110

Ocean Pines, MD Homes for Sale with Pool

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  • Lot #180 River Run Ln, Ocean Pines, MD 21811
    Lot #180 River Run Ln, Ocean Pines, MD 21811
    Lot #180 River Run Ln, Ocean Pines, MD 21811
    /40

    $400,000

    • Land
    • 0.5 Acre
    • $800,000 per Acre

    Lot #180 River Run Ln, Ocean Pines, MD 21811

    Welcome to Lot 180, an extraordinary new offering in the exclusive River Run community in Berlin, Maryland. This is one of the few remaining waterfront lots in the entire community—and certainly one of the finest. Perfectly positioned along the tranquil banks of the St. Martin River, Lot 180 boasts serene water views, easy access for launching kayaks or paddleboards, and a peaceful, natural

    Grant Fritschle Keller Williams Realty Delmarva

    Lot #180 River Run Ln, Ocean Pines, MD 21811
  • 45 Clubhouse Dr, Berlin, MD 21811
    45 Clubhouse Dr, Berlin, MD 21811
    45 Clubhouse Dr, Berlin, MD 21811
    /70

    $1,159,900

    • 7 Beds
    • 4 Baths
    • 3,082 Sq Ft

    45 Clubhouse Dr, Berlin, MD 21811

    Motivated Sellers Boaters, beach lovers, and big families—this one’s for you! This 7-bedroom, 4-bathroom waterfront home sits on 65 feet of canal frontage with a 7,500 lb boat lift—just 1,600 feet from the bay. Whether you're cruising out for a day on the water or relaxing on the oversized back deck, this home makes it easy to live the coastal lifestyle. Inside, you'll find over 3,000 square feet

    Spike Sands Berkshire Hathaway HomeServices PenFed Realty - OP

    45 Clubhouse Dr, Berlin, MD 21811
  • 72 Boston Dr, Berlin, MD 21811
    72 Boston Dr, Berlin, MD 21811
    72 Boston Dr, Berlin, MD 21811
    /25

    $269,000

    • Land
    • 0.18 Acre
    • $1,494,444 per Acre

    72 Boston Dr, Berlin, MD 21811

    Design and build your custom coastal retreat on this rare 0.18-acre waterfront lot offering expansive views of peaceful Manklin Creek. Nestled on Boston Drive in the sought-after Ocean Pines community, this homesite promises privacy and tranquility with unspoiled nature views and minimal development across the creek, a true luxury along the coast. Enjoy the best of coastal living with Ocean

    Anna Spann Coldwell Banker Realty

    72 Boston Dr, Berlin, MD 21811
  • 756 Ocean Pkwy, Berlin, MD 21811
    756 Ocean Pkwy, Berlin, MD 21811
    756 Ocean Pkwy, Berlin, MD 21811
    /40

    $415,000

    • 5 Beds
    • 2 Baths
    • 2,054 Sq Ft

    756 Ocean Pkwy, Berlin, MD 21811

    This lovely home is for your family and all your friends. A spacious well-maintained 5 bedroom rancher featuring an addition that added family room living area and additional bedroom space. The home is complemented with new vinyl plank flooring throughout. Some other renovations include an updated primary bathroom, new roof (home and shed), new gutters/ gutter guards, and down spouts, new

    Beth Miller Berkshire Hathaway HomeServices PenFed Realty - OP

    756 Ocean Pkwy, Berlin, MD 21811
  • 120 Robin Hood Trail, Berlin, MD 21811
    120 Robin Hood Trail, Berlin, MD 21811
    120 Robin Hood Trail, Berlin, MD 21811
    /48

    $439,900

    • 4 Beds
    • 2 Baths
    • 1,402 Sq Ft

    120 Robin Hood Trail, Berlin, MD 21811

    Don't miss out on this incredible opportunity to own a piece of Ocean Pines paradise. With its unbeatable location, stunning design, and endless possibilities, this remodeled 4 bedroom, 2 bath home is the perfect haven for anyone looking to experience the best of coastal living. This home has a new architectural roof, new siding and shutters, high efficiency tilt in windows, new flooring

    Jenny Sheppard Sheppard Realty Inc

    120 Robin Hood Trail, Berlin, MD 21811
  • Lot #192 Medinah Ln, Berlin, MD 21811
    Lot #192 Medinah Ln, Berlin, MD 21811
    Lot #192 Medinah Ln, Berlin, MD 21811
    /39

    $650,000

    • Land
    • 0.58 Acre
    • $1,120,690 per Acre

    Lot #192 Medinah Ln, Berlin, MD 21811

    A true showcase among the newly released home sites in the highly sought-after River Run community in Berlin, Maryland. This is not just another lot—it’s one of the premier waterfront parcels in the entire neighborhood, offering an unparalleled combination of location, view, and lifestyle. With sweeping, unobstructed vistas of the St. Martin River, proximity to the clubhouse and amenities, and

    Grant Fritschle Keller Williams Realty Delmarva

    Lot #192 Medinah Ln, Berlin, MD 21811
  • Lot #165 River Run Ln, Ocean Pines, MD 21811
    Lot #165 River Run Ln, Ocean Pines, MD 21811
    Lot #165 River Run Ln, Ocean Pines, MD 21811
    /42

    $249,000

    • Land
    • 0.33 Acre
    • $754,545 per Acre

    Lot #165 River Run Ln, Ocean Pines, MD 21811

    Lot #165 – River Run, Berlin, Maryland -A Rare Opportunity to Build in One of the Eastern Shore’s Most Coveted Golf Communities.Just Released - Lot #165 in River Run, a pristine new homesite in one of the most desirable and well-preserved golf course communities on Maryland’s Eastern Shore. Never before offered for public sale, this exceptional lot represents a rare opportunity to secure

    Grant Fritschle Keller Williams Realty Delmarva

    Lot #165 River Run Ln, Ocean Pines, MD 21811
  • 2 Cottonwood Ct, Ocean Pines, MD 21811
    2 Cottonwood Ct, Ocean Pines, MD 21811
    2 Cottonwood Ct, Ocean Pines, MD 21811
    /19

    $125,000

    • Land
    • 0.21 Acre
    • $595,238 per Acre

    2 Cottonwood Ct, Ocean Pines, MD 21811

    There are very few vacant lots left in the Award-Winning and Amenity-Filled Community of Ocean Pines! Showcase your new home on this beautiful wooded corner lot located in the Sherwood Forest section, with access to public water and sewer. Just a short walk or ride to multiple parks, restaurants, banks, post office, library and much more. Only a few miles to the Ocean City beaches, boardwalk,

    Debbie Hileman Hileman Real Estate-Berlin

    2 Cottonwood Ct, Ocean Pines, MD 21811
  • 85 King Richard Rd, Berlin, MD 21811
    85 King Richard Rd, Berlin, MD 21811
    /2

    $875,000

    • 4 Beds
    • 2.5 Baths
    • 3,108 Sq Ft

    85 King Richard Rd, Berlin, MD 21811

    Welcome to Triple Crown Estates in the South Gate of Ocean Pines. The Harper Model is a stunning 4‐bedroom, 2.5‐bath custom build by Ultimate Homes, LLC. This coastal‐styled residence offers just over 3,100 sq ft of beautifully designed living space—including a 19 x17 primary bedroom with tray ceilings, a first-floor office for working remotely or opt to make it a first floor 5th bedroom, and

    Jenny Sheppard Sheppard Realty Inc

    85 King Richard Rd, Berlin, MD 21811
  • 502 Tidewater Cove, Ocean Pines, MD 21811
    502 Tidewater Cove, Ocean Pines, MD 21811
    502 Tidewater Cove, Ocean Pines, MD 21811
    /56

    $592,000 Open Sat 3PM - 5PM

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    502 Tidewater Cove, Ocean Pines, MD 21811

    Jessica Lynch Coldwell Banker Realty

    502 Tidewater Cove, Ocean Pines, MD 21811
  • 11818 River Run Ln, Berlin, MD 21811
    11818 River Run Ln, Berlin, MD 21811
    11818 River Run Ln, Berlin, MD 21811
    /65

    $954,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,317 Sq Ft

    11818 River Run Ln, Berlin, MD 21811

    Presenting an amazing Lot-Home Package in the waterfront community of River Run! Built by award-winning builder, Capstone Homes, this custom Hannah floor plan on lot 168 with golf course views will be the first of its kind. The Hannah is Capstone's modernized farmhouse floorplan and boasts an elegant two-story great room, first floor primary suite, office space, and a spacious kitchen layout

    Bradley Absher Keller Williams Realty

    11818 River Run Ln, Berlin, MD 21811
  • 10 Jockey Ct, Ocean Pines, MD 21811
    10 Jockey Ct, Ocean Pines, MD 21811
    10 Jockey Ct, Ocean Pines, MD 21811
    /12

    $849,900 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,457 Sq Ft

    10 Jockey Ct, Ocean Pines, MD 21811

    Brand new construction with an anticipated May completion - just in time for the summer season! This impressive home offers over 3,400 square feet of living space with 5 bedrooms, 3.5 baths, and a bonus room, providing exceptional flexibility for today’s lifestyle. Located on a quiet cul-de-sac in Triple Crown Estates, a community known for its larger lot sizes, this property features a generous

    Cindy Poremski Berkshire Hathaway HomeServices PenFed Realty - OP

    10 Jockey Ct, Ocean Pines, MD 21811
  • 31 Preakness Dr, Ocean Pnes, MD 21811
    31 Preakness Dr, Ocean Pnes, MD 21811
    31 Preakness Dr, Ocean Pnes, MD 21811
    /72

    $735,900 New Construction

    • 5 Beds
    • 3 Baths
    • 2,442 Sq Ft

    31 Preakness Dr, Ocean Pnes, MD 21811

    Welcome to 31 Preakness Dr. !!! You are going to LOVE this ONE! Discover the exquisite new construction by Country Wide Builders in the sought-after Triple Crown Community of Ocean Pines. This stunning home is designed with a harmonious blend of coastal elegance and modern luxury, offering an idyllic setting surrounded by the serenity of abundant wildlife.Coastal Design with Modern

    Sandie Mattes Keller Williams Realty Delmarva

    31 Preakness Dr, Ocean Pnes, MD 21811
  • 4 Preakness Dr, Ocean Pines, MD 21811
    4 Preakness Dr, Ocean Pines, MD 21811
    4 Preakness Dr, Ocean Pines, MD 21811
    /113

    $899,900 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,135 Sq Ft

    4 Preakness Dr, Ocean Pines, MD 21811

    This brand-new 5-bedroom, 3.5-bath coastal farmhouse blends modern luxury with timeless design. Thoughtfully crafted with premium finishes throughout, it features 9-foot ceilings, an 18-foot vaulted great room with a custom fireplace, built-ins, and an open floor plan perfect for entertaining and everyday living.The designer kitchen is truly the heart of the home. It showcases solid wood

    Bethany Drew Hileman Real Estate-Berlin

    4 Preakness Dr, Ocean Pines, MD 21811
  • 71 Hingham Ln, Berlin, MD 21811
    71 Hingham Ln, Berlin, MD 21811
    71 Hingham Ln, Berlin, MD 21811
    /20

    $599,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,199 Sq Ft

    71 Hingham Ln, Berlin, MD 21811

    Welcome to Gemcraft’s newest addition to Ocean Pines! As you walk into the Hamilton , there is a choice room that’s open to the foyer. Use this space as a formal living room or playroom for the kids. Down the hall is the great room containing a fireplace, making an inviting space to gather with the whole family, which opens up to a classically designed kitchen. A small mudroom at the entry to the

    Debbie Hileman Hileman Real Estate-Berlin

    71 Hingham Ln, Berlin, MD 21811
  • 0 River Run Ln, Ocean Pines, MD 21811
    0 River Run Ln, Ocean Pines, MD 21811
    0 River Run Ln, Ocean Pines, MD 21811
    /4

    $985,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,900 Sq Ft

    0 River Run Ln, Ocean Pines, MD 21811

    NEW CUSTOM-BUILT HOME/LOT PACKAGE NOW AVAILABLE BY TWO DUDES BUILDERS! Visit this site and view location for a beautiful custom-built home in Coastal River Run Golf community near Ocean City, Ocean Pines & Berlin. This stunning two-level planned residence boasts an impressive 3,000 square feet of thoughtfully designed living space to create the home you have always wanted! Peaceful water views

    Sandy Dougan Berkshire Hathaway HomeServices PenFed Realty - OP

    0 River Run Ln, Ocean Pines, MD 21811
  • 0 River Run Ln, Ocean Pines, MD 21811
    0 River Run Ln, Ocean Pines, MD 21811
    0 River Run Ln, Ocean Pines, MD 21811
    /7

    $1,249,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,268 Sq Ft

    0 River Run Ln, Ocean Pines, MD 21811

    Take a drive thru the prestigious Golf community of River Run into the newer section in rear- Two Dudes building a stunning new custom home to be completed by Mid-April. Nestled within the highly sought-after waterfront lots of River Run, this spacious residence boasts 5 bedrooms and 3.5 baths. Thoughtfully designed over two levels, with the luxurious master suite conveniently located on the

    Sandy Dougan Berkshire Hathaway HomeServices PenFed Realty - OP

    0 River Run Ln, Ocean Pines, MD 21811
  • 83 King Richard Rd, Berlin, MD 21811
    83 King Richard Rd, Berlin, MD 21811
    /2

    $765,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    83 King Richard Rd, Berlin, MD 21811

    Crafted by Ultimate Homes, LLC, "The Hunter" is a masterfully designed 4-bedroom, 2.5-bath with den/office all in this sprawling rancher located in the prestigious new section of Triple Crown Estates in Ocean Pines. Blending timeless craftsmanship with refined modern finishes, this residence offers an elevated lifestyle just moments from the coast. Inspired Design. Exceptional Comfort, From the

    Jenny Sheppard Sheppard Realty Inc

    83 King Richard Rd, Berlin, MD 21811
  • 72 Boston Dr, Berlin, MD 21811
    72 Boston Dr, Berlin, MD 21811
    /2

    $711,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,767 Sq Ft

    72 Boston Dr, Berlin, MD 21811

    Anna Spann Coldwell Banker Realty

    72 Boston Dr, Berlin, MD 21811
  • 46 Boatswain Dr, Berlin, MD 21811
    46 Boatswain Dr, Berlin, MD 21811
    46 Boatswain Dr, Berlin, MD 21811
    /66

    $1,399,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    46 Boatswain Dr, Berlin, MD 21811

    Welcome to a true waterfront masterpiece in the sought after community Ocean Pines in Berlin, MD. This custom built, 4 bedroom, 3.5 bath home spans over 3,400 square feet and was thoughtfully designed to capture breathtaking water views from nearly every room. Perfectly positioned on the lot, the home’s unique angles, expansive windows, and architectural detail create a one of a kind coastal

    Ryan Haley Atlantic Shores Sotheby's International Realty

    46 Boatswain Dr, Berlin, MD 21811
  • 3 Hatteras St, Berlin, MD 21811
    3 Hatteras St, Berlin, MD 21811
    3 Hatteras St, Berlin, MD 21811
    /29

    $335,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,187 Sq Ft

    3 Hatteras St, Berlin, MD 21811

    Welcome to easy coastal living in one of Maryland’s most sought-after 55+ communities—this upgraded, move-in-ready home in The Parke at Ocean Pines offers privacy, style, and resort-style amenities all in one. Located in the highly desirable 55+ community of The Parke at Ocean Pines, this well-appointed 2-bedroom, 2-bath home at 3 Hatteras Street offers exceptional value, privacy, and modern

    Hoffy Hoffman Berkshire Hathaway HomeServices PenFed Realty - OP

    3 Hatteras St, Berlin, MD 21811
  • 17 Falcon Bridge Rd, Berlin, MD 21811
    17 Falcon Bridge Rd, Berlin, MD 21811
    17 Falcon Bridge Rd, Berlin, MD 21811
    /39

    $349,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,343 Sq Ft

    17 Falcon Bridge Rd, Berlin, MD 21811

    Welcome Home to 17 Falcon Bridge Road. Tucked away in a serene, wooded setting, this charming 2-story retreat perfectly blends cozy comfort with modern elegance. Whether you are looking for a peaceful year-round residence or a seasonal escape, this home offers the warmth you’ve been searching for. Featuring 3 spacious bedrooms and 2 full bathrooms, providing plenty of room for family and guests.

    Ryan Haley Atlantic Shores Sotheby's International Realty

    17 Falcon Bridge Rd, Berlin, MD 21811
  • 185 Windjammer Rd, Berlin, MD 21811
    185 Windjammer Rd, Berlin, MD 21811
    185 Windjammer Rd, Berlin, MD 21811
    /18

    $437,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 2,000 Sq Ft

    185 Windjammer Rd, Berlin, MD 21811

    Ocean Pines Colonial Home – Golf Course Living at Its Finest.Property Overview -- This beautifully appointed colonial home offers the perfect blend of timeless charm and modern comfort. Featuring three spacious bedrooms and three full bathrooms, the residence is fully furnished and is ideally situated along the scenic fairways of the Ocean Pines Golf Course, creating a peaceful and

    Steve Howse Berkshire Hathaway HomeServices PenFed Realty - OP

    185 Windjammer Rd, Berlin, MD 21811
  • 5 Freeport Ln, Berlin, MD 21811
    5 Freeport Ln, Berlin, MD 21811
    5 Freeport Ln, Berlin, MD 21811
    /68

    $529,900 Open Sat 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,106 Sq Ft

    5 Freeport Ln, Berlin, MD 21811

    This sun-filled, 3 bedroom, 3 bath single family home is located in The Parke 55+ community within Ocean Pines southgate and is truly one of the most secluded and peaceful lots out there! This Egret model floor plan is located off the small/low density Freeport Lane, and closely located to the activity filled clubhouse and serene Hidden Lake . Upon entering, you are greeted by 2-story ceiling, a

    Lauren Bunting Keller Williams Realty Delmarva

    5 Freeport Ln, Berlin, MD 21811
  • 82 Sandyhook Rd, Berlin, MD 21811
    82 Sandyhook Rd, Berlin, MD 21811
    82 Sandyhook Rd, Berlin, MD 21811
    /18

    $425,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 1,988 Sq Ft

    82 Sandyhook Rd, Berlin, MD 21811

    Welcome to 82 Sandyhook Rd, located in the highly sought after Ocean Pines community, where lifestyle meets convenience and resort style living!Ocean Pines offers an unmatched list of amenities that truly make it a place you never have to leave. Residents enjoy access to 5 swimming pools, both indoor and outdoor, a championship 18 hole golf course, two marinas, a yacht club with waterfront

    Amber Parsley Keller Williams Flagship

    82 Sandyhook Rd, Berlin, MD 21811
  • 16 Marview Dr, Berlin, MD 21811
    16 Marview Dr, Berlin, MD 21811
    /2

    $399,999 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    16 Marview Dr, Berlin, MD 21811

    Welcome to 16 Marview Drive in Ocean Pines, MD—charming, updated, and perfectly positioned on a spacious corner lot. This inviting 3-bedroom, 2-bath home offers a blend of comfort, style, and outdoor living that’s hard to find. Step outside and enjoy the expansive yard featuring a partially fenced side yard—ideal for pets, play, or entertaining. Unwind on the beautifully designed patio with

    Bethany Drew Hileman Real Estate-Berlin

    16 Marview Dr, Berlin, MD 21811
  • 20 Brandywine Dr, Berlin, MD 21811
    20 Brandywine Dr, Berlin, MD 21811
    20 Brandywine Dr, Berlin, MD 21811
    /91

    $449,000 Open Fri 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    20 Brandywine Dr, Berlin, MD 21811

    20 Brandywine Drive is located in the heart of Ocean Pines—a beautifully maintained home offering comfort, space, and the lifestyle you’ve been looking for. Nestled on a quiet street, this property features a spacious and functional layout perfect for both everyday living and entertaining.Step inside to find a bright and inviting interior with generous living areas, a well-appointed kitchen,

    Shawn Kotwica Coldwell Banker Realty

    20 Brandywine Dr, Berlin, MD 21811
  • 14 Garrett Dr, Berlin, MD 21811
    14 Garrett Dr, Berlin, MD 21811
    /2

    $404,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,244 Sq Ft

    14 Garrett Dr, Berlin, MD 21811

    Beautifully refreshed 3-bedroom, 2-bath home located in the sought-after community of Ocean Pines! This move-in-ready property features a spacious layout with a screened-in deck—perfect for relaxing or entertaining—and a cozy gas fireplace for year-round comfort. Recent upgrades include brand-new luxury plank flooring throughout the main living areas, new carpeting in the bedrooms, and a fully

    Billy Barr Keller Williams Realty Delmarva

    14 Garrett Dr, Berlin, MD 21811
  • 2 Crab Cay Ct, Berlin, MD 21811
    2 Crab Cay Ct, Berlin, MD 21811
    2 Crab Cay Ct, Berlin, MD 21811
    /3

    $599,900 Coming Soon

    • 4 Beds
    • 4 Baths
    • 2,178 Sq Ft

    2 Crab Cay Ct, Berlin, MD 21811

    Kenneth Roche Berkshire Hathaway HomeServices PenFed Realty

    2 Crab Cay Ct, Berlin, MD 21811
  • 18 Southwind Ct, Berlin, MD 21811
    18 Southwind Ct, Berlin, MD 21811
    18 Southwind Ct, Berlin, MD 21811
    /32

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,374 Sq Ft

    18 Southwind Ct, Berlin, MD 21811

    3 bedroom, 2 bathroom rancher nestled in a cul de sac in Ocean Pines Community. Gas fireplace, skylight, enclosed rear porch, Laundry room, over sized one car garage. Primary bedroom and primary bathroom. This property is a Fannie Mae Homepath property.

    LaVon Adkins ERA Martin Associates

    18 Southwind Ct, Berlin, MD 21811

Showing Results 81 - 110, Page 3 of 3

Maryland Worcester County Ocean Pines

Homes for Sale with Pool in Ocean Pines, MD

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In Ocean Pines, there are currently 110 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Ocean Pines, MD and discover your ideal residence.

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