Chester, NY Homes

/35
$210,000 Sold Jun 09, 2025
- 1,296 Sq Ft
- $162/SF
- 165 Days On Market
- 3 Beds
- 1 Bath
- Built 1995
7823 State Route 9, Chester, NY 12860

Looking for the perfect getaway close to Gore Mountain and all the Adirondacks has to offer? If so, this could be the place for you. Enjoy the back deck and listen to the babbling creek that runs through the property. This vacation home is being sold fully furnished, you have nothing to do but start your time away! Currently being used as a successful Airbnb with excellent rental history. Well

Vickie Reed Hunt ERA

7823 State Route 9, Chester, NY 12860

Est $689,622 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,861 Sq Ft
8 Valerie Dr, Chester, NY 10918

8 Valerie Dr, Chester, NY 10918

/2
$57,500
- Land
- 1.73 Acres
- $33,237 per Acre
L37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chester, NY 12817

This property has beach rights to two separate beaches. HOA Fee includes maintenance of beaches and road.Blue Bay Road is a Private Road.

John Palermo John R. Palermo

L37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chester, NY 12817
$800,000 Sold Jun 06, 2025
- 3,418 Sq Ft
- $234/SF
- 110 Days On Market
- 5 Beds
- 4 Baths
- Built 1978
118 Murray Dr, Chester, NY 10918

Nestled on 2.8 acres of lush, mature landscaping that borders the serene Goosepond Mountain State Park, this custom-designed contemporary ranch showcases a timeless blend of materials, with stone and brick construction lending both character and durability. Crafted by its original owners with meticulous attention to detail, the home offers a harmonious connection to its natural surroundings. A

Brian Caplicki Keller Williams Hudson Valley

118 Murray Dr, Chester, NY 10918

Est $681,458 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,904 Sq Ft
3 Stacey Ln, Chester, NY 10918

3 Stacey Ln, Chester, NY 10918

/20
$169,500
- Land
- 23 Acres
- $7,500 per Acre
L2 Friends Lake Rd, Chester, NY 12817

Seller financing now available with decent deposit and good credit. Previously approved 4-lot subdivision with beach rights to Murphy Beach on Friends Lake. 8.6 acre lot, 7.5 acre lot, 3.2 acre lot, and a 3 acre lot. Rough house and septic locations have been approved. (reference survey map) Possible views from the upper areas of the property with some select clearing. Make arrangements to walk

Walter Swartz Gallo Realty ADK Inc

L2 Friends Lake Rd, Chester, NY 12817
$290,000 Sold Jun 05, 2025
- 1,118 Sq Ft
- $259/SF
- 30 Days On Market
- 2 Beds
- 1 Bath
- Built 1989
4401 Whispering Hills Dr, Chester, NY 10918

Move-in ready, this attractive two-bedroom, one-bath townhouse with attached one car garage is located in the sought-after Whispering Hills Community of Chester. This second-floor end unit features hardwood floors in the main living areas, a vaulted ceiling, and inviting wood-burning fireplace. A sliding door off the living room opens to a private deck, perfect for relaxing. The kitchen,

Annmarie Kovacs Howard Hanna Rand Realty

4401 Whispering Hills Dr, Chester, NY 10918

Est $578,236 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,080 Sq Ft
56 Goosepond Mountain Rd, Chester, NY 10918

56 Goosepond Mountain Rd, Chester, NY 10918

/16
$59,900
- Land
- 1.89 Acres
- $31,693 per Acre
71 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

71 Carriage Knoll Rd, Chester, NY 12817
$960,000 Sold Jun 05, 2025
- 5,312 Sq Ft
- $181/SF
- 45 Days On Market
- 5 Beds
- 4 Baths
- Built 2010
53 Gibson Hill Rd, Chester, NY 10918

This house was built custom. You won't find another house like this one. Total privacy with this spectacular home sits in the middle of 3.1 mature acres which includes a beautiful natural waterfall. Surrounded by 400 plus acres of state owned land that can never be developed. Hike from your backyard to the Appalachian trial. Grand entryway with cathedral ceilings and heated marble floors.

Roxanne Hartman Timothy W. Kramer

53 Gibson Hill Rd, Chester, NY 10918

Est $759,494 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,740 Sq Ft
149 Creamery Pond Rd, Chester, NY 10918

149 Creamery Pond Rd, Chester, NY 10918

/18
$74,900
- Land
- 4.17 Acres
- $17,962 per Acre
77 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

77 Carriage Knoll Rd, Chester, NY 12817
/12
$189,500 Sold Jun 02, 2025
- Land
- 97 Acres
- $1,948 per Acre
- 11 Days On Market
L47 Cobble Creek Rd, Chester, NY 12853

Must see property with endless opportunity. 97+ acres with mature timber including close to 40 acres of Maple. Enjoy all your recreational adventures. Dedicated logging road(built wide enough for two vehicles in some places, where needed). Great views of the pond and mountain. Located minutes from Gore Mountain Ski Area, Lake George and the Adirondacks. Build your dream home, enjoy privacy,

Sara Gallipo-Sammis Century 21 - Adirondacks

L47 Cobble Creek Rd, Chester, NY 12853

Est $692,105 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,436 Sq Ft
169 Creamery Pond Rd, Chester, NY 10918

169 Creamery Pond Rd, Chester, NY 10918

/18
$74,900
- 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
$415,000 Sold May 30, 2025
- 1,144 Sq Ft
- $363/SF
- 16 Days On Market
- 3 Beds
- 1 Bath
- Built 1978
18 Miller Dr, Chester, NY 10918

**(10-12 Cancelled- Saturday 4/12 due to weather)** Nestled on a quiet cul-de-sac in the heart of Chester Village, this meticulously maintained 3-bedroom ranch offers all the right elements you're looking for—paired with a village neighborhood location you simply can't beat. With hardwood floors in excellent condition hidden beneath the carpeting, a spacious eat-in kitchen, and the warmth of a

Jennifer DiCostanzo RE/MAX Town & Country

18 Miller Dr, Chester, NY 10918

Est $582,091 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,136 Sq Ft
7 Mount Ridge Ct, Monroe, NY 10950

7 Mount Ridge Ct, Monroe, NY 10950

/22
$76,900
- Land
- 5 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
$609,000 Sold May 30, 2025
- 2,032 Sq Ft
- $300/SF
- 50 Days On Market
- 3 Beds
- 3 Baths
- Built 2019
2 Bell Way, Chester, NY 10918

This STUNNING Chester home with Chester Schools that sits on 0.36 acre of privacy is now available for you to call Home!!In the Center of Chester & Great location! Enter into a spacious Living room with with plenty of natural window light.A formal dining room with modern light fixtures & sliders that lead to a back deck. House is built in 2019 !!! fresh out of the box, trendy and modern, & plenty

Shia Lieberman Blooming Realty

2 Bell Way, Chester, NY 10918

Est $404,771 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,694 Sq Ft
465 Meri Ln, Monroe, NY 10950

465 Meri Ln, Monroe, NY 10950

/24
$78,900
- Land
- 6 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
$1,350,000 Sold May 30, 2025
- 4,350 Sq Ft
- $310/SF
- 24 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2013
154 Hambletonian Rd, Chester, NY 10918

Welcome to this breathtaking equestrian estate nestled on close to 24 acres of Chester’s picturesque farmland in the Warwick Valley School district. This meticulously maintained colonial home offers 4 bedrooms, a den, and 3.5 baths, blending classic charm with modern luxury. A massive entryway greets you into the home. It boasts a chef’s kitchen featuring a Wolf stove, Sub-Zero refrigerator,

Claudia Lepore Keller Williams Realty

154 Hambletonian Rd, Chester, NY 10918

Est $384,561 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,694 Sq Ft
463 Meri Ln, Monroe, NY 10950

463 Meri Ln, Monroe, NY 10950

/23
$74,900
- Land
- 4.31 Acres
- $17,378 per Acre
102 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

102 Carriage Knoll Rd, Chester, NY 12817
$700,000 Sold May 23, 2025
- 3,120 Sq Ft
- $224/SF
- 49 Days On Market
- 5 Beds
- 2.5 Baths
- Built 2002
8 Country Woods Dr, Chester, NY 10918

Welcome to this freshly painted colonial home, perfectly situated on over 4 acres of private, picturesque land. With its timeless wrap-around porch and breathtaking views, this home combines classic elegance with modern upgrades.Inside, you'll find a grand 2-story entry, hardwood floors, and a thoughtfully designed first-floor layout. The living room, with its gas fireplace on a convenient

Sheyla Falesto Howard Hanna Rand Realty

8 Country Woods Dr, Chester, NY 10918

Est $404,761 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,698 Sq Ft
421 Heritage Ln Unit 421, Monroe, NY 10950

421 Heritage Ln Unit 421, Monroe, NY 10950

/19
$68,900
- Land
- 3.26 Acres
- $21,135 per Acre
98 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

98 Carriage Knoll Rd, Chester, NY 12817
$530,000 Sold May 19, 2025
- 1,932 Sq Ft
- $274/SF
- 21 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
3 Grant Dr, Monroe, NY 10950

Welcome to this meticulously cared-for home in the highly sought-after Monroe Woodbury School District, offering a perfect blend of space, comfort, and modern updates. Sitting on a generous, private 1/3-acre lot, this spacious 1,932 sq ft home features three large bedrooms, each with ample closet space, and a dedicated home office ideal for remote work. The home boasts two full bathrooms—one on

Rosalie Cook Weichert Realtors

3 Grant Dr, Monroe, NY 10950

Est $400,816 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,698 Sq Ft
321 Heritage Ln, Monroe, NY 10950

321 Heritage Ln, Monroe, NY 10950

/21
$68,900
- 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
$617,000 Sold May 19, 2025
- 2,676 Sq Ft
- $231/SF
- 146 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1835
1301 Kings Hwy, Chester, NY 10918

Located just outside the quaint village of Sugar Loaf sits this 1835 farm house. Situated on 2.3 acres with a creek, this warm and inviting center hall colonial style house offers plenty of authentic character of yesterday, including a covered porch, mud room, 2 fireplaces and wide plank floors. There are 4 bedrooms and 2 full and 1 half baths. Yet modern day upgrades include renovated baths and

Susan Walski Keller Williams Hudson Valley

1301 Kings Hwy, Chester, NY 10918

Est $479,931 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,880 Sq Ft
66 Pewter Cir, Chester, NY 10918

66 Pewter Cir, Chester, NY 10918

/22
$68,900
- 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
$475,000 Sold May 15, 2025
- 1,500 Sq Ft
- $317/SF
- 22 Days On Market
- 3 Beds
- 2 Baths
- Built 1956
11 N Hudson St Unit N, Chester, NY 10918

WOW! Beautiful, sunny, bright and totally RENOVATED home. Brand new kitchen, new floors, new bathrooms (one just added), new driveway, doors, new roof, new stone stairways, new patio and walkways in the front and back and more. Featuring quality construction throughout, enjoy a modern, clean spacious feeling floorplan with the added conveniences of a finished, walk-up attic, full, dry,

Layla Rose Boyles Century 21 Realty Center

11 N Hudson St Unit N, Chester, NY 10918

Est $532,941 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,210 Sq Ft
53 Pewter Cir, Chester, NY 10918

53 Pewter Cir, Chester, NY 10918

/71
$299,900
- Land
- 166 Acres
- $1,807 per Acre
L9 Atateka Rd, Chester, NY 12817

This is a fantastic opportunity to own your own patch of beautiful Adirondack woods, nearly 166 acres, complete with a perennial stream, beaver pond, mature timber, and plenty of wild game. Use this property as your own recreational playground or build your dream home or camp in this peaceful, wooded retreat. Property is access by a right of way from Atateka Rd. Proceed ~400 feet to property

John O'Donnell Timberland Realty

L9 Atateka Rd, Chester, NY 12817
$750,000 Sold May 15, 2025
- 2,276 Sq Ft
- $330/SF
- 16 Days On Market
- 3 Beds
- 4 Baths
- Built 1999
16 Spectrum Dr, Chester, NY 10918

Set on 5 private acres, this beautifully maintained Colonial offers the perfect combination of tranquility and convenience. With 2,276 sq. ft. of living space (not including the finished basement), this home features a pristine kitchen, a cozy living room with a fireplace, and a versatile lower level ready to suit your needs—whether as a recreation space, home office, or gym. Designed for both

John Olivero Keller Williams Realty

16 Spectrum Dr, Chester, NY 10918

Est $700,458 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,223 Sq Ft
15 Pewter Cir, Chester, NY 10918

15 Pewter Cir, Chester, NY 10918

/22
$68,900
- Land
- 3.11 Acres
- $22,154 per Acre
72 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

72 Carriage Knoll Rd, Chester, NY 12817
$338,000 Sold May 15, 2025
- 1,282 Sq Ft
- $264/SF
- 69 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1989
4120 Whispering Hills Dr, Chester, NY 10918

Beautiful two bedroom townhouse located in the highly desirable community of Whispering Hills. Nothing to do but move right in to this gorgeous condo in a Pet Friendly community. Recently renovated and freshly painted with an updated kitchen and bathrooms make this a lovely place to call home. Throughout the home is freshly painted, new light fixtures, new cordless shades. The spacious family

Joseph Paoli Howard Hanna Rand Realty

4120 Whispering Hills Dr, Chester, NY 10918

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