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$515,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,518 Sq. Ft.
  • 2 Car Garage
  • Updated 7 days ago
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25 High Street is back on the market and newly refreshed, making this Victorian gem more inviting than ever. Brimming with character and ready for your personal touch, this special home welcomes you with original wide-plank wood floors throughout-preserved under carpeting to maintain their timeless authenticity and warmth. Entertain in style in the bright, modern kitchen or host memorable gatherings in the spacious formal dining room. Two large living rooms offer flexible spaces for relaxation and entertainment, while upstairs, four comfortable bedrooms and two full baths (including one on the main floor) ensure plenty of room for family and guests. Two staircases offer convenient access to every level. Additional highlights include a walk-up attic with two unfinished rooms bursting with potential, an unfinished basement for extra storage or workspace, and a large garage plus carport for vehicles or hobbies. Located less than a mile from the heart of Chester's charming village, this property offers a prime location close to local shops, restaurants, and everyday amenities. Just minutes to Route 84 and roughly 1 hour and 40 minutes to New York City, it's perfect for weekend getaways or daily commuting. With its size, layout, and location, this home also presents an outstanding opportunity as a short-term rental or Airbnb, with strong income potential given Chester's desirable setting near Glenmere Lake, Goose Pond Mountain State Park, and The Castle Fun Center.

Full Property Details for 25 High St

General

  • Price: $515,000
  • Taxes: $14,066
  • Status: Pending
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 883804
  • Updated: 1/11/2026
  • Added to Site: 201 day(s) ago

Interior

  • Number of Rooms: 15
  • Interior Features: First Floor Full Bath, Eat-in Kitchen, Kitchen Island, Original Details
  • Fireplace: Yes
  • Fireplace(s): Living Room
  • Appliances: Dishwasher, Electric Range
  • Laundry Facilities: Yes
  • Flooring: Carpet, Ceramic Tile, Hardwood, Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: In Basement

Exterior

  • Porch/Patio/Deck: Covered, Porch

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Driveway, Garage

Location

  • County: Orange County

School Information

  • High School District: Chester
  • Elementary School: Chester Elementary School
  • Middle School: Chester Academy-Middle/High School
  • High School: Chester Academy-Middle/High School

Heating & Cooling

  • Cooling Type: Wall/Window Unit(s)
  • Heating Type: Hot Water, Steam

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Natural Gas Connected, Sewer Connected

Structural Information

  • Architectural Style: Victorian
  • Detached/Attached: Detached
  • Construction: Frame
  • Basement: Yes
  • Basement Desc.: Unfinished
  • Unfinished Attic: Yes
  • Building Size: 3518
  • Square Feet: 3,518
  • Sq. Ft. Source: Public Records
  • Year Built: 1850

Additional Structures

  • Other Structures: Garage(s)

Lot Features

  • Lot Size (Acres): 0.6313
  • Lot Size (Sq. Ft.): 27,500
  • Frontage: County Road
  • Road Maintenance: Public Maintained Road
  • Lot Features: Back Yard, Level

Financial Considerations

  • Tax Amount: $14,066.24

Disclosures and Reports

  • Special Conditions: Probate Listing
  • Property ID: 332201-102-000-0001-050.000-0000

Listed by Christie's Int. Real Estate

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Listing agents

— 25 High St —

  • Christie's Int. Real Estate

  • Christie's Int. Real Estate

914-266-9200

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 25 High St

School District:Chester Union Free School District
NameGradesDistance
Chester Elementary School, Chester, NY
2 Herbert Drive, Chester, NY 10918
K-50.7 mi
Chester Academy Middle High School
64 Hambletonian Avenue, Chester, NY 10918
9-120.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 25 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/08/2025
Price Reduced
$515,000
-1.9%
MLS
7/01/2025
Listed
$525,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 25 High St

Year
Property Taxes
Change
Tax Assessment
Change
2021
$2,880
-49%
$192,500
—
2021
$5,689
-49%
$192,500
—
2020
$11,236
5%
$192,500
—
2018
$10,669
3%
$192,500
—
2017
$10,388
1%
$192,500
—
2016
$10,314
3%
$192,500
—
2015
$10,037
2%
$192,500
—
2015
$9,812
-3%
$192,500
—
2013
$10,124
—
$192,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Christie's Int. Real Estate

25 High Street, Chester, NY 10918 (MLS# 883804) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 25 High Street is currently listed for $515,000 and was received on July 01, 2025. Want to learn more about 25 High Street? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

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