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Chester NY Real Estate & Homes for Sale

73 Properties Found

The median home value in Chester, NY is $262,500. This is higher than the county median home value of $208,300. The national median home value is $185,800. The average price of homes sold in Chester, NY is $262,500. Approximately 79.03% of Chester homes are owned, compared to 19.23% rented, while 1.74% are vacant. Chester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chester real estate agent to arrange a tour today!
Learn more about Chester Real Estate.


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1–25 of 73 properties displayed
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Beds:
2
Baths:
2.00
Sq.Ft.:
1,248
Status:
NEW LISTING
MLS#:
4852049
Type:
Single Family-Detached
Lot size:
0.34 Acres
Year built:
1900
A broker reciprocity listing Courtesy: HomeSmart Homes & Estates
View additional info

Here it is! The perfect starter home. Right in town. Walk to everything. Lovingly updated and maintained. Ready for you to move in. Huge fenced in yard with a large shed and play set. Come see for yourself today.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,331
Status:
NEW LISTING
MLS#:
4851802
Type:
Condo
Year built:
1987
A broker reciprocity listing Courtesy: William Raveis Baer & McIntosh Real Estate
View additional info

This is the largest home available in Whispering Hills. This end unit home with over 1,300 square feet has so much to so offerâ¦. Large and bright rooms, 3-bedrooms, 2 full baths + a half bath on the first floor. Wood burning fireplace, 3-bedrooms, 2 and a half bathsâ¦.All updated within the past year! New roof, skylight, newer furnace, sliders lead to the extra large patio. Wonderful commuter location. Close to all major roadways and shopping including Woodbury Commons.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,792
Status:
NEW LISTING
MLS#:
4851526
Type:
Single Family-Detached
Lot size:
2.4 Acres
Year built:
1995
A broker reciprocity listing Courtesy: Keller Williams Realty Group
View additional info

Beautiful home is located in the growing town of Chester. This home is immaculate and has been recently updated. Features 3 large bedrooms, an additional room, 2 full and 1 half updated bathrooms, beautiful hardwood flooring, wrap around deck, finished walk out basement with office, 2 acres of landscape, two car garage, basketball court, pool, hot tub, privacy, corner lot, lake views. The updated kitchen is perfect for entertaining as it opens to the family room with a warm fireplace. Taxes do not reflect star credits

Open House:

Sunday, 11/18 12:00-2:00PM

Beds:
4
Baths:
4.00
Sq.Ft.:
2,960
Status:
NEW LISTING
MLS#:
4851637
Type:
Single Family-Detached
Lot size:
2.7 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Keller Williams NY Realty
View additional info

Buy This Awesome Home, We Will Buy Yours* Nature lovers rejoice- this is the one youâve been waiting for! Nestled in the unique Artisan hamlet of sugar Loaf, this well-maintained home offers you a serene retreat with views year-round- including majestic wildlife close enough to touch. Enjoy the blazing colors of autumn from any room in this spacious cape cod home. Watch the snow fall while you cozy up in front of the wood burning stove, or enjoy the sunsets on your two-tiered redwood deck. Plenty of room for the kids to play- take advantage of the ability to go snow sledding in your own backyard. 2nd floor has an office with a separate entrance and access to the deck. The zoning allows for a home business, with one employee. The basement has 400 SF of finished space- not included in the listed SF. Enjoy all the area has to offer, including hiking, skiing & boating- then stop by one of the caféâs or restaurants in town. All of this, and Warwick Schools! *call your realtor for details.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,072
Status:
NEW LISTING
MLS#:
4851150
Type:
Single Family-Detached
Lot size:
0.51 Acres
Year built:
2004
A broker reciprocity listing Courtesy: BHG Rand Realty
View additional info

Magnificent Grand Contemporary Colonial that features a beautiful open Airy floor plan.This Gorgeous home features hardwood floors throughout, recessed lighting, crown and chair moldings, a Spectacular Living Room, Spacious Formal Dining Room that hosts large parties and holidays. Family Room with gas fireplace, Gormet Kitchen with high end cabinetry, Corian Countertops, upscale appliances, breakfast bar, open dining area. 1St Floor Bedroom with full bathroom which is great for a inlaw, teen or guest quarters. Private Laundry room. 2nd Floor offers a very Large Master BR suite with cathedral ceilings, beautiful bathroom that offers a double sink vanity and huge walk in closet. 2 more Large bedrooms one of which offers soaring ceilings. Full main bathroom. Overlook Balcony looking over the lower level. Lots of walk in attic storage. Full unfinished workable Basement. Trex Decking on the deck and front porch. Lush Landscaped yard. Sprinkler System, Central Air, Absolutely Stunning Home

Beds:
5
Baths:
3.00
Sq.Ft.:
4,687
Status:
Active
MLS#:
4841440
Type:
Single Family-Detached
Lot size:
5.3 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Keller Williams Realty
View additional info

Bring your vision. This is a great home that needs a special buyer to make it sparkle again. The roof was replaced about 7 years ago and a new furnace installed around 2013. A/C replaced in 2017. With proper permits the first level could be reconfigured for a mini master suite with access to the back deck. Close to major highways, fine dining, entertainment, vineyards, skiing and shopping. You donât want to miss seeing this incredible property that has so much to offer at a great price!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,053
Status:
Active
MLS#:
4850018
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: Monroe Realty Center
View additional info

This beautifully maintained 2 bdrm 1 1/2 ba 2 story condo is located in Whispering Hills in the historic village of Chester. The home features a living rm with wood burning fireplace and opens to the dining area with sliding drs that lead to a private outdoor patio. Upstairs, the spacious master bdrm has cathedral ceilings and walk-in closet. Bathroom upgrades include granite counter top, ceramic tile flr and subway tile bath surround. Furnace/AC and refridge 2-3 yrs old. The skylight comes with a custom cover. There's plenty of built-in storage throughout this condo between the garage, additional closets and attic with pull-down stairs. Walk to everything, pools, clubhouse, tennis cts, basketball cts, tot lot, shops, movies, dining and transportation. NYC commuter bus stops right in complex. Minutes to NYS Thruway, 55 minutes to NYC, 10 minutes to Orange Regional Medical Center and 25 minutes to Stewart International Airport. E-z on E-z off rt 17. This is an ideal commuter location.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,216
Status:
Active
MLS#:
4850837
Type:
Single Family-Detached
Lot size:
0.62 Acres
Year built:
1965
A broker reciprocity listing Courtesy: BHG Rand Realty
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Single level living waiting for you with this Ranch home waiting for some love. Fix it up and make it just the way you want it to call it home. Wood floors throughout. Front and back decks. Great 1/2+ acre w generous backyard with room to roam. Huge unfinished finishable basement. Popular Monroe/Woodbury Schools.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,655
Status:
Active
MLS#:
4849956
Type:
Single Family-Detached
Lot size:
0.37 Acres
Year built:
1850
A broker reciprocity listing Courtesy: BHG Rand Realty
View additional info

Charming Chester turn of the century 2-story home newly renovated. Walk up on your large covered front porch and enjoy the peace and fresh country air. This home is located across the street from the Heritage Trail. Large first floor master bedroom with adjoining bathroom & walk-in closet. Living room, formal dining room, eat-in-kitchen, large laundry room/half bath. Second floor includes 2 bedrooms and full bath. This home is ready for a new family!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,212
Status:
Active
MLS#:
4850165
Type:
Single Family-Detached
Lot size:
1 Acres
Year built:
1979
A broker reciprocity listing Courtesy: BHG Rand Realty
View additional info

Beautiful contemporary style home situated on 1 acre of picturesque, professionally landscaped property. Blue stone walkway and stone walls lead to the front door. The open floor plan and architectural windows flood the space with natural light. The formal living room has bamboo hardwood floors, high-hat lighting and a beautiful stone fireplace. The master suite is conveniently located on the first floor. The large master has a walk-in closet, master bath with whirlpool tub, Corian countertops and Kohler fixtures. An office (with closet), half bath, laundry room and den complete the first floor. The second floor features two additional bedrooms, both generous in size and a hall bathroom. The exterior is equally impressive with a large wrap around deck with pergola, stone patio with awning, Koi pond,fire pit and shed with electric. Mature landscaping surrounds your oasis and provides ultimate privacy. This property is a must see!!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,084
Status:
Active
MLS#:
4850180
Type:
Condo
Lot size:
0.01 Acres
Year built:
1990
A broker reciprocity listing Courtesy: John J Lease REALTORS Inc
View additional info

Great condition! Bright and sunny 2 bed, 1 bath, 1 car garage end unit. This condo offers an open floorplan with cathedral ceilings and a wood burning fireplace. Glass sliders off the living room leading to a balcony overlooking a spacious lawn. The kitchen offers oak cabinets, lightly used appliances and plenty of cabinets and storage space. The entire home has just been freshly painter and both bedrooms have brand new carpet. The master bedroom has a sink w/ vanity and a spacious walk-in closet. Plenty of parking for guests. Enjoy maintenance free living with 2 clubhouses (adult & baby pools) workout center, walking path, tennis, basketball and playgrounds. Located off RT 17, only 55 minuets to NYC. Short line bus stop in the complex or 10 min to Harriman train station! You will not be disappointed

Beds:
2
Baths:
2.00
Sq.Ft.:
1,086
Status:
Active
MLS#:
4849860
Type:
Condo
Year built:
1987
A broker reciprocity listing Courtesy: Catskill Country Real Estate
View additional info

Location is everything! This unit sits in a quiet area yet steps away from tennis, basketball, a playground, clubhouse, and pool. BBQ out on the patio or picnic in the yard surrounded by greenery. This 2 bedroom, 1.5 bath townhouse boasts gleaming floors with a cozy fireplace in the living room and custom built in shelving. An open floorplan makes hosting dinner a breeze. A skylight and vaulted ceilings add to the charm with 2 large bedrooms upstairs, including a master bedroom with spacious walk-in closet and a full bathroom. A two car garage with plenty of storage space is a bonus. Pride of ownership is apparent. This community provides 2 clubhouse locations, a workout room, 4 dog runs, 2 playgrounds, 2 oversized in- ground pools with separate kiddie pools, basketball courts, tennis courts, and an abundance of yard space for the whole family. This is a commuters dream with a NYC bus stop on premises. Take a look today, you won't be disappointed!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,052
Status:
Active
MLS#:
4848270
Type:
Single Family-Detached
Lot size:
6.1 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Keller Williams Realty
View additional info

Here it is! enjoy your re-birth of this 80s colonial set on over 6 quiet acres on sought-after cul-de-sac. Positioned privately from the road, yet convenient to all services. The entire rear is a park-like setting with 36' decking surrounding the in-ground pool oasis. The backdrop is loaded with privacy. Newly installed baths, oak flooring and slate floors. Room in the garage for a workshop with rear entrance to shangrila. The master bedroom is roomy with walk in closet and full bath. Plenty of opportunity to make this home your own. Kitchen has updated stainless appliances and a 30' living/family room with sliders to the expansive decking in rear. Don't miss out on this great price and great location.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,904
Status:
Active
MLS#:
4847141
Type:
Single Family-Detached
Lot size:
1 Acres
Year built:
1950
A broker reciprocity listing Courtesy: Blooming Realty
View additional info

You'll love the unique layout of this home! Yes, it's a bilevel, Perfect for Mother/Daughter or Home Office. Incl. 4 bds, 2.5 bath, Formal Dining room, Eat in kitchen. Master bedroom with master bath. Sparkling hardwood floors. Cozy family room with brick fireplace., plus large den and Full bath in lower level. Laundry room. Over-sized one car garage. Come see it!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,331
Status:
Active
MLS#:
4832943
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: R2M Realty Inc
View additional info

Welcome Home to Whispering Hills! One of Orange Counties Established Premier Communities. This Townhouse has the LARGEST layout, GREAT DESIGN and a CORNER LOT. Two levels of SPACIOUS townhouse living featuring your own private TWO car garage with LOADS of STORAGE. Features include: Hardwood Floors, BEAUTIFUL Updated Bathrooms, Walk-Out Patio from Updated Kitchen with separate Dining Area. Living Room offers a CUSTOM Entertainment Center and Distinctive Fireplace. Laundry Room on the first floor. Second Level includes Master Bedroom with it's Beautifully Private RENOVATED FULL BATHROOM and ample closets; Two LARGE Additional Bedrooms with UPDATED CONTEMPORARY FULL Bathroom. Wider Hallway allows for Multi Purpose use (Office/Sitting Area). Steps away from amenities - CLUBHOUSES (Great for entertaining), POOLS, TENNIS COURTS, BASKETBALL COURTS, WALKING TRAILS, PLAYGROUNDS, DOG PARKS. Direct Commutes to NYC. Close to local shops, Woodbury Commons, Wineries, Farms, and Outdoor Activities.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,114
Status:
Active
MLS#:
4847777
Type:
Single Family
Subdivision:
Surrey Meadows
Lot size:
0.35 Acres
Year built:
1968
A broker reciprocity listing Courtesy: Mary Jane Pastor Realty, Inc.
View additional info

Foreclosure alert! 3,144 square foot Colonial home with 4 bedrooms and 2 full bathrooms and 1 half bathroom in Chester! Level 1: living room, updated kitchen with granite countertops and new stainless steel appliances, dining room, den/office, family room, 1/2 bathroom and extra bonus rooms. Level 2: master bedroom with bathroom, 3 additional bedrooms and a full hall bathroom. This house was built in 1968 and sits on 0.35 acres.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,680
Status:
Active
MLS#:
4847545
Type:
Single Family-Detached
Subdivision:
Woodbridge Estates
Lot size:
1.6 Acres
Year built:
2000
Courtesy: Weichert Realtors
View additional info

On quiet end of cul de sac - 3 bedrooms 2 ½ bath Open floor plan kitchen into into Great room with fireplace. Screened in porch. Enjoy a quiet neighborhood and scenic views. Full heated basement with extra storage room, which would be great for an in-law suite. Sale will include tenant lease of $2,500 which ends May 31, 2019.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,090
Status:
Active
MLS#:
4847695
Type:
Condo
Year built:
1987
A broker reciprocity listing Courtesy: Keller Williams Realty
View additional info

2 Story 2 Bedroom Townhouse style located in a great setting * It is facing a lawn and trees ! Granite Counters * in Kitchen and Bathrooms Very Private! This home features nice sized living room and dining room * Recessed lights* Sliding glass doors to your patio * Laundry area with beautiful washer and dryer included * 2 good sized Bedrooms and skylight in the upstairs hall , Central air, Fireplace Municipal water and Sewer too !! and a 2 car garage with new doors put in 10/11/2018 interior access. Commuter bus comes right into the complex. Complex offers many amenities including 2 pools, 2 clubhouses, fitness center, basketball court, waling trail and playground.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,788
Status:
Active
MLS#:
4847376
Type:
Single Family-Detached
Subdivision:
Kings Tract
Lot size:
0.28 Acres
Year built:
1968
A broker reciprocity listing Courtesy: RE/MAX Benchmark Realty Group
View additional info

Updated split level home on quiet cul-de-sac and Monroe-Woodbury school district. Renovated and remodeled in 2015 and now new energy efficient furnace, new hot water heater, and solar panel lease. Gleaming hardwood flooring, spacious rooms, and great yard! Home features large formal living room and country eat-in kitchen and dining room with skylights! Skylight also in main bathroom with granite counter top, tile shower and jetted tub & heat lamp! Bedrooms have gleaming hardwood flooring and nice size rooms. Recreational/family room is a great space for games, parties, and more...the bonus it a wet bar for entertaining. Convenient door to back trex deck and back yard fun! Chester location for easy commuting access and close to everything! Must see and won't last! Shown by appointment only with notice.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,004
Status:
Active
MLS#:
4847176
Type:
Single Family-Detached
Lot size:
1.8 Acres
Year built:
1863
Courtesy: Weichert Realtors
View additional info

Own a piece of local history, Oodles of Charm await...and affordable too. Fall in love with this Picturesque Farmhouse built in 1860's, with 3 Bedrooms, 1 Bath, Its set on 1.8 level acres. This home is for the person that loves primitive & simple living. It has an Eat in Kitchen, Wood flooring, Wonderful Hand Hewn Beams throughout. The land is fantastic and also has a fenced area which could be for a garden or as its used currently, a Dog Pen! Exterior Barn for the hobbiest. The home as many updates inc new septic in 2016, windows replaced in 2007. Roof was replaced in 2005. Local to Shopping, Restaurants, This Orange county home has much to offer. It would make a great year round or weekend home. Use your imagination. you are invited to take a peek. Serious Inquiries only. Home sold As Is.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,331
Status:
Active
MLS#:
4847198
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: BHG Rand Realty
View additional info

HELLO COMMUTERS!!!!WHAT A BARGAIN...â¦.Spacious Oversized End Unit Townhouse. This Unit has a large Livingroom, Dining Room and a fabulous kitchen with walk out Patio. Lots of cabinetry and counter space. Close to Train and Bus Stop to NYC. Commuter Bus comes right onto Complex. Huge 2 Car Garage. Lots of Windows and sunlight. Great for shopping, near Woodbury Commons, Walmart, Target and more. Very close to Bear Mountain, many hiking trails and great mountain Views. 2 Clubhouses and Pools; Gym and Playground; Basketball, Tennis and Racquet Ball Courts and 4 Dog Runs.... Hurry a Must See, will not Last Long.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,531
Status:
Active
MLS#:
4846669
Type:
Single Family-Detached
Lot size:
5.3 Acres
Year built:
1987
A broker reciprocity listing Courtesy: BHG Rand Realty
View additional info

Welcome Home to Your Country Estate! Enjoy the privacy of this 4 Bedroom Center Hall Colonial, beautifully situated on 5.2 acres of stunningly landscaped property. This home features an updated kitchen with beautiful quartz countertops, a center island, and new soft close cabinets. Sip your coffee and take in the mountain views under the awning of the two tiered deck overlooking the backyard oasis with in-ground pool. Conveniently located with easy access to the highway and close to Sugarloaf Village, this home has it all. Newer 2-Zone Air Conditioning. Hardwood Floors throughout main living area. Tree-lined driveway.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,086
Status:
Active
MLS#:
4845675
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: BHG Rand Realty
View additional info

Just a short walking distance to the Village of Chester, this 2 Bedroom, 1.5 Bathroom Whispering Hills Condo offers * Duplex living * Galley style Kitchen off the Dining Room with sliding glass door overlooking your own Patio * Powder Room * Living Room with Wood-Burning Fireplace * 1st Floor Washer/Dryer * Central Air Conditioning * Large Master Bedroom with vaulted ceiling and walk-in closet adjoined to a full bathroom * Hallway skylight * Spacious 2nd bedroom * 2-car attached garage with door openers * Garage Storage * NYC Shortline Bus stop right in the complex * Amenities include 2 in-ground pools and tot pools, clubhouse, tennis courts, basketball courts, playground * Close to all, shopping, dining, highways, transportation, NY-17 just 1 minute away * Great Commuter Location * Low Taxes!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,331
Status:
Active
MLS#:
4846281
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: BHG Rand Realty
View additional info

Largest model available in Whispering Hills with updated kitchen incl Granite counters Stainless steel apl. update 1/2 bathroom Living room with woodburning fireplace. Front loading washer and dryer incl. Large 2 car garage plus space for storage. The second floor has vaulted ceiling in the master suite with newer tiled full bathroom. Two other bedrooms plus full updated bathroom. Three year old Furnace and central air. Pella Sliding door and new storm door. Updated 6 panel interior doors. Plus many other upgrades. Commuter bus walking distance from front door, Pool, clubhouse/gym and walking trails.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,866
Status:
Active
MLS#:
4846149
Type:
Single Family-Detached
Subdivision:
Star View
Lot size:
5.7 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Coldwell Banker Village Green Realty
View additional info

Welcome home to this beautiful and spacious farmhouse style Colonial! Set back from the road, this lovely home sits on 5.7 partially wooded acres on a dead-end road in a quiet and peaceful subdivision known as Star View. Enter into the open and welcoming 2 story foyer and walk down the center hall into the remodeled kitchen with brand new cherry Kraftmaid cabinets and quartz counter-tops. The kitchen opens into a spacious family room and features a wood-burning fireplace. The living room has a doorway leading out to the wrap-around porch. The formal dining room is ready and waiting to host all of your holiday meals. A spacious full finished basement awaits your exercise equipment, media room/man cave, crafting space...you name it! On the second floor a generous sized Master Bedroom and Master Bath with walk-in closets awaits you, along with three other large bedrooms and another full bathroom. Plenty of room for a large family! Come see this wonderful "off the beaten path" home today!

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The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than the owner of this site are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright © 2018 Hudson Gateway Multiple Listing Service, Inc. AND Hudson Gateway Association of REALTORS, Inc.. All rights reserved.

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