Newest Homes for Sale in Chester, NY

/29
$550,000
- 3 Beds
- 1.5 Baths
- 1,644 Sq Ft
56 Poplar Dr, Monroe, NY 10950

BiLevel/Raised Ranch on Quiet Street with Room to Grow! Come home and relax on the upper level deck overlooking state land that offers additional privacy. This well-maintained home clearly shows the pride of ownership. Open concept living room and dining room features many windows that fill the home with natural sunlight. Enjoy the convenience of the updated full bathroom and three comfortable

Jeffrey Jacobsen Terrie OConnor

56 Poplar Dr, Monroe, NY 10950
/49
$389,000
- 3 Beds
- 1 Bath
- 1,062 Sq Ft
185 Oxford Rd, Chester, NY 10918

Welcome to 185 Oxford Road, Chester! •••••This charming 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 Monroe-Woodbury School District, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful knotted hardwood flooring, cathedral

William Philip Keller Williams Hudson Valley

185 Oxford Rd, Chester, NY 10918
/29
$549,999
- 4 Beds
- 2.5 Baths
- 2,098 Sq Ft
7 Lakeview Dr, Chester, NY 10918

This charming updated 4-bedroom beauty in the Warwick School district offers a private and quiet setting featuring an above ground pool surrounded by a freshly painted deck just 3 minutes from Sugar Loaf Arts and Crafts Village. Its' kitchen has been upgraded boasting stainless steel appliances, granite countertops, and cherrywood cabinetry with undermount lighting and a wine/ beverage cooler.

Sheyla Falesto Howard Hanna Rand Realty

7 Lakeview Dr, Chester, NY 10918
/36
$799,000
- 4 Beds
- 2.5 Baths
- 3,070 Sq Ft
197 Oxford Rd, Chester, NY 10918

Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm

Regina Carmel Howard Hanna Rand Realty

197 Oxford Rd, Chester, NY 10918
/29
$389,900
- 3 Beds
- 2 Baths
- 1,393 Sq Ft
4114 Whispering Hills, Chester, NY 10918

WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door)

Gzim Hakanjin Coldwell Banker Realty

4114 Whispering Hills, Chester, NY 10918
/35
$374,999

$25K PRICE DROP 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

Chativa Bowen

Keller Williams Realty

241 Meadow Ave, Chester, NY 10918
/18
$360,000
- 3 Beds
- 2.5 Baths
- 1,585 Sq Ft
154 Eagleton Dr, Monroe, NY 10950

New Pics!Welcome to easy, low-maintenance living in this beautifully maintained 3-bedroom, 2.5-bath condo townhouse offering 1,585 square feet of comfortable living space in a peaceful community. Wake up to tranquil views overlooking a picturesque lake and enjoy the perfect blend of privacy, convenience, and amenities. The bright and spacious layout features central air conditioning, generous

Bernadette Corrigan Keller Williams Realty

154 Eagleton Dr, Monroe, NY 10950
/3
$750,000
- 5 Beds
- 2.5 Baths
- 2,700 Sq Ft
2 Boville Ct, Chester, NY 10918

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

Moshe Kaufman MK Realty Inc

2 Boville Ct, Chester, NY 10918
/31
$345,000

$54K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
402 Mountain Laurel Dr, Monroe, NY 10950

Waterfront living at its finest! HEAT and HOT WATER Included. 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,

Alexandria Sarki Keller Williams Realty

402 Mountain Laurel Dr, Monroe, NY 10950
/2
$725,000
- 3 Beds
- 2.5 Baths
- 2,677 Sq Ft
1 Arborvitae Ct, Chester, NY 10918

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 9 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

Moshe Kaufman MK Realty Inc

1 Arborvitae Ct, Chester, NY 10918
/40
$634,999

$15K PRICE DROP
- 4 Beds
- 3 Baths
- 2,316 Sq Ft
424 Laroe Rd, Chester, NY 10918

Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment.

Jeffrey Morrissey Epique Realty

424 Laroe Rd, Chester, NY 10918
/2
$1,700,000
- Land
- 46.5 Acres
- $36,559 per Acre
0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914

Incredible opportunity to own approximately 55 acres of land being offered as a package with two adjoining parcels. This expansive property offers endless potential for investors, builders, or those seeking a private estate or recreational retreat. Preliminary information suggests the property may have the potential for approximately 400,000 square feet of warehouse space. Both parcels are being

Lazar Schvimmer Mount Realty

0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
/46
$635,000
- 4 Beds
- 3 Baths
- 3,636 Sq Ft
10 Hidden Dr, Monroe, NY 10950

Tucked away on over an acre with serene lake views and deeded lake rights, this spacious Monroe retreat offers the perfect blend of privacy, comfort, and lifestyle. Wake up to natural light pouring through oversized windows and start your day on the deck overlooking the water. Inside, you’ll find 3/4 generously sized bedrooms and 3 full baths, along with an updated kitchen and baths that bring a

rosemary mcginn Century 21 Full Service Realty

10 Hidden Dr, Monroe, NY 10950
/5
$49,900
- Land
- 1.76 Acres
- $28,352 per Acre
Unlisted Address

Opportunity awaits on this 1.76-acre building lot in the heart of the Adirondacks, just minutes from Gore Mountain. Whether you're dreaming of an affordable year-round home or the perfect basecamp for skiing, hiking, mountain biking, snowmobiling, and everything the Adirondacks have to offer, this property provides an excellent starting point. Existing improvements include electric service, as

Sean Rogge

Howard Hanna Capital Inc

Unlisted Address
/32
$545,000

Open Sun 1PM - 3PM $70K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,908 Sq Ft
11 Chandler Dr, Chester, NY 10918

Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love.Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement

Daniella Restrepo Coldwell Banker Realty

11 Chandler Dr, Chester, NY 10918
/42
$549,000

$10K PRICE DROP
- 3 Beds
- 3 Baths
- 2,374 Sq Ft
44 Wilson Rd, Monroe, NY 10950

Welcome to this beautifully maintained 3-bedroom, 3-bath ranch nestled on a quiet dead-end street in the Lake Hill Farms community in the Town of Chester, within the Monroe-Woodbury School District. Offering municipal services, central air conditioning, and exceptional pride of ownership, this home is truly move-in ready. Step inside to a bright and inviting floor plan featuring a spacious living

Claudia Lepore Keller Williams Realty

44 Wilson Rd, Monroe, NY 10950
/47
$570,000

$9K PRICE DROP
- 3 Beds
- 2 Baths
- 1,644 Sq Ft
152 Highland Ave, Monroe, NY 10950

Impeccably maintained and lovingly cared for, this spacious 3-bedroom, 2-bath , 48 foot bi-level ranch offers comfort, functionality, and timeless appeal in one of Monroe’s desirable private cul-de-sac settings.Step inside to find bright, welcoming living spaces, generous room sizes, and beautiful hardwood floors that add warmth and character throughout much of the home. The inviting main

Aja Marshall Krumpfer Realty Group, LLC

152 Highland Ave, Monroe, NY 10950
/5
$850,000
- 5 Beds
- 2.5 Baths
- 3,200 Sq Ft
5 Hilltop Ln, Chester, NY 10918

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail

Moshe Kaufman MK Realty Inc

5 Hilltop Ln, Chester, NY 10918
/36
$750,000

$50K PRICE DROP
- 4 Beds
- 3.5 Baths
- 3,100 Sq Ft
985 Craigville Rd, Chester, NY 10918

Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

DAVID DEBERARDINIS Serhant LLC

985 Craigville Rd, Chester, NY 10918
/50
$750,000
- 5 Beds
- 2.5 Baths
- 2,700 Sq Ft
3 Boville Ct, Chester, NY 10918

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

Dovid Hoffman MK Realty Inc

3 Boville Ct, 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 Palermo John R

36 Fawn Ridge Rd, Chester, NY 12817
/37
$789,900
- 5 Beds
- 4 Baths
- 4,697 Sq Ft
19 Grand View Terrace, Chester, NY 10918

Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living

Randolph Rogers

eXp Realty

19 Grand View Terrace, Chester, NY 10918
/32
$1,199,000

$100K PRICE DROP
- 4 Beds
- 3.5 Baths
- 5,712 Sq Ft
16 Sunset Ridge, Monroe, NY 10950

NEW PRICE! Ready to sell! Highly motivated seller. Sold as-is. Recent updates include fresh paint in select areas and new pavers for enhanced curb appeal. Located approximately one hour from NYC with convenient access to major roadways.Welcome to this secluded Colonial in desirable Trout Brook Estates, set on nearly 6 private acres with over 5,700 sq ft of living space. This spacious

Carmela Lopez Borrazas Serhant LLC

16 Sunset Ridge, Monroe, NY 10950
/7
$900,000
- 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

Sandra Spector Howard Hanna Rand Realty

651 Lakes Rd, Monroe, NY 10950
/50
$1,195,000
- 4 Beds
- 3.5 Baths
- 4,281 Sq Ft
22 Goshen Rd, Chester, NY 10918

Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on

Martha Randazzo Howard Hanna Rand Realty

22 Goshen Rd, Chester, 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
/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
/50
$990,000

$10K PRICE DROP
- 4 Beds
- 2.5 Baths
- 3,955 Sq Ft
1 Oakland Ave, Chester, NY 10918

Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

Christina Rowan

Howard Hanna Rand Realty

1 Oakland Ave, Chester, NY 10918
/35
$875,000
- 4 Beds
- 2.5 Baths
- 3,656 Sq Ft
49 Stone Mountain Trail, Chester, NY 10918

Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

Arya Rabinovits eRealty Advisors, Inc

49 Stone Mountain Trail, Chester, NY 10918
/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
/38
$1,200,000
- 4 Beds
- 2.5 Baths
- 2,711 Sq Ft
63 Whitetail Run, Chester, NY 10918

This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

Artan Kukaj SPIRAL NY Real Estate LLC

63 Whitetail Run, Chester, NY 10918
/29
$549,900
- 3 Beds
- 2 Baths
- 2,138 Sq Ft
3318 State Route 94, Chester, NY 10918

This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the

Asha Keegan Howard Hanna Rand Realty

3318 State Route 94, Chester, NY 10918
/43
$949,000
- 4 Beds
- 2.5 Baths
- 3,332 Sq Ft
19 Bull Mine Rd, Chester, NY 10918

Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

James Cosenza BHG Real Estate Green Team

19 Bull Mine Rd, Chester, NY 10918
/19
$429,000
- 3 Beds
- 1.5 Baths
- 1,460 Sq Ft
4 Maple Ln, Monroe, NY 10950

Welcome to this beautifully updated Monroe home, ideally located just about 50 minutes from New York City. Set on a lush, well-kept property with mature trees and excellent curb appeal, this move-in-ready home offers a fresh modern look inside and out. The exterior features gray siding, white trim, a black front door, manicured landscaping, a newly paved driveway, and a spacious rear deck

Joseph Rosenfeld Flag Realty Group

4 Maple Ln, Monroe, NY 10950
/9
$375,000

$100K PRICE INCREASE
- Land
- 7.53 Acres
- $49,801 per Acre
L1.34 McPhillips Pine Ln, Chester, NY 12817

Here we have a 7.5 acre ultra-private building lot to be owned along with controlling ownership of a 2 acre shared beach and dock parcel - where through the parcel ownership, you own a dock section and control the use of the parcel by other deeded rights holders. Friends Lake is a private, jet-ski free lake, with a water ski course. Only 2O minutes to Lake George and Gore Mountain Ski Area. About

Michael Lynch Coldwell Banker Prime Properties

L1.34 McPhillips Pine Ln, Chester, NY 12817
/23
$520,000

$70K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,083 Sq Ft
94 Booth Rd, Chester, NY 10918

Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres.Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half

Craig Watters Compass Greater NY, LLC

94 Booth Rd, Chester, NY 10918
/28
$539,000

$41K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,698 Sq Ft
24 Walnut St, Chester, NY 10918

Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NYTucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange

Tara Roufanis Keller Williams Village Sq Rlt

24 Walnut St, Chester, NY 10918
/49
$785,000

$14K PRICE DROP
- 5 Beds
- 5.5 Baths
- 5,403 Sq Ft
4 Debbie Ct, Chester, NY 10918

Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest.From the moment you arrive, you’ll appreciate

Joseph Rosenfeld Flag Realty Group

4 Debbie Ct, 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

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