Chester, NY Homes for Sale

/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
Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/49
$749,999

$50K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,718 Sq Ft
58 Nancy Ln, Chester, NY 10918

Imagine ending every day watching the sun set from your front porch, with breathtaking views that change beautifully through every season. Sunset views, a fenced backyard, brand-new Trex deck, above-ground pool, home office, and the flexibility of **four sleeping spaces** make this property truly stand out. Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial is

Gina Dudgeon Howard Hanna Rand Realty

58 Nancy Ln, Chester, NY 10918
/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
/9
$879,900
- 4 Beds
- 2.5 Baths
- 3,200 Sq Ft
1414 Kings Hwy, 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

1414 Kings Hwy, 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
/37
$340,000
- 2 Beds
- 1 Bath
- 1,004 Sq Ft
166 Bull Mill Rd, Chester, NY 10918

Step into the timeless charm of this historic 1800s farmhouse, where character and history come together in a warm, inviting setting. Original details, classic craftsmanship, and the unique character of a bygone era create a home unlike today’s new construction. Adding to its rich history, the original deed to the property is included and will be conveyed to the new owner—a rare keepsake that

Stephen Ramundo Keller Williams Valley Realty

166 Bull Mill Rd, Chester, NY 10918
/2
$1,975,000
- Land
- 79.2 Acres
- $24,937 per Acre
0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914

A once-in-a-generation opportunity to acquire 79.2 acres in the highly sought-after Town of Blooming Grove. Rarely does a parcel of this size become available in one of Orange County's fastest-growing and most desirable communities. Whether you're a long-term investor, developer, or land banker, this exceptional property offers tremendous upside and the potential to capitalize on the area's

Yoel Kornbluh Mount Realty

0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
/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! 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, showcasing a center island, newer

Alexandria Sarki Keller Williams Realty

402 Mountain Laurel Dr, 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
/8
$425,000
- 3 Beds
- 2 Baths
- 2,460 Sq Ft
23 Pike Ct, Monroe, NY 10950

Welcome to 23 Pike Court. Unlock the potential of this spacious 3-bedroom, 2-bath raised ranch, which offers 2,460 square feet of living space on a generous .75 acre lot, giving you the space and flexibility to create something truly special. Perfect for an investor, contractor, or DIY enthusiast, this home is ready for someone with vision. While it needs work, it is move-in ready and offers an

Patricia Sassi RE/MAX Benchmark Realty Group

23 Pike Ct, Monroe, NY 10950
/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
/6
$88,900
- Land
- 1.79 Acres
- $49,665 per Acre
L4/5 Marina Rd, Chester, NY 12817

This lot has beach rights to two beaches shown on map. Home Owners's associationfee includes beach maintenance only. HOA board is working toward the possibility of installing a boat docking system for the future. Presently there is space of non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's trust of which he is a co-executor. New excavation

John Palermo Palermo John R

L4/5 Marina Rd, Chester, NY 12817
/20
$894,000

$105K 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
/50
$475,000
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
21 Trotting Dr, Chester, NY 10918

Welcome to this impeccably maintained raised ranch in the highly sought-after Surrey Meadows Community. Upon entering the foyer, you'll find a practical area beneath the stairs, providing convenient storage for coats and shoes. The lower level features a spacious bedroom with access to a full bathroom, complemented by a versatile bonus room perfect for a cozy den or guest accommodation. Ascend

Michele Kayser Keller Williams Realty

21 Trotting Dr, Chester, NY 10918
/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
/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
/50
$449,000
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
66 Whitetail Run, Chester, NY 10918

Welcome to 66 Whitetail Run – Chester, NY.Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities.Step inside to a

Soleil Jackman Howard Hanna Rand Realty

66 Whitetail Run, 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
/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
/46
$615,000
- 3 Beds
- 2 Baths
- 1,848 Sq Ft
412 Laroe Rd, Chester, NY 10918

Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The

Nathalie Sessoms Howard Hanna Rand Realty

412 Laroe 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 MS Realty Group USA, Inc

220 Oxford Rd, 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
/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
/34
$650,000
- 3 Beds
- 4 Baths
- 2,520 Sq Ft
29 Murray Dr, Chester, NY 10918

Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances

Liudmila Lobeeva eXp Realty

29 Murray Dr, 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
/38
$699,000
- 5 Beds
- 3.5 Baths
- 3,463 Sq Ft
65 Oxford Springs Rd, Chester, NY 10918

Welcome to 65 Oxford Springs Road! This stunning 5-bedroom, 3.5-bath Colonial offering approximately 3,400 square feet of thoughtfully designed living space in a peaceful, wooded setting. From the inviting covered front porch, step inside to spacious, light-filled rooms that blend comfort and elegance. Rich hardwood floors, soaring ceilings, abundant windows, and a beautiful stone fireplace

Stephanie Dolan HomeSmart Homes & Estates

65 Oxford Springs 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
/32
$389,900
- 3 Beds
- 2.5 Baths
- 1,694 Sq Ft
213 Eagleton Dr, Monroe, NY 10950

Some homes simply make everyday life easier, and 213 Eagleton Drive is one of them. This 3-bedroom, 2.5-bath townhome offers a practical layout with comfortable living spaces, an attached garage, additional driveway parking, and an unfinished basement for lots of storage. During the winter months, the home offers views of the community lake, adding a peaceful backdrop to the changing

Deborah Warner Keller Williams Valley Realty

213 Eagleton Dr, Monroe, NY 10950
/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
/32
$545,000

$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
/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
/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
$88,500

$1K PRICE DROP
- Land
- 12.79 Acres
- $6,919 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
/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
/16
$325,000

$25K PRICE DROP
- 4 Beds
- 1 Bath
- 1,504 Sq Ft
151 Main St, Chester, NY 10918

A Diamond in the Rough! Calling all handymen to bring this Village Charmer back to its' original glory. This home has a large Living Room with a cozy alcove, spacious Dining Room and large Kitchen with sliders to a rear deck and yard. It also features 4 nice sized bedrooms. With a "little love and vision" this home could be a lovely family home! Could be a wonderful opportunity for investors!

Eveline White Hudson Valley Griffith

151 Main St, Chester, NY 10918
/23
$530,000

$529K PRICE INCREASE
- 3 Beds
- 2 Baths
- 1,676 Sq Ft
74 Heaton Rd, Monroe, NY 10950

Step inside to hardwood floors and a welcoming eat-in kitchen featuring stainless steel appliances, ceramic tile flooring and soft-close cabinetry and drawers. Both full bathrooms have been beautifully updated with newer showers, tile and fixtures, plus the everyday luxury of HEATED FLOORS.The major improvements are already done: 200-amp electrical service (2025), rear property-line fencing

Barbara Bloch Coldwell Banker Realty

74 Heaton Rd, Monroe, NY 10950
/19
$459,000
- 4 Beds
- 2.5 Baths
- 2,060 Sq Ft
63 Hubshop Rd, Chester, NY 10918

Welcome Home to 63 Hubshop! This charming colonial boasts 2,100 square feet, 4 Bedrooms, 3 Bathrooms and sits on just under an acre of land. With a spacious kitchen, and both a designated living room and dining room, this home offers an easy-flowing layout, making you feel right at home the moment you walk through the door. Off the kitchen you will find a bonus room that can be transformed into a

Ryan Barrett Keller Williams Realty

63 Hubshop Rd, Chester, NY 10918

Showing Results 41 - 80, Page 2 of 4

New York Orange County

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 Real Estate

More About Living in Chester

Chester Homes for Sale by Style

Homes for Sale in Nearby Cities

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