Chester, NY Homes

• 

  

  

  /37

  $715,000 Pending

  • 3 Beds
  • 4 Baths
  • 2,276 Sq Ft

  16 Spectrum Dr, Chester, NY 10918

  Set on 5 private acres, this beautifully maintained Colonial offers the perfect combination of tranquility and convenience. With 2,276 sq. ft. of living space (not including the finished basement), this home features a pristine kitchen, a cozy living room with a fireplace, and a versatile lower level ready to suit your needs—whether as a recreation space, home office, or gym. Designed for both

  

  John Olivero

  Keller Williams Realty

  (845) 289-8260

  16 Spectrum Dr, Chester, NY 10918
• 

  

  

  /30

  $14,300 per month

  • 7 Beds
  • 5 Baths
  • Condo for Rent

  45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

  Escape to this luxurious 7-bedroom retreat in the heart of Chester, NY! Designed for ultimate relaxation, the home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy stylish furnishings, a chic home office, and elegant touches throughout. A game room with a pool table adds a fun element, making this the perfect mix of comfort and

  45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918
• 

  $560,000 Sold May 02, 2025

  • 2,092 Sq Ft
  • $268/SF
  • 43 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2002

  69 High St, Chester, NY 10918

  This STUNNING Chester home with Chester Schools that sits on 1 acre of privacy is now available for you to call Home!! Enter into a spacious Living room with with plenty of natural window light and a wood burning fireplace. A formal dining room with modern light fixtures & sliders that lead to a back deck. An updated eat-in kitchen with NEW granite counters and island! NEW stainless steel

  Sandra Arnez Keller Williams Hudson Valley

  69 High St, Chester, NY 10918
• 

  Est $1,169,429 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,554 Sq Ft

  5 Primrose Ln, Chester, NY 10918

  5 Primrose Ln, Chester, NY 10918
• 

  

  

  /31

  $1,199,900

  • 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
• 

  

  /6

  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Condo for Rent

  3815 Whispering Hills, Chester, NY 10918

  WHISPERING HILLS!! End Unit! Two Level Living! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Living Room with Fireplace! Dining Area! Master Bedroom Suite with Walk in Closet! Kitchen with Stainless Steel Appliances & Custom Tiled Back Splash! Sliders to Patio! Central Air! Country Club Living! Clubhouses! Pools! Tennis! Basketball! Tot Lot! Perfect Commuter Location! Walk to NYC Bus & Shopping!

  Amanda Dnistrian ARC Realty 1 in Sales

  3815 Whispering Hills, Chester, NY 10918
• 

  $1,450,000 Sold May 02, 2025

  • 5,638 Sq Ft
  • $257/SF
  • 327 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2022

  151 Kings Highway Bypass, Chester, NY 10918

  Nestled on a picturesque 14-acre lot overlooking Sugarloaf, the Adirondack timber frame home stood as a testament to impeccable craftsmanship and luxurious living. Every detail of this 4-bedroom, 5-bath retreat exuded elegance and comfort. The great room, with its soaring ceilings and grand stone fireplace, offered breathtaking views of the rolling landscape. No expense was spared in the gourmet

  John Olivero Keller Williams Realty

  151 Kings Highway Bypass, Chester, NY 10918
• 

  Est $782,414 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,328 Sq Ft

  15 Eagle Crest Way, Chester, NY 10918

  15 Eagle Crest Way, Chester, NY 10918
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  /33

  $395,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,038 Sq Ft

  12 Oak St, Chester, NY 10918

  Located in a peaceful area on a picturesque corner lot in the Village of Chester, this ranch style home in the Cherry Heights neighborhood has been meticulously well maintained with perennial flowers, mature trees, and privacy hedges. Inside, the home boasts a spacious living room with a large picture window that offers views of the front covered porch and a vibrant Japanese maple tree. The

  

  Jennifer Loprieno

  Howard Hanna Rand Realty

  (845) 539-1929

  12 Oak St, Chester, NY 10918
• 

  

  /15

  $1,600 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  13 Jackson St Unit C, Chester, NY 10918

  Welcome to the charming Village of Chester! With bedroom views of the village, a private parking space, and a small patio area this rental has it all. Don't miss out on this opportunity to live in a quaint and convenient location.

  Brooke Lorimer Keller Williams Realty

  13 Jackson St Unit C, Chester, NY 10918
• 

  $405,000 Sold Apr 30, 2025

  • 1,222 Sq Ft
  • $331/SF
  • 35 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1962

  16 Kerner Dr, Chester, NY 10918

  This Kerner Drive classic home is now waiting for its next owner! With 3 bedrooms, this ranch home is brimming with potential and is close to shopping, schools, parks and major roadways. The main level boasts a comfortable layout, while the walk-out lower level provides the perfect opportunity to add extra living space or create a versatile retreat. Hidden beneath the carpeting, the hardwood

  Patricia Sassi RE/MAX Benchmark Realty Group

  16 Kerner Dr, Chester, NY 10918
• 

  Est $178,771 Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  495 Laroe Rd, Chester, NY 10918
• 

  

  /50

  $799,900

  • 5 Beds
  • 4 Baths
  • 3,418 Sq Ft

  118 Murray Dr, Chester, NY 10918

  Nestled on 2.8 acres of lush, mature landscaping that borders the serene Goosepond Mountain State Park, this custom-designed contemporary ranch showcases a timeless blend of materials, with stone and brick construction lending both character and durability. Crafted by its original owners with meticulous attention to detail, the home offers a harmonious connection to its natural surroundings. A

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (845) 409-8716

  118 Murray Dr, Chester, NY 10918
• 

  

  /18

  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Condo for Rent

  1213 Whispering Hills, Chester, NY 10918

  Great 2nd floor corner/end unit with an open floor plan including vaulted ceilings, a wood fireplace new carpeting in this 2nd floor unit. Formal dining room, deck for electric barbeque, full bathroom with glass tub doors and tile, new paint throughout. Large bedroom includes walk-in closet and privacy door to the bathroom. Also includes a second bedroom and private laundry/utility room and a

  Rosemarie Morello Keller Williams Hudson Valley

  1213 Whispering Hills, Chester, NY 10918
• 

  $607,700 Sold Apr 29, 2025

  • 3,385 Sq Ft
  • $180/SF
  • 107 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1981

  142 Laroe Rd, Chester, NY 10918

  Welcome to a stunning retreat at 142 Laroe Rd, Chester, NY 10918—, offering a harmonious blend of elegance, space, and functionality. Covering a generous floor size of 3,385 square feet on an expansive lot of 69,696 square feet, this magnificent property promises spacious living, comfort, and captivating beauty both indoors and outdoors.This five-bedroom, three-bathroom masterpiece is designed to

  Peter Persaud HomeSmart Homes & Estates

  142 Laroe Rd, Chester, NY 10918
• 

  Est $316,832 Not Listed For Sale

  5 Heidi Ln, Chester, NY 10918

  5 Heidi Ln, Chester, NY 10918
• 

  

  /40

  $949,000

  • 4 Beds
  • 4 Baths
  • 4,489 Sq Ft

  11 Saddle Hill Rd, Chester, NY 10918

  Welcome to 11 Saddle Hill Road! This beautiful brick colonial, combines private luxury with convenience! With over 5000 sq. ft of living space, this home has room for everyone! You are welcomed by a grand two story entryway into this beautiful sunlit home with gleaming hardwood floors throughout. The main level features a formal dining room, office/flex space (with french doors), and an updated,

  Alissa Taylor-Vetell Keller Williams Realty

  11 Saddle Hill Rd, Chester, NY 10918
• 

  

  /19

  $750 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  7915 State Route 9 Unit 2, Chester, NY 12860

  Basic 1BR/1BA apartment Pottersville! This unit has a large porch and semi-private yard. Exceptionally easy to access from I-87, close to skiing, 20 minutes to Gore, 25 minutes to Lake George. Heat, hot water, sewer and water included in rent. Landlord plows parking lot, tenant is responsible for their walkway. SF estimated. No smoking, no pets. 3x income and renter's insurance required. This

  Jonathan Van Dyk Equitas Realty

  7915 State Route 9 Unit 2, Chester, NY 12860
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  /5

  $41,500 Sold Apr 28, 2025

  • Land
  • 3.54 Acres
  • $11,723 per Acre

  • 27 Days On Market

  L34 Lane Rd, Chester, NY 12853

  Great location in the heart of the Southern Adirondacks! Build your dream home on this 3.5 acre parcel with a DRILLED WELL! A culvert has been added, and the pole was installed between the power company's poles. The area is cleared. It is close to Schroon Lake, Loon Lake & Minerva Town Beach. It is 10 minutes from Gore Mountain. The possibilities are endless! Don't miss out on this one!

  Julia Pucciarelli Gallo Realty ADK Inc

  L34 Lane Rd, Chester, NY 12853
• 

  Est $797,994 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  25 Eagle Crest Way, Chester, NY 10918

  25 Eagle Crest Way, Chester, NY 10918
• 

  

  /50

  $859,900

  • 4 Beds
  • 3.5 Baths
  • 4,021 Sq Ft

  157 Creamery Pond Rd, Chester, NY 10918

  Welcome to Creamery Estates of Sugarloaf, where your dream home awaits just an hour’s drive from New York City. Nestled within walking distance of the charming downtown hamlet of Sugarloaf, this lovely residence is minutes away from schools, boutique shops, restaurants, grocery stores, the Sugar Loaf Performing Arts Center, wineries, breweries, apple orchards, the Appalachian trails, local

  Carla Terranova Keller Williams Realty

  157 Creamery Pond Rd, Chester, NY 10918
• 

  

  /15

  $2,700 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  62 Main St, Chester, NY 10918

  Tons of square footage in a quiet area with amazing views. With coffe shops , entertainment and restaurants within walking distance , this rental will go quick! Ample parking, a backyard complete with play area, bamboo floors and 5 minutes from commuting highways make this place a unicorn in the real estate world. Come check it out!

  Ryan Case Keller Williams Realty

  62 Main St, Chester, NY 10918
• 

  $750,000 Sold Apr 25, 2025

  • 2,822 Sq Ft
  • $266/SF
  • 53 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2002

  137 Creamery Pond Rd, Chester, NY 10918

  This stunning 4-bedroom, 2.5-bathroom home in Sugar Loaf, NY, offers 2822 sq. ft. of spacious living, nestled within the Warwick School District. The home features a grand fireplace in the great room, a chef’s kitchen, and a walk-out basement with office space. Enjoy breathtaking views of Creamery Pond from the property, creating a tranquil setting for both indoor and outdoor living. Perfectly

  John Stika Keller Williams Realty

  137 Creamery Pond Rd, Chester, NY 10918
• 

  Est $800,661 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  20 Gilmour Way, Twn Palm Tree, NY 10950

  20 Gilmour Way, Twn Palm Tree, NY 10950
• 

  

  /39

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft

  2 Laura Dr, Chester, NY 10918

  Fall in love with this stunning updated 4-bedroom Colonial located in Sugar Loaf Heights within the Warwick School District. You will feel like you apparated into the latest issue of Better Homes & Gardens the moment you enter. Agents - better schedule extra long showings as your clients will never want to leave! Step into the inviting living room featuring warm hardwood floors, soft recessed

  Virginia Corbett eXp Realty

  2 Laura Dr, Chester, NY 10918
• 

  

  /18

  $2,500 per month

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Condo for Rent

  2720 Whispering Hills, Chester, NY 10918

  Welcome to 2720 Whispering Hills in Chester, NY—a charming 2-bedroom, 1.5-bathroom townhouse offering 1,072 square feet of comfortable living space. This home features a cozy fireplace, in-unit laundry, and an attached garage with off-street parking. The community amenities include pools, clubhouses, tennis and basketball courts, and a playground. Conveniently located near shopping, dining, and

  Michael Cahill HomeSmart Homes & Estates

  2720 Whispering Hills, Chester, NY 10918
• 

  $550,000 Sold Apr 23, 2025

  • 3,327 Sq Ft
  • $165/SF
  • 12 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1973

  16 Fernglade Ct, Chester, NY 10918

  This is a must see home, bring some TLC, design skills and imagination! - This large home, complete with a full walkout basement, situated on 1.5 acres in a cul-de-sac offers so much potential. Two "Primary Bedrooms"! First floor - Large foyer with 2 story entry -primary bedroom w/walk-in closet and full bath, formal living room & dining room, open kitchen w/breakfast nook, guest bedroom, full

  Kim Chiapperino RE/MAX Benchmark Realty Group

  16 Fernglade Ct, Chester, NY 10918
• 

  Not Listed For Sale

  • 6 Beds
  • 2 Baths
  • 2,138 Sq Ft

  68 Conklingtown Rd, Chester, NY 10918

  68 Conklingtown Rd, Chester, NY 10918
• 

  

  /33

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,452 Sq Ft

  138 Dug Rd, Chester, NY 10918

  Welcome home to this beautifully maintained Dutch Colonial situated on 2.6 serene acres within the desirable Monroe-Woodbury School District. This inviting home offers 4 spacious bedrooms, 2.5 bathrooms, and 2,452 square feet of well-appointed living space, thoughtfully designed for both comfort and functionality. Upon entering, you'll notice the natural light accentuating the gleaming hardwood

  Jake Garay Serhant LLC

  138 Dug Rd, Chester, NY 10918
• 

  

  /14

  $2,100 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1358 Kings Hwy, Sugar Loaf, NY 10981

  Quintessential Sugar Loaf Cottage, newly renovated inside, featuring expansive windows in the front living space, new LVP Flooring throughout, new kitchen with plenty of cabinetry, open shelving and a bar style countertop for extra prep space or entertaining. The space also features an extra large pantry and a new spacious sunlit bathroom with stand up shower. First bedroom is on the main floor

  Christine DeLuca BHG Real Estate Green Team

  1358 Kings Hwy, Sugar Loaf, NY 10981
• 

  $475,000 Sold Apr 22, 2025

  • 1,452 Sq Ft
  • $327/SF
  • 45 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  397 Bellvale Rd, Chester, NY 10918

  ** FULLY AVAILABLE ** Discover your sanctuary in the highly coveted Warwick Valley School District! Nestled on nearly 2 breathtaking acres, this charming home offers the perfect blend of privacy and modern comfort. With stunning views of Sugar Loaf Mountain, you’ll feel surrounded by nature while enjoying the convenience of one-level living. Step inside to an inviting open floor plan, ideal for

  Juan Bautista Keller Williams Realty

  397 Bellvale Rd, Chester, NY 10918
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 3,182 Sq Ft

  63 Main St, Chester, NY 10918

  63 Main St, Chester, NY 10918
• 

  

  /35

  $899,900

  • 4 Beds
  • 4 Baths
  • 4,854 Sq Ft

  4 Camelback Rd, Chester, NY 10918

  Stunning 4-Bedroom Home with Breathtaking Mountain Views!This is the one you've been waiting for! Nestled on a serene, tree-lined cul-de-sac, this luxurious 4-bedroom, 4-bath home offers the perfect blend of elegance, comfort, and spectacular mountain views.Step inside to a sun-drenched living room, where gleaming hardwood floors create an inviting ambiance. The spacious family room features a

  Veronica Goldzberg 2Win Realty LLC

  4 Camelback Rd, Chester, NY 10918
• 

  

  /22

  $3,050 per month

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • House for Rent

  46 Midway Dr, Monroe, NY 10950

  THE RENTAL YOU HAVE BEEN LOOKING FOR! Beautiful, well-kept fabulous two story home in the Monroe Woodbury School district. Spacious rooms, updated kitchen with plenty of cabinets, four season room fully equipped with new windows and heater can used as office, ample living space, and expansive backyard to enjoy all year round. This lovely home comes with lake rights and all your needs. Call today,

  Eliezer Safdie Sage Realty Center LLC

  46 Midway Dr, Monroe, NY 10950
• 

  $749,900 Sold Apr 18, 2025

  • 3,480 Sq Ft
  • $215/SF
  • 29 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2004

  2 Grand View Terrace, Chester, NY 10918

  ***Welcome Home to this great commuter location in the desirable Valley View subdivision*** The open floor plan seamlessly connects the living, dining, and kitchen areas, providing the ideal setting for gatherings and entertaining. Every room exudes charm and sophistication. Just moments from home you'll find easy access to transportation, ensuring a smooth commute to work or outings.

  Randolph Rogers eXp Realty

  2 Grand View Terrace, Chester, NY 10918
• 

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,488 Sq Ft

  20 High St, Chester, NY 10918

  20 High St, Chester, NY 10918
• 

  

  /38

  $745,000

  • 5 Beds
  • 3.5 Baths
  • 3,464 Sq Ft

  65 Oxford Springs Rd, Chester, NY 10918

  One-of-a-kind custom built Country Contemporary Home on 2.3 Acre on top of the hill. This Unique Open Floor plan welcomes bright warm sunlight in each of the 10 rooms. Top of the line hardwood floors and trim throughout the house, Large open kitchen with modern appliances and plenty of counter space including the granite island. 5 Bedrooms, 3.5 Bathrooms. Master bedroom with fireplace and walk

  Yoel Schwarz Glilos

  65 Oxford Springs Rd, Chester, NY 10918
• 

  

  /16

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Condo for Rent

  3312 Whispering Hills, Chester, NY 10918

  Welcome to lovely Whispering Hills! Don't miss this amazing opportunity to rent this beautiful, centrally located corner unit that was completely renovated in 2018 and has been meticulously maintained. This spacious, 2 bedroom, move-in ready unit has been freshly painted and professionally cleaned. Open floor plan makes for easy entertaining! Enjoy a glass of wine on the deck in warmer weather or

  Marianna LoGiudice Weichert Realtors

  3312 Whispering Hills, Chester, NY 10918
• 

  $415,000 Sold Apr 08, 2025

  • 2,604 Sq Ft
  • $159/SF
  • 24 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  2 Fields Ln, Chester, NY 10918

  Privacy seekers!! Large 3-bedroom ranch with master suite, bright and sunny large living room with fireplace and bow window, hardwood floors and cutout to eat in kitchen. Formal dining room with sliders to rear deck. Large den could be addition sleeping area. Enormous laundry room on living level with lavatory and access to rear yard and walk out garage/basement. Basement adds well over 1000 sq

  Margaret Galatro ARC Realty 1 in Sales

  2 Fields Ln, Chester, NY 10918
• 

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,600 Sq Ft

  21 Hardscrabble Rd, Chester, NY 10918

  21 Hardscrabble Rd, Chester, NY 10918

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