74

Chester, NY Homes for Sale with Acreage

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  • /8

    $39,500

    • Land
    • 1.82 Acres
    • $21,703 per Acre

    34 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    34 Carriage Knolls Rd, Chester, NY 12817
  • /3

    $150,000

    • Land
    • 5.14 Acres
    • $29,183 per Acre

    36 Fawn Ridge Rd, Chester, NY 12817

    Must see building site which has panoramic views overlooking Gore Mountain Range to the North but possible 360 degree Mountain View's with some clearing necessary.

    John Palermo John R. Palermo

    36 Fawn Ridge Rd, Chester, NY 12817
  • /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
  • /33

    $89,500

    • Land
    • 12.79 Acres
    • $6,998 per Acre

    3-4 Adirondack Heights Rd, Chester, NY 12817

    Seller financing now available. 12.79 acres of mixed forest and wetlands. Perc tests and engineered plot plans have been completed. APA approved building sites with well & septic locations identified. (2-lots can each be built upon or just have one large lot) Power at the road pedestal box. Tons of hemlock, spruce, and pine trees throughout. Close to Chestertown, 20-minutes to Gore Mountain or

    Walter Swartz Gallo Realty ADK Inc

    3-4 Adirondack Heights Rd, Chester, NY 12817
  • /43

    $949,000

    • 4 Beds
    • 2.5 Baths
    • 3,332 Sq Ft

    19 Bull Mine Rd, Chester, NY 10918

    Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

    James Cosenza BHG Real Estate Green Team

    19 Bull Mine Rd, Chester, NY 10918
  • /8

    $869,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    10 Well Sweep Ln, Chester, NY 10918

    Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

    Carla Terranova Keller Williams Realty

    10 Well Sweep Ln, Chester, NY 10918
  • /50

    $1,725,000

    • 4 Beds
    • 2.5 Baths
    • 3,348 Sq Ft

    20 Goshen Rd, Chester, NY 10918

    THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

    Ramanjit Dhanoa eXp Realty

    20 Goshen Rd, Chester, NY 10918
  • /35

    $999,999

    • 5 Beds
    • 2.5 Baths
    • 4,772 Sq Ft

    2 Garnett Hill Rd, Chester, NY 10918

    A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

    Rachel Baruchov Platinum Realty Associates

    2 Garnett Hill Rd, Chester, NY 10918
  • /50

    $725,000

    • 6 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    487 Black Meadow Rd, Chester, NY 10918

    A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

    Dominic Santagato Joseph Baratta Company Realty

    487 Black Meadow Rd, Chester, NY 10918
  • /19

    $74,900

    $19K PRICE INCREASE
    • Land
    • 4.05 Acres
    • $18,494 per Acre

    85 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    85 Carriage Knoll Rd, Chester, NY 12817
  • /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
  • /22

    $68,900

    $19K PRICE INCREASE
    • Land
    • 3.37 Acres
    • $20,445 per Acre

    86 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    86 Carriage Knoll Rd, Chester, NY 12817
  • /10

    $119,995

    • Land
    • 30.95 Acres
    • $3,877 per Acre

    1.3 Cobble Creek Rd Unit 3, Chester, NY 12853

    Rarely does a property combine privacy, natural beauty and convenience as well as this 30-acre tract in Chester, New York. Located on a year-round town road, the land offers easy access while maintaining the peaceful feeling of a true Adirondack forest retreat. Several elevated APA-approved building sites are scattered throughout the property, offering ideal locations for an off-grid cabin or

    Marc Christmas CHRISTMAS AND ASSOCIATES INC

    1.3 Cobble Creek Rd Unit 3, Chester, NY 12853
  • /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
  • /2

    $1,700,000

    • Land
    • 46.5 Acres
    • $36,559 per Acre

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914

    Incredible opportunity to own approximately 55 acres of land being offered as a package with two adjoining parcels. This expansive property offers endless potential for investors, builders, or those seeking a private estate or recreational retreat. Preliminary information suggests the property may have the potential for approximately 400,000 square feet of warehouse space. Both parcels are being

    Lazar Schvimmer Mount Realty

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
  • /33

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 1,730 Sq Ft

    107 Pine Hill Rd, Chester, NY 10918

    Something Special! See It and Fall in Love! A pavered walkway welcomes you to this curb appealing 3 BR, 2 1/2 bath Stucco Cape that is privately set on 1.1 acres! Open and sun filled with lots of windows! So many updates! Large primary BR and luxurious bath are on the 1 st floor! Open LR and DR have sliders to private deck to enjoy pastoral views and views of Sugar Loaf Mountain! 2 large BRs with

    Linda Clark Hudson Valley Griffith

    107 Pine Hill Rd, Chester, NY 10918
  • /23

    $76,900

    $14K PRICE INCREASE
    • Land
    • 5.1 Acres
    • $15,078 per Acre

    112 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    112 Carriage Knoll Rd, Chester, NY 12817
  • /10

    $37,500

    • Land
    • 1.62 Acres
    • $23,148 per Acre

    60 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for

    Walter Swartz Gallo Realty ADK Inc

    60 Carriage Knolls Rd, Chester, NY 12817
  • /49

    $785,000

    $14K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,403 Sq Ft

    4 Debbie Ct, Chester, NY 10918

    Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the

    Joseph Rosenfeld Flag Realty Group

    4 Debbie Ct, Chester, NY 10918
  • /25

    $125,000

    • Land
    • 13.33 Acres
    • $9,377 per Acre

    L9 Byrd Pond, Chester, NY 12853

    Open walking trail around the property and very easy to navigate. Private 13+ acre building parcel just minutes from Gore Mountain and the conveniences of North Creek. The land is gently sloping with a roughed-in driveway/road already leading in from Bird Pond Road, offering a great head start for future access and site planning. Several attractive building locations can be found throughout the

    Walter Swartz Gallo Realty ADK Inc

    L9 Byrd Pond, Chester, NY 12853
  • /25

    $78,900

    $14K PRICE INCREASE
    • Land
    • 5.76 Acres
    • $13,698 per Acre

    106 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    106 Carriage Knoll Rd, Chester, NY 12817
  • /50

    $599,000

    Open Sun 1PM - 2PM $251K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,120 Sq Ft

    558 Pine Hill Rd, Chester, NY 10918

    Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

    Charnie Guttmann eRealty Advisors, Inc

    558 Pine Hill Rd, Chester, NY 10918
  • /35

    $675,000

    $40K PRICE DROP
    • 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'Altiiio Coldwell Banker Choice Prop.

    335 Laroe Rd, Chester, NY 10918
  • /2

    $299,000

    $51K PRICE DROP
    • Land
    • 5.7 Acres
    • $52,456 per Acre

    552 Pine Hill Rd, Chester, NY 10918

    Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

    Charnie Guttmann eRealty Advisors, Inc

    552 Pine Hill Rd, Chester, NY 10918
  • /23

    $68,900

    $19K PRICE INCREASE
    • Land
    • 3.05 Acres
    • $22,590 per Acre

    82 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    82 Carriage Knoll Rd, Chester, NY 12817
  • /24

    $74,000

    $10K PRICE DROP
    • Land
    • 2.84 Acres
    • $26,056 per Acre

    38 Granite Ridge Rd, Chester, NY 12817

    Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

    Nicholas Khachadourian KW Platform

    38 Granite Ridge Rd, Chester, NY 12817
  • /7

    $39,500

    • Land
    • 2.38 Acres
    • $16,597 per Acre

    22 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    22 Carriage Knolls Rd, Chester, NY 12817
  • /16

    $37,500

    • Land
    • 2 Acres
    • $18,750 per Acre

    13 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    13 Carriage Knolls Rd, Chester, NY 12817
  • /39

    $799,900

    Open Sun 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,715 Sq Ft

    176 Beverly Rd, Chester, NY 10918

    Welcome to 176 Beverly Road, Colonial-style nestled on 2.5 beautifully landscaped acres in the highly sought-after Warwick Valley School District. From the moment you arrive, you'll appreciate the home's curb appeal featuring custom stone entrance pillars with illuminated house numbers, a beautifully inlaid driveway address, professionally landscaped grounds accented by natural stone and

    Jocelyn Rivera

    176 Beverly Rd, Chester, NY 10918
  • /50

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 4,281 Sq Ft

    22 Goshen Rd, Chester, NY 10918

    Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on

    Martha Randazzo Howard Hanna Rand Realty

    22 Goshen Rd, Chester, NY 10918
  • /16

    $65,000

    • Land
    • 1 Acre
    • $65,000 per Acre

    888 Landon Hill Rd, Chester, NY 12817

    One acre building lot. Property is cleared for building, 200 amp electric service installed and a point well on the property. There is currently a 14x40 ''tiny home'' on the property that can be purchased separately or the seller will remove. Minutes from Pottersville, close to Chestertown and Schroon Lake. Appx 20 mins to Gore Mnt Ski Center, 15 mins to Schroon Lake and only 10 mins from Loon

    Kelli May Better Way Realty

    888 Landon Hill Rd, Chester, NY 12817
  • /46

    $635,000

    Open Sun 2PM - 4PM
    • 4 Beds
    • 3 Baths
    • 3,636 Sq Ft

    10 Hidden Dr, Monroe, NY 10950

    Tucked away on over an acre with serene lake views and deeded lake rights, this spacious Monroe retreat offers the perfect blend of privacy, comfort, and lifestyle. Wake up to natural light pouring through oversized windows and start your day on the deck overlooking the water. Inside, you’ll find 3/4 generously sized bedrooms and 3 full baths, along with an updated kitchen and baths that bring a

    rosemary mcginn Century 21 Full Service Realty

    10 Hidden Dr, Monroe, NY 10950
  • /49

    $999,900

    $200K PRICE DROP
    • 4,032 Sq Ft

    206 Greycourt Rd, Chester, NY 10918

    INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly

    Frank Muccari Cronin & Company Real Estate

    206 Greycourt Rd, Chester, NY 10918

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