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Hollywood, MD Homes for Sale with Pool

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  • 44140 Outrigger Way, California, MD 20619
    44140 Outrigger Way, California, MD 20619
    44140 Outrigger Way, California, MD 20619
    /36

    $299,900

    • 1 Bed
    • 1.5 Baths
    • 1,645 Sq Ft

    44140 Outrigger Way, California, MD 20619

    Step into modern comfort with this beautifully designed 1-bedroom, 1.5-bath condo, featuring an open-concept layout and high-end finishes throughout. The spacious living room boasts dramatic vaulted ceilings, creating a light-filled and airy space perfect for relaxing or hosting. A convenient half bath adds functionality for guests. The impressive kitchen is a true showpiece, complete with

    Agent Photo

    Connie Gunn

    CENTURY 21 New Millennium

    (240) 213-7707

    44140 Outrigger Way, California, MD 20619
  • 23084 Vanda Way, California, MD 20619
    23084 Vanda Way, California, MD 20619
    23084 Vanda Way, California, MD 20619
    /55

    $430,000

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    23084 Vanda Way, California, MD 20619

    Townhome located in the Orchid Park Neighborhood of the highly desirable Wildewood community! This home offers an abundance of upgrades including recessed lighting throughout; upgraded lighting in all bedrooms, LVP flooring on entry and main levels, upgraded carpet on upper level; gourmet kitchen with upgraded cabinetry, under cabinet lighting, quartz countertops, gas range, double oven, and

    Agent Photo

    Edward Tully

    RE/MAX One

    (301) 507-1977

    23084 Vanda Way, California, MD 20619
  • 23660 Pine View Ln, Hollywood, MD 20636
    23660 Pine View Ln, Hollywood, MD 20636
    23660 Pine View Ln, Hollywood, MD 20636
    /9

    $800,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 3,744 Sq Ft

    23660 Pine View Ln, Hollywood, MD 20636

    This property is located in a rapidly developing area of central St. Mary’s County very close to the expanding county airport, offering strong potential for future growth and investment.The parcel is currently zoned RL (Residential Low Density), which allows for one dwelling unit per acre, with the potential for up to five homes per acre under the current zoning ordinance. Additionally,

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 230-6304

    23660 Pine View Ln, Hollywood, MD 20636
  • 23771 Myrtle Glen Way, California, MD 20619
    23771 Myrtle Glen Way, California, MD 20619
    23771 Myrtle Glen Way, California, MD 20619
    /44

    $415,000

    • 4 Beds
    • 4 Baths
    • 2,290 Sq Ft

    23771 Myrtle Glen Way, California, MD 20619

    *Full home inspection performed and available to buyers upon request.* Step inside to an impressive open-concept living space, perfect for both entertaining and relaxing. On the main floor, a versatile room awaits—ideal as a private office or guest suite, complete with its own rear entry. Upstairs, soaring ceilings frame a chef-inspired kitchen that flows seamlessly into the family room, with

    Agent Photo

    Amy Scott

    OE Realty

    (240) 589-5172

    23771 Myrtle Glen Way, California, MD 20619
  • 43998 Swift Fox Dr, California, MD 20619
    43998 Swift Fox Dr, California, MD 20619
    43998 Swift Fox Dr, California, MD 20619
    /29

    $525,000

    • 4 Beds
    • 3.5 Baths
    • 3,413 Sq Ft

    43998 Swift Fox Dr, California, MD 20619

    Welcome to 43998 Swift Fox Dr—an inviting three-story home featuring four bedrooms, three full baths, and a convenient half bath. The heart of the home is the spacious kitchen, complete with rich wood cabinetry, granite countertops, and stainless steel appliances. It opens to a bright, airy living area that’s perfect for entertaining or unwinding after a long day. Upstairs, the primary suite

    John Ippolito Redfin Corp

    43998 Swift Fox Dr, California, MD 20619
  • 45429 Englewood Way, California, MD 20619
    45429 Englewood Way, California, MD 20619
    45429 Englewood Way, California, MD 20619
    /35

    $430,000

    • 3 Beds
    • 3.5 Baths
    • 2,548 Sq Ft

    45429 Englewood Way, California, MD 20619

    Luxury Living in Style describes this stunning end unit townhome with 2,548 finished sq ft in a premium location close to schools, shopping, restaurants and commuter routes in California, Maryland. This beautifully maintained 3-level end-unit of superb living space including a fully finished basement. With 3 spacious bedrooms, 3 full bathrooms, and a convenient half bath, there’s room for

    Mary Chambers JPAR Real Estate Professionals

    45429 Englewood Way, California, MD 20619
  • Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    /30

    $479,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650

    Homesite 102 Oakley D1***March Delivery***Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown,

    Laura Bernth RE/MAX One

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
  • 45118 Saint Cuthbert Farm Rd, Hollywood, MD 20636
    45118 Saint Cuthbert Farm Rd, Hollywood, MD 20636
    45118 Saint Cuthbert Farm Rd, Hollywood, MD 20636
    /67

    $2,490,000

    • 5 Beds
    • 4.5 Baths
    • 4,661 Sq Ft

    45118 Saint Cuthbert Farm Rd, Hollywood, MD 20636

    Welcome to an extraordinary waterfront retreat at 45118 Saint Cuthbert Farm Rd, Hollywood, MD—a truly rare offering on the Patuxent River. Set on nearly 2 acres with 166 feet of water frontage, this stunning, one-of-a-kind custom-built waterfront home delivers a lifestyle that few properties can match.Enjoy breathtaking, unobstructed views spanning over a mile and a half of the Patuxent

    Matthew Burgan Infinitas Realty Group

    45118 Saint Cuthbert Farm Rd, Hollywood, MD 20636
  • 44087 Granite Way, California, MD 20619
    44087 Granite Way, California, MD 20619
    44087 Granite Way, California, MD 20619
    /53

    $375,000

    • 3 Beds
    • 4 Baths
    • 2,947 Sq Ft

    44087 Granite Way, California, MD 20619

    Beautiful 3-Level Home in Wildewood Village 55+ Community — Approx. 3000 of Finished space.! Welcome to this spacious and beautifully maintained single-family home located in the highly desirable Wildewood Village Over 55 Community. Conveniently situated near shopping, dining, theaters, medical facilities, and just across the bridge from Solomon’s Island, where you can enjoy the charm of

    Cris Curtis CENTURY 21 New Millennium

    44087 Granite Way, California, MD 20619
  • Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
    /45

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650

    Homesite 100 Madison D1: ***March Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an

    Laura Bernth RE/MAX One

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
  • 41438 Silver Charm Ct, Leonardtown, MD 20650
    41438 Silver Charm Ct, Leonardtown, MD 20650
    41438 Silver Charm Ct, Leonardtown, MD 20650
    /4

    $690,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft

    41438 Silver Charm Ct, Leonardtown, MD 20650

    Heather Foster RE/MAX One

    41438 Silver Charm Ct, Leonardtown, MD 20650
  • 44045 Fieldstone Way, California, MD 20619
    44045 Fieldstone Way, California, MD 20619
    44045 Fieldstone Way, California, MD 20619
    /37

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,903 Sq Ft

    44045 Fieldstone Way, California, MD 20619

    Welcome to easy, one-level living in the Villages of Wildewood, a premier 55+ community in the heart of St. Mary’s County. This lovely duplex offers comfort, convenience, and a relaxed lifestyle just minutes from shopping, dining, theaters, medical facilities, and local attractions. A welcoming front porch sets the tone as you enter. Make your way to the large living room featuring sliding glass

    Eric Sweeney O'Brien Realty ERA Powered

    44045 Fieldstone Way, California, MD 20619
  • 23104 Sweetbay Ln, California, MD 20619
    23104 Sweetbay Ln, California, MD 20619
    23104 Sweetbay Ln, California, MD 20619
    /35

    $470,000

    • 4 Beds
    • 2.5 Baths
    • 2,147 Sq Ft

    23104 Sweetbay Ln, California, MD 20619

    Updated 4-bedroom, 2.5-bath home on a tree-lined corner lot in the desirable Wildewood community. Custom interior shutters, new luxury vinyl flooring, and thoughtful design details elevate the home, including a geometric accent wall, hand-stenciled half bath, and a board-and-batten feature wall in the primary suite. The floor plan offers an easy, natural flow with a kitchen that includes table

    Colin McHugh O'Brien Realty ERA Powered

    23104 Sweetbay Ln, California, MD 20619
  • 23369 Marview Ct, Leonardtown, MD 20650
    23369 Marview Ct, Leonardtown, MD 20650
    23369 Marview Ct, Leonardtown, MD 20650
    /58

    $435,000

    • 3 Beds
    • 3.5 Baths
    • 2,308 Sq Ft

    23369 Marview Ct, Leonardtown, MD 20650

    Beautiful Clark’s Rest townhome offering three finished levels, a two-car garage, and over 2,300 square feet of living space. The main level features hardwood floors, a gourmet kitchen with granite countertops and 42-inch cabinetry, a separate formal dining space, and a large family room—ideal for both everyday living and entertaining.The fully finished lower level includes a spacious

    Jennifer Goddard CENTURY 21 New Millennium

    23369 Marview Ct, Leonardtown, MD 20650
  • 26445 Peninsular Dr, Hollywood, MD 20636
    26445 Peninsular Dr, Hollywood, MD 20636
    26445 Peninsular Dr, Hollywood, MD 20636
    /4

    $275,000 Coming Soon

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    26445 Peninsular Dr, Hollywood, MD 20636

    Professional photos coming soon. Welcome to the Hollywood Shores neighborhood....a waterfront community! This home features two bedrooms and one bathroom. the home provides a comfortable layout with room for everyone. The front door faces the water though views are limited. A sliding glass door leads to a deck that wraps around to the front and is perfect for outdoor entertaining. More details to

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    26445 Peninsular Dr, Hollywood, MD 20636
  • 44183 Goldenzelle Way, California, MD 20619
    44183 Goldenzelle Way, California, MD 20619
    44183 Goldenzelle Way, California, MD 20619
    /33

    $454,900

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft

    44183 Goldenzelle Way, California, MD 20619

    Welcome to 44183 Goldenzelle Way — a beautifully maintained 4-bedroom, 3.5-bath end-unit townhome nestled in the sought-after Wildewood neighborhood of California, MD. This spacious and light-filled home offers the perfect blend of comfort, style, and convenience. Step inside to discover open-concept living spaces bathed in natural light, ideal for both relaxing and entertaining. The upgraded

    Matthew Burgan Infinitas Realty Group

    44183 Goldenzelle Way, California, MD 20619
  • 23015 Wedgewood Ln, California, MD 20619
    23015 Wedgewood Ln, California, MD 20619
    23015 Wedgewood Ln, California, MD 20619
    /39

    $474,900

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    23015 Wedgewood Ln, California, MD 20619

    23015 Wedgewood Ln | Wildewood Community Welcome to 23015 Wedgewood Lane, a beautifully maintained 3-bedroom, 2.5-bath home tucked away on a peaceful cul-de-sac in the highly sought-after Wildewood community. Designed for comfort and easy living, this home offers a main floor primary suite complete with a private en suite bath — the perfect retreat at the end of the day. Step inside to an

    Matthew Burgan Infinitas Realty Group

    23015 Wedgewood Ln, California, MD 20619
  • 24850 Peaceful View Way Ct, Hollywood, MD 20636
    24850 Peaceful View Way Ct, Hollywood, MD 20636
    24850 Peaceful View Way Ct, Hollywood, MD 20636
    /49

    $699,000 New Construction

    • 4 Beds
    • 2.5 Baths

    24850 Peaceful View Way Ct, Hollywood, MD 20636

    Move in ready new construction coming this spring! Located at 24850 Peaceful View Way in Hollywood, MD, this 4-bedroom home sits on a private 1.5-acre cul-de-sac lot, offering space, privacy, and modern farmhouse-inspired design.The exterior features stone skirting, a side-entry garage, and a welcoming front porch. Inside, the home is designed with high ceilings, upgraded trim details, luxury

    Michele Posey RE/MAX Realty Group

    24850 Peaceful View Way Ct, Hollywood, MD 20636
  • Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650
    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650
    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650
    /45

    $489,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650

    Lot 112 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and the perfect blend

    Laura Bernth RE/MAX One

    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650
  • 45301 Foghorn Way, California, MD 20619
    45301 Foghorn Way, California, MD 20619
    45301 Foghorn Way, California, MD 20619
    /44

    $430,000

    • 3 Beds
    • 3.5 Baths
    • 2,772 Sq Ft

    45301 Foghorn Way, California, MD 20619

    Welcome to 45301 Foghorn Way in the heart of California, MD! This stunning end-unit townhouse is filled with natural light and offers comfort, convenience, and modern living—all in a location that puts you close to everything Southern Maryland has to offer. Nestled in a vibrant community, you’ll enjoy quick access to shopping, restaurants, schools, and local employers such as NAS Patuxent River.

    Jacqueline Houck Keller Williams Real Estate -Exton

    45301 Foghorn Way, California, MD 20619
  • 44535 River Otter Dr, California, MD 20619
    44535 River Otter Dr, California, MD 20619
    44535 River Otter Dr, California, MD 20619
    /58

    $375,000

    • 4 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    44535 River Otter Dr, California, MD 20619

    Welcome Home to Wildewood! This spacious townhome offers a 1 car garage, Large entry level room that can be used as a 4th bedroom, office, or another family/entertainment room with a full bath. The second floor offers your kitchen and living areas with a half bath. The 3rd level offers 3 bedrooms and 2 full bath. This neighborhood offers various pools and recreation areas. Stop by for a look.

    Kimberly Huffnagle CENTURY 21 New Millennium

    44535 River Otter Dr, California, MD 20619
  • 43748 Winterberry Way, California, MD 20619
    43748 Winterberry Way, California, MD 20619
    /2

    $370,000 Coming Soon

    • 3 Beds
    • 3.5 Baths
    • 2,165 Sq Ft

    43748 Winterberry Way, California, MD 20619

    Coming Soon...

    Justin Mika The Southside Group Real Estate

    43748 Winterberry Way, California, MD 20619
  • 23295 White Elm Ct, California, MD 20619
    23295 White Elm Ct, California, MD 20619
    /2

    $470,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,172 Sq Ft

    23295 White Elm Ct, California, MD 20619

    Tucked away at the end of a quiet cul-de-sac, 23295 White Elm Court feels like home the moment you arrive. Set on a spacious third-acre lot in the heart of Wildewood, this charming two-story residence offers the perfect balance of comfort, space, and everyday livability. With over 2,100 square feet of living space and three bathrooms, the layout is designed to give everyone room to spread out

    Matthew Burgan Infinitas Realty Group

    23295 White Elm Ct, California, MD 20619
Maryland St Marys County Hollywood

Homes for Sale with Pool in Hollywood, MD

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In Hollywood, there are currently 23 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 Hollywood, MD and discover your ideal residence.

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