27

Chester, NY Homes for Sale under $400,000

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  • /18

    $399,000

    • Land
    • 46 Acres
    • $8,674 per Acre

    492 Black Meadow Rd, Chester, NY 10918

    Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching,

    Agent Photo

    Ewa Kusmierek

    eXp Realty

    492 Black Meadow Rd, Chester, NY 10918
  • /22

    $329,000

    • 2 Beds
    • 1.5 Baths
    • 1,294 Sq Ft

    4118 Whispering Hills, Chester, NY 10918

    Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer flooring on the main level. Wood burning fireplace in the spacious living room. Sliding door from the dining area to the patio. The primary bedroom with tall vaulted ceilings has a large walk-in closet with custom

    Agent Photo

    Joseph Paoli

    Howard Hanna Rand Realty

    4118 Whispering Hills, Chester, NY 10918
  • /35

    $399,999

    Coming Soon Pre-Foreclosure
    • 4 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    241 Meadow Ave, Chester, NY 10918

    Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship.Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming

    Agent Photo

    Chativa Bowen

    Keller Williams Realty

    241 Meadow Ave, Chester, 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

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
  • /23

    $119,995

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

    1.3 Cobble Creek Rd, 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

    1.3 Cobble Creek Rd, Chester, NY 12853
  • /48

    $400,000

    • 3 Beds
    • 2.5 Baths
    • 1,699 Sq Ft

    174 Eagleton Dr Unit 17D, Monroe, NY 10950

    Welcome to this beautifully maintained end-unit townhouse offering serene lakefront living and an exceptional array of community amenities, including a pool, playground, basketball & tennis courts. Freshly painted throughout the first floor and enhanced with elegant crown molding, this home showcases quality finishes and pride of ownership. Attractive vinyl plank flooring extends through the

    Donna Gennaro Howard Hanna Rand Realty

    174 Eagleton Dr Unit 17D, Monroe, NY 10950
  • /23

    $390,000

    • 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
  • /50

    $280,000

    $161K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 2,016 Sq Ft

    815 Craigville Rd, Chester, NY 10918

    We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property.Originally built

    MaryBeth O'Hara Ellis Sotheby's Intl Realty

    815 Craigville Rd, Chester, NY 10918
  • /18

    $189,000

    • Land
    • 3.14 Acres
    • $60,191 per Acre

    2 Dixon Rd, Chester, NY 12817

    Fish, Paddle, Build! Own an incredible 509' of private frontage on the Schroon River, complete with your very own mini island and over 3 buildable acres to create your Adirondack escape. Driveway is already in place with power available at the road, making your future plans even easier. Located just south of the dam (no direct access to Schroon Lake), this peaceful setting is ideal for fishing,

    Angie Mead Gallo Realty ADK Inc

    2 Dixon Rd, Chester, NY 12817
  • /25

    $159,000

    $6K PRICE DROP
    • Land
    • 31,798 Sq Ft
    • $217,808 per Acre

    L3 Emily Ln Unit Lot 3, Chester, NY 12817

    Rare opportunity to own a .73-acre vacant building lot with deeded dock and lake rights on beautiful Loon Lake. Located within the small and intimate Lakemont Association--featuring just 8 members--this property offers a unique chance to secure one of the few lake rights parcels with guaranteed docking. The lot is level and has already undergone selective clearing, making it an ideal canvas for

    Saraha Millington Gallo Realty ADK Inc

    L3 Emily Ln Unit Lot 3, Chester, NY 12817
  • /13

    $206,000

    $69K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,240 Sq Ft

    503 Mountain Laurel Dr, Monroe, NY 10950

    Peaceful country living in this two-story center lakefront unit with full basement located in Windridge community. Enjoy incredible mountain views from this large private Townhome. Primary bedroom on upper level with walk in closet and large sitting area which can be used as home office. Slider to rear patio with beautiful lake views!! Large living and dining area. Beautiful quiet complex close

    Margaret Galatro ARC Realty 1 in Sales

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

    $299,000

    $41K PRICE DROP
    • 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
  • /20

    $399,000

    • 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
  • /9

    $275,000

    • Land
    • 7.53 Acres
    • $36,521 per Acre

    L1.34 McPhillips Pine Ln, Chester, NY 12817

    If you are looking for an ultra private lot with access (dock and beach rights) to one of the pristine exclusive lakes in the Adirondacks, you found it. Friends Lake is the home to cool people and is private, jet-ski free, with a water ski course and simply no nonsense. Only 2O minutes to Lake George and Gore Mountain Ski Area. About 4 hours from NYC and 2.5 hours to Montreal. Saratoga Springs is

    Michael Lynch Coldwell Banker Prime Properties

    L1.34 McPhillips Pine Ln, Chester, NY 12817
  • /34

    $349,999

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

    3414 Whispering Hills, Chester, NY 10918

    Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with

    Kevin Grier KW Hudson Valley United

    3414 Whispering Hills, 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 MS Realty Group USA, Inc

    220 Oxford 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
  • /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
  • /14

    $129,000

    $30K PRICE DROP
    • Land
    • 20,473 Sq Ft
    • $274,468 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
  • /26

    $379,900

    $45K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft

    7 Hambletonian Ave, Chester, NY 10918

    Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay

    William Scolza HomeSmart Homes & Estates

    7 Hambletonian Ave, Chester, NY 10918
  • /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
  • /35

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,086 Sq Ft

    2604 Whispering Hills, Chester, NY 10918

    Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improvements completed within the last five years include new windows, furnace, water heater, washer, and dryer, providing peace of mind for the new owner. The bright, spacious floor plan is perfect for everyday living and

    Sonia Gonzalez HomeSmart Homes & Estates

    2604 Whispering Hills, 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
  • /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
  • /26

    $275,000

    • 2 Beds
    • 1 Bath
    • 1,062 Sq Ft

    804 Swan Hollow Rd, Monroe, NY 10950

    Welcome Home! Well maintained two bedroom unit with lake and mountain views. Spacious living room with access to a private balcony. Eat in kitchen has updated counter tops and new appliances. Both bedrooms have ample closet space. Windridge is a quiet community conveniently located minutes from town. Great commuter location. Amenities include pool, playground, tennis and basketball courts,

    Valerie Quinn Keller Williams Realty

    804 Swan Hollow Rd, Monroe, NY 10950
  • /33

    $185,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    28 Olmstedville Rd, Chester, NY 12817

    Older home in a completely private location - in the center of a Hamlet. Trees and bushes make the home invisible from the road. The back border is Town land with Public beach area on Trout Brook Good for canoeing. Covered porch is on two sides of the house. The interior has beautiful real wood floors. Main level is kitchen, dining room, living room, full bath and laundry area. Upstairs are 3

    Heidemarie Lane Big Hat Realty

    28 Olmstedville Rd, Chester, NY 12817
  • /4

    $389,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,062 Sq Ft

    185 Oxford Rd, Chester, NY 10918

    Welcome to 185 Oxford Rd, Chester! •••••This charming and updated 3-bedroom Ranch home is now available for $389,000. Offering 1,062 sqft of comfortable one-level living on a generous 0.95-acre lot in the Town of Blooming Grove, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful hardwood flooring, a cathedral ceiling,

    William Philip Keller Williams Hudson Valley

    185 Oxford Rd, Chester, NY 10918

Home Price Trends

Median Sale Price
$498,000
Median Single Family Sale Price
$660,000
Median Townhouse Sale Price
$329,500
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$275
Number of Homes for Sale
57
Last 12 months Home Sales
91
Months of Supply
7.50
Median List Price
$589,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-7%
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