26

Chester, NY Homes for Sale with Pool

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  • /41

    $1,139,900

    $20K PRICE DROP
    • 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

    16 Lori Ln, Chester, NY 10918
  • /36

    $749,900

    • 4 Beds
    • 4 Baths
    • 3,080 Sq Ft

    20 Mountainside Dr, Chester, NY 10918

    20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange

    Agent Photo

    Randolph Rogers

    eXp Realty

    20 Mountainside Dr, Chester, NY 10918
  • /33

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 1,585 Sq Ft

    255 Heritage Ln, Monroe, NY 10950

    Welcome to Windridge! This well-maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfortable, carefree living in a convenient Hudson Valley location. The first floor features a spacious eat-in kitchen with new stainless-steel appliances, a powder room, and an open living/dining area with sliding doors leading to the patio. Upstairs offers two bedrooms, a full bath, and a spacious

    Agent Photo

    Elsa Seguinot

    Coldwell Banker Realty

    255 Heritage Ln, Monroe, NY 10950
  • /33

    $290,000

    $25K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft

    4008 Whispering Hills Dr, Chester, NY 10918

    Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17.Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace,and a separate dining area ideal for

    Karen Taphorn Howard Hanna Rand Realty

    4008 Whispering Hills Dr, Chester, NY 10918
  • /32

    $1,199,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 5,712 Sq Ft

    16 Sunset Ridge, Monroe, NY 10950

    NEW PRICE! Ready to sell! Highly motivated seller. Sold as-is. Recent updates include fresh paint in select areas and new pavers for enhanced curb appeal. Located approximately one hour from NYC with convenient access to major roadways.Welcome to this secluded Colonial in desirable Trout Brook Estates, set on nearly 6 private acres with over 5,700 sq ft of living space. This spacious

    Carmela Lopez Borrazas Serhant LLC

    16 Sunset Ridge, Monroe, NY 10950
  • /2

    $360,000

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

    3409 Whispering Hills, Chester, NY 10918

    Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways.Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace,

    Bernadette Giordano Howard Hanna Rand Realty

    3409 Whispering Hills, Chester, NY 10918
  • /24

    $295,000

    • 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
  • /7

    $900,000

    • 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

    Sandra Spector Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • /29

    $389,900

    • 3 Beds
    • 2 Baths
    • 1,393 Sq Ft

    4114 Whispering Hills, Chester, NY 10918

    WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door)

    Gzim Hakanjin Coldwell Banker Realty

    4114 Whispering Hills, Chester, NY 10918
  • /50

    $1,145,000

    $50K PRICE DROP
    • 9 Beds
    • 6.5 Baths
    • 4,965 Sq Ft

    19 High St, Chester, NY 10918

    Own One of America's Great Equestrian LandmarksSteeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of

    Beth Palma Keller Williams Realty

    19 High St, Chester, NY 10918
  • /36

    $750,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    985 Craigville Rd, Chester, NY 10918

    Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

    DAVID DEBERARDINIS Serhant LLC

    985 Craigville Rd, Chester, NY 10918
  • /49

    $749,999

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Imagine ending every day watching the sun set from your front porch, with breathtaking views that change beautifully through every season. Sunset views, a fenced backyard, brand-new Trex deck, above-ground pool, home office, and the flexibility of **four sleeping spaces** make this property truly stand out. Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial is

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • /31

    $345,000

    $54K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    402 Mountain Laurel Dr, Monroe, NY 10950

    Waterfront living at its finest! Welcome to this beautifully maintained center-unit townhome in one of Monroe's most sought-after communities. Offering over 1,800 square feet of living space, this home features 3 bedrooms, 2 full bathrooms, 1 half bath, and breathtaking lake views right from your backyard. The updated eat-in kitchen is the heart of the home, showcasing a center island, newer

    Alexandria Sarki Keller Williams Realty

    402 Mountain Laurel Dr, Monroe, NY 10950
  • /46

    $615,000

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    412 Laroe Rd, Chester, NY 10918

    Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The

    Nathalie Sessoms Howard Hanna Rand Realty

    412 Laroe Rd, Chester, NY 10918
  • /32

    $295,000

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft

    2119 Whispering Hills, Chester, NY 10918

    Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and

    Jasmine Wadhwa Howard Hanna Rand Realty

    2119 Whispering Hills, 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
  • /32

    $389,900

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

    213 Eagleton Dr, Monroe, NY 10950

    Some homes simply make everyday life easier, and 213 Eagleton Drive is one of them. This 3-bedroom, 2.5-bath townhome offers a practical layout with comfortable living spaces, an attached garage, additional driveway parking, and an unfinished basement for lots of storage. During the winter months, the home offers views of the community lake, adding a peaceful backdrop to the changing

    Deborah Warner Keller Williams Valley Realty

    213 Eagleton Dr, Monroe, NY 10950
  • /32

    $545,000

    $70K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,908 Sq Ft

    11 Chandler Dr, Chester, NY 10918

    Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love.Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement

    Daniella Restrepo Coldwell Banker Realty

    11 Chandler Dr, 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

    $949,000

    $50K PRICE DROP
    • 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
  • /29

    $549,999

    • 4 Beds
    • 2.5 Baths
    • 2,098 Sq Ft

    7 Lakeview Dr, Chester, NY 10918

    This charming updated 4-bedroom beauty in the Warwick School district offers a private and quiet setting featuring an above ground pool surrounded by a freshly painted deck just 3 minutes from Sugar Loaf Arts and Crafts Village. Its' kitchen has been upgraded boasting stainless steel appliances, granite countertops, and cherrywood cabinetry with undermount lighting and a wine/ beverage cooler.

    Sheyla Falesto Howard Hanna Rand Realty

    7 Lakeview Dr, 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
  • /18

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 1,585 Sq Ft

    154 Eagleton Dr, Monroe, NY 10950

    New Pics!Welcome to easy, low-maintenance living in this beautifully maintained 3-bedroom, 2.5-bath condo townhouse offering 1,585 square feet of comfortable living space in a peaceful community. Wake up to tranquil views overlooking a picturesque lake and enjoy the perfect blend of privacy, convenience, and amenities. The bright and spacious layout features central air conditioning, generous

    Bernadette Corrigan Keller Williams Realty

    154 Eagleton Dr, Monroe, NY 10950
  • /50

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,516 Sq Ft

    3 Garnett Hill Rd, Chester, NY 10918

    This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the

    Jacob Fried Keller Williams Realty

    3 Garnett Hill Rd, Chester, NY 10918
  • /46

    $299,000

    • 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
  • /35

    $369,000

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

    2522 Whispering Hills Unit 518, Chester, NY 10918

    Welcome to Whispering Hills! Discover easy living, comfort and privacy while living within a neighborhood community. Perfect for first time home buyers or if you're downsizing for care free, low maintenance living. Enjoy this spacious 3 bedroom, 3 bath townhouse with lots of storage and your private garage with direct entry into your home. Comfortable and spacious bedroom layouts with baths and

    Ann Marie Silvani Howard Hanna Rand Realty

    2522 Whispering Hills Unit 518, Chester, NY 10918

Home Price Trends

Median Sale Price
$500,000
Median Single Family Sale Price
$664,500
Median Townhouse Sale Price
$320,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
69
Last 12 months Home Sales
83
Months of Supply
10.00
Median List Price
$599,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-5%
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