Blooming Real Estate | Blooming Homes and Condos for Sale
  • Home
  • Advanced Search
  • Selling
  • What's My Home Worth?
  • Meet the Team
  • Blog
Login
845-388-1900

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Chester Real Estate Search

TO
Advanced Search

Address Search

Chester Homes for Sale

In the County of Orange, the small town of Chester, New York, is a well-established community with a long history and rich heritage. This delightful town encompasses the village of Chester, a historic settlement around which most of Chester’s real estate is found. The village of Chester encompasses an old train station that is now home to a museum, and along Main Street, you’ll find many beautifully restored heritage structures. The town is the proud birthplace of Philadelphia-style cream cheese and historically has been one of the dairy industry’s centers. 

Further contributing to the appeal of Chester homes, in proximity, you’ll find several state parks and smaller local parks. Many of these recreation destinations offer tennis courts and ball fields, like those found at Goosepond Mountain State Park. The area is also rich with trails for horseback riding and hiking. Following the old Erie Railway line, the Orange County Heritage Trail is an excellent example and passes right through Chester. Beyond recreation, shopping and dining opportunities are also easily accessible. Specifically, there is a ShopRite, several other retailers, and a six-screen movie theatre in the Chester Mall.

Furthermore, this family-friendly community is served by the Chester Union Free School District which oversees the operation of Chester High School, Chester Middle School, and Chester Elementary School, all located within the community. Homes for sale in Chester are diverse, but many fall within the mid-range and are standard single-family properties. That said, there is new construction in Chester, as well as older homes, too. It is not uncommon to find acreage in Chester either, and lots larger than one-quarter acre are also common. For buyers seeking a lower maintenance option, there are a handful of Chester condos from which to choose as well. Please, as soon as it is convenient for you, connect with us and we will happily answer all of your questions about the currently available properties in Chester, New York.

Our website features the best Chester real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in the Chester real estate market? Sign up for a Chester Real Estate Market Report to see what’s active, under contract, and sold!

Contact us today to find out how we can be of assistance to you!

Newest Chester Homes and Condos for Sale

45 Rock Ridge  Road, Chester image
45 Rock Ridge Road, Chester $1,495,000 ▲

13.9 Breathtaking Private Acres w/ Your Own Pond & Fabulous Heated In Ground Pool in Chester w/Warwick Schools. This is a very special 1870's home, w/3235 Sq. Ft. this Co...

board logo
  • 3 Beds
  • 3 Baths
  • H6204568 MLS
board logo
29 Wilson  Road, Monroe image
29 Wilson Road, Monroe $470,000

Welcome to Lake Hill Farms-in the heart of the Hudson Valley. This lovely corner, fenced in property boasts 4 bedrooms & 2 baths, a large kitchen opening up to a dining a...

board logo
  • 4 Beds
  • 2 Baths
  • H6203258 MLS
board logo
28 Hidden  Drive, Monroe image
28 Hidden Drive, Monroe $474,000

Welcome to Your New Home, on 1- acre park like property. This Beautiful Home is located on a quite private road & is move in ready. This property boasts 3 bedrooms & 2 Fu...

board logo
  • 3 Beds
  • 2 Baths
  • H6203743 MLS
board logo
25 Trotting  Drive, Chester image
25 Trotting Drive, Chester $350,000

This home just needs updating. Has been in the same family since it was built. The owner is asking for patience the tenants are in the middle of moving out and are accom...

board logo
  • 4 Beds
  • 2 Baths
  • H6204474 MLS
board logo
47 Maple  Avenue, Chester image
47 Maple Avenue, Chester $449,000

Hurry to see the fabulous layout of this young custom built home with accessory apartment! Spacious 2771 square feet of extended living space features an upper section w...

board logo
  • 5 Beds
  • 3 Baths
  • H6202601 MLS
board logo
109 Restdale  Road, Chester image
109 Restdale Road, Chester $649,900

If your looking for a private setting this is it. Small stream down below.Stone barbecue next to the stream for relaxing times.3500 square ft Colonial with wonderful fron...

board logo
  • 4 Beds
  • 3 Baths
  • H6199478 MLS
board logo
143 Conklingtown  Road, Chester image
143 Conklingtown Road, Chester $1,200,000

Perfect meticulously maintained custom built Colonial ready for you to move in! Located in the most desirable neighborhood of Chester. Enjoy the picturesque views of 1....

board logo
  • 4 Beds
  • 4 Baths
  • H6201954 MLS
board logo
20A High  Street, Chester image
20A High Street, Chester $220,000

Your home can feel like the perfect private Zen getaway. Come home to picturesque views and birds chirping. Your cares melt away as your drive down the tree lined drivewa...

board logo
  • 1 Beds
  • 1 Baths
  • H6203652 MLS
board logo
902 Swan Hollow  Road, Monroe image
902 Swan Hollow Road, Monroe $280,000

Tastefully renovated bright and airy Townhouse with tiled entry. Large living room with fireplace, updated kitchen with newer stainless steel appliances. updated lava...

board logo
  • 3 Beds
  • 2 Baths
  • H6202415 MLS
board logo
9 Hickory  Lane, Monroe image
9 Hickory Lane, Monroe $250,000

Three bedroom ranch in a quiet residential locaton in the Monroe Woodbury School District. Enjoy one level living and have easy access to Walton Lake during the summer. H...

board logo
  • 3 Beds
  • 2 Baths
  • H6203101 MLS
board logo
49 Hambletonian  Road, Chester image
49 Hambletonian Road, Chester $549,000

Located in Chester, this contemporary style home was built in 1992 and boasts 2 bedrooms, 2 full bathrooms and 1 half bathroom. Walk into the entry foyer which takes you...

board logo
  • 2 Beds
  • 3 Baths
  • H6201362 MLS
board logo
3 Marion  Street, Chester image
3 Marion Street, Chester $599,999

Come and see this beautiful Colonial style house in the village of Chester, Offering 2,744 Sq Ft of spacious living area, Big kitchen with ceramic tiles, central AC, hig...

board logo
  • 3 Beds
  • 3 Baths
  • H6201603 MLS
board logo
95 Creamery Pond  Road, Chester image
95 Creamery Pond Road, Chester $609,900

Gorgeous Four Bedroom Colonial Located On Creamery Pond In The Hamlet Of Sugar Loaf! Only Minutes From Downtown Warwick And Chester, This Home Offers Close Proximity To H...

board logo
  • 4 Beds
  • 3 Baths
  • H6200973 MLS
board logo
144 Kings Highway Bypass, Sugar Loaf image
144 Kings Highway Bypass, Sugar Loaf $925,000

Brand new stunning homes being built in an 8 lot subdivision. Fully loaded; these homes include all the high end materials and finishes most builders consider extras such...

board logo
  • 4 Beds
  • 4 Baths
  • H6201733 MLS
board logo
29 Grand View  Terrace, Chester image
29 Grand View Terrace, Chester $650,000

Welcome Home! Meticulously maintained 5 Bedroom 4 Bath home in the Village of Chester with an open floor plan. Cathedral ceilings with a balcony overlooking the living ar...

board logo
  • 5 Beds
  • 4 Baths
  • H6201844 MLS
board logo


Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Copyright 2022 OneKey All rights reserved.

Like or Share
Loading likes...

Address Search

Popular Areas

  • Central Valley
  • Chester
  • Hamptonburgh
  • Harriman
  • Highland Mills
  • Kiryas Joel
  • Middletown
  • Newburgh
  • New Windsor
  • Town of Blooming Grove
  • Town of Monroe
  • Town of Woodbury
  • Village of Monroe
  • Village of South Blooming Grove
  • Washingtonville

Market Reports

  • Central Valley
  • Chester
  • Hamptonburgh
  • Harriman
  • Highland Mills
  • Kiryas Joel
  • Middletown
  • Newburgh
  • New Windsor
  • Town of Blooming Grove
  • Town of Monroe
  • Town of Woodbury
  • Village of Monroe
  • Village of South Blooming Grove
  • Washingtonville

Interactive Map Search

Interactive Map Search image

Buying & Selling Made Easy

Freshest Data Available Freshest Data Available
Active Listings Active Listings Only
Customizable Search Options Customizable Search Options
New Listing Alerts New Listing Alerts
Instant Home Value Assessments Instant Home Value Assessments

 

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years
Calculate

Does not include any taxes or fees.
Please consult a financial professional.

 

Translate Site

  • Home
  • Advanced Search
  • Buying
  • Featured Properties
  • Foreclosures
  • Selling
  • What's My Home Worth?
  • Recently Sold Listings
  • Market Reports
  • Meet the Team
  • Standard Operating Procedures
  • Blog
  • Contact Us

 

Blooming Realty
(845) 388-1900
info@bloomingrealty.com

© 2021 All Rights Reserved | Privacy Policy

Standard Operating Procedures

Notification of Fair Housing Laws

9 Dallas Dr
Monroe, NY 10950

 

Advanced Searches

  • Condo Search
  • MLS # Search
  • Foreclosure Search
  • Zip Search
  • Sold Search
  • Address Search
IDX Real Estate Websites by
• Accessibility • Terms • Privacy