29

Highland, NY Homes for Sale under $400,000

Section Image Section Image
  • /37

    $195,000

    • 1 Bed
    • 1 Bath
    • 777 Sq Ft

    223 Yulan Barryville Rd, Barryville, NY 12719

    Charming Country Bungalow — Turnkey & Fully FurnishedTucked away in the scenic hamlet of Barryville, this delightful one-bedroom country bungalow is ready for you to simply unpack and unwind. Being sold fully furnished and equipped with all appliances — just showup, bring your suitcase and settle in.Inside, you'll find warm wood floors flowing throughout a thoughtfully arranged layout.

    Agent Photo

    Barry Becker

    KW Hudson Valley United

    223 Yulan Barryville Rd, Barryville, NY 12719
  • /38

    $399,900

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    173 Yulan Barryville Rd, Barryville, NY 12719

    Located in the peaceful countryside of Yulan, this beautifully maintained ranch style home offers the perfect opportunity to enjoy year-round living or create your own weekend retreat in the heart of Sullivan County. Designed for effortless one-level living, this inviting home blends comfort, privacy, and modern convenience with the natural beauty of the Catskills.Step inside to discover a

    Agent Photo

    Kathy White

    Exit Realty Connections

    173 Yulan Barryville Rd, Barryville, NY 12719
  • /18

    $199,900

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 884 Sq Ft

    94 Airport Rd, Eldred, NY 12732

    This quintessential Catskills cottage welcomes you home with a warm embrace and exudes relaxation, peace and quiet. Simply the epitome of a sweetness, refreshing your soul and recharging your energy. The kind of place where you sleep all night without a worry in the world and you wake up to sunshine and birds singing their song. There are an abundance of windows throughout the home letting in the

    Agent Photo

    Donna Geba

    Century 21 Geba Realty

    94 Airport Rd, Eldred, NY 12732
  • /31

    $350,000

    $49K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    87 Airport Rd, Eldred, NY 12732

    Stop the search! This 2,000 sq ft home offers the perfect blend of comfort and country living. Features include a large living room with hardwood floors and a cozy stone fireplace, a custom chef's kitchen to prepare your perfect meals and a dining area that opens to a screened-in porch for dining al fresco. Enjoy the convenience of 3 bedrooms and 2 baths on the main level. Need more space? The

    Agent Photo

    Donna Geba

    Century 21 Geba Realty

    87 Airport Rd, Eldred, NY 12732
  • /8

    $195,000

    • Land
    • 22.3 Acres
    • $8,744 per Acre

    0 Crawford Rd Unit KEY821449, Highland, NY 12528

    Beautiful wooded 22.3 acre parcel along quaint Crawford Road just outside of the charming Delaware river hamlet of Barryville. Close to Eldred, Yulan, Barryville, Narrowsburg and the Delaware River.

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate LLC

    0 Crawford Rd Unit KEY821449, Highland, NY 12528
  • /3

    $150,000

    • Land
    • 6.7 Acres
    • $22,388 per Acre

    0 Highland Lake Rd Unit KEY868497, Highland, NY 12732

    Located just outside of the charming hamlet of Eldred, this wooded parcel provides access to the spectacular Halfway Brook with rushing waters and waterfall along the rear property line. This area of the Hudson Valley provides easy access to the Delaware River for fishing, rafting & canoeing. It also provides plenty of opportunities for outdoor recreation, camping and hunting. It's a hop, skip

    Theresa Powers

    Keller Williams Realty

    0 Highland Lake Rd Unit KEY868497, Highland, NY 12732
  • /18

    $129,900

    $29K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft

    250 County Road 21, Barryville, NY 12719

    Home Sweet Home can describe this comfortable manufactured home tucked away on 3/4 of an acre this home features a spacious living room, eat in kitchen with wood cabinets, laundry closet, 3 bedrooms and 2 bathrooms. A great location in between Yulan and Barryville NY close to area amenities including farmers markets, library, the Delaware river for recreation, grocery store, schools and so much

    Agent Photo

    Donna Geba

    Century 21 Geba Realty

    250 County Road 21, Barryville, NY 12719
  • /20

    $199,000

    $50K PRICE DROP
    • Land
    • 6.38 Acres
    • $31,191 per Acre

    0 Browning Blvd Unit 27248900, Highland, NY 12719

    Escape to the beauty of lake living with this stunning 6.38-acre property in the private gated community of York Lake Shores. Enjoy boating, sailing, swimming, and fishing on the pristine lake while surrounded by peace and nature. Ideally located just two hours from New York City and under 20 minutes to the Metro-North train, this property offers the perfect balance of seclusion and convenience.

    Cathy Nation Premier Land Hub

    0 Browning Blvd Unit 27248900, Highland, NY 12719
  • /7

    $175,000

    • Land
    • 6.01 Acres
    • $29,118 per Acre

    0 Split Rock Dr Unit KEY921291, Highland, NY 12719

    Waterfront...NOT Kidding! Rare wooded waterfront parcel..privacy in nature with towering trees and tucked away within this secluded setting overlooking the water.. the perfect ingredients for your harmonious getaway upstate in the Catskills. Begin dreaming about your custom design home and everything you will be able to finally create. Minutes from Eldred, Barryville, the Delaware river and

    Debbie Jagel Cabins & Canoes Real Estate

    0 Split Rock Dr Unit KEY921291, Highland, NY 12719
  • /14

    $399,000

    • Land
    • 7.47 Acres
    • $53,414 per Acre

    0 York Lake Estates Rd Unit KEY987214, Highland, NY 12719

    Gorgeous lakefront property with possible owner financing! Build your dream waterfront retreat. This rare, southern-exposure lakefront property offers the ultimate canvas for your dream home, tucked within a private gated community. Spanning over 7.47 extraordinary acres along the shores of a pristine glacial lake, this secluded retreat is designed for those who value privacy, nature, and

    Dawn Payne Payne Team LLC

    0 York Lake Estates Rd Unit KEY987214, Highland, NY 12719
  • /26

    $395,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    30 Woods Rd, Yulan, NY 12792

    Tucked into 6.3 private wooded acres along a quiet country road, this thoughtfully updated two-bedroom one-bathroom turnkey 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

    Dawn Payne PAYNE TEAM LLC

    30 Woods Rd, Yulan, NY 12792
  • /14

    $399,000

    • Land
    • 7.47 Acres
    • $53,414 per Acre

    0 York Lake Estates Rd Unit 11927216, Highland, NY 12719

    Gorgeous lakefront property with possible owner financing! Build your dream waterfront retreat. This rare, southern-exposure lakefront property offers the ultimate canvas for your dream home, tucked within a private gated community. Spanning over 7.47 extraordinary acres along the shores of a pristine glacial lake, this secluded retreat is designed for those who value privacy, nature, and

    Dawn Payne PAYNE TEAM LLC

    0 York Lake Estates Rd Unit 11927216, Highland, NY 12719
  • /7

    $180,000

    • Land
    • 6.29 Acres
    • $28,617 per Acre

    0 Split Rock Dr Unit KEY921280, Highland, NY 12719

    WATERFRONT!!!! Yes it is...with the views and sounds of the water and most of all serenity....Wooded, peaceful and awaiting you!! lots with mossy ground, sculptural boulders, and gentle contours create a magical setting for your future home site. Your house can sit perfectly tucked among the trees, offering a natural sense of utmost privacy. The subtle land contours are well suited for a walkout

    Debbie Jagel Cabins & Canoes Real Estate

    0 Split Rock Dr Unit KEY921280, Highland, NY 12719
  • /23

    $379,000

    • 3 Beds
    • 2 Baths
    • 1,384 Sq Ft

    171 Yulan Barryville Rd, Barryville, NY 12719

    Upstate dreams do exist. Imagine opening your patio doors and realizing your favorite room Is actually outside. You will fall in love every day with your woodsy backyard! The Silence! This contemporary chic ranch blends simplicity in the finishes and the added bonus of exciting indoor-outdoor living. The light filled interior features a skim-coated fireplace, a redesigned kitchen with a cozy

    Chris Somerville Cabins & Canoes Real Estate

    171 Yulan Barryville Rd, Barryville, NY 12719
  • /19

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    5 Steges Rd, Eldred, NY 12732

    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

    5 Steges Rd, Eldred, NY 12732
  • /34

    $249,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft

    140 Highland Lake Rd, Highland Lake, NY 12743

    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

    140 Highland Lake Rd, Highland Lake, NY 12743
  • /18

    $189,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 792 Sq Ft

    148 Lakeview Drive Rd, Highland Lake, NY 12743

    CHARMING RANCH IN HIGHLAND LAKE, NY - Welcome to this affordable two bedroom/1 bath home that is all you need for your weekend getaway in the Sullivan Catskills. This can also be the perfect full-time home that's easy to maintain while keeping costs down. Five minutes down the road is a grocery store, Eldred Central School and restaurants, making this location extremely convenient. Approximately

    Caroline Akt Caroline Akt Realty LLC

    148 Lakeview Drive Rd, Highland Lake, NY 12743
  • /14

    $299,700

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,164 Sq Ft

    50 Park Rd, Yulan, NY 12792

    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

    50 Park Rd, Yulan, NY 12792
  • /22

    $199,000

    $50K PRICE DROP
    • Land
    • 6.38 Acres
    • $31,191 per Acre

    0 Browning Blvd Unit KEY997085, Highland, NY 12719

    Escape to this beauty lakefront property sitting on 6.38 gorgeous acres in the private gated community of York Lake Shores. Enjoy boating, sailing, swimming, and fishing on the pristine lake while surrounded by peace and nature. Ideally located just two hours from New York City and under 20 minutes to the Metro-North train, this property offers the perfect balance of seclusion and convenience.

    Dawn Payne Payne Team LLC

    0 Browning Blvd Unit KEY997085, Highland, NY 12719
  • /7

    $145,600

    • 2 Beds
    • 1 Bath
    • 1,440 Sq Ft

    3426 State Route 97, Barryville, NY 12719

    2-bedroom, 1 bath, 1,440 square foot single family ranch home sitting on a 15,246 square foot lot. Make it your own. Jump on this great deal before it’s gone! All buyers are responsible to confirm City, County, Zoning, Tax, and other records to their satisfaction before bidding. No inspection contingencies in contract. Absolutely no repairs before closing. This property is sold As-Is. This is a

    Jamarr Zellner REALHome Services & Solutions

    3426 State Route 97, Barryville, NY 12719
  • /38

    $319,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    114 Proctor Rd, Eldred, NY 12732

    FRESH NEW PRICE. YOUR OPPORTUNITY JUST GOT BETTER!! 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,

    Dawn Payne Payne Team LLC

    114 Proctor Rd, Eldred, NY 12732
  • /13

    $265,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    24 Frazier Rd, Eldred, NY 12732

    Great opportunity for investor or rehab. Recent improvements including a newer electric system, newer well pump, and newer furnace. The septic system was pumped last year. The property offers a spacious lot that provides plenty of outdoor space and privacy. Shed in the front yard, jacuzzi and shipping container will be leaving with owner.

    Sean Walker Keller Williams Realty

    24 Frazier Rd, Eldred, NY 12732
  • /2

    $399,000

    • Land
    • 3.9 Acres
    • $102,308 per Acre

    0 Hartung Rd, Eldred, NY 12743

    Your lakefront escape awaits! Nestled on 3.90 acres along a beautiful motorboat lake, this property offers the perfect blend of tranquility, recreation, and convenience. Spend your days boating, fishing, swimming, or jet skiing right from your own waterfront retreat, all while being just two hours from New York City and only 20 minutes to Metro-North train service for an easy getaway or commute.

    Dawn Payne Payne Team LLC

    0 Hartung Rd, Eldred, NY 12743
  • /20

    $340,000

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

    328 Lakeview Drive Rd, Highland Lake, NY 12743

    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

    328 Lakeview Drive Rd, Highland Lake, NY 12743
  • /50

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft

    91 Airport Rd, Eldred, NY 12732

    Welcome to your own private Catskills retreat. Tucked away among towering trees and surrounded by nature, this beautiful log home offers the perfect blend of rustic charm, comfort, and privacy. Set on 4.71 acres with exclusive lake rights to Washington Lake, this is where peaceful mornings, star-filled nights, and unforgettable memories begin. Inside, you'll find 3 spacious bedrooms, 2 full

    Dawn Payne PAYNE TEAM LLC

    91 Airport Rd, Eldred, NY 12732
  • /28

    $399,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,500 Sq Ft

    943 State Route 55, Eldred, NY 12732

    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

    943 State Route 55, Eldred, NY 12732
  • /20

    $369,000

    • 3 Beds
    • 1.5 Baths
    • 1,252 Sq Ft

    220 Mail Rd, Barryville, NY 12719

    Set on Mail Road in the heart of Barryville, this Cape Cod sits in one of Sullivan County's most peaceful pockets — minutes from the Delaware River yet completely removed from the noise of everyday life. The oversized rear deck is the true heart of this property: expansive enough for al fresco dining, evening gatherings, and soaking in the hot tub while surrounded by mature trees. French doors

    Loretta Wolff NexLvl Real Estate Inc.

    220 Mail Rd, Barryville, NY 12719
  • /15

    $169,900

    $5K PRICE DROP
    • Land
    • 5.84 Acres
    • $29,092 per Acre

    0 Crawford Rd Unit KEY983986, Highland, NY 12528

    Escape to the peace and beauty of the Sullivan County Catskills with this lovely 5.8-acre parcel on Crawford Rd in the Town of Highland. Partially cleared and very private, this property offers the perfect setting to build your dream home in the country. Imagine relaxing on your future front porch or back deck while watching eagles soar overhead, enjoying star-filled skies, and taking in the

    Dominick Tufano RE/MAX Benchmark Realty Group

    0 Crawford Rd Unit KEY983986, Highland, NY 12528
  • /50

    $274,900

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,241 Sq Ft

    111 Delaware Dr, Lackawaxen, PA 18435

    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

    111 Delaware Dr, Lackawaxen, PA 18435
How to Buy a Home How to Finance a Home How to Sell a Home