Newest Homes for Sale in Chester, NY

/50
$580,000
- 4 Beds
- 2.5 Baths
- 2,112 Sq Ft
150 Lake Region Blvd, Monroe, NY 10950

Welcome to 150 Lake Region Blvd — a well-maintained home located in Monroe’s desirable Lake Region / Walton Park area. The moment you step inside, you’re greeted by warm hardwood floors and an open, comfortable layout that feels welcoming without being overwhelming. The home offers a natural flow from room to room, making everyday living and entertaining easy and functional. With 4 oversized

Pete Wolven Hudson Valley Home Connection

150 Lake Region Blvd, Monroe, NY 10950
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/8
$699,990
- 4 Beds
- 3 Baths
- 1,867 Sq Ft
34 Mountainside Dr, Chester, NY 10918

ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

Karen Gauvin Our House Real Estate Group

34 Mountainside Dr, Chester, NY 10918
/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
/23
$62,000
- Land
- 11.11 Acres
- $5,581 per Acre
62 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

62 Carriage Knolls Rd, Chester, NY 12817
/7
$49,500
- Land
- 3.36 Acres
- $14,732 per Acre
20 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

20 Carriage Knolls Rd, Chester, NY 12817
/22
$450,000
- 4 Beds
- 2 Baths
- 1,932 Sq Ft
3 Tulip Ln, Monroe, NY 10950

Spacious raised ranch style home offering three bedrooms and two full bathrooms with 1,932 square feet of comfortable living space. Features a 1-car garage and a functional layout perfect for everyday living. The home has been freshly painted, giving it a bright, clean, move-in ready feel. A great opportunity for buyers seeking space, style, and value.

Geni Silva Ethos Realty LLC

3 Tulip Ln, Monroe, NY 10950
/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 topographyâ€”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
/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
/3
$675,000
- Land
- 2 Acres
- $337,500 per Acre
50 Elkay Dr, Chester, NY 10918

Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

Leib Glanz Point Realty USA

50 Elkay Dr, Chester, NY 10918
/13
$460,000
- 3 Beds
- 1.5 Baths
- 1,728 Sq Ft
1367 Kings Hwy, Chester, NY 10918

Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

Mark Karten Karten Real Estate Svcs LLC

1367 Kings Hwy, Chester, NY 10918
/34
$999,000
- 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
/24
$275,000
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
2113 Whispering Hills Unit 178, Chester, NY 10918

Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

Valerie Quinn Keller Williams Realty

2113 Whispering Hills Unit 178, Chester, NY 10918
/7
$500,000
- Land
- 9.78 Acres
- $51,125 per Acre
30 Harding Way, Chester, NY 10950

An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

Ida Payne Keller Williams Realty

30 Harding Way, Chester, NY 10950
/27
$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
$699,000
- 3 Beds
- 3 Baths
- 3,000 Sq Ft
360 Prospect Rd, Chester, NY 10918

B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

Joseph Mendlowitz eRealty Advisors, Inc

360 Prospect Rd, Chester, NY 10918
/3
$75,000
- Land
- 12 Acres
- $6,250 per Acre
L62.2 Moffitt Rd, Chester, NY 12817

12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

Carol Monroe Najer Realty

L62.2 Moffitt Rd, Chester, NY 12817
/28
$305,000
- 2 Beds
- 1.5 Baths
- 1,072 Sq Ft
3917 Whispering Hills, Chester, NY 10918

Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

Jie Liu Keller Williams Hudson Valley

3917 Whispering Hills, Chester, NY 10918
/2
$639,000
- 3 Beds
- 1.5 Baths
- 1,816 Sq Ft
101 Oxford Rd, Chester, NY 10918

This nice quiet house is a great place to call home. With almost 11 acres of land, there's a lot of space to enjoy activities and outdoor fun. The first floor of the house offers a nice layout with big living room, family room, kitchen, dining room, and a half bath. and a washer and dryer room . Bedrooms are nice and big making it very comfortable . The house will need some TLC and will need

Nathan Landau Loop Realty Inc

101 Oxford Rd, Chester, NY 10918
/13
$239,900
- 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
/45
$1,300,000
- 4 Beds
- 2.5 Baths
- 3,866 Sq Ft
2948 State Route 94, Chester, NY 10918

Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

Elizabeth Broderick Tuxedo Hudson Realty Corp

2948 State Route 94, Chester, NY 10918
/33
$289,500
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
1401 Whispering Hills, Chester, NY 10918

Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

Debbie Goldstein Howard Hanna Rand Realty

1401 Whispering Hills, Chester, NY 10918
/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
/14
$129,000
- Land
- 0.47 Acre
- $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
/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
$400,000
- 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
/8
$849,900
- 4 Beds
- 2.5 Baths
- 2,603 Sq Ft
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 will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

Karen Gauvin Our House Real Estate Group

32 Mountainside Dr, 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
/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 of

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

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