55 Pleasant St #2, Windham, NH 03087
OFF MARKET

$498,400

Trulia Estimate
  • 2 Beds
  • 3 Baths
  • 1,940 sqft

55 Pleasant St #2, Windham, NH 03087

Est. Refi. Payment $3,218/mo*
Refinance Your Home

Home Value

Trulia Estimate
$498K
Since last month
Decreased$8K (-1.5%)
Since last year
Increased$22K (+4.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +14% in the last 10 years
MonthEstimated value
2026
August 2026$499K
August 2026$498K
July 2026$507K
June 2026$502K
May 2026$489K
April 2026$494K
March 2026$480K
February 2026$472K
January 2026$467K
2025
2024
2023
2020

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Pleasant Street, Windham, NH
0.04
Condo
$430,000
05/15/26
2
2.5
1,522
20 Brookview Road, Windham, NH
0.13
Condo
$720,000
06/22/26
2
2
2,640
11 Misty Meadow Road, Windham, NH
0.10
Condo
$735,000
11/21/25
3
3
3,148
11 Venus Way, Pelham, NH
0.29
Condo
$605,000
03/17/26
2
2
1,700
10 Sullivan Road, Hudson, NH
0.37
Condo
$420,000
08/14/26
3
2
2,041
13B Hedgerow Drive, Hudson, NH
0.48
Condo
$560,000
04/10/26
3
2.5
2,183
11A Lund Drive, Hudson, NH
0.55
Condo
$360,000
02/03/26
2
1.5
1,287
15 Lund Drive #A, Hudson, NH
0.59
Condo
$405,000
02/26/26
2
1.5
1,146
11 Lund Dr #A, Hudson, NH
0.57
Condo
$360,000
02/02/26
2
2
1,248
9A York Road, Hudson, NH
0.85
Condo
$515,000
04/28/26
3
2.5
2,193

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
34 Pleasant Street, Windham, NH 03087
0.02
$399,900
2
2.5
1,522
Recently Sold
74 Pleasant Street, Windham, NH 03087
0.03
$402,500
2
2.5
1,642
Recently Sold
67 Pleasant Street #67, Windham, NH 03087
0.05
$451,000
2
2.5
1,522
Recently Sold
18 Pleasant Street, Windham, NH 03087
0.04
$430,000
2
2.5
1,522
Recently Sold
19 Pleasant Street #19, Windham, NH 03087
0.05
$456,900
3
2.5
1,715
Off Market
63 Pleasant Street, Windham, NH 03087
0.05
$435,000
2
2.5
1,522
Recently Sold
24 Pleasant Street, Windham, NH 03087
0.05
$446,800
2
2.5
1,522
Off Market
33 Pleasant Street, Windham, NH 03087
0.05
$452,000
2
2.5
1,529
Off Market
81 Pleasant Street, Windham, NH 03087
0.08
$464,500
2
2.5
2,098
Off Market
51 Brookview Road, Windham, NH 03087
0.12
$475,000
2
2.5
1,529
Recently Sold
75 Brookview Road, Windham, NH 03087
0.12
$425,000
2
2.5
1,606
Recently Sold
11 Misty Meadow Road, Windham, NH 03087
0.10
$735,000
3
3
3,148
Recently Sold

Local Information

  • Map ViewExplore the area around 55 Pleasant St #2.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 2002
1,940 sqft
$257/sqft
Garage

About this House

One of the most elite units in the active adult community of Whispering Winds. Plenty of upgrades to make life simpler! Beautiful natural sunlight fills the open concept living unit. The main floor offers a generous sized master suite, formal dining, kitchen/informal dining and 1/2 bath. Best of all is the 3 season porch great for sipping your morning tea while looking over the natural landscaping of Whispering Winds. Up a flight of stairs to a large loft area used as a second bedroom complete with full bath and walk-in closet. Sit by the fire on a cold chilly night in the finished basement in this unit. One of the many upgrades made. This unit would not be complete without the central vacuum system, automatic generator big enough to power the whole unit and of course the luxury of a one car attached garage. 3 Season Porch furniture and washer/dryer included in sale. This unit is priced to move fast! Don't wait!
55 Pleasant St #2, Windham, NH 03087 is a 2 bedroom, 3 bathroom, 1,940 sqft condo built in 2002. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $498,400, with a rent estimate of $3,958/month.

Home Details for 55 Pleasant St #2

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Interior Details
Additional StorageNumber of Rooms: 6Types of Rooms: Walk In Closet, Dining RoomStorage
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: VinylPatioPorch
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: CondoArchitecture: Other

Building

Levels, Entrance, & Accessibility
Disabled Access

Additional Information

On Site Laundry Available

Price and Tax history

DateEventPrice
Apr 30, 2015
Source: Agent Provided
ListingRemoved
$234,900
Apr 21, 2015
Source: Agent Provided
Pending
$234,900
Nov 4, 2014
Source: Agent Provided
Listed For Sale
$234,900

Market trends in Windham

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50
2MoM

Around this home

What Locals Say about Windham

At least 42 Trulia users voted on each feature.

  • 96 % Say car is needed

  • 94 % Say it's dog friendly

  • 92 % Say parking is easy

  • 89 % Say people would walk alone at night

  • 88 % Say it's quiet

  • 87 % Say there's holiday spirit

  • 85 % Say yards are well-kept

  • 82 % Say there's wildlife

  • 69 % Say kids play outside

  • 61 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 52 % Say there are community events

  • 14 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

  • 12 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • M Rideout
    "Nicest town in New Hampshire by far, safe, good schools, easy access to 93. Taxes are high but you get what you pay for I guess. "
    0
    Flag
  • Viren.patel
    "You see dog owners walking here all the time. Everyone is so friendly & nice that you feel like a part of one big family. "
    1
    Flag
  • Renee C.
    "Recreation department has a lot of town events at the park at the library They have dog Halloween parade Town beach hs many water activity’s "
    5
    Flag
  • Caitlinschiffer
    "Strawberry Festival, concerts in the common, Griffen Park sports and recreation fields, tennis, basketball. Great community restaurants, Old School, Reds Tavern, Common Man, Windham Restuarant. "
    5
    Flag
  • Tammy V.
    "all the dogs in my neighborhood are small and friendly, everyone picks up after their dogs for the most part. "
    2
    Flag
  • Morgan.pm
    "Everyone has a dog and everyone knows all the neighbors dogs names and they are all friends. Okay people allow their dogs to run around leash free during the day. A great neighborhood for walking your dogs. Everyone is super friendly. Everyone cleans up after their pups"
    2
    Flag
  • Rebekah S.
    "Lots of room to run in yards, lots of doggy friends and neighbors, lots of great vets and hospitals and safe to walk on road anytime of day "
    3
    Flag
  • 13mnesti
    "Quiet small town community with all the necessary shops, delicious restaurants, and close proximity to the mountains, beach, and city "
    2
    Flag
  • Vismay S.
    "It’s an awesome town to raise kids & live your entire life in. It is very conveniently located suburb. "
    4
    Flag
  • deborahemyers
    "I think it is a little piece of heaven close enough to Boston to be worth the extra 1/2 hour drive from a "normal" commute."
    0
    Flag
  • deborahemyers
    "Used to live there and going back ASAP. Windham has spoiled me for other areas, if you need to be in the southern New Hampshire, or Boston area at all. "
    0
    Flag
  • cb_bullock
    "Snob Quotient very high. Has become over-built Easy access to rte 93; state rtes 111, 128, 3"
    0
    Flag
  • karting4fun
    "The area is well kept, quiet, friendly, and clean. Very close to schools. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 55 Pleasant St #2

  • What is 55 Pleasant St #2 estimated to be worth?
    Trulia's estimated value for 55 Pleasant St #2 in Windham, NH is $498,400.
  • Is Windham a buyer's or seller's market?
    Windham is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Windham?
    Residents describe Windham, NH as dog-friendly, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Windham, NH.
  • What are the closest schools to 55 Pleasant St #2?
    The closest schools to 55 Pleasant St #2 in Windham, NH are Golden Brook Elementary School (Pre-K, rated 8/10), Windham Center School (Elementary, rated 9/10), Windham High School (rated 9/10).
  • Does 55 Pleasant St #2 have air conditioning?
    Yes, 55 Pleasant St #2 in Windham, NH has air conditioning.
  • Does 55 Pleasant St #2 have laundry facilities?
    Yes, 55 Pleasant St #2 in Windham, NH has in-unit laundry.

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

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