Chester, NY Homes for Sale under $800,000

Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal.Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious

Danielle Hinton Redfin Real Estate

Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment.

Jeffrey Morrissey Epique 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 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

This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a

Carla Terranova Keller Williams Realty

Welcome to this charming three bedroom, two and a half bath colonial nestled in a welcoming neighborhood just minutes from the highway and the charming hamlet of Sugar Loaf. This inviting home offers a comfortable layout with plenty of space for everyday living and gathering. Outside, enjoy a flat, level yard that provides space for relaxing, entertaining, gardening, or outdoor activities.

Michele Tobin Keller Williams Realty

3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

Bernadette Corrigan Keller Williams Realty

Welcome to this beautifully maintained 3-bedroom, 3-bath ranch nestled on a quiet dead-end street in the Lake Hill Farms community in the Town of Chester, within the Monroe-Woodbury School District. Offering municipal services, central air conditioning, and exceptional pride of ownership, this home is truly move-in ready. Step inside to a bright and inviting floor plan featuring a spacious living

Claudia Lepore Keller Williams 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 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

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

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

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

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

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

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

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

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

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

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

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

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

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 deck just 3 minutes from Sugar Loaf Arts and Crafts Village. Its' kitchen has been upgraded boasting stainless steel appliances, granite countertops, and cherrywood cabinetry with undermount lighting and a wine/ beverage cooler.

Sheyla Falesto Howard Hanna Rand Realty

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

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

Moshe Kaufman MK Realty Inc

The search for your DREAM HOME ends when you visit this property, since it will check all your boxes ! LOCATION which is perfect for commuters, just a few feet away from the charming Sugar Loaf Craft Village, situated between Warwick and Chester for your enjoyment and convenience of both town's amenities and activities. Corner lot, vinyl siding, deck overlooking the private backyard with a raised

Patricia Brady Keller Williams Realty

Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest.From the moment you arrive, you’ll appreciate

Joseph Rosenfeld Flag 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 inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm

Regina Carmel Howard Hanna Rand Realty

This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the

Jacob Fried Keller Williams Realty

Showings begin on 8/28. More information and pics coming soon.

Gina Dudgeon 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 and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The

Moses Schreiber MS Realty Group USA, Inc

BiLevel/Raised Ranch on Quiet Street with Room to Grow! Come home and relax on the upper level deck overlooking state land that offers additional privacy. This well-maintained home clearly shows the pride of ownership. Open concept living room and dining room features many windows that fill the home with natural sunlight. Enjoy the convenience of the updated full bathroom and three comfortable

Jeffrey Jacobsen Terrie OConnor

Highly sought-after Warwick Schools, this Colonial offers curb appeal with custom stone entrance pillars featuring illuminated house numbers, an inlaid driveway address, professionally landscaped grounds accented by natural stone and in-ground lighting, and an insulated two-car carriage-style garage with glass doors. A grand two-story foyer with soaring ceilings, elegant wainscoting, and abundant

David White Owner Entry.com

Tucked away on over an acre with serene lake views and deeded lake rights, this spacious Monroe retreat offers the perfect blend of privacy, comfort, and lifestyle. Wake up to natural light pouring through oversized windows and start your day on the deck overlooking the water. Inside, you’ll find 3/4 generously sized bedrooms and 3 full baths, along with an updated kitchen and baths that bring a

rosemary mcginn Century 21 Full Service Realty

Impeccably maintained and lovingly cared for, this spacious 3-bedroom, 2-bath , 48 foot bi-level ranch offers comfort, functionality, and timeless appeal in one of Monroe’s desirable private cul-de-sac settings.Step inside to find bright, welcoming living spaces, generous room sizes, and beautiful hardwood floors that add warmth and character throughout much of the home. The inviting main

Aja Marshall Krumpfer Realty Group, LLC