02-Photo-1 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
01-Twilight-1 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
ENTRANCE - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
LIVING ROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
LIVING ROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
ENTRANCE - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
LIVING ROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
FIREPLACE WITH INSERT - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
FIREPLACE WITH INSERT - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
LIVING/DINING ROOMS - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
DINING ROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
DINING ROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
KITCHEN - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
KITCHEN - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
KITCHEN - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
1ST FLOOR BATHROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
1ST FLOOR BEDROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
1ST FLOOR BEDROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
LAUNDRY ROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
LAUNDRY - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
STAIRCASE - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
STAIRCASE - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
46-Photo-45 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
47-Photo-46 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
48-Photo-47 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
BEDROOM 2 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
BEDROOM2 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
BEDROOM 3 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
BEDROOM 3 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
2ND FLOOR BATHROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
2ND FLOOR BATHROOM - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
BEDROOM 4 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
BEDROOM 4 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
03-Photo-2 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
04-Photo-3 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
05-Photo-4 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
06-Photo-5 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
FENCED GARDEN - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
08-Photo-7 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
BACKYARD - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
11-Photo-10 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
FIRE PIT - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
PORTABLE HOT SPA - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
13-Photo-12 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
DECK - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
DECK - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
16-Photo-15 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
PORTABLE HOT SPA - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
19-Photo-18 - 2385 Winding Way, Tobyhanna, PA 18466, Tobyhanna
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54 photos

$299,900

2385 Winding Way, Tobyhanna, PA 18466
Tobyhanna, PA 18466
Listed by Izabella Glinska · eXp Realty, LLC - East Stroudsburg
Bedrooms
3
Bathrooms
2
Living area
N/A
Year built
1988

About this home

Welcome to this beautifully renovated and well-maintained home with flexible living space, including an extra room converted from the garage. The main level offers convenient first-floor living with a bedroom, a full bath with shower, sunken living room, dining room, and kitchen with Stainless Steel appliances. Luxury vinyl and tile flooring flow throughout the home. Upstairs you'll find additional 3 bedrooms and a second full bath. Two pellet stoves keep the home cozy and warm year-round. Enjoy outdoor living on the rear deck overlooking the yard, complete with a fire pit, grill, and portable hot spa. Three sheds provide plenty of storage. Located in a gated community with lakes, beaches, swimming pools, playgrounds, tennis courts, and a clubhouse. Use it as a full-time residence, vacation getaway, or short-term rental investment. Convenient to major highways, shopping, dining, skiing, golf, water parks, casinos, and all the Pocono Mountains have to offer.

Highlights

Fireplace

Property details

MLS #
PM-144449
Property type
Single Family Residence
Subdivision
A Pocono Country Place
Status
Active
Days on market
35
On market date
September 3, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.35 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Clear Run Intrmd Sch
5.03 mi away · Grades 3-6
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
973
Student:teacher ratio
10.7:1
District
Pocono Mountain SD
Middle
Swiftwater Interm Sch
8.67 mi away · Grades 4-6
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
729
Student:teacher ratio
10.3:1
District
Pocono Mountain SD
HighCharter
Evergreen Community CS
6.28 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
101
Student:teacher ratio
9.2:1
District
Evergreen Community CS

Walkability

Blended score for Tobyhanna's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

33
Car-dependent
out of 100
EPA National Walkability Index
8.2 / 20 -- Below average walkable
Google Places amenity density
20 / 100
Restaurants & cafes0
Grocery stores0
Parks2
Schools0
Transit stops4
Pharmacies0

Market position

How this listing compares to current activity in Tobyhanna, from live MLS data.

On the market 35 days -- 65 fewer days than Tobyhanna's current average of 100 days.
For reference, the median list price across 292 active listings in Tobyhanna right now is $265,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Adjust tax / insurance estimates
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Est. monthly payment
$1,956/mo
$59,980 down
$239,920 loan
Principal & interest$1,556
Property tax (est.)$250
Home insurance (est.)$150

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Data source: Listing information provided by Pocono Mountains Association of REALTORS® via Trestle/CoreLogic. Last updated September 3, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.