5433 Highway 23

Windham, NY 12496

$1,999,999
Price
5
Beds
3,409 Sq. Ft.
$587 / Sq. Ft.
3,409
Sq. Ft.
$587
per Sq. Ft.
P1434049
DJI_0269
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P1434039

Description

A One-of-a-Kind Masterpiece in the Heart of Windham, NY! Welcome to Main Street Magic—an exceptional, fully reimagined 5-bedroom, 4-bathroom home (2 full, 2 half) located just 2 hours from NYC in the sought-after Catskills town of Windham. This stunning property perfectly blends historic charm with modern luxury and lifestyle-driven design. Step inside to soaring 13' vaulted ceilings and an incredible custom kitchen featuring quartz countertops, a 100-year-old reclaimed wood island, tiled backsplash,...A One-of-a-Kind Masterpiece in the Heart of Windham, NY! Welcome to Main Street Magic—an exceptional, fully reimagined 5-bedroom, 4-bathroom home (2 full, 2 half) located just 2 hours from NYC in the sought-after Catskills town of Windham. This stunning property perfectly blends historic charm with modern luxury and lifestyle-driven design. Step inside to soaring 13' vaulted ceilings and an incredible custom kitchen featuring quartz countertops, a 100-year-old reclaimed wood island, tiled backsplash, built-in table with bench seating, stainless steel appliances, and a stone bar with beverage center—ideal for hosting unforgettable gatherings. Enjoy cozy nights by the gas fireplace, unwind in the private sauna, and soak in the curated ambiance with custom fixtures, stained glass accents, and a 4-zone multimedia system. The home also includes two mudrooms, tile walk-in showers, recessed lighting throughout (interior + exterior), and a spacious first-floor primary suite for comfort and convenience. French doors lead you to an insulated upper deck, lower deck, and a generous, flat yard perfect for entertaining, relaxing, or playing. A rare find, the property also includes a plumbed 1930s barn—ready to be converted into a studio, guest house, or event space. Located on Main Street (NY-23) and connected to public utilities, you're walking distance to shops, dining, and all Windham has to offer. With exterior architectural details and old world charm with new modern flare, this house has it all. Whether you're looking for a luxury vacation retreat, income-generating property, or forever home, this residence delivers it all. With skiing, hiking, mountain biking, and the growing appeal of Windham—including PGA golf coming soon—this is a year-round destination on the rise. Showings available now — Offers being accepted! Don't miss your chance to own a truly unique piece of Windham.

Property Details for 5433 Highway 23

Senior Community YN
No
Zoning
210 - 1 Family
Zoning Description
01 - Single Family Residence
Waterfront YN
No
Waterfront YN
No
Senior Community YN
No
Basement YN
No
LISTING UPDATED: 10/13/2025 02:31 AM

Property Details for 5433 Highway 23

StatusActive
MLS #20254478
Days on Market87
Taxes$3,806 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1930
Lot Size0.34 AC / 14,810 SF
CountyGreene County

Location

Listing Courtesy of Hunt Real Estate ERA
Add your commute

Building Information for 5433 Highway 23

Stories2Year Built1930Building Size-Lot Size0.34 AC / 14,810 SF

Payment Calculator

$10,200 per month

30 year fixed, 6.28% Interest

Principal and Interest

$9,883

Property Taxes

$317

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 5433 Highway 23

Summary
Location and General Information
  • Directions: Take NY-23 to House. Located directly on NY-23.
  • Township: Windham
  • MLS Area Major: Windham
  • County: Greene
  • Latitude: 42.307176
  • Longitude: -74.255548
  • MLS Area Major: Windham
  • Sign On Property YN: Yes
  • Mountain(s): Yes
Taxes and HOA
  • Association YN: No
  • Association Fee: $.00
  • Parcel Number: 78.18-2-39
  • Tax Block: 2
  • Tax Legal Description: Single Family Dwelling
  • Tax Annual Amount: $3,806.00
  • Association YN: No
Parking
  • Attached Garage YN: No
  • Garage YN: No
  • Garage YN: No
  • Driveway: Yes
  • Off Street: Yes
Property
Lot Information
  • New Construction YN: No
  • Lot Size Acres: 0.34
  • Above Grade Finished Area: 3409.0
  • Below Grade Finished Area: 0.0
  • Living Area: 3409.0
  • Lot Size Area: 0.34
  • Lot Size Units: Acres
  • Lot Size Square Feet: 14810.4
  • Above Grade Finished Area: 3409.0
  • Below Grade Finished Area: 0.0
  • Lot Size Acres: 0.34
  • Other: Yes
  • Clapboard: Yes
  • Stone: Yes
  • Cleared: Yes
  • Landscaped: Yes
  • Level: Yes
  • Views: Yes
Property and Assessments
  • Owner Name: Hughes
  • Total Floor Plans Count: 0
  • Property Type: Residential,Single Family Residence
  • Year Built: 1930
  • Property Sub Type: Single Family Residence
  • New Construction YN: No
  • Page: 0
  • Section: 0
  • Close Of Escrow: Yes
Taxes and HOA
  • Tax Assessed Value: 334525.0
  • Tax Lot: 39
Utilities
  • Public Sewer: Yes
  • Public: Yes
Interior and Exterior Features
Exterior Features
  • Stories: 2
  • Balcony: Yes
  • Fire Pit: Yes
  • Lighting: Yes
  • Barn(s): Yes
  • Front Porch: Yes
  • Porch: Yes
  • Rear Porch: Yes
  • Wrap Around: Yes
  • Shingle: Yes
Interior Features
  • Basement YN: No
  • Spa YN: No
  • Fireplaces Total: 1
  • Fireplace YN: Yes
  • Room Total: 7
  • Bathrooms Total (Integer): 4
  • Bathrooms Total (Decimal): 3.0
  • Bathrooms Total (Notational): 2.2
  • Cooling: Yes
  • Heating: Yes
  • Bedrooms Total: 5
  • Bathrooms Full: 2
  • Bathrooms Half: 2
  • Rooms Total: 7.0
  • Bathrooms Half: 2.0
  • Fireplace YN: Yes
  • Spa YN: No
  • Bar Fridge: Yes
  • Dishwasher: Yes
  • Disposal: Yes
  • Dryer: Yes
  • Electric Oven: Yes
  • Ice Maker: Yes
  • Microwave: Yes
  • Oven: Yes
  • Range: Yes
  • Refrigerator: Yes
  • Stainless Steel Appliance(s): Yes
  • Tankless Water Heater: Yes
  • Wine Cooler: Yes
  • Central Air: Yes
  • ENERGY STAR Qualified Doors: Yes
  • French Doors: Yes
  • Living Room: Yes
  • Ceramic Tile: Yes
  • Engineered Hardwood: Yes
  • Slab: Yes
  • Forced Air: Yes
  • Bar: Yes
  • Built-in Features: Yes
  • Cathedral Ceiling(s): Yes
  • High Ceilings: Yes
  • Kitchen Island: Yes
  • Open Floorplan: Yes
  • Pantry: Yes
  • Primary Downstairs: Yes
  • Sound System: Yes
  • Stone Counters: Yes
  • Tile Counters: Yes
  • Vaulted Ceiling(s): Yes
  • Walk-In Closet(s): Yes
  • Wet Bar: Yes
  • Wired for Data: Yes
  • Wired for Sound: Yes
  • Laundry Room: Yes
  • Lower Level: Yes
  • Main Level: Yes
  • Two: Yes
  • Double Pane Windows: Yes
  • ENERGY STAR Qualified Windows: Yes
  • Shutters: Yes
Room Information
Room Information
  • Dining Room Level: Second
  • Laundry Level: First
  • Living Room Level: Second
  • Primary Bedroom Level: First
Mobile Home
Mobile Home Information
  • Sign On Property YN: Yes
Rental
Rental Information
  • Occupant Type: Vacant
  • Occupant Type: Vacant

Property History for 5433 Highway 23

DateEvent & SourcePriceAppreciation
Dec 6, 2023

Sold (Public Record)

Public Record #1524953803

$185,000

+7.6% / yr

Jul 8, 2021

Sold (Public Record)

Public Record #1467562905

$155,000—
DateEvent & SourcePrice
12/06/2023

Sold (Public Record)

Public Record #1524953803

$185,000

+7.6% / yr

07/08/2021

Sold (Public Record)

Public Record #1467562905

$155,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5433 Highway 23

Taxable ValueLand$20,600Additions$183,800Total$204,400
Tax Record2024$3,459 ($288 / month)
Home Facts
Beds5Baths2Total Finished SqFt3,256 SqFtAbove Grade Finished SqFt3,256 SqFtStories2Lot Size14,810 SqFtStyleSingle Family ResidenceYear Built1930Zoning01 - NOT ZONECountyGREENEAPN194600 78.18-2-39

Schools near 5433 Highway 23

This home is within Windham-Ashland-Jewett Central School District.
Rating
School
Type
Grades
Distance
Windham Ashland Central School
Public - PK to 12
Rating
School
Distance
Windham Ashland Central School
PublicPK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5433 Highway 23, Windham, NY 12496

5433 Highway 23 is a single family home for sale in Windham, NY 12496. This property was listed for sale on September 19, 2025 by Hunt Real Estate ERA, it's currently listed at $1,999,999. It has been on the market for a total of 87 days and was last sold on December 6, 2023. This listing's school district is Windham-Ashland-Jewett Central School District. Nearby schools include Windham Ashland Central School. 5433 Highway 23 is a 5-bed, 4-bath, 3,409 sqft single family home built in 1930.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Hunt Real Estate ERA

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale or lease on this webpage comes from the the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. Real estate listings held by brokerage firms other than Compass are marked with a OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS or Ulster County Board of REALTORS Logo. Use of these search facilities other than by a consumer seeking to purchase or lease real estate is prohibited. The accuracy of all information is deemed reliable but not guaranteed and should be verified through personal inspection by and/or with appropriate professionals. The data contained herein is copyrighted by the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Information Copyright 2025, OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. All rights reserved. Data last updated: 10/13/2025 02:31 AM