Newest Homes for Sale in Chester, NY

/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
/7
$874,400
- 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
/5
$54,900
- Land
- 10.14 Acres
- $5,414 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
/48
$730,000
- 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

(845) 447-0221

7 Park Place, Chester, NY 10918
/31
$59,500
- Land
- 5.42 Acres
- $10,978 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
/30
$725,000
- 5 Beds
- 2.5 Baths
- 3,124 Sq Ft
9 Country Woods Dr, Chester, NY 10918

Thoughtfully repositioned with a nearly $15,000 price adjustment makes this Country Woods colonial an unbeatable value! Now priced to allow for updates while securing a prime location, generous living space, a beautiful setting, and room to add your personal style. Country Woods is one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers

Kimberly Starks Howard Hanna Rand Realty

9 Country Woods Dr, Chester, NY 10918
/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
/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
/24
$479,000
- 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
/11
$349,999
- Land
- 4.9 Acres
- $71,428 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 block

James Feldhaus eXp Realty

8 Camelback 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
/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
/48
$1,100,000
- 4 Beds
- 3.5 Baths
- 4,467 Sq Ft
53 Odyssey Dr, Chester, NY 10918

Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

Hilary Ryan Goldman Howard Hanna Rand Realty

53 Odyssey Dr, Chester, NY 10918
/28
$1,498,888
- 4 Beds
- 4 Baths
- 7,308 Sq Ft
37 Main St, Chester, NY 10918

Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank Street Nestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades. The property features:•

James Feldhaus eXp Realty

37 Main St, Chester, NY 10918
/4
$350,000
- 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.

Theresa Powers Keller Williams Realty

0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
/5
$74,900
- Land
- 1.79 Acres
- $41,844 per Acre
L4-5 Marina Rd, Chester, NY 12817

This is two lots combined for better access and development and has beach rights to two beaches shown on map. HOA Owner's association fee includes beach maintenance. HOA board is working toward the possibility of installing a boat docksystem for the future. Presently there is space for non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's LLC

John Palermo John R. Palermo

L4-5 Marina Rd, Chester, NY 12817
/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
/17
$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
/19
$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
/20
$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
/19
$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
/22
$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
/23
$76,900
- 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
/25
$78,900
- 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
/23
$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
/24
$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
/23
$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
/71
$299,900
- Land
- 165.92 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
/5
$259,000
- Land
- 20.18 Acres
- $12,834 per Acre
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 can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

Karen Gauvin Our House Real Estate Group

32 Mountainside Dr, Chester, NY 10918
/8
$225,000
- Land
- 1 Acre
- $225,000 per Acre
34 Mountainside Dr, Chester, NY 10918

Lovely 1-Acre lot w/MOUNTAIN VIEWS & NATURAL GAS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at

Karen Gauvin Our House Real Estate Group

34 Mountainside Dr, Chester, NY 10918
/78
$699,900
- Land
- 337 Acres
- $2,077 per Acre
L 13.2 Friends Lake Rd, Chester, NY 12817

2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of State Forest Preserve, the Hudson River Woods & Wildwater property is the ''complete package'' of Adirondack property. With over 4,500 feet of road frontage (with electric) on Friends Lake Road, it's an ideal location for a camp, second home, or subdivision.

John O'Donnell Timberland Realty

L 13.2 Friends Lake Rd, Chester, NY 12817
/27
$129,000
- Land
- 13.33 Acres
- $9,677 per Acre
L9 Bird Pond Rd, Chester, NY 12853

Private 13+ acres of gently sloping land just minutes from Gore Mountain. Roughed-in driveway/Road leading from Bird Pond Rd. Several nice building locations around the property. One house-site staked-out for reference. Possible views from higher on the property with some select clearing. Listing agent will provide one set of existing preliminary building plans for the future homeowner from

Walter Swartz Gallo Realty ADK Inc

L9 Bird Pond Rd, Chester, NY 12853
/2
$500,000
- Land
- 0.83 Acre
- $603,355 per Acre
0 Main St, Chester, NY 10918

Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

Claude Brischoux Keller Williams Realty

0 Main St, Chester, NY 10918

Showing Results 41 - 73, Page 2 of 2

New York Orange County Chester

How to Buy a Home How to Finance a Home How to Sell a Home

Chester Types of Homes for Sale

Chester Homes by Price

Chester Homes for Sale under $100K

More About Living in Chester

Homes in Nearby Cities

Homes in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage