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Rare Turnkey Income Producer! 2nd-Floor Winwood End Unit with Ski Slope Views Welcome to The Winwood, where affordability meets premium four-season Catskills living. This unique and well-appointed second-floor end unit condominium offers one of the most accessible and value-packed opportunities to own in the highly desirable Windham market. Whether you are searching for a carefree weekend retreat, a smart full-time mountain residence, or a high-yielding investment property, this rare turnkey gem delivers location, lifestyle, and proven income potential. The Residence: Step inside this premium end unit to discover a relaxed, sun-drenched layout designed for effortless living. The bright, comfortable living area flows seamlessly to your own private balcony, where you can sip your morning coffee or unwind with an evening beverage while taking in breathtaking, picturesque views of Windham's ski slopes. Exclusive Mountain Perks: Winwood owners and guests enjoy top-tier convenience, including: Guaranteed lift tickets to the mountain. Free shuttle service directly to the ski slopes. On-site parking equipped with Tesla EV charging stations. Resort-Style Amenities: The Winwood offers an impressive collection of on-site amenities rarely found at this price point. Just outside your door, enjoy a refreshing outdoor saltwater pool and a community firepit for cool mountain nights, a fully equipped fitness center to keep you active, a private on-site movie theater and a dedicated game room, plus convenient coin-operated laundry facilities. The Location: Positioned perfectly for four-season adventure, you are just a short, scenic stroll from town. Immerse yourself in everything the local area has to offer, from championship golf courses and alpine hiking/biking trails to local farmers' markets, antique shopping, and fabulous dining. Value, location, and a turnkey income stream come together perfectly here. Welcome home to your ultimate mountain getaway! **Monthly HOA fee 425.38 **

Highlights

  • Residential
  • Condominium
  • Built in 1960
  • 0.01 Acre Lot
  • 101 days on Market

  • Bedrooms
    1
  • Bathrooms
    1
  • Year Built
    1960
  • Architectural Style
    Other
  • Construction Materials
    Stone
  • Living Area
    435.0
  • Appliances
    Dishwasher, Electric Cooktop, Free-Standing Refrigerator
  • Flooring
    Carpet, Ceramic Tile, Stone
  • Patio And Porch
    Other
  • Pool Features
    In Ground
  • Cooling
    Multi Units

  • Acres
    0.01
  • View
    Mountain(s), Other

  • Area
    Windham
  • County
    Greene
  • City
    Windham
  • Zip Code
    12496

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Frequently Asked Questions

How do I schedule a tour of 5220 Route 23 229?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 5220 Route 23 229.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 5220 Route 23 229?

Click Ask a Question to talk with our team. You already know it is a 1 bed, 1 bath, listed for $199,000. We can talk through recent upgrades, potential seller motivation, how this condominium compares to others in Windham, and can even get you in to see the property quickly.

How do I get a virtual tour of 5220 Route 23 229?

Yes! A virtual tour is available for 5220 Route 23 229. Click here to view the full walkthrough and explore every room at your own pace. If you would like a guided virtual showing or have questions along the way, we can connect you with our local expert to walk you through it live.

How much is the monthly mortgage payment for 5220 Route 23 229?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 5220 Route 23 229 at around $1,317. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 5220 Route 23 229?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Greene County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 5220 Route 23 229?

In most cases, yes. Whether 5220 Route 23 229 is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Windham's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 5220 Route 23 229?

We can handle that for you. Our preferred local agent specializes in residentials in Windham and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $199,000 with 435 sqft of space—that comes out to approximately $457 per square foot.

How long has this property been on the market?

5220 Route 23 229 was listed on July 30, 2026, which means it's been on the market for 101 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1960, making it approximately 66 years old.

What is the lot size of this property?

5220 Route 23 229 sits on a 0.01-acre lot, which is 436 square feet.

What are the property taxes for 5220 Route 23 229?

The most recent public record shows annual property taxes for 5220 Route 23 229 were approximately $2,217. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 5220 Route 23 229 still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively 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 deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS). All rights reserved.

Last Updated: November 06, 2026 at 03:15PM | Source: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS) | MLS#: 20264331