27 Winchester Ave
Peekskill, NY 10566
- 2 Beds
- 3 Baths
- 1,900 sqft
2 Beds
3 Baths
1,900 sqft
Home Value
Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.
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 |
|---|---|---|---|---|---|---|---|
0.12 | Apartment | $340,000 | 10/08/25 | 2 | 2 | 1,100 | |
1.18 | Apartment | $595,000 | 12/24/25 | 2 | 2.5 | 1,300 | |
0.87 | Apartment | $700,000 | 09/23/25 | 1 | 1 | 700 | |
0.87 | Apartment | $240,000 | 10/09/25 | 1 | 1 | - | |
0.80 | Apartment | $210,000 | 11/03/25 | 1 | 1 | - | |
0.80 | Apartment | $175,000 | 10/14/25 | - | - | ||
0.79 | Apartment | $200,000 | 10/01/25 | - | - | ||
0.83 | Apartment | $225,600 | 11/05/25 | - | - | ||
0.25 | Apartment | $150,000 | 11/12/25 | - | - | ||
0.80 | Apartment | $335,000 | 04/02/26 | - | - |
Home facts updated by county records
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 |
|---|---|---|---|---|---|---|
0.06 | $427,000 | 2 | 2.5 | 1,600 | Recently Sold | |
0.06 | $453,600 | 2 | 2.5 | 1,550 | Off Market | |
0.07 | $422,100 | 2 | 2.5 | 1,600 | Off Market | |
0.00 | $510,000 | 2 | 2.5 | 1,800 | Recently Sold | |
0.08 | $459,900 | 3 | 2.5 | 1,600 | For Sale | |
0.03 | $476,400 | 2 | 2.5 | 1,295 | Off Market | |
0.03 | $455,900 | 2 | 2.5 | 1,290 | Off Market | |
0.02 | $538,000 | 2 | 2.5 | 1,800 | Off Market | |
0.04 | $398,300 | 2 | 2 | 1,200 | Off Market | |
0.04 | $404,300 | 2 | 2 | 1,205 | Off Market | |
0.04 | $700,200 | 4 | 2.5 | 2,240 | Off Market | |
0.03 | $460,100 | 2 | 2.5 | 1,300 | Off Market |
Local Information
-- mins to
Home Highlights
Property Type
Apartment
Year Built
1988
Living Area
1,900 sqft
Parking
None
About this House
Updated 3 level unit in Society Hill II. 1st floor: powder room, eat-in kitchen, counter-tops, stove, microwave, dishwasher and title floors. Kitchen has a pass-through to dining area/living room w/hardwood floors, sliding glass doors lead to balcony. 2nd floor: 2 bedrooms both w/ renovated full baths. Entire 2nd floor has hardwood floors. washer and gas dryer conveniently located on the 2nd floor. Lower level: half bathroom, den/ office/ workout room and family room with sliding glass doors to the patio. 5 min walk to Beach Shopping Center. 2 min walk to the clubhouse, enjoy community amenities including resort-style indoor pool with lovely sundeck, racquetball, exercise room, basketball, meeting rooms with kitchen, and a full schedule of classes. One assigned parking space; plenty of guest parking.
27 Winchester Ave, Peekskill, NY 10566 is a 2 bedroom, 3 bathroom, 1,900 sqft apartment built in 1988. It last sold for $175,000 on Dec 13, 2011. More recently, it was listed as a rental in June 2022 with an asking price of $3,000 per month. That rental listing was removed on June 12, 2022. It is currently off market. The Trulia Estimate rent is $2,584/month.
Home Details for 27 Winchester Ave
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Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Interior Details Number of Rooms: 6 |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Levels, Entrance, & Accessibility Floors: Hardwood |
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Exterior Home Features Roof: OtherExterior: Brick |
Parking & Garage Parking: None |
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Year Built Year Built: 1988 |
Property Type / Style Property Type: ApartmentArchitecture: Other |
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Units in Building: 1 |
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Lot Area: 435 sqft |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jun 12, 2022 Source: BHHS broker feed | ListingRemoved | |
Jun 9, 2022 Source: BHHS broker feed #H6186695 | Listed For Rent | $3,000 |
May 29, 2022 Source: BHHS broker feed | ListingRemoved | |
May 21, 2022 Source: BHHS broker feed #H6186695 | Listed For Rent | $3,000 |
Aug 27, 2017 Source: Agent Provided | ListingRemoved | $2,500 |
Aug 16, 2017 Source: Agent Provided | Listed For Rent | $2,500 |
Aug 10, 2016 Source: Agent Provided | ListingRemoved | $2,375 |
Apr 22, 2016 Source: Agent Provided | ListingRemoved | $2,500 |
Feb 14, 2015 Source: Agent Provided | ListingRemoved | $2,350 |
Feb 14, 2015 Source: Agent Provided | Pending | $2,350 |
Feb 7, 2015 Source: Agent Provided | PriceChange | $2,350 Price decreased by 4% |
Jan 29, 2015 Source: Agent Provided | PriceChange | $2,450 Price decreased by 2% |
Jan 10, 2015 Source: Agent Provided | Listed For Rent | $2,500 |
Dec 13, 2011 Source: N/A | Sold | $175,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | Unavailable | $321,711 |
Home facts updated by county records
Market trends in Peekskill
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
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 27 Winchester Ave
- What is the price history for 27 Winchester Ave?27 Winchester Ave in Peekskill, NY last sold for $175,000 in December 2011.
- 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.
- What are the closest schools to 27 Winchester Ave?The closest schools to 27 Winchester Ave in Peekskill, NY are Hillcrest School (Elementary, rated 6/10), Oakside School (Elementary, rated 3/10), Peekskill High School (rated 3/10).
- Does 27 Winchester Ave have air conditioning?Yes, 27 Winchester Ave in Peekskill, NY has air conditioning.
- Does 27 Winchester Ave have laundry facilities?Yes, 27 Winchester Ave in Peekskill, NY has in-unit laundry.

