Highland, NY Homes for Sale under $500,000

A Little Work, A Lot of Wonder!! Cape Cod Retreat with a Pond!Your Peaceful Catskills Getaway Awaits.Just two hours from New York City and 15 minutes to the Metro-North train, this charming Cape Cod offers the perfect blend of country tranquility and small town charm. Set on 2.17 picturesque acres, this property invites you to slow down, breathe deep, and truly enjoy life in the

Gibson McKean Payne Team LLC

Retro Lakefront Charm with Stunning Views – A Hidden Gem Just Two Hours from NYC. Step back into the classic charm of the 1960s with this inviting 3-bedroom, 2-bath lakefront home nestled in a beloved community where generations of families have made lasting memories. Located on a pristine glacier lake, this home offers year-round beauty and recreation—from kayaking and sailing to fishing and

Dawn Payne Payne Team LLC

Cozy ranch home in Eldred, NY. Eldred is part of the Town of Highland and is situated near the Delaware River in the scenic Catskill Mountains region. This ranch offers the perfect canvas for your personal updates and creative vision. This home and serene setting with 3 bedrooms, a country eat in kitchen, living area and a full bath on one level for easy living. The property sits in a desirable,

Dali Levy KW Hudson Valley United

Lake Rights to Highland Lake ! Extra lot included in sale. Cute home with two Bedrooms and two Full baths, nice sized living room, dining area, kitchen, good sized landing upstairs that could be used for office area, enclosed sun room, black topped driveway on a nice sized lot. ( home sits on 3/4 acre and extra lot on left of home is 1/3 acre, for a Total of 1.10 acres.) Quiet area. Lake access

Lorraine Smith Century 21 Geba Realty

Discover the perfect blend of comfort, privacy, and natural beauty at 50 Park Road in Yulan. Set on just under an acre along the tranquil banks of Beaver Brook, this charming 3-bedroom, 2-bath home includes Lots 11, 12, and 13, offering a rare opportunity to own waterfront property with creek frontage—all outside the flood zone. Whether you're looking for a full-time residence, a weekend retreat,

Nick Ralph Nestquest Direct LLC

Beautiful property offering a wonderful opportunity for homeowners, investors, or those seeking a peaceful retreat. This home features a spacious layout with endless potential to customize and make it your own. Conveniently located near local amenities, outdoor recreation, and major roadways. Property is being sold as is. Buyer is responsible for verifying all information, including taxes,

Ron Martinez Listing Pro Realty Services

Stunning Colonial 4 Bedroom Farmhouse Retreat in the Heart of the Catskills ,on over 1 acre of private landscape, this house offers a serene escape for seeking comfort and lifestyle. Key Features: Open floor plan with vaulted ceilings, with two fireplaces (gas and wood), skylights in the living and kitchen area. 3 full bathrooms, jacuzzi tub, cathedral master ceiling, spacious dining area

Michael Friedmann eRealty Advisors, Inc

Tucked into 6.3 private wooded acres along a quiet country road, this thoughtfully updated two-bedroom one-bathroom home offers the privacy, tranquility, and natural beauty that define life in the Upper Delaware River Valley. Surrounded by mature pines, hardwoods, and native ferns, the property feels secluded from the world while remaining just minutes from Barryville and Eldred. Whether enjoying

Myra Rappoport Payne Team LLC

2 Houses for the price of one! Recently renovated, these homes are perfect for living in one and renting out the other or use as a guest house when you have friends and family visit. Both have 2 bedrooms, 1 full bath, kitchen, dining room and living room. Plenty of natural lights. Walk up attic with lots of storage space. Circular driveway makes for easy parking and the 2 car garage is handy for

Gibson Mc Kean Gibson E McKean Inc

Welcome to this lovingly cared for 1920s farmhouse a place where memories have been made for generations and where timeless country charm welcomes you from the moment you arrive. Set on 2.20 picturesque acres in the heart of the Catskills, this immaculate home offers over 1,600 square feet of warm, inviting living space designed for comfort, connection, and relaxation.Inside, you’ll find 3

Dawn Payne Payne Team LLC

Welcome to Dogwood Lake House, a charming 20th-century Colonial Revival with deeded lake access on Highland Lake. Tucked under a canopy of ornamental dogwoods and hydrangeas, this cozy four bedroom home overlooks Highland Lake, and features lake views from almost every window. At the heart of the home, a striking wood-burning fireplace anchors the living room, surrounded by wood paneling,

Owen Boller Boller Properties

Looking for that "peaceful, easy feeling"? This charming cabin is the ultimate prescription for rest, relaxation, and outdoor adventure. Located in a beautiful, vibrant pocket of Sullivan County, you’ll be minutes from local breweries, antique hunting, and dining.Situated on a usable, naturally landscaped acre with mature trees, the property features a 2-bedroom, 1-bath layout that perfectly

Jonathan Sunshine The Sunshine Group Real Estate

Unique opportunity to own a live/work property on two separate lots totaling nearly 2 acres, offered together. A-frame (swiss chalet) contemporary home features vaulted ceilings, fire place, wood burning stove, 3 bedrooms, 2.5 baths, 2,088 square feet living space.The adjoining commercial lot includes a two-bay garage with lifts, and radiant heat run by water baseboards via home heating oil.

Jennifer Townsend Iron Valley RE Tri-State

3 Acres * Stunning Newly Renovated homeCompletely, totally, and newly renovated (2025) home featuring a spacious open-concept floor plan, the home boasts 4 generous bedrooms and 2 beautifully updated full bathrooms. Offering updated interior throughout, including new appliances, beautiful floors, and new windows with Minisplits.Conveniently located on Route 55 in Eldred, close to Bethel

Pamela Henning KW Hudson Valley United

Move right into this beautifully renovated colonial tucked away at the end of the road, offering privacy, peace, and a setting that feels a world away. Set on a serene 5.65-acre lot, 142 Split Rock Drive is a spacious 2006-built home with 2,240 square feet, featuring four bedrooms and two and a half bathrooms. Thoughtful recent updates include new flooring throughout, a renovated bathroom, and a

Alan Wieder Catskills Home Services

Delaware Riverview Farmhouse Cottage!!Own the last house on a dead end street in the quaint, historic River town of Lackawaxen, PA. This privately set, move in condition home is full of character & charm! Apply for a short term rental permit and gain income when you are not there relaxing yourself. Welcoming covered front porch w/ original custom wood work and cabinetry inside, hardwood flooring,

Shaun Burger, Assoc Broker Keller Williams RE Milford