81

Chester, NY Homes for Sale

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  • 2812 Whispering Hills Unit 577, Chester, NY 10918
    2812 Whispering Hills Unit 577, Chester, NY 10918
    2812 Whispering Hills Unit 577, Chester, NY 10918
    /30

    $290,000 Coming Soon

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

    2812 Whispering Hills Unit 577, Chester, NY 10918

    Motivated sellers. Welcome to Whispering Hills, one of the most sought-after communities in the area with resort style amenities and unbeatable commuter convenience. Picture yourself coming home to this beautiful space. The large living room opens to sliding glass doors that lead out to your private deck, the perfect spot to unwind after a long day. Cathedral ceilings create an open, airy feel,

    Agent Photo

    Kathy White

    Exit Realty Connections

    (845) 390-2310

    2812 Whispering Hills Unit 577, Chester, NY 10918
  • 16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    /49

    $779,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 2,870 Sq Ft

    16 Oxford Springs Rd, Chester, NY 10918

    Discover modern living at its finest in this beautifully designed 2,870 sq ft contemporary home set on 4.1 stunning acres featuring a peaceful pond and a seasonal babbling brook. Offering wonderful privacy and an effortless indoor–outdoor lifestyle, this property is a rare retreat surrounded by nature. Inside, oak hardwood floors flow across both levels, setting a warm yet sophisticated tone. The

    Jennifer Gold RE/MAX Benchmark Realty Group

    16 Oxford Springs Rd, Chester, NY 10918
  • 80 Pewter Cir, Chester, NY 10918
    80 Pewter Cir, Chester, NY 10918
    80 Pewter Cir, Chester, NY 10918
    /49

    $534,900 Open Sat 11AM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,946 Sq Ft

    80 Pewter Cir, Chester, NY 10918

    Welcome to the Villas at Sugar Loaf — an unbeatable location that rarely sees homes come on the market! Just half a mile from the charming hamlet of Sugar Loaf, this beautifully maintained move-in ready townhome is in the highly sought-after Warwick School District. With easy access to major highways and train stations, this home is ideal for commuters. Inside, you’ll love the bright, open floor

    Julie Klein BHG Real Estate Green Team

    80 Pewter Cir, Chester, NY 10918
  • 1503 Whispering Hills, Chester, NY 10918
    1503 Whispering Hills, Chester, NY 10918
    /2

    $339,900

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

    1503 Whispering Hills, Chester, NY 10918

    Nice end unit 3 bedroom 2.5 bath condo with 2 car garage in whispering hills. Primary bedroom with private full bath and 2 nice size extra bedrooms plus a hall bath on the 2nd floor. Warm up on those cold nights with the fireplace in the living room. Enjoy a quiet moment on your private patio sipping your coffee. Great location with playground and tennis across the street, pool, clubhouse and bus

    Darlene Provino Century 21 E & M Williams Rlty

    1503 Whispering Hills, Chester, NY 10918
  • L30 Lane Rd, Chester, NY 12853
    L30 Lane Rd, Chester, NY 12853
    L30 Lane Rd, Chester, NY 12853
    /5

    $35,000

    • Land
    • 7.07 Acres
    • $4,950 per Acre

    L30 Lane Rd, Chester, NY 12853

    You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

    Julia Pucciarelli Gallo Realty ADK Inc

    L30 Lane Rd, Chester, NY 12853
  • 2104 Whispering Hills, Chester, NY 10918
    2104 Whispering Hills, Chester, NY 10918
    /2

    $299,900

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

    2104 Whispering Hills, Chester, NY 10918

    WHISPERING HILLS!! SOLD AS IS!!! Largest Model! Two Level Living! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Living Room! Master Bedroom Suite with Walk in Closet! Patio! Country Club Living! Clubhouses! Pools! Tennis! Basket Ball! Tot Lot! Dog Walk! Perfect Commuter Location! Walk to NY Bus! Close to Major Highway & Shopping!

    Amanda Dnistrian ARC Realty 1 in Sales

    2104 Whispering Hills, Chester, NY 10918
  • 3 Hickory Ln, Monroe, NY 10950
    3 Hickory Ln, Monroe, NY 10950
    3 Hickory Ln, Monroe, NY 10950
    /38

    $324,000

    • 4 Beds
    • 1 Bath
    • 1,760 Sq Ft

    3 Hickory Ln, Monroe, NY 10950

    A spacious ranch style home offering incredible potential and plenty of living space. Features an open concept main level with a large living/dining area, updated flooring, and sliding doors leading to a generous rear deck. The renovated full bathroom adds a modern touch. Lower level includes multiple finished rooms, ideal for extra bedrooms, office space, or storage. Set on a wide, open lot with

    Lazar Schvimmer Blooming Realty

    3 Hickory Ln, Monroe, NY 10950
  • 1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    /33

    $295,000

    • 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
  • 18 Oakland Ave, Chester, NY 10918
    18 Oakland Ave, Chester, NY 10918
    18 Oakland Ave, Chester, NY 10918
    /33

    $369,900

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

    18 Oakland Ave, Chester, NY 10918

    This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated appliances and a custom pantry with large pull-out drawers. The Living room wood floors were refinished and are immaculate. The bathroom has been updated and built to be ADA-compliant with a space-saving "pocket door." There is a large shed in the backyard, all near all the activities the Village has to offer.

    Claude Brischoux Keller Williams Realty

    18 Oakland Ave, Chester, NY 10918
  • 36 Marian Ct, Warwick, NY 10990
    36 Marian Ct, Warwick, NY 10990
    36 Marian Ct, Warwick, NY 10990
    /27

    $395,000

    • 2 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    36 Marian Ct, Warwick, NY 10990

    Turnkey Townhome with Scenic Views – No HOA – Warwick School District. Welcome to your newly renovated 2-bedroom, 1.5-bath townhome in the heart of Warwick, just 60 minutes from NYC. This beautifully updated home is perfect for first-time buyers or anyone seeking a stylish, low-maintenance lifestyle in a quiet, commuter-friendly setting—without the restrictions of an HOA. Set against a backdrop

    Courtney Tablante Keller Williams Realty

    36 Marian Ct, Warwick, NY 10990
  • 65 Hudson St, Chester, NY 10918
    65 Hudson St, Chester, NY 10918
    65 Hudson St, Chester, NY 10918
    /24

    $345,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    65 Hudson St, Chester, NY 10918

    A truly rare opportunity to secure over two acres of prime land in the highly desirable and rapidly appreciating town of Chester. This charming property isn't just a home; it's a foundation for your future and a strategic long-term investment. Set on a sprawling 2.1+ acre lot, this property offers the space and privacy that is simply unmatched in today's market. The current single-level structure

    Nikki Grzegorzewski Keller Williams Realty

    65 Hudson St, Chester, NY 10918
  • 2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /31

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    2 Pine Hill Rd, Chester, NY 10918

    Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center.

    Debbie Walsh SHAHAR Management LLC

    2 Pine Hill Rd, Chester, NY 10918
  • 651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    /7

    $874,900

    • 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
  • 4 Camelback Rd, Chester, NY 10918
    4 Camelback Rd, Chester, NY 10918
    4 Camelback Rd, Chester, NY 10918
    /50

    $1,098,888 Pre-Foreclosure

    • 5 Beds
    • 4 Baths
    • 5,080 Sq Ft

    4 Camelback Rd, Chester, NY 10918

    The one you don't to miss. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This meticulously

    Alexander Fayn Prominent Properties Sotheby's

    4 Camelback Rd, Chester, NY 10918
  • 451 Meri Ln, Monroe, NY 10950
    451 Meri Ln, Monroe, NY 10950
    451 Meri Ln, Monroe, NY 10950
    /37

    $399,000

    • 3 Beds
    • 3.5 Baths
    • 1,698 Sq Ft

    451 Meri Ln, Monroe, NY 10950

    *Highest and best offers are due Thursday November 13th by 6pm. Welcome to the most current phase of Windridge built in 2001. This rare end unit with basement sits in a premium location backing to hundreds of acres of woods as your backdrop. If you love the outdoors, you just hit a home run by clicking into this new listing. You can hike the Appalachian Trail right outside your front door without

    Gary Silberstein Keller Williams Valley Realty

    451 Meri Ln, Monroe, NY 10950
  • 15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    /5

    $65,000

    • Land
    • 10.14 Acres
    • $6,410 per Acre

    15 Deer Run, Chester, NY 12817

    10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

    Patricia Seitz McAlonen Pearsall Realty

    15 Deer Run, Chester, NY 12817
  • 10 Damian Ct, Chester, NY 10918
    10 Damian Ct, Chester, NY 10918
    10 Damian Ct, Chester, NY 10918
    /33

    $1,375,000

    • 11 Beds
    • 6.5 Baths
    • 4,327 Sq Ft

    10 Damian Ct, Chester, NY 10918

    Welcome to 10 Damian Court — a stunning custom Colonial set on 2.6 acres of beautifully landscaped grounds in a peaceful Chester cul-de-sac. Built in 2004, this impressive home offers over 4,300 sq ft of elegant living space, featuring 11 bedrooms and 6.5 baths designed for comfort and flexibility. Enjoy a spacious eat-in kitchen with granite counters and pantry, a formal dining area, and a

    Elimelech Kremer MS Realty Group USA, Inc

    10 Damian Ct, Chester, NY 10918
  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /50

    $699,000 Open Sun 2PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    220 Oxford Rd, Chester, NY 10918

    Step into this newly renovated contemporary ranch, where comfort meets value on 6.3 acres of peaceful living. Featuring 4 spacious bedrooms and 3.5 bathrooms, this home has been beautifully renovated with new plumbing, spotlights, flooring, kitchen, painting, and full wiring for a camera and security system. Enjoy a large eat-in kitchen, formal dining room, cozy family room, and a bright attic

    Chaim Weiss Exit Realty Venture

    220 Oxford Rd, Chester, NY 10918
  • 23 W Meadow Way, Warwick, NY 10990
    23 W Meadow Way, Warwick, NY 10990
    23 W Meadow Way, Warwick, NY 10990
    /48

    $920,000

    • 4 Beds
    • 2.5 Baths
    • 2,969 Sq Ft

    23 W Meadow Way, Warwick, NY 10990

    Views abound from this stunning colonial in the Warwick Ridge Sub-Division. Don't miss out on this custom built colonial.includes Chefs kitchen, quartz counters, extensive trim package, custom tile, hardwood the works

    Robert Valentine BHG Real Estate Green Team

    23 W Meadow Way, Warwick, NY 10990
  • 16 Mari Rd, Chester, NY 10918
    16 Mari Rd, Chester, NY 10918
    16 Mari Rd, Chester, NY 10918
    /38

    $500,000

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

    16 Mari Rd, Chester, NY 10918

    Set back on a quiet street, just steps from downtown Sugar Loaf is this large home on almost an acre. Walk into the open living room and dining room, open to the kitchen with stainless steel appliances. The primary bedroom has access to the back deck, perfect for sipping your morning coffee overlooking the large peaceful backyard. Two additional bedrooms and a full bath complete the main floor.

    Kimberly Corkum Keller Williams Realty

    16 Mari Rd, Chester, NY 10918
  • 7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    /48

    $740,000

    • 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

    Luanne McGann Century 21 Full Service Realty

    7 Park Place, Chester, NY 10918
  • L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    /31

    $69,000

    • Land
    • 5.42 Acres
    • $12,731 per Acre

    L7 Macglashan Ln, Chester, NY 12817

    Very nice 5.42 acres of property with plenty of secluded building options. Gently sloping topography with mixed hardwood and conifers throughout. An abundance of wildlife signs from end to end of this parcel. This property is zoned ''Rural Use'' and would be used ideally for a home or cabin (one-primary single family residence) with garage or other auxiliary building. Seller financing possible

    Walter Swartz Gallo Realty ADK Inc

    L7 Macglashan Ln, Chester, NY 12817
  • 3 Derose Ln, Chester, NY 10918
    3 Derose Ln, Chester, NY 10918
    3 Derose Ln, Chester, NY 10918
    /50

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 2,550 Sq Ft

    3 Derose Ln, Chester, NY 10918

    This colonial home is truly designed for both family living and entertaining. Upon entering, a two-story entry provides easy access to all areas without needing to pass through other rooms unnecessarily. The spacious kitchen is a highlight, featuring oak cabinets, a pantry, updated appliances and a tiled backsplash and floor. For more casual gatherings, the family room offers hardwood floors. For

    Donna Gennaro Howard Hanna Rand Realty

    3 Derose Ln, Chester, NY 10918
  • 84 Pine Hill Rd, Chester, NY 10918
    84 Pine Hill Rd, Chester, NY 10918
    84 Pine Hill Rd, Chester, NY 10918
    /18

    $425,000

    • 3 Beds
    • 1 Bath
    • 1,266 Sq Ft

    84 Pine Hill Rd, Chester, NY 10918

    Welcome to your dream home! This beautifully renovated ranch-style house sits on a stunning 5-acre lot, offering privacy and tranquility amidst nature's beauty. Step inside to discover a tastefully updated interior featuring modern finishes and top-notch upgrades throughout. The spacious open-concept living areas are perfect for entertaining, and the gourmet kitchen boasts brand-new appliances

    Samuel Kohn eRealty Advisors, Inc

    84 Pine Hill Rd, Chester, NY 10918
  • 9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    /34

    $739,900

    • 5 Beds
    • 2.5 Baths
    • 3,124 Sq Ft

    9 Country Woods Dr, Chester, NY 10918

    Welcome to Country Woods, one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers over 3,100 square feet of comfortable living space. A wrap-around front porch invites you inside, where a two-story foyer and 9-foot ceilings create a bright and spacious feel. The formal living and dining rooms flow seamlessly into the kitchen, complete with

    Kimberly Starks Howard Hanna Rand Realty

    9 Country Woods Dr, Chester, NY 10918
  • 69 Cedar Pond Ln, Chester, NY 10918
    69 Cedar Pond Ln, Chester, NY 10918
    69 Cedar Pond Ln, Chester, NY 10918
    /93

    $1,975,000

    • 6 Beds
    • 7.5 Baths
    • 7,034 Sq Ft

    69 Cedar Pond Ln, Chester, NY 10918

    Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets.A three-story entry

    Emily Iason Four Seasons Sotheby's Int.

    69 Cedar Pond Ln, Chester, NY 10918
  • L31 Clarkson Rd, Chester, NY 12817
    L31 Clarkson Rd, Chester, NY 12817
    L31 Clarkson Rd, Chester, NY 12817
    /14

    $144,900

    • Land
    • 0.47 Acre
    • $308,298 per Acre

    L31 Clarkson Rd, Chester, NY 12817

    Build Your Adirondack Getaway on Loon Lake!Enjoy beach rights on beautiful Loon Lake with this just-under-half-acre lot, the perfect spot to create your own year-round retreat or seasonal escape. Whether you dream of summer days by the water, paddling and swimming, or cozy winter weekends in the mountains, this property offers an ideal starting point for your Adirondack lifestyle.

    Brooke Clark Four Seasons Sotheby's International Realty

    L31 Clarkson Rd, Chester, NY 12817
  • 70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    /23

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 1,357 Sq Ft

    70 Main St, Chester, NY 10918

    Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you

    Kassandra Mott Keller Williams Hudson Valley

    70 Main St, Chester, NY 10918
  • 5 Berkley Terrace, Monroe, NY 10950
    5 Berkley Terrace, Monroe, NY 10950
    5 Berkley Terrace, Monroe, NY 10950
    /24

    $530,000

    • 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
  • 8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    /11

    $375,000

    • Land
    • 4.9 Acres
    • $76,531 per Acre

    8 Camelback Rd, Chester, NY 10918

    Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY.The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets.This shovel-ready, fully approved, and engineered building lot features Belgian

    James Feldhaus eXp Realty

    8 Camelback Rd, Chester, NY 10918
  • 2 Dawn Ct, Chester, NY 10918
    2 Dawn Ct, Chester, NY 10918
    2 Dawn Ct, Chester, NY 10918
    /34

    $689,900

    • 4 Beds
    • 2.5 Baths
    • 3,092 Sq Ft

    2 Dawn Ct, Chester, NY 10918

    Spectacular 4 bedrooms, 2.5 bathrooms colonial in the very desirable Sugarloaf Heights. This magnificent home offers heavenly views right from your rear deck. You never have to leave home when you can step outside and enjoy your own personal refuge with a fully fenced-in yard that brings privacy to your in-ground pool. Home offers many recent upgrades which include updated kitchen, recess

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 203-6068

    2 Dawn Ct, Chester, NY 10918
  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /2

    $350,000

    • Land
    • 2 Acres
    • $175,000 per Acre

    220 Oxford Rd, Chester, NY 10918

    A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

    Chaim Weiss Exit Realty Venture

    220 Oxford Rd, Chester, NY 10918
  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    /23

    $430,000

    • 3 Beds
    • 1 Bath
    • 1,561 Sq Ft

    33 Meadow Ave, Chester, NY 10918

    One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

    Ernie Acampora River Realty Services, Inc.

    33 Meadow Ave, Chester, NY 10918
  • 12 Juniper Ln, Monroe, NY 10950
    12 Juniper Ln, Monroe, NY 10950
    12 Juniper Ln, Monroe, NY 10950
    /42

    $559,000

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft

    12 Juniper Ln, Monroe, NY 10950

    Welcome to this 4-bedroom, 3 full bath raised ranch offering a flexible and spacious layout designed for comfortable everyday living. Hardwood floors run throughout the main level, adding warmth and character to the home's living spaces. The primary bedroom features a private en-suite bath, creating a quiet and comfortable retreat. Three additional bedrooms provide plenty of room for family,

    Agent Photo

    Shaylene Neumann

    Houlihan Lawrence Inc.

    (329) 208-1641

    12 Juniper Ln, Monroe, NY 10950
  • 23 Renies Rd, Chester, NY 10918
    23 Renies Rd, Chester, NY 10918
    23 Renies Rd, Chester, NY 10918
    /35

    $690,000

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

    23 Renies Rd, Chester, NY 10918

    Escape to your own sanctuary in this stunning 3 bedroom 3 full bath contemporary cedar home, perfectly blending modern comfort with natural charm. Inside you'll find an open-concept layout with soaring ceilings, large windows, and natural wood finishes that create a warm, modern vibe. The spacious kitchen features stainless appliances, hickory cabinets and an island ideal for entertaining. Two

    Kristie Jacques Century 21 Full Service Realty

    23 Renies Rd, Chester, NY 10918
  • 0 Renies Rd, Chester, NY 10918
    0 Renies Rd, Chester, NY 10918
    0 Renies Rd, Chester, NY 10918
    /3

    $199,000

    • Land
    • 1.85 Acres
    • $107,568 per Acre

    0 Renies Rd, Chester, NY 10918

    Seize the opportunity to own this serene, buildable lot nestled in a quiet, desirable location. Perfect for your dream home. This parcel offers privacy, natural beauty, and close to everything! Convenient access yet tucked away for peace and quiet. Don’t miss out—schedule your visit today!

    Kristie Jacques Century 21 Full Service Realty

    0 Renies Rd, Chester, NY 10918
  • 32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    /8

    $849,900

    • 4 Beds
    • 2.5 Baths
    • 2,603 Sq Ft

    32 Mountainside Dr, Chester, NY 10918

    A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

    Karen Gauvin Our House Real Estate Group

    32 Mountainside Dr, Chester, NY 10918
  • 507 Bull Mill Rd, Chester, NY 10918
    507 Bull Mill Rd, Chester, NY 10918
    507 Bull Mill Rd, Chester, NY 10918
    /45

    $674,999

    • 5 Beds
    • 2.5 Baths
    • 3,115 Sq Ft

    507 Bull Mill Rd, Chester, NY 10918

    Welcome to this beautifully maintained colonial with a charming wrap-around front porch, set on 1.5 private acres within the sought-after Monroe-Woodbury School District. Offering over 3,100 square feet of living space, this 5-bedroom, 2.5-bath home blends timeless style with thoughtful design.Step inside the two-story foyer and you’ll find a bright, flowing layout designed for both

    Agent Photo

    Alison Orlando

    Keller Williams Hudson Valley

    (845) 385-2902

    507 Bull Mill Rd, Chester, NY 10918
  • 34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, Chester, NY 10918
    /8

    $699,990

    • 4 Beds
    • 3 Baths
    • 1,867 Sq Ft

    34 Mountainside Dr, Chester, NY 10918

    ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.).

    Karen Gauvin Our House Real Estate Group

    34 Mountainside Dr, Chester, NY 10918
  • 391 Bull Mill Rd, Chester, NY 10918
    391 Bull Mill Rd, Chester, NY 10918
    391 Bull Mill Rd, Chester, NY 10918
    /30

    $519,999

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    391 Bull Mill Rd, Chester, NY 10918

    Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular

    Agent Photo

    Alexandra Zinko

    Century 21 Realty Center

    (845) 412-9860

    391 Bull Mill Rd, Chester, NY 10918

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New York Orange County Chester

Real Estate & Homes for Sale in Chester, NY

Frequently Asked Questions

What is the average home price in Chester, NY?
Homes for sale in Chester, NY have an average home price of $615,791.
How many homes have sold over the last 12 months in Chester, NY?
129 homes have sold in Chester, NY over the last 12 months.
What are the most popular zip codes in Chester, NY?
The most popular zip codes in Chester, NY include 10918, 10990, 10950, 10924 and 10921.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $554,000. If you put a 20% down payment of $110,800 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $2,730 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $117K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, NY?
Chester, NY has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Greenwood Lake Elementary School, Scotchtown Avenue School and Warwick Valley High School. Browse all the schools in Chester, NY to learn more.

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 69 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, NY over the last 12 months is $526,000, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$526,000
Median Single Family Sale Price
$581,000
Median Townhouse Sale Price
$325,000
Median 2 Bedroom Sale Price
$299,950
Median 1 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$267
Number of Homes for Sale
37
Last 12 months Home Sales
129
Months of Supply
3.40
Median List Price
$554,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
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