sq ft
219 Highland Dr, Stroudsburg, PA 18360
SOLD JUL 2, 2026
$560,000
B
4 beds2.5 baths2,732 sq ft
119 Godfreys Gate, Stroudsburg, PA 18360
SOLD MAR 17, 2026
$385,000
C
4 beds4.5 baths3,328 sq ft
2 Shepard Ct, Delaware Water Gap, PA 18327
SOLD DEC 22, 2025
$610,000
D
5 beds3.5 baths3,698 sq ft
7297 Cherry Valley Rd, Stroudsburg, PA 18360
SOLD JUN 9, 2026
$699,000
E
6 beds4 baths4,634 sq ft
2506 Red Fox Ln, Stroudsburg, PA 18360
SOLD JUL 30, 2026
$485,000
F
3 beds2.5 baths4,129 sq ft
220 Highland Dr, Stroudsburg, PA 18360

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,167/mo

Redfin rental estimate

List your home for rent

Market trends in 18360, PA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.9%

0.2% MoM

Median sale price

$422K

$21K MoM

Avg. days on market

17d

4 days MoM

Recently sold homes

7 MoM

New listings for sale

$339,500
4 beds3 baths3,318 sq ft
810 Scott St, Stroudsburg, PA 18360
$325,000
5 beds3 baths2,344 sq ft
507 Starlite Ct, Stroudsburg, PA 18360
(717) 755-5599
$420,000
— beds3.5 baths2,244 sq ft
728-730 Ann St, Stroudsburg, PA 18360
3D WALKTHROUGH
$305,000
4 beds2 baths1,716 sq ft
127 Broad St, Stroudsburg, PA 18360
$220,000
3 beds1.5 baths1,513 sq ft
2254 Chipperfield Dr, East Stroudsburg, PA 18301
3D WALKTHROUGH
$355,356
3 beds2.5 baths1,872 sq ft
238 Becca Ln, Stroudsburg, PA 18360
$645,000
5 beds2 baths3,113 sq ft
5333 Hickory Cir, Stroudsburg, PA 18360
$385,000
4 beds2 baths2,136 sq ft
1004 Tara View Dr, Stroudsburg, PA 18360
$345,500
3 beds1.5 baths2,199 sq ft
1317 Coolbaugh St, Stroudsburg, PA 18360
(570) 421-8950
$729,900
5 beds4 baths4,380 sq ft
1657 Rachel Rd, Stroudsburg, PA 18360
See all

Provided by Redfin

Sale history for 101 Rolling Hills Rd

Date

Event

Price

PMAR #PM-102285

Oct 26, 2023

Sold

$775,000

$111/sq ft

Aug 26, 2023

Relisted

—

Aug 12, 2023

Delisted

—

Jul 30, 2023

Price Changed

$824,999

$118/sq ft

Jul 30, 2023

Relisted

—

Jun 20, 2023

Price Changed

$834,999

$120/sq ft

Jun 6, 2023

Price Changed

$839,999

$120/sq ft

May 15, 2023

Relisted

—

Apr 15, 2023

Price Changed

$849,999

$122/sq ft

Apr 2, 2023

Price Changed

$859,999

$123/sq ft

Feb 3, 2023

Price Changed

$874,999

$126/sq ft

Jan 1, 2023

Price Changed

$899,999

$129/sq ft

Dec 5, 2022

Price Changed

$914,999

$131/sq ft

Nov 14, 2022

Listed

$924,999

$133/sq ft

GLVRMLS #585162

Oct 4, 2018

Sold

$685,000

$98/sq ft

Jul 6, 2018

Listed

$695,000

$100/sq ft

PMAR #PM-59219

Oct 4, 2018

Sold

$685,000

$98/sq ft

Jul 3, 2018

Listed

$695,000

$100/sq ft

PMAR #PM-49770

Aug 6, 2017

Listed

$695,000

$100/sq ft

PWMLS #173518

Jul 30, 2017

Listed

$695,000

$100/sq ft

PMAR #PM-30878

Dec 30, 2015

Listed

$799,999

$115/sq ft

PMAR #PM-22408

Apr 17, 2015

Listed

$899,800

$129/sq ft

PMAR #PM-13759

Jun 27, 2014

Listed

$899,800

$129/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$25,861 (−2.9%)

$64,900 + $593,260

$658,160

2025

$26,636 (+4.8%)

$64,900 + $623,840

$688,740

2024

$25,424 (+3.9%)

$64,900 + $623,840

$688,740

2023

$24,458 (+0.1%)

$64,900 + $623,840

$688,740

2022

$24,427 (+0.5%)

$64,900 + $623,840

$688,740

2021

$24,300 (+1.6%)

$64,900 + $623,840

$688,740

2020

$23,922 (+13.9%)

$64,900 + $623,840

$688,740

2019

$20,997

$22,700 + $80,120

$102,820

2018

$20,997

$22,700 + $80,120

$102,820

2017

$20,996 (−1.4%)

$22,700 + $80,120

$102,820

2015

$21,300

$22,700 + $80,120

$102,820

Tax history for 101 Rolling Hills Rd

Year

Property tax

Land + Additions

Assessment*

2026

$25,861 (−2.9%)

$64,900 + $593,260

$658,160

2025

$26,636 (+4.8%)

$64,900 + $623,840

$688,740

2024

$25,424 (+3.9%)

$64,900 + $623,840

$688,740

2023

$24,458 (+0.1%)

$64,900 + $623,840

$688,740

2022

$24,427 (+0.5%)

$64,900 + $623,840

$688,740

2021

$24,300 (+1.6%)

$64,900 + $623,840

$688,740

2020

$23,922 (+13.9%)

$64,900 + $623,840

$688,740

2019

$20,997

$22,700 + $80,120

$102,820

2018

$20,997

$22,700 + $80,120

$102,820

2017

$20,996 (−1.4%)

$22,700 + $80,120

$102,820

2015

$21,300

$22,700 + $80,120

$102,820

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

Public record

Public record
Zoning

Beds

Baths

Stories

1.7

Lot width

—

Lot depth

—

Lot size

2.17 Acres

Year renovated

—

Sq. Ft.

5,661

Year built

2006

Style

Single Family Residential

County

Monroe County

APN

16 98046

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2026.

Low Density Residential District

This District includes large land areas that should, to the degree practical, be developed in a manner that preserves their open space character and natural amenities. Permanent and seasonal residences at low density, as well as recreational uses, resorts, camps, wildlife preserves and other types of uses compatible with the natural environment are appropriate.

Permitted uses

Include but are not limited to:

Housing-Single unit
Recreation
Communications tower

Property details

Parking

Parking/Garage Information
Has Garage
Has Attached Garage
# of Garage Spaces: 3
Parking Features: Attached

Interior

Bathroom Information
# of Full Bathrooms: 5
# of Half Bathrooms: 2

Heating & Cooling
Has Cooling
Cooling: Ceiling Fan(s), Central Air
Has Heating
Heating: Oil, Propane

Interior Features
Interior Features: Pantry, Kitchen Island, Granite Counters, Cathedral Ceiling(s), Walk-In Closet(s), In-Law Floorplan, Central Vacuum, Storage, Other, See Remarks
Appliances: Gas Range, Water Heater, Dishwasher, Microwave
Flooring: Hardwood, Tile
Has Fireplace
# of Fireplaces: 2
Fireplace Features: Living Room

Room Information
# of Rooms Total: 13
Has Basement
Basement Details: Full

Exterior

Exterior Features
Patio And Porch Features: Patio, Deck, Covered
Roof: Asphalt, Fiberglass

Building Information
Above Grade Finished Area: 5,671
Below Grade Finished Area: 1,300
Construction Materials: Brick

Property Features
Has View

Property Information
Property Type: Residential
Property Sub Type: Single Family Residence
Raw Mls Property Sub Type: Residential
Common Walls: No Common Walls

Lot Information
Lot Features: Corner Lot, Cleared
Road Surface Type: Paved
Lot Size Area: 2.17
Lot Size Units: Acres
Lot Size Acres: 2.17
Zoning Description: Residential

Financial

Tax Information
Tax Annual Amount: $24,427.07

Utilities

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

Location

Location Information
Directions: From Main Street Delaware Water Gap: Cherry Valley Road to left on Totts Gap Road to left on Wolf Hollow to left on Rolling Hill, house on left.
Subdivision Name: None

Public facts

Beds: 4
Baths: 6.0
Sq. Ft.: 5,661
Stories: 1.7
Lot Size: 2.17 acres
Style: Single Family Residential
Year Built: 2006
Year Renovated: —
County: Monroe County
APN: 16 98046

Home facts updated by county records on Jul 20, 2026

Around this home

Schools

Smithfield El School

Public K-5 • Assigned • 2.2mi

6/10

J T Lambert Intermediate School

Public 6-8 • Assigned • 3.3mi

5/10

East Stroudsburg Senior High School South

Public 9-12 • Assigned • 2.6mi

5/10

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

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

13% 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

Stroudsburg, PA • 18360

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 8.8 hours in June and 3.8 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

3.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$907,000 – $1.10M

Sell confidently with a local market expert in Stroudsburg. 3 minutes to get started.

Nearby similar homes

$1,000,000

3 beds3 baths3,125 sq ft

224 Doctor Ln, East Stroudsburg, PA 18301

$419,900

3 beds2 baths3,421 sq ft

6277 Franklin Hill Rd, East Stroudsburg, PA 18301

$281,500

3 beds1 bath1,040 sq ft

22 Independence Rd, East Stroudsburg, PA 18301

$419,000

4 beds3 baths2,385 sq ft

106 Independence Rd, East Stroudsburg, PA 18301

$650,000

6 beds3.5 baths4,268 sq ft

170 Music Center Dr, East Stroudsburg, PA 18301

$299,000

3 beds1 bath963 sq ft

1139 Old Mill Rd, East Stroudsburg, PA 18301

New listings for sale in 18360

$339,500

4 beds3 baths3,318 sq ft

810 Scott St, Stroudsburg, PA 18360

$325,000

5 beds3 baths2,344 sq ft

507 Starlite Ct, Stroudsburg, PA 18360

(717) 755-5599

$420,000

— beds3.5 baths2,244 sq ft

728-730 Ann St, Stroudsburg, PA 18360

3D WALKTHROUGH

$305,000

4 beds2 baths1,716 sq ft

127 Broad St, Stroudsburg, PA 18360

$220,000

3 beds1.5 baths1,513 sq ft

2254 Chipperfield Dr, East Stroudsburg, PA 18301

3D WALKTHROUGH

$355,356

3 beds2.5 baths1,872 sq ft

238 Becca Ln, Stroudsburg, PA 18360

$645,000

5 beds2 baths3,113 sq ft

5333 Hickory Cir, Stroudsburg, PA 18360

$385,000

4 beds2 baths2,136 sq ft

1004 Tara View Dr, Stroudsburg, PA 18360

$345,500

3 beds1.5 baths2,199 sq ft

1317 Coolbaugh St, Stroudsburg, PA 18360

(570) 421-8950

Home values near 101 Rolling Hills Rd

Data from public records.

Address	Redfin Estimate
108 Rolling Hills Rd, Stroudsburg, PA 4 Beds \| 2.5 Baths \| 3198 Sq. Ft.	$668,278
5 Rolling Hills Rd, Stroudsburg, PA 4 Beds \| 2.5 Baths \| 2891 Sq. Ft.	$601,904

Address	Redfin Estimate
112 Rolling Hills Rd, Stroudsburg, PA 4 Beds \| 3 Baths \| 4214 Sq. Ft.	$711,396
145 Wolf Hollow Dr, Stroudsburg, PA 2 Beds \| 1 Baths \| 2447 Sq. Ft.	$496,845

Address	Redfin Estimate
109 Rolling Hills Rd, Stroudsburg, PA 4 Beds \| 2.5 Baths \| 2756 Sq. Ft.	$566,149
1682 Totts Gap Rd, Stroudsburg, PA 3 Beds \| 1.5 Baths \| 1738 Sq. Ft.	$422,905

Property information provided by PMAR when last listed in 2022. This data may not match . Learn more.

More real estate resources

Minor Civil Divisions
Neighborhoods
Cities
Zip Codes
Popular Searches

Clinton Township homes for sale
Fredon Township homes for sale
Stillwater Township homes for sale
Washington Township homes for sale
Washington Township homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Stroudsburg	Agents near me	Bethlehem, PA homes for sale	Stroudsburg Housing Market
Houses for sale near me	Philadelphia, PA homes for sale	Allentown, PA homes for sale
Land for sale near me	Pittsburgh, PA homes for sale	Media, PA homes for sale
Open Houses near me	West Chester, PA homes for sale	Stroudsburg Property Records
Condos for sale near me	Lancaster, PA homes for sale	PA New Listings

Academy Hill Historic District homes for sale
Downtown Stroudsburg homes for sale
Northgate Estates homes for sale

Nazareth homes for sale
Easton homes for sale
Mount Pocono homes for sale

18301 homes for sale
07832 homes for sale
18360 homes for sale