Chester, NY Homes for Sale

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  /29

  $550,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  391 Bull Mill Rd, Chester, NY 10918

  Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
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  /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
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  /33

  $711,000

  • 4 Beds
  • 2.5 Baths
  • 3,092 Sq Ft

  2 Dawn Ct, Chester, NY 10918

  Spectacular 4 bedrooms, 2.5 bathrooms colonial in the very desirable Sugarloaf Heights. This magnificent home offers heavenly views right from your rear deck. You never have to leave home when you can step outside and enjoy your own personal refuge with a fully fenced-in yard that brings privacy to your in-ground pool and hot tub. Home offers many recent upgrades which include updated kitchen,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 203-6068

  2 Dawn Ct, Chester, NY 10918
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  /42

  $575,000

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft

  12 Juniper Ln, Monroe, NY 10950

  Welcome to this 4-bedroom, 3 full bath raised ranch offering a flexible and spacious layout designed for comfortable everyday living. Hardwood floors run throughout the main level, adding warmth and character to the home's living spaces. The primary bedroom features a private en-suite bath, creating a quiet and comfortable retreat. Three additional bedrooms provide plenty of room for family,

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (329) 208-1641

  12 Juniper Ln, Monroe, NY 10950
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  /2

  $369,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  4703 Whispering Hills Unit 320, Chester, NY 10918

  Rare end unit in Whispering Hills. 3 bedrooms, 2 1/2 bathroom in spectacular location in the highly sought after Chester School district. Coming soon. Stay tuned....

  

  Erin Connolly

  Artisan Realty

  (845) 328-6250

  4703 Whispering Hills Unit 320, Chester, NY 10918
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  /50

  $979,000

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  893 Laroe Rd, Monroe, NY 10950

  When you walk in the front door, the artful design and carefully curated surroundings immediately banish the outside world. The open floor plan and copious windows bring in the sunshine and natural light. Begin in the spacious living room with woodburning fireplace that opens into the family room. The living room flows naturally to the family room with its own fireplace, and it is surrounded by

  Lisa Fountain Corcoran Country Living

  893 Laroe Rd, Monroe, NY 10950
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  /22

  $345,000

  • 3 Beds
  • 2.5 Baths
  • 1,392 Sq Ft

  65 Darin Rd, Warwick, NY 10990

  Charming and move-in ready townhouse in desirable Kings Estates of Warwick, NY, located in the Warwick Valley Central School District with no HoA fees and 60 mins to/from NYC. This cozy 3-bedroom, 2.5-bath home offers an open-concept living and dining area filled with natural light. The updated kitchen boats stainless steel appliances, offering a modern touch to this warm and inviting home. A

  Sandra Laramore Redfin Real Estate

  65 Darin Rd, Warwick, NY 10990
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  /44

  $674,999 Open Sun 11AM - 1PM

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Tucked away on a quiet cul-de-sac, 9 Mount Ridge Court offers a rare opportunity to own a lovingly maintained 5-bedroom, 3-bath home with 3,000 square feet of light-filled living space. Owned and cared for by the original homeowner since day one, this residence combines warmth, comfort, and flexibility—ready for its next chapter.Step inside to find spacious, sun-filled rooms with an easy

  James Feldhaus eXp Realty

  9 Mount Ridge Ct, Monroe, NY 10950
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  /40

  $769,000

  • 4 Beds
  • 2.5 Baths
  • 3,063 Sq Ft

  48 Brennan Ct, Chester, NY 10918

  Welcome to this stunning home nestled on 5 acres near the heart of Chester, NY. Tucked away for ultimate privacy, yet just minutes from shopping, dining, and major highways-it's the perfect blend of seclusion and convenience. Step inside this spacious 4-bedroom 3-bathroom retreat, designed for comfort and style. This open layout flows seamlessly with plenty of natural light pouring in through

  Claude Brischoux Keller Williams Realty

  48 Brennan Ct, Chester, NY 10918
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  /35

  $690,000

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  23 Renies Rd, Chester, NY 10918

  Escape to your own sanctuary in this stunning 3 bedroom 3 full bath contemporary cedar home, perfectly blending modern comfort with natural charm. Inside you'll find an open-concept layout with soaring ceilings, large windows, and natural wood finishes that create a warm, modern vibe. The spacious kitchen features stainless appliances, hickory cabinets and an island ideal for entertaining. Two

  Kristie Jacques Century 21 Full Service Realty

  23 Renies Rd, Chester, NY 10918
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  /43

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  165 Creamery Pond Rd, Chester, NY 10918

  The timeless, elegant Colonial in the Warwick School District is ready for a new hallmark. Situated just behind the Sugarloaf Arts Village—home to over 50 vibrant small shops, restaurants, and unique places to explore—this residence offers both charm and convenience. Spacious and filled with natural light, it’s perfect for peaceful enjoyment with your loved ones. A gas fireplace adds warmth and

  Kichka Pascaru Christie's Int. Real Estate

  165 Creamery Pond Rd, Chester, NY 10918
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  /8

  $899,900

  • 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
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  /50

  $879,000

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

  11 Saddle Hill Rd, Chester, NY 10918

  **Welcome to 11 Saddle Hill Road – A Perfect Blend of Luxury, Space & Location**This stunning brick Colonial offers the perfect balance of private luxury and everyday convenience. With over **5,000 square feet** of impeccably finished living space, this home provides ample room for everyone to **live, work, and relax in comfort**.Step into the **grand two-story foyer**, flooded with

  Alissa Taylor-Vetell Keller Williams Realty

  11 Saddle Hill Rd, Chester, NY 10918
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  /45

  $674,999

  • 5 Beds
  • 2.5 Baths
  • 3,115 Sq Ft

  507 Bull Mill Rd, Chester, NY 10918

  Welcome to this beautifully maintained colonial with a charming wrap-around front porch, set on 1.5 private acres within the sought-after Monroe-Woodbury School District. Offering over 3,100 square feet of living space, this 5-bedroom, 2.5-bath home blends timeless style with thoughtful design.Step inside the two-story foyer and you’ll find a bright, flowing layout designed for both

  Alison Orlando Keller Williams Hudson Valley

  507 Bull Mill Rd, Chester, NY 10918
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  /8

  $799,999

  • 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.).

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  /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
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  /50

  $975,000 Open Sun 3:30PM - 6PM

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft

  2 Primrose Ln, Chester, NY 10918

  Introducing an exceptional opportunity to own your dream property with over 18 acres wooded land! This stunning colonial is a perfect blend of luxury and functionality. Spanning 2370 square footage plus finished basement with 4 spacious bedrooms and 3 elegantly designed bathrooms, this home boasts an inviting atmosphere that caters to both relaxation and entertaining.As you step inside,

  Joel Friedman MS Realty Group USA, Inc

  2 Primrose Ln, Chester, NY 10918
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  /37

  $724,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 3,977 Sq Ft

  278 Gibson Hill Rd, Chester, NY 10918

  AMAZING PROPERTY -- offers something for everyone! Gorgeously restored 3,977 square foot colonial farmhouse on 5.1 private acres, and with a pool, 5 bay carport, a 38x40 garage (with it's own entrance from road -- can rent out for income), and so much more! . . . Located in the Warwick Valley School District (and just a half mile to the Warwick town line). Just minutes to all downtown Warwick has

  Dean Diltz Keller Williams Realty

  278 Gibson Hill Rd, Chester, NY 10918
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  /45

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,817 Sq Ft

  23 Eagle St, Monroe, NY 10950

  This beautifully upgraded Cape-style home in the top-rated Monroe-Woodbury School District features 3 bedrooms and 2 full baths with modern comfort and style. The primary suite boasts a walk-in closet and custom shower, while upstairs laundry, wide plank floors, and a cozy fireplace add convenience and charm. The 16x20 chef's kitchen includes a commercial oven, modern appliances, and a 4x8

  Patricia Culianos Joseph Baratta Company Realty

  23 Eagle St, Monroe, NY 10950
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  /11

  $34,000

  • Land
  • 1.8 Acres
  • $18,889 per Acre

  L27 Carriage Knolls Rd, Chester, NY 12817

  Seller financing now available! This property has been cleared and excavated in preparation for a new home. Site-plans are complete, perc tests are complete, septic plans have been completed, and an electric pedestal has been installed. (The small shed on-site is included as part of this transaction. Larger building also available separately and would need to be removed once the house certificate

  Walter Swartz Gallo Realty ADK Inc

  L27 Carriage Knolls Rd, Chester, NY 12817
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  /24

  $489,900

  • 4 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  22 Bridle Ln, Chester, NY 10918

  This well-maintained 4-bedroom raised ranch located in Surrey Meadows, is just a short walk to a town park and local schools. The home features an updated kitchen and bathrooms, a bright and functional layout, and 400 square feet of finished space in the basement with a family room, bedroom, storage and laundry area. Let’s not forget about the inviting sunroom—perfect for morning coffee,

  Jennifer Lucas Keller Williams Realty

  22 Bridle Ln, Chester, NY 10918
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  /45

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  11 Lakeview Dr, Chester, NY 10918

  Split-level spacious home in desirable Chester neighborhood within Warwick Valley School District! This home features newer vinyl siding, a custom front entry door, hardwood floors, ceiling fans, and radiant electric ceiling heat. The 2-car garage includes windows and an automatic opener. Enjoy the fully fenced-in yard with an in-ground pool, deck with gazebo, shed, and play set—all included.

  Nicole Renda IBNA Real Estate Group

  11 Lakeview Dr, Chester, NY 10918
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  /3

  $199,000

  • Land
  • 1.85 Acres
  • $107,568 per Acre

  0 Renies Rd, Chester, NY 10918

  Seize the opportunity to own this serene, buildable lot nestled in a quiet, desirable location. Perfect for your dream home. This parcel offers privacy, natural beauty, and close to everything! Convenient access yet tucked away for peace and quiet. Don’t miss out—schedule your visit today!

  Kristie Jacques Century 21 Full Service Realty

  0 Renies Rd, Chester, NY 10918
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  /13

  $620,800

  • Land
  • 194 Acres
  • $3,200 per Acre

  68 Walter Foote Rd, Chester, NY 12853

  194 Acres in the Adirondack Park - Endless Possibilities. Two contiguous lots 32.-1-24 and 32.-1-23 located on the side of a mountain, minutes to Gore Mountain skiing, whitewater rafting & hiking trails. It offers privacy & seclusion with close proximity to amenities in North Creek. There are existing logging roads for access. Features include: a brook, pond, small wetland area, tool shed, old

  Cindy Brower Coldwell Banker Prime Properties

  68 Walter Foote Rd, Chester, NY 12853
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  /48

  $499,000

  • 5 Beds
  • 2.5 Baths
  • 3,120 Sq Ft

  358 Bull Mill Rd, Chester, NY 10918

  CHARM, SPACE and OPPORTUNITY in the highly rated Monroe-Woodbury School District! Classic vintage 5 bedroom colonial on 3.10 level acres offering the perfect blend of character and potential - all just 50 miles from NYC yet a world away from the hustle and bustle of city life. Located on a winding country road, the home sits on a large, level lot with mature trees and an in ground pool (condition

  Amy Wilhelm Corcoran Baer & McIntosh

  358 Bull Mill Rd, Chester, NY 10918
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  /41

  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  47 Greycourt Ave, Chester, NY 10918

  Classic farmhouse feel with contemporary updates on a generous 1.3-acre lot, with this home you get it all! This 3/4bedroom, 1.5-bath home combines classic warmth with modern comforts, including a kitchen featuring granite countertops, hardwood flooring and a spacious island perfect for prep and entertaining. along with a huge sunken living room with recessed lighting and a pellet stove to save

  Pedro Garcia Curasi Realty, Inc.

  47 Greycourt Ave, Chester, NY 10918
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  /10

  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  264 Heritage Ln, Monroe, NY 10950

  Move-In Ready 3-Bedroom Condo in the Monroe-Woodbury School District. Discover comfort, convenience, and community in this 3-bedroom, 1.5-bath condo located in one of the most desirable areas of the Hudson Valley. The open-concept main level features a bright and spacious living room, a dining area, and a well-appointed kitchen—perfect for everyday living and entertaining. Upstairs, you’ll find

  Frank Golio Howard Hanna Rand Realty

  264 Heritage Ln, Monroe, NY 10950
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  /26

  $225,000

  • 2 Beds
  • 1 Bath
  • 484 Sq Ft

  42 Heaton Rd, Monroe, NY 10950

  This quaint two-bedroom home is located in the lake region of Monroe. It is a short walk down Heaton rd. to Walton Lake. There is an enclosed porch when you enter the home that has bright sunny windows. The kitchen and living room are one open room. There is one bathroom, both bedrooms have nice size closets. Full attic with pull down stairs for storage. Great starter home or perfect for

  Maureen Schroder Keller Williams Valley Realty

  42 Heaton Rd, Monroe, NY 10950
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  /39

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,898 Sq Ft

  25 High St, Chester, NY 10918

  25 High St in Chester, NY, is a Victorian gem rich with character and ready for your personal touch. Step inside to discover original wide-plank wood floors throughout and preserved under carpeting, offering timeless warmth and authenticity. The bright modern kitchen is ready for gatherings, while the spacious formal dining room sets the stage for memorable meals. Two large living rooms provide

  Alicia Goldman Christie's Int. Real Estate

  25 High St, Chester, NY 10918
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  /13

  $89,900

  • Land
  • 14.7 Acres
  • $6,116 per Acre

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817

  Beautiful 14.7 acres located in Adirondack Heights! Private & secluded. Some clearing has been done- roughed in driveway. Site plan available- approved building lot. 20 minutes to Gore Mountain. Close to all the local lakes, restaurants, & shopping. Your Adirondack adventure awaits!

  Julia Pucciarelli Gallo Realty ADK Inc

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
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  /2

  $139,900

  • Land
  • 45.83 Acres
  • $3,053 per Acre

  0 William Hill Rd, Chester, NY 12817

  Lovely large lot on William Hill Road, more pics to come.AO 6/28

  Jason Minch William Raveis-New York LLC

  0 William Hill Rd, Chester, NY 12817
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  /13

  $86,500

  • Land
  • 2.84 Acres
  • $30,458 per Acre

  38 Granite Ridge Rd, Chester, NY 12817

  Great opportunity to build your own Adirondack dream home not far from Lake George. Seller financing available . Includes 2.84 acres of gently rolling property cleared for a potential house or a cabin. All stumps and undergrowth have been removed. 200 amp underground electrical service with 30 amp and 50 amp receptacles for camper hook up. Extra sleeve for future broadband or satellite. Winding

  Walter Swartz Gallo Realty ADK Inc

  38 Granite Ridge Rd, Chester, NY 12817
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  /50

  $1,775,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating.Nature lovers and hobby farmers will

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
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  /37

  $569,999

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  78 Pickerel Rd, Monroe, NY 10950

  Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

  Dylan Piazza Howard Hanna Rand Realty

  78 Pickerel Rd, Monroe, NY 10950
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  /48

  $1,099,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Exquisite Colonial Estate: Timeless Grandeur Meets Modern LuxuryNestled gracefully on a private cul-de-sac amidst meticulously manicured grounds, this sprawling Colonial estate offers an unparalleled blend of classic elegance and contemporary comfort. From the moment you approach the stately wrought-iron fenced property and enter through the grand foyer, you are greeted by a magnificent staircase

  Beth Palma Keller Williams Realty

  5 Gabriels Dr, Chester, NY 10918
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  /50

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  90 Main St, Chester, NY 10918

  "The House on the Hill" Proudly offered for the first time in over 70 years. This expansive and character-rich home overlooks the heart of the village while offering nearly 10 acres of space, privacy, and endless potential. Set across three separate parcels totaling 9.68 acres, the property features a main house with approximately 4,000 sq ft, a charming 2-bedroom guest cottage, a large dairy

  STEVEN WROBEL JR. Serhant LLC

  90 Main St, Chester, NY 10918
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  /35

  $1,650,000

  • 6 Beds
  • 4.5 Baths
  • 3,512 Sq Ft

  17 Bonnie Brook Rd, Monroe, NY 10950

  Over 20 sprawling acres with serene life, pond frontage, this is a true sanctuary. Located in Monroe-Woodbury this unique property offer two distinct residences and a spacious barn, providing endless possibilities. House 1: Contemporary Modern originally built in 1965. The first home boasts a generous 3,500+ sq ft of premium living space. Designed with a flexible layout, the home features two

  Pamela Henning Keller Williams Hudson Valley

  17 Bonnie Brook Rd, Monroe, NY 10950
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  /31

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  2 Pine Hill Rd, Chester, NY 10918

  Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts

  Debbie Walsh SHAHAR Management LLC

  2 Pine Hill Rd, Chester, NY 10918
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  /35

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  576 Bull Mill Rd, Chester, NY 10918

  A fantastic opportunity for investors or future homeowners! This well-maintained home is set on a large, flat lot in a quiet, nature-filled neighborhood and offers strong rental potential with long-term flexibility. Inside, you’ll find a spacious living room, formal dining area, kitchen, and comfortable layout ideal for everyday living. Recent updates include fresh interior paint (2021), and a

  Lazar Schvimmer Blooming Realty

  576 Bull Mill Rd, Chester, NY 10918
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  /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

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