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Chester, NY Homes for Sale with Pool

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  • /31

    $549,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,844 Sq Ft

    13 Tulip Ln Unit 4, Monroe, NY 10950

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the heart of Monroe, NY. This inviting property offers an ideal blend of comfort, functionality, and outdoor enjoyment. Step inside to discover a sun-filled living room, formal dining room, and an eat-in kitchen complete with granite countertops, stainless steel appliances, and sliding doors that open to a spacious

    Courtney Tablante Keller Williams Realty

    13 Tulip Ln Unit 4, Monroe, NY 10950
  • /50

    $859,900

    • 4 Beds
    • 3.5 Baths
    • 4,021 Sq Ft

    157 Creamery Pond Rd, Chester, NY 10918

    Welcome to Creamery Estates of Sugarloaf, where your dream home awaits just an hour’s drive from New York City. Nestled within walking distance of the charming downtown hamlet of Sugarloaf, this lovely residence is minutes away from schools, boutique shops, restaurants, grocery stores, the Sugar Loaf Performing Arts Center, wineries, breweries, apple orchards, the Appalachian trails, local

    Carla Terranova Keller Williams Realty

    157 Creamery Pond Rd, Chester, NY 10918
  • /47

    $675,000

    • 4 Beds
    • 2.5 Baths
    • 2,608 Sq Ft

    174 Creamery Pond Rd, Chester, NY 10918

    Welcome to this beautifully maintained 4 bedroom, 2.5 bath Colonial nestled in the historic craft village of Sugar Loaf and award winning Warwick Valley Schools. This classic home offers timeless curb appeal, a spacious layout perfect for entertaining. The great room features an elegant stone fireplace, perfect for cozy evenings. A flowing layout with separate living, dining and great rooms

    Michele Tobin Keller Williams Realty

    174 Creamery Pond Rd, Chester, NY 10918
  • /38

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    12 Bianca Blvd, Chester, NY 10918

    Charming Colonial with Endless Potential – Priced to Sell!This stately Colonial is bursting with character and waiting for the right owner to bring it back to life! Nestled in a desirable neighborhood, this home offers classic architectural details, generous living spaces, and a layout perfect for modern living. While it needs some TLC, the potential here is undeniable—original hardwood

    Aoife Freeman Howard Hanna Rand Realty

    12 Bianca Blvd, Chester, NY 10918
  • /36

    $624,242

    • 4 Beds
    • 2.5 Baths
    • 2,236 Sq Ft

    20 Hubshop Rd, Chester, NY 10918

    CAPTIVATING CAPE COD! 1.5 Private Acres! 4 Bedrooms! 2 1/2 Bathrooms! 1 Car Garage! Gorgeous Updated Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Breakfast Nook! Master Bedroom Suite with Walk In Closet Located on the First Floor! Living Room with Double Sided Fireplace! Gleaming Hard Wood Floors! New Carpeting! Recessed Lighting! Laundry Room! Full Basement! Rocking

    Amanda Dnistrian ARC Realty 1 in Sales

    20 Hubshop Rd, Chester, NY 10918
  • /45

    $850,000

    • 4 Beds
    • 2.5 Baths
    • 3,656 Sq Ft

    49 Stone Mountain Trail, Chester, NY 10918

    Nestled in a peaceful and private cul-de-sac, this stunning three-story contemporary colonial offers the perfect blend of elegance, space, and modern comfort. Set on an over 7 acre expansive lot, this home features a sprawling front and backyard, ideal for outdoor activities year-round—whether it’s summer fun by the pristine inground pool or winter ice sliding across the gentle slopes. A 2-car

    Leon Klein Keller Williams Hudson Valley

    49 Stone Mountain Trail, Chester, NY 10918
  • /41

    $349,999

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

    4503 Whispering Hills, Chester, NY 10918

    WELCOME TO WHISPERING HILLS CONDOMINIMUM COMMUNITY!!! Check out this 3 Bedroom, 2.5 Bathroom Condominium nestled in the Village of Chester and in the Chester School District. This Condo is located a mile from the Village of Chester featuring a variety of Village amenities including local restaurants, shopping centers, medical offices, banking services, home improvement stores, close to

    Richard Baxter Keller Williams Realty

    4503 Whispering Hills, Chester, NY 10918
  • /7

    $899,900

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

    651 Lakes Rd, Monroe, NY 10950

    Build and Customize your dream home today on this compound in Monroe, Only one of its kind! The owner/builder has three plans for you tochoose from starting at 2600 sq feet - 5000 sq feet. This elegant, multi-family property consists of 3 residences nestled on over 3.5 statelylandscaped acres affording you peace and privacy. Surrounded by the original stone walls of this compound, this

    Frank Golio Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • /33

    $569,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    92 Pickerel Rd, Monroe, NY 10950

    Year end gifts are always wonderful to receive. Welcome to 92 Pickerel road Monroe, New York. A meticulous home awaiting its new owners and features including 3 to 4 bedrooms, 2 full baths, hardwood flooring, recently installed windows, roof, and boiler. A large eat in custom kitchen with granite, stainless appliances and Sub-Zero refrigeration. Dining room is adjacent and well placed.

    Richard Wawrynek Howard Hanna Rand Realty

    92 Pickerel Rd, Monroe, NY 10950
  • /36

    $334,900

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

    1610 Whispering Hills, Chester, NY 10918

    Discover your perfect commuter condo in the Whispering Hills Neighborhood of Chester! This beautiful end unit features three spacious bedrooms and two and a half baths. As you step inside, you'll find a bright and airy open living space that showcases the well maintained hardwood floors and charming fireplace, which provides a cozy atmosphere for gatherings during the cooler months. Off the side

    Patricia Sassi RE/MAX Benchmark Realty Group

    1610 Whispering Hills, Chester, NY 10918

Home Trends in Chester, NY

Home Trends

Median Price (12 Mo)
$493,650
Median Single Family Price
$555,000
Median Townhouse Price
$320,000
Median 2 Bedroom Price
$289,000
Median 1 Bedroom Price
$185,000
Average Price Per Sq Ft
$266
Number of Homes for Sale
24
Last 12 months Home Sales
132
Months of Supply
2.20
Median List Price
$499,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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