21

Homes for Sale in 10918 with Pool

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  • /41

    $1,159,900

    • 4 Beds
    • 5 Baths
    • 4,624 Sq Ft

    16 Lori Ln, Chester, NY 10918

    Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the

    Agent Photo

    Randolph Rogers

    eXp Realty

    (845) 493-2930

    16 Lori Ln, Chester, NY 10918
  • /37

    $424,999

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

    2722 Whispering Hills Unit 542, Chester, NY 10918

    New beginnings offered in this light and bright fully refreshed end unit in the highly sought after Whispering Hills community. Featuring new designer paint throughout, brand new luxury vinyl plank (LVP) flooring, new stainless steel appliances, two car garage with recently installed garage doors and so much more. Located close to major highway, NYC bus and shopping. Club house with gym,

    Agent Photo

    Erin Connolly-Frontino

    Artisan Realty

    (845) 932-1237

    2722 Whispering Hills Unit 542, Chester, NY 10918
  • /47

    $985,000

    • 5 Beds
    • 3.5 Baths
    • 3,764 Sq Ft

    86 Long Vista Ln, Chester, NY 10918

    Some properties are simply worth talking about... this one has all the bells & whistles you're seeking! Privately set on 5.2 scenic acres within the Warwick School District and just one hour from NYC, this distinguished Colonial pairs timeless elegance with resort-style outdoor living, mountain views, and exceptional multi-generational flexibility. A gracious front porch sets the tone, welcoming

    Agent Photo

    Jennifer DiCostanzo

    RE/MAX Town & Country

    (845) 606-3942

    86 Long Vista Ln, Chester, NY 10918
  • /50

    $370,000

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

    3815 Whispering Hills Dr, Chester, NY 10918

    Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest

    David Kraus MK Realty Inc

    3815 Whispering Hills Dr, Chester, NY 10918
  • /50

    $1,195,000

    • 9 Beds
    • 6.5 Baths
    • 4,965 Sq Ft

    19 High St, Chester, NY 10918

    Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

    Beth Palma Keller Williams Realty

    19 High St, Chester, NY 10918
  • /49

    $769,000

    Open Fri 2AM - 4PM $31K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Brand new to the market! Perched atop the desirable Fieldcrest subdivision with sweeping panoramic views and unforgettable sunsets, this spectacular Colonial offers exceptional space, comfort, and versatility both inside and out. Set on 1.3 picturesque acres, this beautifully maintained home is designed for everyday living and effortless entertaining.A charming oversized front porch overlooks

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • /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
  • /50

    $3,400,000

    • 4 Beds
    • 4 Baths
    • 7,750 Sq Ft

    19 Greentree Ln, Chester, NY 10918

    Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

    Jake Garay Serhant LLC

    19 Greentree Ln, Chester, NY 10918
  • /12

    $640,000

    • 3 Beds
    • 1.5 Baths
    • 2,136 Sq Ft

    4 Greycourt Rd, Chester, NY 10918

    Welcome to 4 Greycourt Road, your dream home awaits! This delightful residence boasts a spacious 6-room layout, featuring 3 generous bedrooms and 1.5 baths, all nestled on over 2.5 acres of stunning greenery. Imagine whipping up culinary masterpieces in the well-appointed kitchen, complete with ample cabinetry and modern appliances—perfect for any cooking enthusiast! Each bedroom is a serene

    Nathen Singer MK Realty Inc

    4 Greycourt Rd, Chester, NY 10918
  • /45

    $1,300,000

    $95K PRICE DROP
    • 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

    $260,000

    $35K PRICE DROP
    • 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
  • /40

    $500,000

    • 4 Beds
    • 2 Baths
    • 1,730 Sq Ft

    37 Surrey Rd, Chester, NY 10918

    Looking for a 4-bed home in Chester, NY with a pool, major system updates, generous outdoor living space, and convenient access to schools, parks, shopping, and commuter routes? Welcome to 37 Surrey Road, a beautifully maintained raised ranch offering 4 bedrooms, 2 full bathrooms, approximately 1,730 square feet of living space, and a backyard designed for entertaining and relaxation. Set on a

    Lady Castro eXp Realty

    37 Surrey Rd, Chester, NY 10918
  • /42

    $849,900

    • 4 Beds
    • 3 Baths
    • 2,370 Sq Ft

    2 Primrose Ln, Chester, NY 10918

    Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

    Janet Rendle Weichert Realtors

    2 Primrose Ln, 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
  • /35

    $875,000

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

    49 Stone Mountain Trail, Chester, NY 10918

    Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

    Arya Rabinovits eRealty Advisors, Inc

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

    $1,090,000

    • 4 Beds
    • 3.5 Baths
    • 4,130 Sq Ft

    102 Beverly Rd, Chester, NY 10918

    Located in the Warwick School district on a coveted street sits this larger than life home with impressive presence. The curved driveway welcomes you to the wide porch, perfect for rocking chairs and relaxing. The impressive entrance with custom stairway and window seat is just the first of impressive touches in this home. Large kitchen overlooks the yard and is well appointed with Thor

    Kimberly Corkum Keller Williams Realty

    102 Beverly Rd, Chester, NY 10918
  • /32

    $319,900

    $4K PRICE INCREASE
    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft

    2820 Whispering Hills, Chester, NY 10918

    Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

    Anne Marie Scouarnec R2M Realty Inc.

    2820 Whispering Hills, Chester, NY 10918
  • /35

    $715,000

    • 4 Beds
    • 2.5 Baths
    • 2,784 Sq Ft

    335 Laroe Rd, Chester, NY 10918

    Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal

    Christina D'Altilio Coldwell Banker Choice Prop.

    335 Laroe Rd, Chester, NY 10918
  • /29

    $720,000

    • 4 Beds
    • 2.5 Baths
    • 1,718 Sq Ft

    26 Bridle Ln, Chester, NY 10918

    From the moment you arrive, it's clear this is a home whose character and setting are best experienced firsthand. The bright, open-concept living area features vaulted ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. A beautiful den with two walls of windows and a gas fireplace overlooks the pool and surrounding landscape. The thoughtfully

    David White Owner Entry.com

    26 Bridle Ln, Chester, NY 10918
  • /50

    $624,900

    $124K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    17 Woodridge Dr, Chester, NY 10918

    Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4 years young. The pools heating system runs on propane tank. Entire home was freshly

    Sharon Kushner eXp Realty

    17 Woodridge Dr, Chester, NY 10918
  • /32

    $329,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    1311 Whispering Hills Unit 96, Chester, NY 10918

    Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

    Michael Jenney Keller Williams Realty

    1311 Whispering Hills Unit 96, Chester, NY 10918
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