Chester, NY Homes for Sale under $500,000

Welcome to your dream home at 108 Pine Hill Rd, Chester, NY, where comfort meets elegance in a spacious single-family abode. This charming home offers a thoughtfully designed layout, featuring a welcoming kitchen with direct outdoor access, perfect for morning coffees or entertaining. The first floor also hosts a cozy living room and a bright family room, both filled with natural light. Upstairs,

Avi Samet Avion

Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you

Kassandra Mott Keller Williams Hudson Valley

Set on nearly half an acre in the Village of Chester, this charming brick Cape Cod offers a rare combination of privacy and convenience, featuring a flexible four room layout and a fully finished lower level with full bath. Positioned well back from the road with a long private driveway and no homes directly across the street, the setting feels peaceful and tucked away while remaining minutes

Geoffrey Green BHG Real Estate Green Team

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 ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

Ernie Acampora River Realty Services, Inc.

Spacious raised ranch style home offering three bedrooms and two full bathrooms with 1,932 square feet of comfortable living space. Features a 1-car garage and a functional layout perfect for everyday living. The home has been freshly painted, giving it a bright, clean, move-in ready feel. A great opportunity for buyers seeking space, style, and value.

Geni Silva Ethos Realty LLC

Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat

William Scolza HomeSmart Homes & Estates

Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

Mark Karten Karten Real Estate Svcs LLC

Welcome to this beautifully fully renovated 4-bedroom, 2-bath home, thoughtfully updated in 2026 with modern finishes throughout. This spacious property offers a bright open-concept layout featuring a large living room, dining area, and a stunning modern kitchen complete with a skylight and abundant natural light. Enjoy new flooring and moldings throughout, freshly painted interiors, and

Pearl Ungar eRealty Advisors, Inc

Quaint ranch offering comfort, convenience, and room to make it your own. This 2-bedroom, 2-full bathroom home features hardwood floors and a practical layout with great natural light. The finished walk-out basement adds valuable living space with plenty of possibilities: home office, recreation area or guest space. There is also abundant storage throughout the home. Enjoy outdoor living with a

Maria Kriesel Century 21 Full Service Realty

Is there a 3-bed ranch in Monroe NY under $500K with a finished basement, pool, and commuter convenience? 35 Maple Ln is a 3-bedroom, 2-bathroom ranch offered at $499,999 with 1,460 sq ft of living space, including 960 sq ft above grade and a 500 sq ft finished basement. Built in 1964, this single family residence offers true single level living plus flexible lower level space ideal for

Kewin Garabito eXp Realty

Lake Rights! Low Taxes! Welcome home to this lovely cape, beautifully situated on a double lot allowing for plenty of yard space for peace and privacy. This home features 4 bedrooms and 2 full bathrooms with a large eat-in kitchen, wood floors and a spacious unfinished, walk-out basement. Walk-out from the kitchen onto a lovely deck for grilling, dining and relaxing as you take in the tree-top

Layla Rose Boyles Century 21 Realty Center