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Chester, NY Homes for Sale with Pool

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  • /48

    $730,000

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft

    7 Park Place, Chester, NY 10918

    Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

    Agent Photo

    Luanne McGann

    Century 21 Full Service Realty

    (845) 447-0221

    7 Park Place, Chester, NY 10918
  • /24

    $275,000

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    2113 Whispering Hills Unit 178, Chester, NY 10918

    Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

    Valerie Quinn Keller Williams Realty

    2113 Whispering Hills Unit 178, Chester, NY 10918
  • /13

    $239,900

    • 2 Beds
    • 1.5 Baths
    • 1,240 Sq Ft

    503 Mountain Laurel Dr, Monroe, NY 10950

    Peaceful country living in this two-story center lakefront unit with full basement located in Windridge community. Enjoy incredible mountain views from this large private Townhome. Primary bedroom on upper level with walk in closet and large sitting area which can be used as home office. Slider to rear patio with beautiful lake views!! Large living and dining area. Beautiful quiet complex close

    Margaret Galatro ARC Realty 1 in Sales

    503 Mountain Laurel Dr, Monroe, NY 10950
  • /36

    $395,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,694 Sq Ft

    223 Eagleton Dr, Monroe, NY 10950

    Welcome home to this tastefully updated and meticulously maintained 3 bedroom, 2.5 bath unit in a highly sought after community in the Monroe Woodbury school district. The Windridge community is clustered around ponds adding to the country feel. Located near the back of the cul-de-sac, this home features an open floorplan for easy living and entertaining. Step out of the sliding door in the

    Theresa Powers Keller Williams Realty

    223 Eagleton Dr, Monroe, NY 10950
  • /39

    $319,900

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    607 Mountain Laurel Dr, Monroe, NY 10950

    Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

    Rosalie Cook Weichert Realtors

    607 Mountain Laurel Dr, Monroe, NY 10950
  • /48

    $925,000

    • 5 Beds
    • 3.5 Baths
    • 3,680 Sq Ft

    21 Bull Mine Rd, Chester, NY 10918

    Welcome to this distinguished colonial residence offering five bedrooms and three and a half baths, gracefully positioned on 2.3 acres of private, scenic grounds. Set back from the road, the home is surrounded by expansive green lawns, providing an unparalleled sense of privacy and sophistication. The inviting front porch presents an ideal space to enjoy your morning coffee while taking in the

    Donna Gennaro Howard Hanna Rand Realty

    21 Bull Mine Rd, Chester, NY 10918
  • /7

    $874,400

    • 4 Beds
    • 2 Baths
    • 2,466 Sq Ft

    651 Lakes Rd, Monroe, NY 10950

    Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

    Frank Golio Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • /48

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,467 Sq Ft

    53 Odyssey Dr, Chester, NY 10918

    Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

    Hilary Ryan Goldman Howard Hanna Rand Realty

    53 Odyssey Dr, Chester, NY 10918
  • /2

    $249,900

    • 2 Beds
    • 1.5 Baths
    • 1,053 Sq Ft

    1005 Whispering Hills, Chester, NY 10918

    ONLY CASH OFFERS!! LOW TAXES! Two Level Living! 2 Bedrooms! 1 1/2 Bathrooms! 1 Car Garage! Updated Kitchen! Updated Bathrooms! Living Room with Fireplace! Sliders To Patio! Perfect Commuter Location! Walk to NYC Bus & Shopping! Close to Major Highways! Country Club Living! Clubhouses! Pools! Tennis! Tot Lot! Basketball! Dog Walk!

    Amanda Dnistrian ARC Realty 1 in Sales

    1005 Whispering Hills, Chester, NY 10918
  • /45

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 3,866 Sq Ft

    2948 State Route 94, Chester, NY 10918

    Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

    Elizabeth Broderick Tuxedo Hudson Realty Corp

    2948 State Route 94, Chester, NY 10918
  • /33

    $289,500

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    1401 Whispering Hills, Chester, NY 10918

    Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

    Debbie Goldstein Howard Hanna Rand Realty

    1401 Whispering Hills, Chester, NY 10918
  • /34

    $999,000

    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft

    12 Damian Ct, Chester, NY 10918

    Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

    Elimelech Kremer MS Realty Group USA, Inc

    12 Damian Ct, Chester, NY 10918
  • /28

    $305,000

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft

    3917 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

    Jie Liu Keller Williams Hudson Valley

    3917 Whispering Hills, Chester, NY 10918
  • /25

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,355 Sq Ft

    4116 Whispering Hills, Chester, NY 10918

    Beautifully updated 3-bedroom, 2.5-bath Dogwood model townhouse located in Whispering Hills, a desirable corner unit setting. This home offers a perfect blend of comfort and modern upgrades.Step inside to find a thoughtfully refreshed interior with remodeled and freshly painted bathrooms, along with a bright, open layout. The kitchen is equipped with a brand-new refrigerator and dishwasher,

    Michael Casarella William Raveis-New York, LLC

    4116 Whispering Hills, Chester, NY 10918
  • /50

    $699,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    360 Prospect Rd, Chester, NY 10918

    B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

    Joseph Mendlowitz eRealty Advisors, Inc

    360 Prospect Rd, Chester, NY 10918
  • /24

    $362,900

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2203 Whispering Hills, Chester, NY 10918

    Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

    Marie Altieri Howard Hanna Rand Realty

    2203 Whispering Hills, Chester, NY 10918
  • /42

    $305,000

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    3601 Whispering Hills, Chester, NY 10918

    Welcome to effortless living in the highly sought-after Whispering Hills community! This beautifully maintained 2-bedroom, 1-bath condo with a 1-car garage offers the perfect blend of comfort, style, and convenience.Step inside to discover a warm and inviting space enhanced by custom wall detailing, stylish flooring, and a cozy fireplace, creating the perfect setting for relaxing and

    Janet Rendle Weichert Realtors

    3601 Whispering Hills, Chester, NY 10918
  • /48

    $499,999

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    35 Maple Ln, Monroe, NY 10950

    Is there a 3-bed ranch in Monroe NY under $500K with a finished basement, pool, and commuter convenience? 35 Maple Ln is a 3-bedroom, 2-bathroom ranch offered at $499,999 with 1,460 sq ft of living space, including 960 sq ft above grade and a 500 sq ft finished basement. Built in 1964, this single family residence offers true single level living plus flexible lower level space ideal for

    Kewin Garabito eXp Realty

    35 Maple Ln, Monroe, NY 10950
  • /24

    $479,000

    • 4 Beds
    • 2 Baths
    • 1,322 Sq Ft

    5 Berkley Terrace, Monroe, NY 10950

    Lake Rights! Low Taxes! Welcome home to this lovely cape, beautifully situated on a double lot allowing for plenty of yard space for peace and privacy. This home features 4 bedrooms and 2 full bathrooms with a large eat-in kitchen, wood floors and a spacious unfinished, walk-out basement. Walk-out from the kitchen onto a lovely deck for grilling, dining and relaxing as you take in the tree-top

    Layla Rose Boyles Century 21 Realty Center

    5 Berkley Terrace, Monroe, NY 10950

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$517,500
Median Single Family Sale Price
$639,000
Median Townhouse Sale Price
$325,000
Median 2 Bedroom Sale Price
$305,000
Average Price Per Sq Ft
$267
Number of Homes for Sale
34
Last 12 months Home Sales
102
Months of Supply
4.00
Median List Price
$525,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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