Chester, NY Homes for Sale

/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 10X10 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 living room

Asha Keegan Howard Hanna Rand Realty

3318 State Route 94, Chester, NY 10918
/46
$319,900

$20K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,320 Sq Ft
607 Mountain Laurel Dr, Monroe, NY 10950

Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

Rosalie Cook Weichert Realtors

607 Mountain Laurel Dr, Monroe, NY 10950
/37
$385,000
- 2 Beds
- 2.5 Baths
- 1,490 Sq Ft
152 Eagleton Dr, Monroe, NY 10950

Move right into this beautifully maintained townhouse in the highly desirable Windridge Complex, offering approximately 1,500 square feet of comfortable living space and peaceful lake views. This inviting home features 2 spacious bedrooms, 2.5 bathrooms, and a functional floor plan designed for today's lifestyle.The main level boasts a dramatic two-story living room with a cozy gas fireplace,

Alissa Taylor-Vetell Keller Williams Realty

152 Eagleton Dr, Monroe, NY 10950
/9
$275,000
- Land
- 7.53 Acres
- $36,521 per Acre
L1.34 McPhillips Pine Ln, Chester, NY 12817

If you are looking for an ultra private lot with access (dock and beach rights) to one of the pristine exclusive lakes in the Adirondacks, you found it. Friends Lake is the home to cool people and is private, jet-ski free, with a water ski course and simply no nonsense. Only 2O minutes to Lake George and Gore Mountain Ski Area. About 4 hours from NYC and 2.5 hours to Montreal. Saratoga Springs is

Michael Lynch Coldwell Banker Prime Properties

L1.34 McPhillips Pine Ln, Chester, NY 12817
/78
$699,900

$140K PRICE DROP
- 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
/3
$899,000

$100K PRICE DROP
- 3 Beds
- 3.5 Baths
- 3,535 Sq Ft
220 Oxford Rd, Chester, NY 10918

220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern

Moche Halpern Blooming Realty

220 Oxford Rd, Chester, NY 10918
/23
$550,000

$40K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,083 Sq Ft
94 Booth Rd, Chester, NY 10918

94 Booth Road represents a rare find in the current Chester market, offering an exceptional balance of space and value on a sprawling 1.84-acre lot. Positioned at the end of a quiet cul-de-sac that borders protected state parkland, this property provides a unique sense of seclusion and a lasting connection to the natural landscape. Inside, the residence spans 2,083 square feet of thoughtfully

Craig Watters Compass Greater NY, LLC

94 Booth Rd, Chester, NY 10918
/50
$849,900

$38K PRICE DROP
- 3 Beds
- 3 Baths
- 2,740 Sq Ft
149 Creamery Pond Rd, Chester, NY 10918

Welcome to the highly sought-after Creamery Estate! This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow layout designed for everyday living. The updated kitchen,

Carla Terranova Keller Williams Realty

149 Creamery Pond Rd, Chester, NY 10918
/20
$68,900

$19K PRICE INCREASE
- 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
/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 MS Realty Group USA, Inc

220 Oxford Rd, Chester, NY 10918
/44
$869,000

$31K PRICE DROP
- 5 Beds
- 3 Baths
- 3,846 Sq Ft
2 Heidi Ln, Chester, NY 10918

Set at the end of a quiet executive cul-de-sac, this refined modern colonial offers a rare blend of quality, scale, and effortless livability on over two acres of level, park-like grounds framed by mature trees. Designed for both everyday comfort and elevated entertaining, the home unfolds with a sense of openness and intention, where natural light and thoughtful craftsmanship define every

Frank Muccari Cronin & Company Real Estate

2 Heidi Ln, Chester, NY 10918
/50
$3,400,000
- 4 Beds
- 4 Baths
- 7,750 Sq Ft
19 Greentree Ln, Chester, NY 10918

Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

Jake Garay Serhant LLC

19 Greentree Ln, Chester, NY 10918
/28
$579,999
- 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
/12
$640,000
- 3 Beds
- 1.5 Baths
- 2,136 Sq Ft
4 Greycourt Rd, Chester, NY 10918

Welcome to 4 Greycourt Road, your dream home awaits! This delightful residence boasts a spacious 6-room layout, featuring 3 generous bedrooms and 1.5 baths, all nestled on over 2.5 acres of stunning greenery. Imagine whipping up culinary masterpieces in the well-appointed kitchen, complete with ample cabinetry and modern appliances—perfect for any cooking enthusiast! Each bedroom is a serene

Nathen Singer MK Realty Inc

4 Greycourt Rd, 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
/39
$365,000

Open Sat 11AM - 1PM
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
2703 Whispering Hills, Chester, NY 10918

Welcome to 2703 Whispering Hills in Chester, NY — a beautifully updated home that stands out from the rest. This well-maintained unit features numerous recent improvements, including new windows, a new garage door, and a new hot water heater, providing peace of mind for years to come. The central air conditioning system is approximately five years old and keeps the home comfortable throughout the

Rebecca Matta-Candela Keller Williams Realty

2703 Whispering Hills, Chester, NY 10918
/7
$900,000
- 4 Beds
- 2.5 Baths
- 2,588 Sq Ft
60 Whitetail Run, Chester, NY 10918

Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and

Isaac Rottenberg Realty Blue Corp

60 Whitetail Run, 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
/45
$1,300,000

$95K PRICE DROP
- 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
$260,000

$35K PRICE DROP
- 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
/40
$500,000
- 4 Beds
- 2 Baths
- 1,730 Sq Ft
37 Surrey Rd, Chester, NY 10918

Looking for a 4-bed home in Chester, NY with a pool, major system updates, generous outdoor living space, and convenient access to schools, parks, shopping, and commuter routes? Welcome to 37 Surrey Road, a beautifully maintained raised ranch offering 4 bedrooms, 2 full bathrooms, approximately 1,730 square feet of living space, and a backyard designed for entertaining and relaxation. Set on a

Lady Castro eXp Realty

37 Surrey Rd, Chester, NY 10918
/29
$499,900

$50K PRICE DROP
- 3 Beds
- 3 Baths
- 2,032 Sq Ft
35 Maple Ave, Chester, NY 10918

Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances,

Joanne Timperio RE/MAX Benchmark Realty Group

35 Maple Ave, Chester, NY 10918
/42
$849,900
- 4 Beds
- 3 Baths
- 2,370 Sq Ft
2 Primrose Ln, Chester, NY 10918

Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

Janet Rendle Weichert Realtors

2 Primrose Ln, Chester, NY 10918
/34
$949,000

$50K PRICE DROP
- 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
/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
/13
$89,995
- Land
- 25.03 Acres
- $3,595 per Acre
1.1 Cobble Creek Rd Unit 1, Chester, NY 12853

Adirondack Mountain Retreat with Stream and Trails Discover 25 acres of classic Adirondack wilderness in Chester, New York, tucked along a year-round, town-maintained road. This exceptional property rises gently from the roadside to several attractive, APA-approved building locations, offering excellent opportunities for an off-grid cabin, or vacation retreat. The land is heavily wooded with a

Marc Christmas CHRISTMAS AND ASSOCIATES INC

1.1 Cobble Creek Rd Unit 1, Chester, NY 12853
/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
/8
$869,900

New Construction
- 4 Beds
- 2.5 Baths
- 3,000 Sq Ft
10 Well Sweep Ln, Chester, NY 10918

Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

Carla Terranova Keller Williams Realty

10 Well Sweep Ln, Chester, NY 10918
/36
$419,000
- 3 Beds
- 2.5 Baths
- 1,694 Sq Ft
332 Heritage Ln, Monroe, NY 10950

Spacious and well-maintained 3BR/2.5BA townhouse in desirable Windridge community. Features include updated laminate hardwood flooring, fireplace, eat-in kitchen, stainless steel appliances, private balcony off primary bedroom, sliding glass doors to private patio, attached 1-car garage with storage loft, and pull-down attic access. Community amenities include pool, clubhouse, and park.

Martin Remo RE/MAX Prime Properties

332 Heritage Ln, Monroe, NY 10950
/44
$569,000

$11K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,112 Sq Ft
150 Lake Region Blvd, Monroe, NY 10950

Welcome to 150 Lake Region Blvd, a beautifully maintained home in Monroe’s sought-after Lake Region / Walton Park community. Step inside to warm hardwood floors and a thoughtfully designed layout that feels both inviting and functional. The main living spaces flow effortlessly, creating an ideal setting for everyday living and entertaining. Offering 4 spacious bedrooms and 3 full bathrooms, the

Pete Wolven Hudson Valley Home Connection

150 Lake Region Blvd, Monroe, NY 10950
/50
$1,725,000
- 4 Beds
- 2.5 Baths
- 3,348 Sq Ft
20 Goshen Rd, Chester, NY 10918

THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

Ramanjit Dhanoa eXp Realty

20 Goshen Rd, Chester, NY 10918
/35
$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
$725,000
- 6 Beds
- 3.5 Baths
- 4,204 Sq Ft
487 Black Meadow Rd, Chester, NY 10918

A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

Dominic Santagato Joseph Baratta Company Realty

487 Black Meadow Rd, Chester, NY 10918
/26
$399,900

$25K PRICE DROP
- 2 Beds
- 1 Bath
- 1,026 Sq Ft
7 Hambletonian Ave, Chester, NY 10918

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay

William Scolza HomeSmart Homes & Estates

7 Hambletonian Ave, Chester, NY 10918
/19
$74,900

$19K PRICE INCREASE
- 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
/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
/22
$68,900

$19K PRICE INCREASE
- 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
/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
/49
$1,090,000
- 4 Beds
- 3.5 Baths
- 4,130 Sq Ft
102 Beverly Rd, Chester, NY 10918

Located in the Warwick School district on a coveted street sits this larger than life home with impressive presence. The curved driveway welcomes you to the wide porch, perfect for rocking chairs and relaxing. The impressive entrance with custom stairway and window seat is just the first of impressive touches in this home. Large kitchen overlooks the yard and is well appointed with Thor

Kimberly Corkum Keller Williams Realty

102 Beverly Rd, Chester, NY 10918
/33
$549,000
- 3 Beds
- 2.5 Baths
- 1,730 Sq Ft
107 Pine Hill Rd, Chester, NY 10918

Something Special! See It and Fall in Love! A pavered walkway welcomes you to this curb appealing 3 BR, 2 1/2 bath Stucco Cape that is privately set on 1.1 acres! Open and sun filled with lots of windows! So many updates! Large primary BR and luxurious bath are on the 1 st floor! Open LR and DR have sliders to private deck to enjoy pastoral views and views of Sugar Loaf Mountain! 2 large BRs with

Linda Clark Hudson Valley Griffith

107 Pine Hill Rd, Chester, NY 10918

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