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Welcome to Whispering Winds, a desirable 55+ community nestled in a peaceful, wooded setting in Windham! This spacious townhouse-style condominium offers 1,522 square feet of comfortable living space, featuring 2 bedrooms, 2.5 bathrooms, and a versatile floor plan designed for convenience and flexibility. The main level offers a welcoming living room with cathedral ceilings, a spacious kitchen with adjoining dining area, and a separate den perfect for a home office, sitting room, or hobby space. A first-floor bedroom, full bathroom, and convenient first-floor laundry provide the option for single-level living. Upstairs, you'll find a generously sized suite complete with a private full bathroom and walk-in closet. Additional highlights include hardwood flooring, central air conditioning, a private deck, and an attached one-car garage. The full, unfinished basement provides approximately 1,080 square feet of additional storage space. This home also comes with an on demand, whole house generator! Enjoy the benefits of condominium living with an association that provides landscaping, snow removal, trash removal, and access to a community clubhouse. Tucked away in a beautifully landscaped neighborhood with a private, cul-de-sac setting, Whispering Winds offers a wonderful combination of privacy, convenience, and low-maintenance living. An excellent opportunity to enjoy the next chapter in one of Windham's established 55+ communities!

Highlights

  • Residential
  • Condominium
  • Built in 2001
  • $415/mo HOA
  • 1 Car Garage
  • 6 days on Market

  • Bedrooms
    2
  • Bathrooms
    2 full · 1 half
  • Year Built
    2001
  • Stories
    2.0
  • Architectural Style
    Townhouse
  • Construction Materials
    Vinyl Siding
  • Garage Spaces
    1.0
  • Parking Features
    Driveway, Paved, Garage
  • Living Area
    1522.0
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer
  • Flooring
    Hardwood, Tile, Carpet
  • Patio And Porch
    Deck
  • Cooling
    Central Air
  • Heating
    Forced Air
  • Basement
    Full, Concrete, Storage Space

  • Lot Features
    Wooded, Private, Landscaped
  • Utilities
    Propane
  • Senior Community
    Yes


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Frequently Asked Questions

How do I schedule a tour of 44 Pleasant St?

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 44 Pleasant St.

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 44 Pleasant St?

Click Ask a Question to talk with our team. You already know it is a 2 bed, 2 bath, listed for $419,900. 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 much is the monthly mortgage payment for 44 Pleasant St?

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 44 Pleasant St at around $2,870. 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 44 Pleasant St?

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 Rockingham 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 44 Pleasant St?

In most cases, yes. Whether 44 Pleasant St 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 44 Pleasant St?

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 $419,900 with 1,522 sqft of space—that comes out to approximately $276 per square foot.

How long has this property been on the market?

44 Pleasant St was listed on November 04, 2026, which means it's been on the market for 6 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 2001, making it approximately 25 years old.

What are the property taxes for 44 Pleasant St?

The most recent public record shows annual property taxes for 44 Pleasant St were approximately $5,763. 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 there an HOA fee for this property, and what does it cover?

This home has an HOA fee of $415 paid monthly.

This covers access to community features including: Snow Removal, Clubhouse, Landscaping.

Is 44 Pleasant St 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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This information is deemed reliable, but not guaranteed.

The data relating to real estate displayed on this web site comes in part from the IDX Program of PrimeMLS. The information being provided is 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. Data last updated November 10, 2026 at 04:47AM