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Hollywood, MD Homes for Sale with Pool

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  • /90

    $834,900 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 5,198 Sq Ft

    41170 Glenwood Place, Mechanicsville, MD 20659

    You have found the home for entertaining. A guest house, a pool, Fenced in back yard, Super sized deck, Fire pit area, and so much more. Sellers have updated with new windows, doors, one HVAC, Garage door openers, Solar lights, etc. Main house has primary bedroom and primary bath, with 3 more bedrooms on 2nd level with laundry room and 2nd bath. Main level has super kitchen with backsplash,

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (227) 232-1681

    41170 Glenwood Place, Mechanicsville, MD 20659
  • /40

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,742 Sq Ft

    23230 Willow Creek Way, California, MD 20619

    Charming One-Level Home in Sought-After California NeighborhoodWelcome to this delightful and well-maintained home, ideal for first-time buyers or those looking to downsize to the ease of single-level living. Nestled in a serene, park-like setting, this home offers both comfort and convenience in one of California’s most desirable communities.Enjoy peaceful mornings and cozy

    Agent Photo

    Trish Brow

    EXP Realty, LLC

    (240) 820-2372

    23230 Willow Creek Way, California, MD 20619
  • /26

    $364,900

    • 2 Beds
    • 3.5 Baths
    • 1,698 Sq Ft

    43695 Winterberry Way, California, MD 20619

    This house comes with a REDUCED RATE as low as 5.75% (APR 5.988%) as of 09/05/2025 through List & LockTM. This is a seller paid rate-buydown that reduces the buyer’s interest rate and monthly payment. Terms apply, see disclosures for more information.Welcome to this 3-level townhome, boasting two extra-large bedrooms on the upper level, with an open floor plan on the main floor. Located

    Agent Photo

    Connie Gunn

    CENTURY 21 New Millennium

    (240) 896-2937

    43695 Winterberry Way, California, MD 20619
  • /36

    $334,900

    • 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) 901-9263

    44140 Outrigger Way, California, MD 20619
  • /48

    $439,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 87 23670 Dragonfly Ln, Leonardtown, MD 20650

    Unit 87 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,604 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus

    Laura Bernth RE/MAX One

    Lot 87 23670 Dragonfly Ln, Leonardtown, MD 20650
  • /35

    $520,000

    • 4 Beds
    • 3.5 Baths
    • 3,158 Sq Ft

    43998 Swift Fox Dr, California, MD 20619

    Home is sold As-Is. Welcome to 43998 Swift Fox Dr, a thoughtfully designed three-story home offering four bedrooms, three full bathrooms, and one half bathroom. The kitchen features rich wood cabinetry, granite countertops, and stainless steel appliances, and flows seamlessly into a bright living area—ideal for gatherings or quiet evenings at home. The primary bedroom offers a comfortable retreat

    John Ippolito Redfin Corp

    43998 Swift Fox Dr, California, MD 20619
  • /55

    $459,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 89 23676 Dragonfly Ln, Leonardtown, MD 20650

    Unit 89 Oakley D1New Construction – Oakley D1 End Unit at Meadows at Town Run II2,966 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, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect

    Laura Bernth RE/MAX One

    Lot 89 23676 Dragonfly Ln, Leonardtown, MD 20650
  • /46

    $439,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 88 23676 Dragonfly Ln, Leonardtown, MD 20650

    Unit 88 Madison D2: New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a

    Laura Bernth RE/MAX One

    Lot 88 23676 Dragonfly Ln, Leonardtown, MD 20650
  • /58

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 2,130 Sq Ft

    23807 Myrtle Glen Way, California, MD 20619

    Welcome to 23807 Myrtle Glen Way, tucked into the highly sought-after Woods at Myrtle Point community! This beautifully maintained 3-bedroom, 3.5-bath home offers the perfect blend of style, comfort, and functionality.Step into the heart of the home, a gorgeous upgraded kitchen featuring an oversized 6-person island, ideal for entertaining. Enjoy seamless indoor-outdoor living with a deck

    Katherine Dean RE/MAX One

    23807 Myrtle Glen Way, California, MD 20619
  • /51

    $599,900

    • 4 Beds
    • 2.5 Baths
    • 3,118 Sq Ft

    23185 Piney Wood Cir, California, MD 20619

    Beautifully Updated Colonial on One Acre in WildwoodThis stunning colonial home sits on a spacious one-acre lot in Wildwood and features numerous high-end updates throughout. The heart of the home is the beautifully remodeled kitchen (2022), showcasing new cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining.The main

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    23185 Piney Wood Cir, California, MD 20619
  • /33

    $420,000

    • 3 Beds
    • 3.5 Baths
    • 2,822 Sq Ft

    23305 Hyacinth Ln, California, MD 20619

    Step inside this beautiful, spacious duplex in the sought-after Dahlia Park community of Wildewood. With its open, sun-filled layout, you’ll enjoy the feel of single-family living—without the extra upkeep.The main level offers a large kitchen, a formal dining area, multiple living spaces, a half bath, and access to your maintenance-free back deck—perfect for entertaining or quiet evenings

    Lauren Garner EXP Realty, LLC

    23305 Hyacinth Ln, California, MD 20619
  • /65

    $609,900

    • 4 Beds
    • 3.5 Baths
    • 3,234 Sq Ft

    44628 Cedar Ct, California, MD 20619

    This is the story of a charming home in Wildewood's premier neighborhood. Situated on a 1.21 acre lot on a peaceful cul-de-sac, with a lush green lawn dappled with shade trees, where the scenery is beautiful all year round. Gorgeous hardscape patio out back with a stone fire pit, complete with a seasoned woodpile, is ideal for outdoor gatherings. A large 2-car garage includes a utility

    Kimberly St. Laurent RE/MAX One

    44628 Cedar Ct, California, MD 20619
  • /99

    $635,000

    • 5 Beds
    • 3.5 Baths
    • 4,046 Sq Ft

    41402 Silver Charm Ct, Leonardtown, MD 20650

    Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuries of Leonard's Grant community that has it all from a spacious pool, basketball court, tennis court, playground, or feel free to frolic in the wide open green field. Designed to bring that beachy tranquility to your everyday life with a coastal design reminiscent of cool breezes and sandy beaches.

    Kelly Padgett CENTURY 21 New Millennium

    41402 Silver Charm Ct, Leonardtown, MD 20650
  • /35

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 3,416 Sq Ft

    23920 Druid Hills Dr, California, MD 20619

    House includes a $30K solar systems where future homeowners will enjoy for a long time. Installed only couple years ago

    nugent nguyen Westgate Realty Group, Inc.

    23920 Druid Hills Dr, California, MD 20619
  • /36

    $434,990

    • 4 Beds
    • 3.5 Baths
    • 2,716 Sq Ft

    43643 Evening Primrose Ct, California, MD 20619

    Welcome Home to 43643 Evening Primrose CourtElegance. Comfort. Lifestyle.Step into a home where every detail reflects thoughtful design and pride of ownership. Tucked away on a quiet, no-through street in the prestigious Wildewood community, this rare duet-style residence offers over 2,800 square feet of refined living space, blending modern comfort with timeless

    Shelia Kuhfahl CENTURY 21 New Millennium

    43643 Evening Primrose Ct, California, MD 20619
  • /79

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    41430 Challedon Way, Leonardtown, MD 20650

    Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality.The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your

    Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
  • /59

    $629,900

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft

    23264 Lindsay Dr, Leonardtown, MD 20650

    Main Level living at its finest in the heart of Leonardtown! Built on an oversized premium corner lot. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which transfers to the new homeowner. VA assumable loan available (to veteran only) at 2.75%. This exquisite home boasts an open floorplan that flows

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • /82

    $685,000

    • 4 Beds
    • 4.5 Baths
    • 4,399 Sq Ft

    22951 Cattail Ln, California, MD 20619

    Welcome to 22951 Cattail Ln, a beautifully maintained custom brick home in the sought-after Redwood subdivision of Wildewood. Perfectly situated near top-rated schools, shopping, and PAX River NAS, this home offers a blend of elegance, functionality, and modern updates. Step inside to find grand-scale living with 4 spacious bedrooms and 3 full baths upstairs, plus a flex room and full bath in the

    Charlotte Long EXP Realty, LLC

    22951 Cattail Ln, California, MD 20619
  • /81

    $599,900

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

    41536 Fairwood Ct, Leonardtown, MD 20650

    Welcome to your dream home, the Pinehurst model built by Marrick Homes, nestled in the highly sought-after Clark's Rest Community. From the moment you pull into the driveway, this timeless Colonial immediately impresses with its classic charm and spacious, modern living. This 3/level home offers 4/bedrooms, 3.5 baths with 4,664 sq ft of living space. The spacious front-load 2-car garage

    Teresa Klopfer RE/MAX Realty Group

    41536 Fairwood Ct, Leonardtown, MD 20650
  • /92

    $515,000

    • 4 Beds
    • 2.5 Baths
    • 2,120 Sq Ft

    44021 Silverwood Ln, California, MD 20619

    Immaculate Colonial in Prestigious Wildewood Welcome to this stunning colonial in the highly sought-after Wildewood community, where timeless charm meets modern luxury. Every detail of this home has been carefully designed to offer comfort, elegance, and functionality. The primary suite boasts a spa-inspired bathroom with heated floors and an oversized walk-in shower—large enough

    Jessica Raley CENTURY 21 New Millennium

    44021 Silverwood Ln, California, MD 20619
  • /43

    $385,000

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

    43640 Winterberry Way, California, MD 20619

    Nestled in the highly desirable Evergreen Park section of Wildwood, this 4-bedroom, 3.5-bath townhome is the perfect blend of comfort, convenience, and community charm. From the moment you step inside, you’re greeted with a bright and open foyer. On the entry level, you’ll find a thoughtfully designed large walkout bedroom with its own full bath, walk-in closet, and private sliding glass door

    Diana Washabaugh CENTURY 21 New Millennium

    43640 Winterberry Way, California, MD 20619
  • /36

    $439,000

    • 3 Beds
    • 2 Baths
    • 1,523 Sq Ft

    23125 Winterberry Ln, California, MD 20619

    Come and see! This is a lovely home on a corner lot with 2 car garage and paved drive. Covered front porch and beautiful patio out back. Trees trimmed and landscaped so very little to mow to maintain it. Open floor plan inside with formal living area and dining area open to the kitchen and den/sun room area. Tons of light as it has extra windows. Kitchen has large pantry and laundry closet for

    Jan Kleponis O'Brien Realty ERA Powered

    23125 Winterberry Ln, California, MD 20619
  • /29

    $512,000

    • 5 Beds
    • 4.5 Baths
    • 3,455 Sq Ft

    44018 Bellflower Way, California, MD 20619

    Welcome to a wonderfully updated and maintained 5-bedroom, 4.5-bathroom colonial home in the highly sought-after Dahlia Park of Wildewood community. This spacious oasis has been restored to new-like condition with new paint and carpet throughout, new bathroom updates on all four levels of living. The main level features a open-concept layout (no doors) which connects the living, dining, family

    Christina Proctor HomeSmart

    44018 Bellflower Way, California, MD 20619
  • /35

    $499,990

    • 4 Beds
    • 2.5 Baths
    • 2,553 Sq Ft

    44014 Silverwood Ln, California, MD 20619

    Welcome to 44014 Silverwood Lane, a stunning Colonial home nestled in the highly sought-after Wildewood community. This exquisite property boasts four spacious bedrooms, two and a half well-appointed bathrooms, and a suite of modern amenities that blend seamlessly with its timeless architectural charm.As you approach the residence, you are greeted by the inviting ambiance of the covered front

    Shelia Kuhfahl CENTURY 21 New Millennium

    44014 Silverwood Ln, California, MD 20619
  • /41

    $449,000

    • 4 Beds
    • 2.5 Baths
    • 2,545 Sq Ft

    44313 Poplar Wood Dr, California, MD 20619

    Welcome to 44313 Poplar Wood Dr, a spacious 4-bedroom, 2.5-bath home nestled on a serene, wooded lot in the heart of the highly sought-after Wildewood community. Perched atop a gentle hill, this home offers exceptional privacy and beautiful views of the surrounding landscape.Step inside to discover a sun-filled interior with generously sized rooms and an open layout perfect for

    Matthew Burgan Infinitas Realty Group

    44313 Poplar Wood Dr, California, MD 20619
  • /10

    $229,000

    • 2 Beds
    • 1.5 Baths
    • 936 Sq Ft

    23311 Sugar Maple Ct, California, MD 20619

    This conveniently located 2 bedroom 1.5 bathroom condo has been recently renovated to include new flooring throughout. With upgraded lighting, breakfast bar, granite countertops, and stainless steel appliances, the kitchen is open concept and opens into the living area. There is an updated and tiled full hall bathroom with a laundry room with included washer and dryer. The master bedroom has a

    brandy Sutor EXP Realty, LLC

    23311 Sugar Maple Ct, California, MD 20619
  • /78

    $679,900

    • 3 Beds
    • 2 Baths
    • 1,372 Sq Ft

    43088 Island View, Hollywood, MD 20636

    POSSIBLE OWNER FINANCING TO QUALIFIED BUYER - WATERFRONT - PERFECT FOR THE HOT WEATHER AND it is WAITING FOR YOU! Completely Renovated Home - New Roof, New Well, New Windows, New HVAC, New Water Heater, New Attic Insulation, New doors, siding, and gutters, New Kitchen and Appliances with Quartz Countertops, New Bathrooms with porcelain, New paint throughout, refinished hardwood floors, new

    Donna Lacey CENTURY 21 New Millennium

    43088 Island View, Hollywood, MD 20636
  • /35

    $450,000 New Construction

    • 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
  • /7

    $470,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,633 Sq Ft

    23585 Goodwill Way, California, MD 20619

    ******COMING SOON******* Welcome to your dream home!! This spacious, modern 4 bedroom 3.5 bathroom end unit townhome features a 2-car garage and has been barely lived in, offering a fresh, like new feel. Boasting an array of amenities including stunning granite countertops in the gourmet kitchen, recessed lighting throughout, generously sized deck that is ideal for outdoor gatherings or

    Edward Tully RE/MAX One

    23585 Goodwill Way, California, MD 20619
  • /2

    $395,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    23190 Falling Leaf Ln, California, MD 20619

    Welcome to 23190 Falling Leaf Ln, a beautifully renovated 4-bedroom, 2.5-bath home located in the highly sought-after Wildewood community. This property has undergone extensive upgrades, blending modern style with everyday functionality.Step inside to find a stunningly remodeled kitchen featuring upgraded cabinetry, sleek countertops, and premium appliances—perfect for both entertaining

    Matthew Burgan Infinitas Realty Group

    23190 Falling Leaf Ln, California, MD 20619
  • /2

    $449,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,642 Sq Ft

    23165 Heatherwood Ln, California, MD 20619

    Welcome to 23165 Heatherwood Ln, a charming 3-bedroom, 2-bath rambler tucked away at the end of a private cul-de-sac in Wildewood’s sought-after Pepper Ridge neighborhood. With thoughtful updates and a spacious open layout, this home is move-in ready and perfect for modern living.A 2017 remodel transformed the great room and kitchen into a stunning open-concept design by removing the

    Matthew Burgan Infinitas Realty Group

    23165 Heatherwood Ln, California, MD 20619
  • /24

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft

    22405 Indian Bridge Rd, California, MD 20619

    Sited on a one-acre level lot, this spacious ranch-style home is waiting for you to make it yours. It has over 1800 sqft of living space, a large entertainment room, and a formal living room. The home has hardwood floors and ceramic tile, and it has a pool house with a large inground deep pool. Conveniently located

    Pennie Platt Home Towne Real Estate

    22405 Indian Bridge Rd, California, MD 20619
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