55 Winchester Ave
Peekskill, NY 10566
- 3 Beds
- 3 Baths
- 1,293 sqft
3 Beds
3 Baths
1,293 sqft
Home Value
Trulia Estimate
$463KSince last month
Decreased$2K (-0.5%)Since last year
Increased$23K (+5.2%)Since last sale
Increased$201K (+76%)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 +75% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $465K |
| July 2026 | $467K |
| June 2026 | $470K |
| May 2026 | $473K |
| April 2026 | $461K |
| March 2026 | $440K |
| February 2026 | $439K |
| January 2026 | $439K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
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 |
|---|---|---|---|---|---|---|---|
0.02 | Condo | $525,000 | 06/12/26 | 3 | 2.5 | 1,472 | |
0.03 | Condo | $455,000 | 02/03/26 | 2 | 2.5 | 1,200 | |
0.03 | Condo | $372,000 | 01/21/26 | 2 | 2 | 1,200 | |
0.03 | Condo | $372,000 | 12/04/25 | 2 | 2 | 1,200 | |
0.03 | Condo | $370,000 | 10/09/25 | 2 | 2 | 1,100 | |
0.01 | Condo | $510,000 | 04/08/26 | 2 | 2.5 | 1,800 | |
0.05 | Condo | $417,123 | 05/11/26 | 2 | 2 | 1,200 | |
0.11 | Condo | $340,000 | 09/19/25 | 2 | 2 | 1,100 | |
0.08 | Condo | $492,875 | 04/06/26 | 2 | 2.5 | 1,780 | |
0.11 | Condo | $366,000 | 12/29/25 | 2 | 2 | 1,100 |
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 |
|---|---|---|---|---|---|---|
0.02 | $525,000 | 3 | 2.5 | 1,472 | Recently Sold | |
0.02 | $502,900 | 3 | 2.5 | 1,600 | Off Market | |
0.02 | $455,000 | 2 | 2.5 | 1,200 | Recently Sold | |
0.02 | $460,100 | 2 | 2.5 | 1,300 | Off Market | |
0.03 | $372,000 | 2 | 2 | 1,200 | Recently Sold | |
0.04 | $433,400 | 2 | 2 | 1,221 | Off Market | |
0.03 | $425,000 | 2 | 2 | 1,200 | For Sale | |
0.04 | $400,200 | 2 | 2 | 1,100 | Off Market | |
0.02 | $538,000 | 2 | 2.5 | 1,800 | Off Market | |
0.03 | $404,300 | 2 | 2 | 1,205 | Off Market | |
0.05 | $417,123 | 2 | 2 | 1,200 | Recently Sold | |
0.02 | $455,900 | 2 | 2.5 | 1,290 | Off Market |
Local Information
-- mins to
Home Highlights
Property Type
Condo
Year Built
1988
Living Area
1,293 sqft
Price/Sqft
$358
Parking
None
About this House
Great three bedroom Townhouse is available for rent on Society Hill II. Main floor has a guest bathroom, laundry, living room, dining room and kitchen with sliding doors to level backyard. Second level leads you to a master bedroom with in suite bathroom, two additional bedrooms and a hall bathroom. Enjoy Society Hill Clubhouse amenities has to offer, indoor heated pool, gym sauna & fitness center. Two parking spaces, Tenant pays for all utilities electric & gas. No pets Tenants are subject to credit and background check, proof of income and references and complete rental application attached. Credit score must be 675 or higher. No pets. COVID-19 disclosure must be signed prior appointment approval. Use all COVID-19 PPE precautions
55 Winchester Ave, Peekskill, NY 10566 is a 3 bedroom, 3 bathroom, 1,293 sqft condo built in 1988. It last sold for $264,000 on Jul 7, 2004. More recently, it was listed as a rental in July 2021 with an asking price of $2,800 per month. That rental listing was removed on July 29, 2021. It is currently off market. The Trulia Estimate is $462,700, with a rent estimate of $3,785/month.
Home Details for 55 Winchester Ave
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Heating & Cooling Heating: Forced Air, GasHeating Fuel: Forced Air |
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Year Built Year Built: 1988 |
Property Type / Style Property Type: Condo |
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Parking & Garage Parking: None |
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Units in Building: 1 |
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Lot Area: 435 sqft |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Oct 1, 2025 Source: OneKey® MLS as distributed by MLS GRID #866419 | ListingRemoved | $445,000 |
Jul 21, 2025 Source: OneKey® MLS as distributed by MLS GRID #866419 | PriceChange | $445,000 Price decreased by 1% |
Jun 26, 2025 Source: OneKey® MLS as distributed by MLS GRID #866419 | PriceChange | $449,900 Price decreased by 1% |
May 23, 2025 Source: OneKey® MLS as distributed by MLS GRID #866419 | Listed For Sale | $454,900 |
Jul 29, 2021 Source: Berkshire Hathaway HomeServices | ListingRemoved | |
Jul 8, 2021 Source: Berkshire Hathaway HomeServices #H6128498 | Listed For Rent | $2,800 |
Aug 1, 2020 Source: Agent Provided | ListingRemoved | $2,550 |
Jun 15, 2020 Source: Agent Provided | PriceChange | $2,550 Price decreased by 2% |
Mar 4, 2020 Source: Agent Provided | Listed For Rent | $2,600 |
Jul 7, 2004 Source: N/A | Sold | $264,000 |
Dec 19, 2000 Source: N/A | Sold | $172,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | Unavailable | $319,737 |
Home facts updated by county records
Market trends in Peekskill
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
—
Available listings
70
8MoM
Around this home
What Locals Say about Peekskill
At least 317 Trulia users voted on each feature.
81 % Say it's dog friendly
78 % Say there are sidewalks
76 % Say car is needed
73 % Say it's walkable to restaurants
72 % Say there's holiday spirit
71 % Say yards are well-kept
68 % Say parking is easy
66 % Say it's walkable to grocery stores
66 % Say kids play outside
63 % Say people would walk alone at night
61 % Say streets are well-lit
59 % Say neighbors are friendly
58 % Say it's quiet
56 % Say there's wildlife
55 % Say they plan to stay for at least 5 years
47 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Frequently asked questions about 55 Winchester Ave
- What is 55 Winchester Ave estimated to be worth?Trulia's estimated value for 55 Winchester Ave in Peekskill, NY is $462,700.
- What is the price history for 55 Winchester Ave?55 Winchester Ave in Peekskill, NY last sold for $264,000 in July 2004.
- Is Peekskill a buyer's or seller's market?Peekskill is currently a seller's market, based on recent for-sale activity.
- What do residents say about Peekskill?Residents describe Peekskill, NY as dog-friendly, pedestrian-friendly, and walkable to restaurants. See recently sold homes in Peekskill, NY.

