Newest Homes for Sale in Chester, NY

/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
$515,000
- 4 Beds
- 2.5 Baths
- 2,898 Sq Ft
25 High St, Chester, NY 10918

25 High Street is back on the market and newly refreshed, making this Victorian gem more inviting than ever. Brimming with character and ready for your personal touch, this special home welcomes you with original wide-plank wood floors throughout—preserved under carpeting to maintain their timeless authenticity and warmth. Entertain in style in the bright, modern kitchen or host memorable

Alicia Goldman

Christie's Int. Real Estate

(845) 244-4823

25 High St, Chester, NY 10918
/18
$83,500
- Land
- 2.84 Acres
- $29,401 per Acre
38 Granite Ridge Rd, Chester, NY 12817

Great opportunity to build your own Adirondack dream home not far from Lake George. Seller financing available . Includes 2.84 acres of gently rolling property cleared for a potential house or a cabin. All stumps and undergrowth have been removed. 200 amp underground electrical service with 30 amp and 50 amp receptacles for camper hook up. Extra sleeve for future broadband or satellite. Winding

Walter Swartz Gallo Realty ADK Inc

38 Granite Ridge Rd, Chester, NY 12817
/45
$650,000
- 5 Beds
- 3.5 Baths
- 3,617 Sq Ft
65 Oxford Springs Rd, Chester, NY 10918

Welcome to 65 Oxford Springs Road, Chester, NY — a custom-built Country Contemporary set on a private 2.3-acre hilltop. This one-of-a-kind property offers the perfect balance of privacy, space, and convenience, just minutes from the NYS Thruway, state parks, and only 45 minutes to NYC. Inside, the bright open floor plan is filled with natural light, featuring rich hardwood floors, custom trim

Ammar Iqbal eXp Realty

65 Oxford Springs Rd, Chester, NY 10918
/50
$1,775,000
- 4 Beds
- 2.5 Baths
- 3,348 Sq Ft
20 Goshen Rd, Chester, NY 10918

Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating.Nature lovers and hobby farmers

Ramanjit Dhanoa eXp Realty

20 Goshen Rd, Chester, NY 10918
/37
$569,999
- 4 Beds
- 2.5 Baths
- 2,040 Sq Ft
78 Pickerel Rd, Monroe, NY 10950

Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

Dylan Piazza Howard Hanna Rand Realty

78 Pickerel Rd, Monroe, NY 10950
/37
$722,000
- 4 Beds
- 2.5 Baths
- 3,977 Sq Ft
278 Gibson Hill Rd, Chester, NY 10918

FULLY AVAILABLE. Amazing property, offers something for everyone! Gorgeously restored 3,977 square foot colonial farmhouse on 5.1 private acres, and with a NEW above-ground pool (replaced October 2025), 5 bay carport, a 38x40 garage (with its own entrance from road -- can rent out for income), and so much more! . . . Located in the Warwick Valley School District (and just a half mile to the

Dean Diltz Keller Williams Realty

278 Gibson Hill Rd, 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
/48
$1,099,000
- 4 Beds
- 2.5 Baths
- 2,722 Sq Ft
5 Gabriels Dr, Chester, NY 10918

Exquisite Colonial Estate: Timeless Grandeur Meets Modern LuxuryNestled gracefully on a private cul-de-sac amidst meticulously manicured grounds, this sprawling Colonial estate offers an unparalleled blend of classic elegance and contemporary comfort. From the moment you approach the stately wrought-iron fenced property and enter through the grand foyer, you are greeted by a magnificent

Beth Palma Keller Williams Realty

5 Gabriels Dr, Chester, NY 10918
/35
$399,000
- 2 Beds
- 1 Bath
- 1,484 Sq Ft
576 Bull Mill Rd, Chester, NY 10918

A fantastic opportunity for investors or future homeowners! This well-maintained home is set on a large, flat lot in a quiet, nature-filled neighborhood and offers strong rental potential with long-term flexibility. Inside, you’ll find a spacious living room, formal dining area, kitchen, and comfortable layout ideal for everyday living. Recent updates include fresh interior paint (2021), and a

Lazar Schvimmer Blooming Realty

576 Bull Mill Rd, 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
/31
$1,160,000
- 4 Beds
- 5 Baths
- 4,624 Sq Ft
16 Lori Ln, Chester, NY 10918

Indulge in luxury living at this resort-style residence in Chester, NY, within the prestigious Monroe Woodbury School District. Set on a tranquil cul-de-sac, this home graces one of MW Schools' most beautiful streets. Crafted with precision by Paul Janus Building Arts, custom millwork, arched windows, and detailed moldings evoke the charm of Westchester and Bergen County homes. From the

Randolph Rogers

eXp Realty

(845) 681-2264

16 Lori Ln, Chester, NY 10918
/49
$1,500,000
206 Greycourt Rd Unit 190, Chester, NY 10918

**Endless Opportunities Await on This Rare 3.2-Acre Property!** ZONED COMMMERCIAL INDUSTRIAL USEFor the first time in over 50 years, this prime piece of real estate is hitting the market! Nestled right off Route 17 with unbeatable exposure, this unique 3.2-acre property offers **unlimited potential** for investors, developers, or those looking for a special place to call home.

Susan McMullen eXp Realty

206 Greycourt Rd Unit 190, 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
/20
$169,500
- Land
- 22.6 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
/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
/4
$479,900
- Land
- 8.38 Acres
- $57,250 per Acre
30 Harding Way, Chester, NY 10950

Opportunity is knocking on the door for all builders/investors in the Town Of Chester, Monroe - Woodbury School District. You buy 2 lots for the price of one. 30 Harding Way is SOLD TOGETHER with the lot next to it of 8.2 acres which is located in Section 15, Block 1, Lot 32. Subdivision potential.

Ida Payne Keller Williams Realty

30 Harding Way, Chester, NY 10950
/2
$499,000
- Land
- 4.5 Acres
- $110,889 per Acre
1414 Kings Hwy, Chester, NY 10918

5 Lot subdivision which has been engineered and submitted to Chester planning board for approvals with water and sewer. Not approved but in the process. Buyer must finish. Site plan in documents as well as addressed planning board comments. Additional Information: SoilType:Unknown,

Joe Distelburger Keller Williams Realty

1414 Kings Hwy, Chester, NY 10918
/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
/22
$37,500
- Land
- 1.62 Acres
- $23,148 per Acre
60 Carriage Rd, Chester, NY

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 steeper 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

60 Carriage Rd, Chester, NY
/9
$62,000
- Land
- 11.11 Acres
- $5,581 per Acre
62 Carriage Rd, Chester, NY

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 steeper 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

62 Carriage Rd, Chester, NY
/18
$39,500
- Land
- 2.38 Acres
- $16,597 per Acre
22 Carriage Rd, Chester, NY

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 steeper 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

22 Carriage Rd, Chester, NY
/12
$39,500
- Land
- 1.82 Acres
- $21,703 per Acre
34 Carriage Rd, Chester, NY

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 steeper 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

34 Carriage Rd, Chester, NY
/25
$39,000
- Land
- 2.48 Acres
- $15,726 per Acre
37 Carriage Rd, Chester, NY

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 steeper 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

37 Carriage Rd, Chester, NY
/13
$37,500
- Land
- 2 Acres
- $18,750 per Acre
13 Carriage Rd, Chester, NY

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 steeper 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

13 Carriage Rd, Chester, NY

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