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Jill A. Lehmann
Associate Real Estate Broker
REALTOR®
(607) 267-0313 Cell
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5433 New York 23 , Windham, NY 12496

New - 11 Hours Ago

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Property Description

Contemporary design blends with historic character in this thoughtfully renovated single-family classic colonial home located on charming Main Street in Windham. Originally built in 1930 and fully redesigned in 2024, this turnkey home creates the perfect environment for hosting lavish get-togethers and unforgettable family memories. Gaze into the skies to celebrate summer fireworks from your enclosed balcony or sip hot cocoa as you follow skiers as they slalom down Windham Mountain trails from your generous eat-in-kitchen. The distinct layout of this home design features a 2nd level entertainers paradise with sprawling kitchen island, custom beverage center, and unobstructed mountain views. An insulated covered deck off the great room and kitchen brings the outside into your entertainment space. After the sun goes down, the gas fireplace is a perfect place to cozy up and enjoy listening to music from one of the 4-zone multimedia systems. Downstairs, five spacious and bright bedrooms encircle the center staircase on the 1st level with 2 well-appointed full baths, a powder room, and laundry room equipped with an oversized washer and dryer. Enter through the elegant front foyer with its grand staircase or trudge around the side entrance into a massive snow room to remove and store all your winter gear. Soaring high ceilings on both sleeping and living floors. Rear barn with plumbing, electric, and metal roof is ready to become your studio, workshop, or recreation space. The covered wrap-around front porch with exterior recessed lighting completes the picture and invites you sit, relax, and unwind. A perfect blend of style, comfort, lifestyle, and modern luxury. All this is just steps away from dining, shopping, and all the wonderful reasons why people have sought out Windham for generations. A rare opportunity to own a home of this quality and location. Come create the memories your family will enjoy for a lifetime!

5433 New York 23 | MLS# 20264601

This single family home located at 5433 New York 23 , Windham, NY 12496 is currently listed for sale with an asking price of $1,599,000. This property was built in 1930 and has 5 bedrooms and 2 full and 2 partial baths with 4056 sq. ft. New York 23 is located within the Wind-Ash-Jewett school district. Search Windham real estate on jill-ogden.timberlandproperties.com today.

Gallery

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Heating: ENERGY STAR Qualified Equipment, Forced Air, Zoned
Home Style: Colonial
Lot Size: 0.34 Acres
Roof Type: Asphalt, Shingle
Taxes: $3,277
Year Built: 1930

Amenities

Bar
Breakfast Bar
Built-in Features
Cathedral Ceiling(s)
Ceiling Fan(s)
Crown Molding
Eat-in Kitchen
Entrance Foyer
Granite Counters
High Ceilings
High Speed Internet
Kitchen Island
Open Floorplan
Primary Downstairs
Recessed Lighting
Smart Camera(s)/Recording
Smart Home
Sound System
Stone Counters
Storage
Vaulted Ceiling(s)
Walk-In Closet(s)
Wet Bar
Wired for Data
Wired for Sound
Balcony
Lighting
Private Yard
Smart Camera(s)/Recording

Feature Descriptions

Appliances: Wine Refrigerator, Washer/Dryer, Washer, Tankless Water Heater, Stainless Steel Appliance(s), Refrigerator, Range Hood, Microwave, Ice Maker, Gas Range, Gas Oven, Freezer, Exhaust Fan, ENERGY STAR Qualified Water Heater, ENERGY STAR Qualified Refrigerator, ENERGY STAR Q
Exterior: Frame, Spray Foam Insulation, Stone, Vinyl Siding
Flooring: Hardwood, Tile
Laundry: Laundry Room, Main Level
Lot: Back Yard, Front Yard, Paved, Views
Parcel #: 39
Parking: Asphalt, Paved, Off Street, Driveway, Additional Parking
Patio/Porch: Enclosed, Front Porch, Patio, Rear Porch, Side Porch, Wrap Around
Road Frontage: Town, City Street, State Road
Road Surface: Asphalt, Paved
Security Features: Carbon Monoxide Detector(s), Closed Circuit Camera(s), Prewired, Smoke Detector(s)
Sewer: Public Sewer
SQFT Total: 4056
Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water Connected, Propane
Water: Public

Local Schools

School District: Wind-Ash-Jewett

Estimate Your Payment

Estimated Payment

$ 4,298.14 per month $3,558.68 Principal & Interest $273.08 Property Tax $466.38 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Windstar Realty Group, LLC

Shown By

Agent Name: Jill A. Lehmann
Agent Phone: (607) 267-0313 Cell
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 08/12/2026. The listing information on this page last changed on 08/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 08/12/2026 12:00:01 AM EST) or Global MLS (last updated Tue 08/11/2026 11:52:30 PM EST) or New York State Alliance MLS (last updated Tue 08/11/2026 11:59:01 PM EST) or Hudson Valley Catskill Region MLS (last updated Tue 08/11/2026 11:51:14 PM EST) or OneKey MLS (last updated Tue 08/11/2026 11:53:21 PM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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