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$449,900

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,420 Sq. Ft.
  • 1 Car Garage
  • Updated 3 days ago
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Welcome! This well-maintained 3-bedroom, 2.5-bath home in the desirable East Stroudsburg South area offers three finished levels of living space connected by a beautiful wide staircase. With a functional layout, the home provides plenty of space for everyday living or entertaining. Built for comfort, efficiency, and peace of mind, the home features two wood-burning stoves capable of heating the entire residence, helping to keep utility costs low during the colder months. A durable metal roof provides long-lasting protection, while the whole-house generator ensures you're prepared for any season. The attached one-car garage and convenient mudroom add practicality and storage, Situated on a beautifully cleared 1.46-acre corner lot, this property offers exceptional outdoor living space. Enjoy gatherings on the spacious patio, relax around the fire pit, and take advantage of the ample parking available for guests, equipment, or recreational vehicles. A detached workshop on the large side lot provides endless possibilities and is ideal for a small business, hobbyist, craftsman, or additional storage. Combining versatile indoor and outdoor spaces this property offers a unique opportunity to enjoy country living with room to work, entertain, and grow.

Full Property Details for 206 Winchester Dr

General

  • Price: $449,900
  • Taxes: $7,565 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 2102
  • MLS ID: PM-141763
  • Updated: 6/1/2026
  • Added to Site: 17 day(s) ago

Interior

  • Number of Rooms: 11
  • Appliances: Electric Range, Refrigerator, Dishwasher, Microwave, Washer, Dryer
  • Furnishings: Negotiable

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Lower Level

Exterior

  • Exterior Features: Rain Gutters, Fire Pit
  • Porch/Patio/Deck: Patio, Deck

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 1
  • Parking Type: Plenty of parking on both sides of the home. Left side is gated.

Location

  • County: Monroe
  • Subdivision: None

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ceiling Fan(s), Window Unit(s)
  • Heating Type: Oil, Wood

Utilities

  • Sewer: Septic Tank
  • Water: Well
  • Well: Yes

Structural Information

  • Architectural Style: Split Level
  • Exterior Const.: Brick, Vinyl Siding
  • Roof: Metal
  • Stories/Levels: 3
  • Square Feet: 3,420
  • Sq. Ft. Source: Estimated
  • Living Area: 3,420 Sq. Ft.
  • Current Bldg. Use: Residential
  • Year Built: 1976

Additional Structures

  • Other Structures: Workshop

Lot Features

  • Lot Size (Acres): 1.46
  • Lot Size (Sq. Ft.): 63,597.6
  • Lot Features: Cleared

Financial Considerations

  • Tax Amount: $7,565.39
  • Tax Year: 2025
  • Terms: Cash, Conventional, FHA, VA Loan

Disclosures and Reports

  • Special Conditions: Standard
  • Legal Description: Lot 401 Sec I
  • Inclusions: Refrigerator, Stove, Microwave, Dishwasher, Washer/Dryer, Two Wood Stoves, AC Window Units, Whole Home Generator, Detached Garage/Workshop
  • APN: 16.6A.1.54

Listed by Smart Way America Realty, Stephanie Tutty

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Listing agent

— 206 Winchester Dr —

  • Stephanie Tutty

    Smart Way America Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 206 Winchester Dr

School District:East Stroudsburg Area School District
NameGradesDistance
Smithfield El School
245 River Road, East Stroudsburg, PA 18301
K-53.6 mi
J T Lambert Intermediate School
2000 Milford Road, East Stroudsburg, PA 18301
6-81.9 mi
East Stroudsburg Shs South
279 North Courtland Street, East Stroudsburg, PA 18301
9-123.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 206 Winchester Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/18/2026
Listed
$449,900
65.61%
MLS
8/25/2006
Sold
$271,666
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 206 Winchester Dr

Year
Property Taxes
Change
Tax Assessment
Change
2026
$7,405
364%
$188,460
—
2025
$1,597
22%
$188,460
—
2024
$1,314
48%
$188,460
—
2023
$890
15%
$188,460
—
2022
$775
-88%
$188,460
—
2021
$6,207
4%
$188,460
543%
2019
$5,987
—
$29,320
—
2018
$5,987
—
$29,320
—
2017
$5,987
—
$29,320
—
2016
$5,999
4%
$29,320
5%
2015
$5,792
—
$27,960
—
2014
$5,792
—
$27,960
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Smart Way America Realty, Stephanie Tutty

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206 Winchester Drive, East Stroudsburg, PA 18301 (MLS# PM-141763) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 206 Winchester Drive is currently listed for $449,900 and was received on May 18, 2026. Want to learn more about 206 Winchester Drive? Do you have questions about finding other Single Family real estate for sale in East Stroudsburg? You can browse all East Stroudsburg real estate or contact a Coldwell Banker agent to request more information.

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