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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 de...
Listing courtesy of Listing Agent: Sheyla L. Falesto (sheyla.falesto@randrealty.com) from Listing Office: Howard Hanna Rand Realty.
Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Che...
Listing courtesy of Listing Agent: Derek J. Greene (office@thegreenerealtygroup.com) from Listing Office: Greene Realty Group.
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 invitin...
Listing courtesy of Listing Agent: Regina Carmel (regina.carmel@randrealty.com) from Listing Office: Howard Hanna Rand Realty.
Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities...
Listing courtesy of Listing Agent: Moses Schreiber (Moses@exitrv.com) from Listing Office: MS Realty Group USA, Inc.
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 se...
Listing courtesy of Listing Agent: Liudmila Lobeeva (Liudmila.Lobeeva@exprealty.com) from Listing Office: eXp Realty.
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 brig...
Listing courtesy of Listing Agent: Gzim Hakanjin (gzim.hakanjin@cbmoves.com) from Listing Office: Coldwell Banker Realty.
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 brigh...
Listing courtesy of Listing Agent: Moshe Kaufman (sales@mkrealtyusa.com) from Listing Office: MK Realty Inc.
Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improv...
Listing courtesy of Listing Agent: Sonia N. Gonzalez (Soniarealestateangel@gmail.com) from Listing Office: HomeSmart Homes & Estates.
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 ...
Listing courtesy of Listing Agent: Chativa Bowen (chativabowen@kw.com) from Listing Office: Keller Williams Realty.
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 gene...
Listing courtesy of Listing Agent: William Philip (WilliamPhilipRE@Gmail.com) from Listing Office: Keller Williams Hudson Valley.
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...
Listing courtesy of Listing Agent: Moshe Kaufman (sales@mkrealtyusa.com) from Listing Office: MK Realty Inc.
Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. ...
Listing courtesy of Listing Agent: Kevin Grier (kevingrier@kw.com) from Listing Office: KW Hudson Valley United.
Welcome to 76 Surrey Road, Chester, NY—a beautifully renovated ranch that is truly move-in ready. This turnkey home offers 3 bedrooms, 2 full bathrooms, and a thoughtfull...
Listing courtesy of Listing Agent: Ammar Iqbal (ammar.iqbal@exprealty.com) from Listing Office: eXp Realty.
Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer...
Listing courtesy of Listing Agent: Joseph Paoli (joe.paoli@randrealty.com) from Listing Office: Howard Hanna Rand Realty.
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 ...
Listing courtesy of Listing Agent: Daniella Restrepo (daniella.restrepo@cbrealty.com) from Listing Office: Coldwell Banker Realty.
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,...
Listing courtesy of Listing Agent: Moshe Kaufman (sales@mkrealtyusa.com) from Listing Office: MK Realty Inc.
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 brigh...
Listing courtesy of Listing Agent: Dovid Hoffman (dh@mkrealtyusa.com) from Listing Office: MK Realty Inc.
Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgett...
Listing courtesy of Listing Agent: David Deberardinis (david.deberardinis2@gmail.com) from Listing Office: Serhant LLC.
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...
Listing courtesy of Listing Agent: Jasmine Wadhwa (jasminewadhwa78@gmail.com) from Listing Office: Howard Hanna Rand Realty.
Private 2.5-Acre Contemporary Retreat with Expansive Deck – Chester, NY Welcome to 424 Laroe Road — a rare opportunity to own 2.5 private acres in sought-after Chester. T...
Listing courtesy of Listing Agent: Jeffrey Morrissey (jeffreymorrisseyrealtor@gmail.com) from Listing Office: Epique Realty.
We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part ...
Listing courtesy of Listing Agent: MaryBeth O'Hara (marybethohara@gmail.com) from Listing Office: Ellis Sotheby's Intl Realty.
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 approxima...
Listing courtesy of Listing Agent: Randolph Rogers (randolph.rogers@exprealty.com) from Listing Office: eXp Realty.
Welcome to 24 Boville Court that sits on 3.7 acres a beautifully maintained home perfectly positioned on a quiet cul-de-sac in the highly desirable Town of Chester. Nestl...
Listing courtesy of Listing Agent: Jennifer Acevedo (jenacevedo@kw.com) from Listing Office: Keller Williams Hudson Valley.
This company operates in one of the Hudson Valley’s fastest-growing suburban markets. The Company generates ~$3.19M in revenue across design-build landscaping, hardscapin...
Listing courtesy of Listing Agent: Peter Berman (peteberman@kwcommercial.com) from Listing Office: Keller Williams Realty.
One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ra...
Listing courtesy of Listing Agent: Ernest Acampora (eacampora@riverrealty.com) from Listing Office: River Realty Services, Inc..
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 archite...
Listing courtesy of Listing Agent: Martha Randazzo (martha.randazzo@randrealty.com) from Listing Office: Howard Hanna Rand Realty.
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 o...
Listing courtesy of Listing Agent: Arya Rabinovits (rabinovitsa@gmail.com) from Listing Office: eRealty Advisors, Inc.
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 th...
Listing courtesy of Listing Agent: Artan Kukaj (artan@spiralny.com) from Listing Office: SPIRAL NY Real Estate LLC.
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...
Listing courtesy of Listing Agent: Christina Rowan (christina.rowan@randrealty.com) from Listing Office: Howard Hanna Rand Realty.
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...
Listing courtesy of Listing Agent: James J. Cosenza (james.j.cosenza@gmail.com) from Listing Office: BHG Real Estate Green Team.
This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive prim...
Listing courtesy of Listing Agent: Asha Keegan (Asha.keegan@randrealty.com) from Listing Office: Howard Hanna Rand Realty.
Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step ...
Listing courtesy of Listing Agent: Christina E. D'Altilio (christina.daltilio@coldwellbankerchoice.com) from Listing Office: Coldwell Banker Choice Prop..
INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart ...
Listing courtesy of Listing Agent: Frank Muccari (frankmproperties@gmail.com) from Listing Office: Cronin & Company Real Estate.
INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart ...
Listing courtesy of Listing Agent: Frank Muccari (frankmproperties@gmail.com) from Listing Office: Cronin & Company Real Estate.
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, ...
Listing courtesy of Listing Agent: Kimberly A Corkum (kimcorkumbroker@gmail.com) from Listing Office: Keller Williams Realty.
Now offered at $899,000. Settle in before the new school year and start living your best life here. Privately set on over 5 scenic acres within the Warwick School Distric...
Listing courtesy of Listing Agent: Jennifer DiCostanzo (jendicorealestate@gmail.com) from Listing Office: RE/MAX Town & Country.
Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NY Tucked on a generous half-acre lot in the charming Village of Chester, t...
Listing courtesy of Listing Agent: Tara Roufanis (tara.roufanis@kw.com) from Listing Office: Keller Williams Village Sq Rlt.
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...
Listing courtesy of Listing Agent: Craig Watters (craig.watters@compass.com) from Listing Office: Compass Greater NY, LLC.
Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of ...
Listing courtesy of Listing Agent: Ewa Kusmierek (Ewa.Kusmierek@exprealty.com) from Listing Office: eXp Realty.
Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout wi...
Listing courtesy of Listing Agent: Sholom Torim (samtorim@gmail.com) from Listing Office: Realty Blue Corp.
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-l...
Listing courtesy of Listing Agent: Moche Halpern (moshe@bloomingrealty.com) from Listing Office: Blooming Realty.
Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND j...
Listing courtesy of Listing Agent: Melissa M Forsyth (hvhomeconnection@gmail.com) from Listing Office: Hudson Valley Home Connection.
A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sop...
Listing courtesy of Listing Agent: Rachel L Baruchov (rachel@platinumrealtyny.com) from Listing Office: Platinum Realty Associates.
Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lif...
Listing courtesy of Listing Agent: Joseph Rosenfeld (jr@flagrealtygroup.com) from Listing Office: Flag Realty Group.
Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The m...
Listing courtesy of Listing Agent: Charles W. Moore (charleswmoore@kw.com) from Listing Office: Keller Williams Realty.
Imagine ending everyday watching the sun set from your front porch, experiencing views that change with every season. Sunset views, fenced yard, brand new Trex deck, pool...
Listing courtesy of Listing Agent: Gina Dudgeon (gina.dudgeon@randrealty.com) from Listing Office: Howard Hanna Rand Realty.
Own One of America's Great Equestrian Landmarks Steeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built ...
Listing courtesy of Listing Agent: Beth Palma (bethpalma@kw.com) from Listing Office: Keller Williams Realty.
Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home f...
Listing courtesy of Listing Agent: Janet A Rendle (jarendle@gmail.com) from Listing Office: Weichert Realtors.
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...
Listing courtesy of Listing Agent: Joanne M Timperio (jmt2286@gmail.com) from Listing Office: RE/MAX Benchmark Realty Group.
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 pr...
Listing courtesy of Listing Agent: Jake Garay (jakegaray@serhant.com) from Listing Office: Serhant LLC.
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