5,275

Homes in ZIP Code 10918

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  • 3910 Whispering Hills, Chester, NY 10918
    3910 Whispering Hills, Chester, NY 10918
    3910 Whispering Hills, Chester, NY 10918
    /11

    $369,900

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

    3910 Whispering Hills, Chester, NY 10918

    Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley

    Agent Photo

    Randolph Rogers

    eXp Realty

    (845) 957-9249

    3910 Whispering Hills, Chester, NY 10918
  • 28 Academy Ave Unit 2, Chester, NY 10918
    28 Academy Ave Unit 2, Chester, NY 10918
    28 Academy Ave Unit 2, Chester, NY 10918
    /20

    $2,695 Per Month

    • 3 Beds
    • 1 Bath
    • 2,386 Sq Ft
    • Apartment for Rent

    28 Academy Ave Unit 2, Chester, NY 10918

    Available for Rent! Spacious 3-bedroom, 1-bath second-floor apartment located in the heart of Chester. This well-maintained unit features a finished attic, providing additional flexible living space perfect for a home office, playroom, or storage. Conveniently located close to shopping, restaurants, parks, schools, and major commuter routes. Enjoy all that the Village of Chester has to offer

    Agent Photo

    Ammar Iqbal

    eXp Realty

    (845) 493-3043

    28 Academy Ave Unit 2, Chester, NY 10918
  • 10 Damian Ct, Chester, NY 10918

    $1,225,000

    Sold Apr 17, 2026

    10 Damian Ct, Chester, NY 10918

    • 11 Beds
    • 6.5 Baths
    • 4,327 Sq Ft
    • Built 2004

    Last Sold Summary

    • 11% Below List Price
    • $283/SF
    • 47 Days On Market

    Current Estimated Value $1,278,785

    Last Listing Agent Elimelech Kremer MS Realty Group USA, Inc

    10 Damian Ct, Chester, NY 10918
  • 5 Roggia Rd, Chester, NY 10918
    5 Roggia Rd, Chester, NY 10918
    5 Roggia Rd, Chester, NY 10918
    /32

    $450,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    5 Roggia Rd, Chester, NY 10918

    Welcome to this spacious and versatile home nestled at a dead end st. in the desirable town of Chester. Offering an abundance of living space, this property is ideal for those seeking privacy, comfort, flexibility, and room to grow. The home features a functional layout with generously sized bedrooms, a bright and inviting living area, and a well-appointed kitchen designed for everyday living and

    Agent Photo

    Nazma Sooknanan

    Nazma Real Estate LLC

    (845) 606-3972

    5 Roggia Rd, Chester, NY 10918
  • 5 Laroc Rd, Chester, NY 10918
    5 Laroc Rd, Chester, NY 10918
    5 Laroc Rd, Chester, NY 10918
    /7

    $4,000 Per Month

    • 6 Beds
    • 2 Baths
    • House for Rent

    5 Laroc Rd, Chester, NY 10918

    Property Id: 1802590Stunning Home with Expansive Yard and Abundant Storage!Welcome to this incredible property, boasting a massive backyard perfect for outdoor entertaining! Enjoy warm weather gatherings on the spacious deck, and make the most of the two sheds for storing tools, equipment, and more.This fantastic home also features:- 1 garage for secure vehicle

    (845) 572-1279

    5 Laroc Rd, Chester, NY 10918
  • 25 Sugarloaf Mountain Rd, Chester, NY 10918

    $635,000

    Sold Jun 22, 2026

    25 Sugarloaf Mountain Rd, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft
    • Built 1999

    Last Sold Summary

    • $325/SF
    • 29 Days On Market

    Current Estimated Value $627,942

    Last Listing Agent Frank Muccari Cronin & Company Real Estate

    25 Sugarloaf Mountain Rd, Chester, NY 10918
  • 53 Gibson Hill Rd, Chester, NY 10918
    53 Gibson Hill Rd, Chester, NY 10918
    53 Gibson Hill Rd, Chester, NY 10918
    /48

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 5,312 Sq Ft

    53 Gibson Hill Rd, Chester, NY 10918

    Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene

    Agent Photo

    Ammar Iqbal

    eXp Realty

    (845) 328-2396

    53 Gibson Hill Rd, Chester, NY 10918
  • 1358 Kings Hwy, Chester, NY 10918
    1358 Kings Hwy, Chester, NY 10918
    1358 Kings Hwy, Chester, NY 10918
    /12

    $2,100 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1358 Kings Hwy, Chester, NY 10918

    Quintessential Sugar Loaf Cottage, newly renovated inside, featuring expansive windows in the front living space, new LVP Flooring throughout, new kitchen with plenty of cabinetry, open shelving and a bar style countertop for extra prep space or entertaining. The space also features an extra large pantry and a new spacious sunlit bathroom with stand up shower. First bedroom is on the main floor

    Christine DeLuca Corcoran Baer & McIntosh

    1358 Kings Hwy, Chester, NY 10918
  • 2912 Whispering Hills, Chester, NY 10918

    $320,000

    Sold Mar 11, 2026

    2912 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Above List Price
    • $295/SF
    • 19 Days On Market

    Current Estimated Value $312,730

    Last Listing Agent Rebecca Matta-Candela Keller Williams Realty

    2912 Whispering Hills, Chester, NY 10918
  • 7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    /48

    $730,000

    $10K PRICE DROP Pending
    • 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
  • 4 Wright Rd, Chester, NY 10918
    4 Wright Rd, Chester, NY 10918
    4 Wright Rd, Chester, NY 10918
    /43

    $3,795 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft
    • Spacious Mountain View Home in Sugar Loaf – Pet Friendly & Move-In Ready

    4 Wright Rd, Chester, NY 10918

    Welcome to this beautifully maintained home nestled in a quiet, family-friendly neighborhood with stunning mountain views. Located less than a 10-minute walk from Valkyrie Coffee, the Indigo Collective salon, and the heart of Sugar Loaf, you'll enjoy easy access to unique shops, restaurants, and local attractions. The village's annual May festival transforms the streets into a vibrant

    4 Wright Rd, Chester, NY 10918
  • 2104 Whispering Hills, Chester, NY 10918

    $260,000

    Sold Mar 11, 2026

    2104 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1984

    Last Sold Summary

    • 13% Below List Price
    • $195/SF
    • 24 Days On Market

    Current Estimated Value $277,956

    Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

    2104 Whispering Hills, Chester, NY 10918
  • 2323 Whispering Hills Unit 213, Chester, NY 10918
    2323 Whispering Hills Unit 213, Chester, NY 10918
    2323 Whispering Hills Unit 213, Chester, NY 10918
    /38

    $327,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft

    2323 Whispering Hills Unit 213, Chester, NY 10918

    Rare Opportunity in Whispering Hills! Discover this uniquely reimagined end-unit condo, expertly converted from a three-bedroom layout into a sprawling, sun-drenched two-bedroom retreat. This home is a masterclass in modern comfort, featuring eight brand-new Andersen windows and a matching Andersen door (2025) that perfectly frames spectacular, far-reaching horizon views. Much of the interior has

    Agent Photo

    Luanne McGann

    Century 21 Full Service Realty

    (845) 516-8714

    2323 Whispering Hills Unit 213, Chester, NY 10918
  • 66 Murray Dr, Chester, NY 10918
    66 Murray Dr, Chester, NY 10918
    66 Murray Dr, Chester, NY 10918
    /37

    $5,300 Per Month

    • 4 Beds
    • 2 Baths
    • 3,412 Sq Ft
    • House for Rent

    66 Murray Dr, Chester, NY 10918

    Welcome to Refined Living — A Contemporary Ranch renovated for Elevated Year-Round Living with ease, entertainment and privacy! Perfectly set on 1.2 acres with Mountain views just one hour from New York City, this FULLY FURNISHED and fully equipped 3,412 square-foot home provides the convenience of one level living blended with the luxury of upscale design features. The bright and open Foyer

    Tehillah Deslandes Howard Hanna Rand Realty

    66 Murray Dr, Chester, NY 10918
  • 189 Creamery Pond Rd, Chester, NY 10918

    $735,000

    Sold Jul 21, 2025

    189 Creamery Pond Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,980 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Above List Price
    • $247/SF
    • 19 Days On Market

    Current Estimated Value $732,824

    Last Listing Agent Patricia Brady Keller Williams Realty

    189 Creamery Pond Rd, Chester, NY 10918
  • 16 Lori Ln, Chester, NY 10918
    16 Lori Ln, Chester, NY 10918
    16 Lori Ln, Chester, NY 10918
    /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

    (845) 493-2930

    16 Lori Ln, Chester, NY 10918
  • 1907 Whispering Hills, Chester, NY 10918
    1907 Whispering Hills, Chester, NY 10918
    1907 Whispering Hills, Chester, NY 10918
    /16

    $2,670 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Townhouse for Rent

    1907 Whispering Hills, Chester, NY 10918

    Welcome home to the highly desirable Whispering Hills Community in Chester School District. This rental features 2 bedrooms, 1.5 bathrooms, and a two car garage for extra storage. Enjoy a cozy fireplace in your spacious living room, kitchen with tile flooring for easy cleanup, and a patio right outside your front sliding doors for summer night enjoyment after taking a dip in the community pool.

    Erin Hansford Stonewall Realty Group LLC

    1907 Whispering Hills, Chester, NY 10918
  • 3308 Whispering Hills Dr, Chester, NY 10918

    $290,000

    Sold Apr 09, 2026

    3308 Whispering Hills Dr, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $271/SF
    • 39 Days On Market

    Current Estimated Value $293,327

    Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

    3308 Whispering Hills Dr, Chester, NY 10918
  • 1 N Hudson St Unit N, Chester, NY 10918
    1 N Hudson St Unit N, Chester, NY 10918
    1 N Hudson St Unit N, Chester, NY 10918
    /38

    $499,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,778 Sq Ft

    1 N Hudson St Unit N, Chester, NY 10918

    Welcome home to 1 North Hudson Street — a meticulously maintained Cape Cod that is truly beautiful inside and out. From the moment you arrive, the curb appeal speaks for itself. Lush, manicured grounds frame this charming brick and white-sided Cape Cod, where mature trees, vibrant landscaping, and a stunning bluestone patio set the stage for a lifestyle of comfort and ease. Whether you're hosting

    Agent Photo

    Alison Orlando

    KW Hudson Valley Untied

    (845) 407-8986

    1 N Hudson St Unit N, Chester, NY 10918
  • 168 Pine Hill Rd Unit 1, Chester, NY 10918
    168 Pine Hill Rd Unit 1, Chester, NY 10918
    168 Pine Hill Rd Unit 1, Chester, NY 10918
    /13

    $2,900 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Apartment for Rent

    168 Pine Hill Rd Unit 1, Chester, NY 10918

    INLCUDES UTILITIES, HEAT & HOT WATER!! Welcome to Unit #1 of 168 Pine Hill Rd. This lovely three bedroom, 1.5 bath apartment offers beautiful views with lots of natural light, an eat in kitchen with stainless steel refrigerator and stove (gas) as well as washer and dryer for added convenience, 3 nice sized bedroom. Easy access- no steps to enter the two level unit. There is a wrap around driveway

    Claudia Lepore Keller Williams Realty

    168 Pine Hill Rd Unit 1, Chester, NY 10918
  • 98 High St, Chester, NY 10918

    $323,500

    Sold Aug 11, 2025

    98 High St, Chester, NY 10918

    • 4 Beds
    • 1.5 Baths
    • 1,360 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 35 Days On Market

    Current Estimated Value $348,670

    Last Listing Agent Zachary Foley eXp Realty

    98 High St, Chester, NY 10918
  • 0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    /4

    $350,000

    $50K PRICE INCREASE
    • Land
    • 5.1 Acres
    • $68,627 per Acre

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

    Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

    Agent Photo

    Theresa Powers

    Keller Williams Realty

    (845) 713-9754

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
  • 82 High St Unit 5, Chester, NY 10918
    82 High St Unit 5, Chester, NY 10918
    82 High St Unit 5, Chester, NY 10918
    /10

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    82 High St Unit 5, Chester, NY 10918

    Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of

    Lynda Hoss Weichert Realtors

    82 High St Unit 5, Chester, NY 10918
  • 44 Cedar Pond Ln, Chester, NY 10918

    $610,000

    Sold Mar 12, 2026

    44 Cedar Pond Ln, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,876 Sq Ft
    • Built 1991

    Last Sold Summary

    • 2% Above List Price
    • $325/SF
    • 48 Days On Market

    Current Estimated Value $638,624

    Last Listing Agent Ammar Iqbal eXp Realty

    44 Cedar Pond Ln, Chester, NY 10918
  • 1 Oakland Ave, Chester, NY 10918
    1 Oakland Ave, Chester, NY 10918
    1 Oakland Ave, Chester, NY 10918
    /50

    $1,000,000

    • 4 Beds
    • 2.5 Baths
    • 3,955 Sq Ft

    1 Oakland Ave, Chester, NY 10918

    Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    (845) 237-3716

    1 Oakland Ave, Chester, NY 10918
  • 15 Old Dominion Rd, Blooming Grove, NY 10914
    15 Old Dominion Rd, Blooming Grove, NY 10914
    15 Old Dominion Rd, Blooming Grove, NY 10914
    /46

    $3,995 Per Month

    • 4 Beds
    • 2.5 Baths
    • 3,112 Sq Ft
    • House for Rent

    15 Old Dominion Rd, Blooming Grove, NY 10914

    With over 3,000 sq ft of refined living space set on 7.5 pristine, level acres, this sun-drenched Colonial offers a rare opportunity for luxury rental living with exceptional privacy, scale, and serenity. A sweeping approach sets the tone, revealing open skies, manicured grounds, and long pastoral views that create an immediate sense of calm and exclusivity. Inside, the home unfolds with a

    Lazar Schvimmer Mount Realty

    15 Old Dominion Rd, Blooming Grove, NY 10914
  • 2812 Whispering Hills Unit 577, Chester, NY 10918

    $320,000

    Sold Feb 13, 2026

    2812 Whispering Hills Unit 577, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Above List Price
    • $295/SF
    • 22 Days On Market

    Current Estimated Value $314,539

    Last Listing Agent Kathy White Exit Realty Connections

    2812 Whispering Hills Unit 577, Chester, NY 10918
  • 2722 Whispering Hills Unit 542, Chester, NY 10918
    2722 Whispering Hills Unit 542, Chester, NY 10918
    2722 Whispering Hills Unit 542, 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
  • 1502 Whispering Hills, Chester, NY 10918
    1502 Whispering Hills, Chester, NY 10918
    1502 Whispering Hills, Chester, NY 10918
    /33

    $2,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Townhouse for Rent

    1502 Whispering Hills, Chester, NY 10918

    Beautiful 3 bedrooms and 2 baths in Whispering Hills. Updated and freshly painted. New carpeting. Fire place and vaulted ceiling.Enjoy resort style living with pools, tennis courts, club house, gym, playgrounds and basketball courts. Located close to major highways for an easy commute. Additional Information: ParkingFeatures:1 Car Attached,Storage: Garage,

    Nikki Grzegorzewski Keller Williams Realty

    1502 Whispering Hills, Chester, NY 10918
  • 4703 Whispering Hills Dr, Chester, NY 10918

    $382,000

    Sold Jan 12, 2026

    4703 Whispering Hills Dr, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1991

    Last Sold Summary

    • 4% Above List Price
    • $287/SF
    • 61 Days On Market

    Current Estimated Value $370,987

    Last Listing Agent Erin Connolly-Frontino Artisan Realty

    4703 Whispering Hills Dr, Chester, NY 10918

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