5433 State Route 23, Windham

$2,200,000

5 Beds
3 Baths
3,409 Sqft
.34 Acre
0 Garage

🏡 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.

Essential Information
MLS® #20252448
Price$2,200,000
Bedrooms5
Bathrooms3.00
Full Baths2
Half Baths2
Square Footage3,409
Acres0.34
Year Built1930
TypeResidential
Sub-TypeSingle Family Residence
StyleOther
StatusActive
Community Information
Address5433 State Route 23
AreaGreene
CityWindham
CountyGreene
StateNY
Zip Code12496
Amenities
ParkingPaved, Off Street, Driveway
ViewMountain(s)
Interior
HeatingForced Air, Propane
CoolingCentral Air
FireplaceYes
# of Fireplaces1
FireplacesGas, Living Room
StoriesTwo
Interior Features

Bar, Built-in Features, Cathedral Ceiling(s), High Ceilings, Kitchen Island, Open Floorplan, Pantry, Primary Downstairs, Sauna, Sound System, Stone Counters, Tile Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Wired for Data, Wired for Sound

Appliances

Wine Cooler, Washer/Dryer, Tankless Water Heater, Stainless Steel Appliance(s), Refrigerator, Range, Oven, Microwave, Ice Maker, Electric Oven, Dryer, Disposal, Dishwasher, Bar Fridge

Exterior
ExteriorClapboard, Stone
Exterior FeaturesBalcony, Fire Pit, Lighting
RoofAsphalt, Metal, Shingle
ConstructionClapboard, Stone
FoundationSlab
Lot Description

Cleared, Landscaped, Level, Views

School Information
DistrictWind-Ash-Jewett
Additional Information
Zoning210 - 1 Family
Listing Details
AgentCaitlin Cucchiella
Listing Courtesy of Core Real Estate Team
Property History
Price Increased from $220,000 to $2,200,000
LISTING MAP

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