29

Hollywood, MD Homes for Sale with Pool

Section Image Section Image
  • 23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    /31

    $439,900

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,634 Sq Ft

    23801 Mcintosh Rd, Hollywood, MD 20636

    BIG PRICE IMPROVEMENT – Now Offered at $439,900. Pool is open and ready for summer. Welcome to this well-maintained split foyer home situated on a 1.25-acre lot in Hollywood, MD, offering the perfect blend of space, comfort, and convenience. Located in the sought-after Leonardtown school district—Duke Elementary, Leonardtown Middle, and Leonardtown High School—this home offers NO HOA and no

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    23801 Mcintosh Rd, Hollywood, MD 20636
  • 43569 Marguerite Way, California, MD 20619
    43569 Marguerite Way, California, MD 20619
    /2

    $386,964

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    43569 Marguerite Way, California, MD 20619

    Beautiful end-unit townhome showcasing exceptional care and attention to detail throughout. Tastefully decorated and move-in ready, this home is waiting for your personal touch. The spacious kitchen features granite countertops, abundant workspace, and plenty of room for entertaining. Overlooking a huge family room, the layout embodies today's sought after open concept design. Step directly from

    Agent Photo

    Trish Brow

    O'Brien Realty ERA Powered

    43569 Marguerite Way, California, MD 20619
  • 23627 Deerfoot Way, California, MD 20619
    23627 Deerfoot Way, California, MD 20619
    23627 Deerfoot Way, California, MD 20619
    /54

    $679,900

    • 4 Beds
    • 3.5 Baths
    • 3,757 Sq Ft

    23627 Deerfoot Way, California, MD 20619

    Offered for the first time, this single-owner custom home in The Woods at Myrtle Point delivers 3479 finished square feet of thoughtful upgrades and modern, energy-smart systems. Built in 2012 on a private 0.72-acre lot — one of just five homes on the street — it features a customized Abberly elevation with 2-foot extensions to the kitchen, office, and third bedroom. The gourmet kitchen showcases

    Michelle Camaioni RE/MAX One

    23627 Deerfoot Way, California, MD 20619
  • Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    /19

    $449,900

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

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ***Estimated Late October Delivery****To Be Built*** 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 main-level entry that opens into a finished rec room or 4th bedroom with a full

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • 23302 Misty Pond Ln, California, MD 20619
    23302 Misty Pond Ln, California, MD 20619
    23302 Misty Pond Ln, California, MD 20619
    /44

    $532,400

    $8K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,003 Sq Ft

    23302 Misty Pond Ln, California, MD 20619

    Amazing colonial in quiet cul-da-sac. Home has a new roof in 2022 with the transferable warranty. Basement is finished fully in 2026, new paint in foyer and upstairs hall, new SHUTTERS and fresh paint on the front door too 2026, Both HVAC system were replaced in 2022-2023. Home features open floor plan in the traditional colonial style. Kitchen island and deck overlooking a small pond in the

    James Dick Long & Foster Real Estate, Inc.

    23302 Misty Pond Ln, California, MD 20619
  • 45397 Englewood Way, California, MD 20619
    45397 Englewood Way, California, MD 20619
    45397 Englewood Way, California, MD 20619
    /60

    $419,900

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

    45397 Englewood Way, California, MD 20619

    Welcome to 45397 Englewood Way, a beautiful 3-level end-unit townhome in The Woods at Myrtle Point, located just minutes from NAS Patuxent River in desirable California, Maryland. Built in 2020, this newer home offers the quality, comfort, and modern finishes buyers want — without the wait for new construction. Inside, you’ll find 3 bedrooms, 2 full baths, and 2 half baths across three bright and

    Bill Oosterink CENTURY 21 New Millennium

    45397 Englewood Way, California, MD 20619
  • Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    /12

    $454,900

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

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    Hurry in! Secure your new home now and personalize it with your choice of interior colors. Expected December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! Homesite 157 Madison D1: 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

    Laura Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • 23609 Crosswinds Way, California, MD 20619
    23609 Crosswinds Way, California, MD 20619
    23609 Crosswinds Way, California, MD 20619
    /29

    $432,000

    $23K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,452 Sq Ft

    23609 Crosswinds Way, California, MD 20619

    Motivated seller!!!! Ready to make a deal!!!! 2025 Build. Why wait for new construction when this home is completely move-in ready and loaded with upgrades. This beautiful home offers 4 bedrooms and 3.5 bathrooms with a versatile and highly desirable layout. The entry level features an oversized two-car garage equipped with an electric vehicle charging plug, a rare and valuable feature. This

    Boyd Grainger Pearson Smith Realty, LLC

    23609 Crosswinds Way, California, MD 20619
  • 41531 Kalitan Ln, Leonardtown, MD 20650
    41531 Kalitan Ln, Leonardtown, MD 20650
    41531 Kalitan Ln, Leonardtown, MD 20650
    /83

    $665,000

    • 5 Beds
    • 3.5 Baths
    • 3,570 Sq Ft

    41531 Kalitan Ln, Leonardtown, MD 20650

    Welcome to this beautiful Wingate model in the highly desirable Leonard’s Grant community! Situated in the front of the neighborhood, this home offers charming curb appeal with a welcoming front porch, side-load garage, and a large fenced backyard complete with a composite deck—perfect for entertaining and outdoor enjoyment. Inside, the main level features new carpet, a spacious formal dining

    Heather Foster RE/MAX One

    41531 Kalitan Ln, Leonardtown, MD 20650
  • Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

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

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #116 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 2,554 sq ft of beautifully finished living space. This interior unit features an oversized

    Laura Hefley RE/MAX One

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    /2

    $645,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Photos coming soon

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • 24249 Mcintosh Rd, Hollywood, MD 20636
    24249 Mcintosh Rd, Hollywood, MD 20636
    24249 Mcintosh Rd, Hollywood, MD 20636
    /65

    $950,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3.5 Baths
    • 2,934 Sq Ft

    24249 Mcintosh Rd, Hollywood, MD 20636

    Rare opportunity to own a breathtaking Horse Farm that features an exquisite custom farmhouse on 21.95 breathtaking acres just 2 miles from downtown Leonardtown! This unbelievable location offers the perfect balance of privacy and convenience with easy access to schools, shopping, restaurants, coffee shops, and commuter routes while enjoying the peace and tranquility of country living. The

    Mary Chambers JPAR Real Estate Professionals

    24249 Mcintosh Rd, Hollywood, MD 20636
  • 23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    /74

    $670,000

    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this well-maintained Belmont model in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment.Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    /43

    $449,900

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

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650

    BUILDER INCENTIVE: Receive $12,500 in Closing Help or Rate Buydown with use of Builder's Preferred Lender and Title. ****Available Now***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

    Laura Hefley RE/MAX One

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
  • 43901 Eucalyptus Way, California, MD 20619
    43901 Eucalyptus Way, California, MD 20619
    43901 Eucalyptus Way, California, MD 20619
    /52

    $405,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft

    43901 Eucalyptus Way, California, MD 20619

    Welcome to this exceptional end-unit townhome in the highly sought-after Wildewood community! Built in 2020 and offering approximately 2,200 square feet of beautifully designed living space, this three-level home combines modern finishes, functional design, and outstanding community amenities. Step inside to discover luxury vinyl plank flooring throughout the entire main level and lower-level

    DJ Hayes RLAH @properties

    43901 Eucalyptus Way, California, MD 20619
  • 23323 Jonquil Ln, California, MD 20619
    23323 Jonquil Ln, California, MD 20619
    23323 Jonquil Ln, California, MD 20619
    /16

    $426,000

    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    23323 Jonquil Ln, California, MD 20619

    Welcome Home to 23323 Jonquil Ln Awaits! If you have kids or just love a view of green grass, you are going to fall in love with the setting of this home. It sits directly across from a wonderful, wide public yard.Giving the kids a perfect, safe place to run around and play right outside your front door. Parking is a breeze, too, with your own attached garage and rear driveway. MAIN LEVELStep

    Thaira Aarabi Home Towne Real Estate

    23323 Jonquil Ln, California, MD 20619
  • 45363 Concord Way, California, MD 20619
    45363 Concord Way, California, MD 20619
    45363 Concord Way, California, MD 20619
    /25

    $440,000

    • 3 Beds
    • 4 Baths
    • 2,080 Sq Ft

    45363 Concord Way, California, MD 20619

    Welcome home to this like-new townhome in the beautiful community of The Woods at Myrtle Point! As you enter this immaculate townhome, you're greeted with a lovely foyer area, a bonus room and half bath, as well as a sliding door to your fully fenced back yard and patio. Walk up the stairs to your spacious and bright main level, which includes a gourmet kitchen with an amazing granite island,

    Deborah Radvany EXP Realty, LLC

    45363 Concord Way, California, MD 20619
  • Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

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

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ** Homesite #114 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 2,554 sq ft of beautifully finished living space. This interior unit features an oversized

    Laura Hefley RE/MAX One

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
  • Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    /40

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    ***SPRING SPECIAL $5,000 Builder Credit Plus $12,500 in Closing Help with Builder's preferred lender and title co*** (special is for this Homesite #99 Madison D3 only). ***Available NOW*** Homesite #99 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

    Laura Hefley RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
  • 23240 Rosewood Ct, California, MD 20619
    23240 Rosewood Ct, California, MD 20619
    /2

    $255,000

    Coming Soon
    • 2 Beds
    • 1.5 Baths
    • 936 Sq Ft

    23240 Rosewood Ct, California, MD 20619

    Welcome to 23240 Rosewood Ct #9 — a beautifully updated top-floor condo offering comfort, convenience, and low-maintenance living. This move-in ready home features 2 spacious bedrooms and 1.5 bathrooms, along with recent upgrades throughout. Enjoy luxury vinyl plank flooring in the main living areas, an updated kitchen with newer appliances, and a breakfast bar that opens to the living space. A

    Matthew Burgan Infinitas Realty Group

    23240 Rosewood Ct, California, MD 20619
  • 23606 Crosswinds Way, California, MD 20619
    23606 Crosswinds Way, California, MD 20619
    23606 Crosswinds Way, California, MD 20619
    /40

    $455,000

    • 3 Beds
    • 3.5 Baths
    • 2,436 Sq Ft

    23606 Crosswinds Way, California, MD 20619

    Welcome to 23606 Crosswinds Way – Like-New Luxury Townhome LivingThis stunning three-story townhouse, built just three years ago, offers the perfect blend of modern style and effortless functionality. Featuring 3 bedrooms, two car garage, private deck, and concrete patio, this home provides plenty of space to live and entertain both indoors and out. Step inside to discover a thoughtfully

    Tanya Becraft Real Estate Professionals, Inc.

    23606 Crosswinds Way, California, MD 20619
  • 44042 Eucalyptus Way, California, MD 20619
    44042 Eucalyptus Way, California, MD 20619
    44042 Eucalyptus Way, California, MD 20619
    /41

    $404,900

    • 4 Beds
    • 2.5 Baths
    • 2,045 Sq Ft

    44042 Eucalyptus Way, California, MD 20619

    Welcome to 44042 Eucalyptus Way in the sought-after Wildewood community of California, MD — a beautifully maintained, nearly new townhome offering modern finishes, flexible living space, and a location that’s hard to beat. Built in 2021, this desirable end-unit location offers added privacy with just one adjoining neighbor, extra windows that fill the home with natural light, and additional green

    Debbie Friedrich Berkshire Hathaway HomeServices PenFed Realty

    44042 Eucalyptus Way, California, MD 20619
  • 23423 Canna Ct, California, MD 20619
    23423 Canna Ct, California, MD 20619
    23423 Canna Ct, California, MD 20619
    /87

    $579,000

    • 5 Beds
    • 4.5 Baths
    • 4,145 Sq Ft

    23423 Canna Ct, California, MD 20619

    NEW PRICE + FRESH UPDATES IN WILDEWOOD!23423 Canna Court is now offered at $579,000! More space. More flexibility. More value — and now even more move-in ready. The sellers have just installed brand-new carpet and padding throughout and had the entire property professionally powerwashed, giving this spacious Wildewood home a fresh, clean feel inside and out. Welcome to a beautifully sized

    Bill Oosterink CENTURY 21 New Millennium

    23423 Canna Ct, California, MD 20619
  • 44555 Aspen Ln, California, MD 20619
    44555 Aspen Ln, California, MD 20619
    44555 Aspen Ln, California, MD 20619
    /56

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,983 Sq Ft

    44555 Aspen Ln, California, MD 20619

    Welcome to 44555 Aspen Ln — a beautifully maintained 4-bedroom, 2.5-bath colonial tucked away in the highly desirable Wildewood community, offering the perfect blend of privacy, space, and convenience. This home is thoughtfully positioned on a quiet, private lot, creating a peaceful setting while still being just minutes from everything you need. Inside, you’ll find expansive living spaces

    Matthew Burgan Infinitas Realty Group

    44555 Aspen Ln, California, MD 20619
  • Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    /7

    $454,900

    New Construction $5K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

    ***** Hurry in! Secure your new home now and personalize it with your choice of interior colors. December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! ***** Homesite #156 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

    Laura Hefley RE/MAX One

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
  • 24730 Half Pone Point Rd, Hollywood, MD 20636
    24730 Half Pone Point Rd, Hollywood, MD 20636
    24730 Half Pone Point Rd, Hollywood, MD 20636
    /40

    $4,595,000

    Coming Soon
    • 4 Beds
    • 7 Baths
    • 13,665 Sq Ft

    24730 Half Pone Point Rd, Hollywood, MD 20636

    A legacy waterfront estate at the tip of coveted Half Pone Point.Commanding one of the most prestigious waterfront settings in Southern Maryland, this extraordinary residence offers more than 14,000 square feet of meticulously crafted living space designed to capture breathtaking panoramic views of the Patuxent River from nearly every room. Architectural excellence and exceptional

    Christopher Carr HomeZu

    24730 Half Pone Point Rd, Hollywood, MD 20636
  • 23048 Mountain Laurel Ln, California, MD 20619
    23048 Mountain Laurel Ln, California, MD 20619
    23048 Mountain Laurel Ln, California, MD 20619
    /33

    $389,999

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,188 Sq Ft

    23048 Mountain Laurel Ln, California, MD 20619

    Welcome to 23048 Mountain Laurel Lane, a beautifully appointed townhome nestled within the highly desirable Wildewood community in California, Maryland. Offering three spacious bedrooms, thoughtfully designed living spaces, and an exceptional location, this residence perfectly balances comfort, style, and convenience. The heart of the home is the well-appointed kitchen, featuring granite

    John Gatton CENTURY 21 New Millennium

    23048 Mountain Laurel Ln, California, MD 20619
  • 23628 Belmar Dr, Leonardtown, MD 20650
    23628 Belmar Dr, Leonardtown, MD 20650
    /2

    $730,000

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    23628 Belmar Dr, Leonardtown, MD 20650

    PROFESSIONAL PHOTOS COMING!

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • 44313 Ocelot Way, California, MD 20619
    44313 Ocelot Way, California, MD 20619
    44313 Ocelot Way, California, MD 20619
    /43

    $374,995

    $5K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    44313 Ocelot Way, California, MD 20619

    MOVE-IN READY AND READY TO CLOSE! Why wait on another home when so much of the work has already been done? This beautifully maintained 4-bedroom, 3.5-bath townhome offers over 2,000 square feet of thoughtfully designed living space, including a finished lower level with a full bath that's perfect for guests, a recreation room, or a home office. The bright, open-concept main level features a

    Tina Marie Biggs EXP Realty, LLC

    44313 Ocelot Way, California, MD 20619
Maryland St Marys County Hollywood

Homes for Sale with Pool in Hollywood, MD

How to Buy a Home How to Finance a Home How to Sell a Home

In Hollywood, there are currently 29 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.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group