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$2,250,000

Experience breathtaking water views from this expansive three-level waterfront home designed for comfort, convenience, and entertaining. Featuring a private elevator, two garages, concrete driveway, and a whole-house generator, this property offers exceptional space for everyday living and hosting guests. The home has also undergone a complete exterior overhaul, including the installation of a brand-new metal roof, providing both durability and long-term peace of mind. The main living area showcases a spacious island kitchen with granite countertops, stainless steel appliances, and a breakfast room, along with formal living and dining rooms. Additional spaces include a family room, office, sunroom, exercise room, studio, entertainment room, workshop, and abundant storage. Two impressive primary suites provide luxurious retreats. The main suite features a private deck, walk-in closets, gas fireplace with marble hearth, a spa-style bath with whirlpool tub, marble floors and tile, and a separate powder room. The second suite includes a walk-in whirlpool tub/shower combination. Additional highlights include hardwood floors, surround sound, central vacuum, security system, two washer/dryer sets, two water heaters, and three-zone heating and cooling. Outdoor living is just as impressive with five decks, front and rear paver patios, and exceptional boating amenities, including a 90’ vinyl bulkhead, a 6’ x 33’ dock, and two boat lifts installed in 2020. Prepare to be impressed by the space, views, and waterfront lifestyle this remarkable home offers.

5 Beds ⋅ 7 Baths

Experience breathtaking water views from this expansive three-level waterfront home designed for comfort, convenience, and entertaining. Featuring a private elevator, two garages, concrete driveway, and a whole-house generator, this property offers exceptional space for everyday living and hosting guests. The home has also undergone a complete exterior overhaul, including the installation of a brand-new metal roof, providing both durability and long-term peace of mind. The main living area showcases a spacious island kitchen with granite countertops, stainless steel appliances, and a breakfast room, along with formal living and dining rooms. Additional spaces include a family room, office, sunroom, exercise room, studio, entertainment room, workshop, and abundant storage. Two impressive primary suites provide luxurious retreats. The main suite features a private deck, walk-in closets, gas fireplace with marble hearth, a spa-style bath with whirlpool tub, marble floors and tile, and a separate powder room. The second suite includes a walk-in whirlpool tub/shower combination. Additional highlights include hardwood floors, surround sound, central vacuum, security system, two washer/dryer sets, two water heaters, and three-zone heating and cooling. Outdoor living is just as impressive with five decks, front and rear paver patios, and exceptional boating amenities, including a 90’ vinyl bulkhead, a 6’ x 33’ dock, and two boat lifts installed in 2020. Prepare to be impressed by the space, views, and waterfront lifestyle this remarkable home offers.

26 Leigh Dr, Ocean Pines

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$697,000

Rare opportunity to build your dream home on this homesite with Bay to Beach Builders! Please note: no home is currently built on this property. The list price reflects a proposed construction package and includes the lot, estimated lot preparation/site work, and the featured Bluewater floor plan. The Bluewater offers 1,767 square feet of thoughtfully designed living space with 3 bedrooms, 2.5 bathrooms, a first-floor primary suite, soaring ceilings in the main living area, and timeless coastal-inspired architecture. Designed for comfortable everyday living and effortless entertaining, this home blends modern functionality with classic beach-town charm. The Bluewater is just one of several floor plans that have been reviewed for this lot and meet setback requirements. Additional home designs available through Bay to Beach Builders include The Oxford (1,126 sq. ft.), The Driftwood (1,820 sq. ft.), The Surfside (1,614 sq. ft.), The Fenwick (2,029 sq. ft.), The Chesapeake (2,455 sq. ft.), The Bethany (2,584 sq. ft.), The Rehoboth (2,584 sq. ft.), and The Ocean View (3,424 sq. ft.). The maximum recommended footprint for this homesite is approximately 38' x 66', and these plans have been selected accordingly. Many of these designs are part of Bay to Beach Builders' popular Coastal Collection and Cottage Series, specifically designed to maximize living space on narrower lots. Homes shown on pilings may also be constructed on a traditional foundation depending on buyer preference and site conditions. As a custom builder, Bay to Beach Builders can modify floor plans to better suit your lifestyle, budget, and vision. Buyers are encouraged to explore available floor plans and design options through Bay to Beach Builders and consult directly with the builder regarding pricing, customization opportunities, and included features. Whether you're dreaming of a full-time residence, vacation retreat, or investment property near the coast, this property offers the flexibility to create a home tailored to your needs. The property offers navigable waterfront with the ability to construct a dock and pier. Neighboring owners currently keep a pontoon boat on the creek, demonstrating recreational boating access. Buyers should verify water depths for their specific vessel.

3 Beds ⋅ 3 Baths

Rare opportunity to build your dream home on this homesite with Bay to Beach Builders! Please note: no home is currently built on this property. The list price reflects a proposed construction package and includes the lot, estimated lot preparation/site work, and the featured Bluewater floor plan. The Bluewater offers 1,767 square feet of thoughtfully designed living space with 3 bedrooms, 2.5 bathrooms, a first-floor primary suite, soaring ceilings in the main living area, and timeless coastal-inspired architecture. Designed for comfortable everyday living and effortless entertaining, this home blends modern functionality with classic beach-town charm. The Bluewater is just one of several floor plans that have been reviewed for this lot and meet setback requirements. Additional home designs available through Bay to Beach Builders include The Oxford (1,126 sq. ft.), The Driftwood (1,820 sq. ft.), The Surfside (1,614 sq. ft.), The Fenwick (2,029 sq. ft.), The Chesapeake (2,455 sq. ft.), The Bethany (2,584 sq. ft.), The Rehoboth (2,584 sq. ft.), and The Ocean View (3,424 sq. ft.). The maximum recommended footprint for this homesite is approximately 38' x 66', and these plans have been selected accordingly. Many of these designs are part of Bay to Beach Builders' popular Coastal Collection and Cottage Series, specifically designed to maximize living space on narrower lots. Homes shown on pilings may also be constructed on a traditional foundation depending on buyer preference and site conditions. As a custom builder, Bay to Beach Builders can modify floor plans to better suit your lifestyle, budget, and vision. Buyers are encouraged to explore available floor plans and design options through Bay to Beach Builders and consult directly with the builder regarding pricing, customization opportunities, and included features. Whether you're dreaming of a full-time residence, vacation retreat, or investment property near the coast, this property offers the flexibility to create a home tailored to your needs. The property offers navigable waterfront with the ability to construct a dock and pier. Neighboring owners currently keep a pontoon boat on the creek, demonstrating recreational boating access. Buyers should verify water depths for their specific vessel.

72 Boston, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$379,900

Spacious and open floor plan designed for easy living and effortless entertaining . This inviting home features 3 generously sized bedrooms and 2 full baths * Sliding glass doors open to a large screened porch * The charming front porch is perfect for enjoying your morning coffee or relaxing in the evenings with your favorite beverage * Roof replaced in 2022 with 50 year warranty * Central Heat /AC for year round comfort * Abundant closet space and storage shed for all of your beach and boating essentials * You'll love being part of a vibrant waterfront community offering exceptional amenities including 5 pools, tennis, pickleball, yacht club, restaurants, Robert Trent Jones, Sr designed championship golf course as well as a beachfront pool, parking and restaurant in Ocean City * EVERYTHING you need to embrace the Coastal Lifestyle to the fullest * Ocean Pines is located just 5 miles inland from Ocean City and blends wooded serenity with Coastal Charm * Fresh paint, new carpeting in bedrooms... Let's make this your home yours *

3 Beds ⋅ 2 Baths

Spacious and open floor plan designed for easy living and effortless entertaining . This inviting home features 3 generously sized bedrooms and 2 full baths * Sliding glass doors open to a large screened porch * The charming front porch is perfect for enjoying your morning coffee or relaxing in the evenings with your favorite beverage * Roof replaced in 2022 with 50 year warranty * Central Heat /AC for year round comfort * Abundant closet space and storage shed for all of your beach and boating essentials * You'll love being part of a vibrant waterfront community offering exceptional amenities including 5 pools, tennis, pickleball, yacht club, restaurants, Robert Trent Jones, Sr designed championship golf course as well as a beachfront pool, parking and restaurant in Ocean City * EVERYTHING you need to embrace the Coastal Lifestyle to the fullest * Ocean Pines is located just 5 miles inland from Ocean City and blends wooded serenity with Coastal Charm * Fresh paint, new carpeting in bedrooms... Let's make this your home yours *

61 Abbyshire Rd, Ocean Pines

Listing courtesy of Sea Grace @ North Beach Realtors. Contact: 443-614-3901

$352,000

Welcome to 26 Castle Drive in Ocean Pines — a beautifully renovated 3-bedroom, 2-bath home originally built in 1984 and thoughtfully updated from top to bottom. This property offers peace of mind with major upgrades already completed, including a new roof, new siding, new windows and doors, new duct work. Inside, you’ll find fresh paint throughout, modern railings, a completely remodeled kitchen, and updated bathrooms designed with today’s style and functionality in mind. The new kitchen features contemporary finishes and a clean, modern aesthetic, making it perfect for everyday living and entertaining. Both bathrooms have been tastefully updated, offering a fresh and cohesive design throughout the home. Located in the sought-after Ocean Pines community, residents enjoy amenities including pools, parks, marina access, golf, and proximity to Ocean City beaches, dining, and shopping. Move-in ready and worry-free — this is the perfect opportunity for a primary residence, second home, or investment property

3 Beds ⋅ 2 Baths

Welcome to 26 Castle Drive in Ocean Pines — a beautifully renovated 3-bedroom, 2-bath home originally built in 1984 and thoughtfully updated from top to bottom. This property offers peace of mind with major upgrades already completed, including a new roof, new siding, new windows and doors, new duct work. Inside, you’ll find fresh paint throughout, modern railings, a completely remodeled kitchen, and updated bathrooms designed with today’s style and functionality in mind. The new kitchen features contemporary finishes and a clean, modern aesthetic, making it perfect for everyday living and entertaining. Both bathrooms have been tastefully updated, offering a fresh and cohesive design throughout the home. Located in the sought-after Ocean Pines community, residents enjoy amenities including pools, parks, marina access, golf, and proximity to Ocean City beaches, dining, and shopping. Move-in ready and worry-free — this is the perfect opportunity for a primary residence, second home, or investment property

26 Castle Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$325,000

BIG PRICE REDUCTION! MOTIVATED SELLER! BRING ALL OFFERS! OVERSIZED FLOOR PLAN! You'll feel like you're in the mountains in this Extra Large Home on an Extra Large lot that backs to Parkland! The second level contains the main living areas, including a tiled backsplash kitchen, a living room with two story ceilings, balcony access, and rustic wooden walls. A large 16x12 Bedroom and 11x8 Bath complete the main floor. Enter the carpeted stairway to a loft area, two additional bedrooms and a full bath on the upper level, overlooking the living room. Accommodate the in-laws / grandparents / large families in the Lower Level living quarters with an additional bedroom, bath, laundry room, kitchen and living area. A one car garage will store all of your beach gear, toys, and tools! Easy access from the South entrance to Ocean Pines. Enjoy top-notch amenities and a short drive to the beaches of Ocean City and Assateague National Seashore. Sold in As-Is condition.

4 Beds ⋅ 3 Baths

BIG PRICE REDUCTION! MOTIVATED SELLER! BRING ALL OFFERS! OVERSIZED FLOOR PLAN! You'll feel like you're in the mountains in this Extra Large Home on an Extra Large lot that backs to Parkland! The second level contains the main living areas, including a tiled backsplash kitchen, a living room with two story ceilings, balcony access, and rustic wooden walls. A large 16x12 Bedroom and 11x8 Bath complete the main floor. Enter the carpeted stairway to a loft area, two additional bedrooms and a full bath on the upper level, overlooking the living room. Accommodate the in-laws / grandparents / large families in the Lower Level living quarters with an additional bedroom, bath, laundry room, kitchen and living area. A one car garage will store all of your beach gear, toys, and tools! Easy access from the South entrance to Ocean Pines. Enjoy top-notch amenities and a short drive to the beaches of Ocean City and Assateague National Seashore. Sold in As-Is condition.

850 Ocean Parkway, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200

$824,900

Brand new construction now completed ready 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 125’ x 100’ homesite. The home offers two primary suites — one on each level. The first-floor primary suite features a beautifully tiled shower, while all full bathrooms are equipped with double-bowl vanities. The stunning kitchen showcases quartz countertops and stainless steel appliances and flows seamlessly into the dining area, which opens to a screened porch and deck, perfect for indoor-outdoor living. The family room is warm and inviting with a linear electric fireplace and a beam-accented vaulted ceiling. Additional highlights include 9’ ceilings on the first floor, LVP flooring throughout the first floor and staircase, a dedicated laundry room, and an 80-gallon hot water heater. The fully insulated, oversized two-car garage features 12’ ceilings, offering excellent potential for additional storage space. The bonus room is separately conditioned with its own split HVAC system, making it ideal for a media room, home office, playroom, or guest retreat. Enjoy all that Ocean Pines has to offer, including multiple pools, golf course, marina, yacht club, beach club in Ocean City, parks, walking trails, and year-round community amenities. Builder Registration #9569.

5 Beds ⋅ 4 Baths

Brand new construction now completed ready 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 125’ x 100’ homesite. The home offers two primary suites — one on each level. The first-floor primary suite features a beautifully tiled shower, while all full bathrooms are equipped with double-bowl vanities. The stunning kitchen showcases quartz countertops and stainless steel appliances and flows seamlessly into the dining area, which opens to a screened porch and deck, perfect for indoor-outdoor living. The family room is warm and inviting with a linear electric fireplace and a beam-accented vaulted ceiling. Additional highlights include 9’ ceilings on the first floor, LVP flooring throughout the first floor and staircase, a dedicated laundry room, and an 80-gallon hot water heater. The fully insulated, oversized two-car garage features 12’ ceilings, offering excellent potential for additional storage space. The bonus room is separately conditioned with its own split HVAC system, making it ideal for a media room, home office, playroom, or guest retreat. Enjoy all that Ocean Pines has to offer, including multiple pools, golf course, marina, yacht club, beach club in Ocean City, parks, walking trails, and year-round community amenities. Builder Registration #9569.

10 Jockey Ct, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$2,249,000

Welcome to a rare waterfront masterpiece on a premier point lot in Ocean Pines. Located at 26 W Mallard Drive on a quiet cul-de-sac, this exceptional direct bayfront coastal-style home offers breathtaking, unobstructed views of the Isle of Wight Bay and the Ocean City skyline. Built in 1983 and impeccably maintained, the residence spans just over 5,000 sq. ft. with 8 bedrooms and 8.5 baths, ideal for large gatherings or multi-generational living. Designed to maximize waterfront living, the home features multiple balconies and expansive decks, an outdoor summer kitchen, hot tub, private pier with boat lift, and generous outdoor entertaining spaces perfect for hosting unforgettable bayfront gatherings. Inside, an elevator servicing up to the third level adds convenience and accessibility. The chef’s kitchen is outfitted with 42” cabinetry, granite countertops, stainless steel appliances, multiple ovens, and a GE induction cooktop, complemented by an abundance of storage and prep space. Additional highlights include six refrigerators, a dedicated laundry room, 200-amp whole-house generator, storm shutters, four storage sheds, and an encapsulated crawlspace with dehumidifier and sump pump. Situated within amenity-rich Ocean Pines, residents enjoy access to parks and recreation, aquatics, championship golf, marina, beach club, and more. This extraordinary bayfront property combines space, luxury, and lifestyle—an unparalleled opportunity on Maryland’s Eastern Shore.

8 Beds ⋅ 9 Baths

Welcome to a rare waterfront masterpiece on a premier point lot in Ocean Pines. Located at 26 W Mallard Drive on a quiet cul-de-sac, this exceptional direct bayfront coastal-style home offers breathtaking, unobstructed views of the Isle of Wight Bay and the Ocean City skyline. Built in 1983 and impeccably maintained, the residence spans just over 5,000 sq. ft. with 8 bedrooms and 8.5 baths, ideal for large gatherings or multi-generational living. Designed to maximize waterfront living, the home features multiple balconies and expansive decks, an outdoor summer kitchen, hot tub, private pier with boat lift, and generous outdoor entertaining spaces perfect for hosting unforgettable bayfront gatherings. Inside, an elevator servicing up to the third level adds convenience and accessibility. The chef’s kitchen is outfitted with 42” cabinetry, granite countertops, stainless steel appliances, multiple ovens, and a GE induction cooktop, complemented by an abundance of storage and prep space. Additional highlights include six refrigerators, a dedicated laundry room, 200-amp whole-house generator, storm shutters, four storage sheds, and an encapsulated crawlspace with dehumidifier and sump pump. Situated within amenity-rich Ocean Pines, residents enjoy access to parks and recreation, aquatics, championship golf, marina, beach club, and more. This extraordinary bayfront property combines space, luxury, and lifestyle—an unparalleled opportunity on Maryland’s Eastern Shore.

26 West Mallard, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$879,900

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 cabinetry in soft sage and dove tones, Calacatta Prado quartz countertops and backsplash, and a large center island with a built-in microwave, prep sink, and elegant brass chandelier. The kitchen is equipped with high-end GE stainless steel appliances, including a gas range with an air fryer, French door refrigerator, and a quiet dishwasher. A pot filler, brushed brass fixtures, and soft-close cabinetry add to the thoughtful details, while a spacious walk-in pantry provides additional storage and convenience. The first-floor primary suite offers a relaxing retreat with a spa-like bathroom featuring a freestanding soaking tub, double vanity, and tiled shower. Upstairs, you will find additional bedrooms, a versatile loft, and a beautifully appointed bathroom. This home is designed with efficiency and durability in mind, featuring a Bosch dual-zone HVAC system, Rinnai tankless water heater, sound-insulated six-inch exterior walls, and a sprinkler and fire suppression system. Outside, enjoy covered front and rear porches, a finished two-car garage, and a newly paved driveway. Every detail of this home reflects quality, comfort, and thoughtful design, creating an exceptional coastal living experience. Photos are digital renders.

5 Beds ⋅ 4 Baths

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 cabinetry in soft sage and dove tones, Calacatta Prado quartz countertops and backsplash, and a large center island with a built-in microwave, prep sink, and elegant brass chandelier. The kitchen is equipped with high-end GE stainless steel appliances, including a gas range with an air fryer, French door refrigerator, and a quiet dishwasher. A pot filler, brushed brass fixtures, and soft-close cabinetry add to the thoughtful details, while a spacious walk-in pantry provides additional storage and convenience. The first-floor primary suite offers a relaxing retreat with a spa-like bathroom featuring a freestanding soaking tub, double vanity, and tiled shower. Upstairs, you will find additional bedrooms, a versatile loft, and a beautifully appointed bathroom. This home is designed with efficiency and durability in mind, featuring a Bosch dual-zone HVAC system, Rinnai tankless water heater, sound-insulated six-inch exterior walls, and a sprinkler and fire suppression system. Outside, enjoy covered front and rear porches, a finished two-car garage, and a newly paved driveway. Every detail of this home reflects quality, comfort, and thoughtful design, creating an exceptional coastal living experience. Photos are digital renders.

4 Preakness Dr, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200

$2,295,000

The opportunity to own the premier property in Ocean Pines comes around only once in a blue moon. Situated on a point lot on Leigh Drive with the most unobstructed views in the Tern’s Landing neighborhood. The 3 level Mediterranean masterpiece has been tastefully curated blending elevated style, design, and architecture. Privately nestled at the end of a cul-de-sac, this 4-bedroom home promotes an indoor-outdoor lifestyle with balconies and decks on every level to admire the panoramic views of Ocean City. Posh customizations including Walker Zanger tiles, Emtek doorknobs, Ralph Lauren pure wool carpet, Kohler faucets, Subzero and Bosch appliances to name a few. Featuring an expansive primary suite with secluded balcony and telescope lookout. Maintenance free exterior with Techo-Bloc pavers and 200 feet of vinyl bulkhead with dock and boat lift. This home radiates coastal luxury and sophistication. Call today for more information!

4 Beds ⋅ 4 Baths

The opportunity to own the premier property in Ocean Pines comes around only once in a blue moon. Situated on a point lot on Leigh Drive with the most unobstructed views in the Tern’s Landing neighborhood. The 3 level Mediterranean masterpiece has been tastefully curated blending elevated style, design, and architecture. Privately nestled at the end of a cul-de-sac, this 4-bedroom home promotes an indoor-outdoor lifestyle with balconies and decks on every level to admire the panoramic views of Ocean City. Posh customizations including Walker Zanger tiles, Emtek doorknobs, Ralph Lauren pure wool carpet, Kohler faucets, Subzero and Bosch appliances to name a few. Featuring an expansive primary suite with secluded balcony and telescope lookout. Maintenance free exterior with Techo-Bloc pavers and 200 feet of vinyl bulkhead with dock and boat lift. This home radiates coastal luxury and sophistication. Call today for more information!

36 Leigh Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$425,000

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. Brand new 2.5 ton Rheem heat pump system and Honeywell thermostat just installed June 2026. This home in 2022 went under major rehab with new architectural roof, new siding and shutters, high efficiency tilt in windows, new flooring throughout, vanities and a beautiful gourmet kitchen with a large granite breakfast bar that seats 6. One of the larger lots in the Pines with the home situated to easily add a two-car garage. South gate living at its best and just a few houses over from the bay. Schedule a showing today and make your dreams a reality!

4 Beds ⋅ 2 Baths

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. Brand new 2.5 ton Rheem heat pump system and Honeywell thermostat just installed June 2026. This home in 2022 went under major rehab with new architectural roof, new siding and shutters, high efficiency tilt in windows, new flooring throughout, vanities and a beautiful gourmet kitchen with a large granite breakfast bar that seats 6. One of the larger lots in the Pines with the home situated to easily add a two-car garage. South gate living at its best and just a few houses over from the bay. Schedule a showing today and make your dreams a reality!

120 Robin Hood, Ocean Pines

Listing courtesy of Sheppard Realty Inc. Contact: 4437830299