13,214

Hollywood, MD Homes

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  • /35

    $345,000

    • 2 Beds
    • 2 Baths
    • 1,422 Sq Ft

    44034 Fieldstone Way, California, MD 20619

    Nicely updated cul-de-sac duplex in the 55+ Wildewood Retirement Village. This 2-bed, 2-bath home features Luxury Vinyl Plank flooring throughout, attractive light Oak cabinets in both kitchen and bath, Quartz counters, tile backsplash, stainless appliances, and a comfortable 3-season sunroom/open deck combo that backs to trees. New Andersen sliding doors w/ in-glass blinds are a highlight in the

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (240) 237-9524

    44034 Fieldstone Way, California, MD 20619
  • /33

    $2,050 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Condo for Rent

    23520 F D R Blvd Unit 305, California, MD 20619

    Prime Commuter Location!!! Upper level condo with private balcony! Beautifully Maintained 2BR/2BA Condo | Granite Counters | Stainless Steel Appliances Meticulously maintained 2-bedroom, 2-bath condominium ideally located for convenient commuting to Washington, DC, Andrews AFB, Pax River, and surrounding military installations.This well-appointed unit features granite countertops, stainless

    Agent Photo

    Danielle Sloan

    Samson Properties

    (240) 820-3083

    23520 F D R Blvd Unit 305, California, MD 20619
  • /2

    $110,000

    Sold May 12, 2026

    0 Steer Horn Neck Rd Unit MDSM2031254, Hollywood, MD 20636

    • Land
    • 22,651 Sq Ft
    • $211,538 per Acre

    Last Sold Summary

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    0 Steer Horn Neck Rd Unit MDSM2031254, Hollywood, MD 20636
    • /70

      Est $685,179

      Not Listed For Sale

      43490 Greg St, Hollywood, MD 20636

      • 4 Beds
      • 2.5 Baths
      • 2,970 Sq Ft
      • Built 2017
      43490 Greg St, Hollywood, MD 20636

      Last Sold Summary

      • 5% Above List Price
      • $221/SF
      • 4 Days On Market
      • Last Sold Price $655,000
      • May 16, 2025

      Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

  • /42

    $464,900

    • 3 Beds
    • 3 Baths
    • 1,634 Sq Ft

    23801 Mcintosh Rd, Hollywood, MD 20636

    OPEN HOUSE SUNDAY 1PM-3PM. Leonardtown schools, NO HOA or Leonardtown taxes! 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 also provides easy access to

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 770-1422

    23801 Mcintosh Rd, Hollywood, MD 20636
  • /31

    Starting at $1,742 Per Month

    • 1 - 3 Beds

    45086 Voyage Path, California, MD 20619

    Discover luxury apartments in California, MD at Settler's Landing. Our beautiful apartment homes feature one-, two-, and three-bedroom layouts designed to give you ample living and storage space. Our apartments are complete with granite countertops, ceramic floors, and private patios. You'll also enjoy our 24-hour fitness center, bark park for resident pets, resort-style pool, and outdoor fire

    Settler's Landing

    (240) 434-0483

    45086 Voyage Path, California, MD 20619
  • /83

    $655,000

    Sold Apr 24, 2026

    41497 Affirmed Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,934 Sq Ft
    • Built 2008

    Last Sold Summary

    • $166/SF
    • 2 Days On Market

    Current Estimated Value $651,362

    Last Listing Agent Heather Foster RE/MAX One

    41497 Affirmed Way, Leonardtown, MD 20650
    • /78

      Est $672,650

      Not Listed For Sale

      42824 Dudley Digges Ln, Hollywood, MD 20636

      • 4 Beds
      • 3.5 Baths
      • 3,216 Sq Ft
      • Built 2002
      42824 Dudley Digges Ln, Hollywood, MD 20636

      Last Sold Summary

      • 4% Above List Price
      • $202/SF
      • 54 Days On Market
      • Last Sold Price $649,000
      • May 16, 2025

      Last Listing Agent Brooke Matthews RE/MAX

  • /2

    $675,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,673 Sq Ft

    22929 Camden Ct, Hollywood, MD 20636

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 232-1763

    22929 Camden Ct, Hollywood, MD 20636
  • /32

    Starting at $2,250 Per Month

    • 2 - 3 Beds

    44980 Hamptons Blvd, Leonardtown, MD 20650

    The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE

    The Hamptons at Leonardtown

    (443) 342-9476

    44980 Hamptons Blvd, Leonardtown, MD 20650
  • /33

    $390,000

    Sold Oct 30, 2025

    23305 Hyacinth Ln, California, MD 20619

    • 3 Beds
    • 3.5 Baths
    • 2,822 Sq Ft
    • Built 2009

    Last Sold Summary

    • $138/SF
    • 46 Days On Market

    Current Estimated Value $402,161

    Last Listing Agent Lauren Garner EXP Realty, LLC

    23305 Hyacinth Ln, California, MD 20619
    • /53

      Est $608,536

      Not Listed For Sale

      41403 Heritage Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,340 Sq Ft
      • Built 2016
      41403 Heritage Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $181/SF
      • 6 Days On Market
      • Last Sold Price $605,000
      • May 16, 2025

      Last Listing Agent Wanda White Century 21 New Millennium

  • /28

    $410,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23116 Lilac St, California, MD 20619

    Welcome to this rare 30-foot-wide end-unit townhome offering the space, upgrades, and lifestyle today’s buyers are searching for. Ideally located just minutes from shopping, dining, waterfront recreation, and only 15 minutes to Naval Air Station Patuxent River, this home blends convenience with comfort. The light-filled main level features hardwood floors throughout, a formal dining area, and a

    Agent Photo

    Sharyn Ahmad

    RE/MAX Realty Group

    (240) 652-2300

    23116 Lilac St, California, MD 20619
  • /34

    Starting at $1,695

    Total Monthly Price

    • 1 - 3 Beds

    23314 Surrey Way, California, MD 20619

    The Apartments of Wildewood is Saint Mary’s premier rental community! Centrally located to everything from employment to entertainment! Our residents have access to many amenities such as two beautiful clubhouses, two sparkling pools, and 24 hour fitness center and on site storage. Friends and family will be awed by your spacious new home with a garage, fireplace, soaring ceilings and soaking

    Apartments of Wildewood

    (240) 434-0763

    23314 Surrey Way, California, MD 20619
  • /41

    $856,681

    Sold Jun 17, 2025

    25055 Preston Ct, Hollywood, MD 20636

    • 4 Beds
    • 2.5 Baths
    • 3,158 Sq Ft
    • Built 2025

    Last Sold Summary

    • $271/SF
    • 179 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    25055 Preston Ct, Hollywood, MD 20636
    • /29

      Est $444,897

      Not Listed For Sale

      41434 Margrove Cir, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,356 Sq Ft
      • Built 2020
      41434 Margrove Cir, Leonardtown, MD 20650

      Last Sold Summary

      • 2% Above List Price
      • $185/SF
      • 30 Days On Market
      • Last Sold Price $435,000
      • May 16, 2025

      Last Listing Agent Jonathan Boss RE/MAX

  • /71

    $530,000

    • 4 Beds
    • 3.5 Baths
    • 3,190 Sq Ft

    43980 Swift Fox Dr, California, MD 20619

    Wow in Wildewood! Welcome to this 4-bedroom, 3.5 bath, Colonial that features gorgeous Oak hardwoods throughout the main floor. A 2-year-young roof, 9-ft ceilings, chair rail, gas fireplace, upgraded kitchen, and finished lower-level are just some of the attractive features of this more than 3,000 sq ft home. Tall Maple cabinets, granite counters, large island w/ breakfast bar, pantry, stainless

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (240) 929-2653

    43980 Swift Fox Dr, California, MD 20619
  • /20

    $2,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Townhouse for Rent

    23352 Black Oak Ct, California, MD 20619

    Property Id: 1776868Welcome to California! This stunning large 3 bedroom, 2.5 bathroom with 3 levels offers modern amenities in a park-like setting among mature trees, walking trails, community center, pool, park, and shopping centers. Enjoy hardwood floors, energy efficient central heat/AC, and off-street reserved parking. New stainless steel refrig/freezer, stove, chef sink/faucet,

    (571) 261-8137

    23352 Black Oak Ct, California, MD 20619
  • /86

    $633,000

    Sold Sep 19, 2025

    22272 Orchard Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,745 Sq Ft
    • Built 2004

    Last Sold Summary

    • $169/SF
    • 1 Day On Market

    Current Estimated Value $643,208

    Last Listing Agent Christina Reed RE/MAX One

    22272 Orchard Ct, Leonardtown, MD 20650
    • /28

      Est $398,112

      Not Listed For Sale

      23165 Foxglove Way, California, MD 20619

      • 3 Beds
      • 3.5 Baths
      • 2,104 Sq Ft
      • Built 2013
      23165 Foxglove Way, California, MD 20619

      Last Sold Summary

      • 1% Above List Price
      • $188/SF
      • 18 Days On Market
      • Last Sold Price $394,600
      • May 16, 2025

      Last Listing Agent Shelia Kuhfahl Century 21 New Millennium

  • /29

    $420,000

    $5K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,006 Sq Ft

    24665 E Montiego Rd, Hollywood, MD 20636

    Welcome to 24665 E. Montiego Road in Hollywood, MD a split foyer home offering exceptional space, flexibility, and comfort. This thoughtfully designed residence features generous living areas on both levels, enhanced by durable and stylish LVP flooring throughout. The main level welcomes you with a spacious living room filled with natural light, a formal dining area perfect for gatherings, and an

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (227) 275-9698

    24665 E Montiego Rd, Hollywood, MD 20636
  • /13

    $900

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • House for Rent

    41515 Singletree Dr, Leonardtown, MD 20650

    Large bedroom with walk in closet, can be furnished or unfinished and I can provide any other items needed for your comfort.Access to whole house with high speed internet House is walking distance to college of southern Maryland and St. Mary’s hospital in a very safe and quiet neighborhood.

    41515 Singletree Dr, Leonardtown, MD 20650
  • /37

    $225,000

    Sold Nov 05, 2025

    44790 Locust Ridge Ct, California, MD 20619

    • 2 Beds
    • 1.5 Baths
    • 936 Sq Ft
    • Built 1992

    Last Sold Summary

    • $240/SF
    • 13 Days On Market

    Current Estimated Value $225,563

    Last Listing Agent Adam Boerckel Home Sweet Home Real Estate LLC

    44790 Locust Ridge Ct, California, MD 20619
    • /32

      Est $327,309

      Not Listed For Sale

      43529 Marguerite Way, California, MD 20619

      • 3 Beds
      • 2 Baths
      • 1,636 Sq Ft
      • Built 2013
      43529 Marguerite Way, California, MD 20619

      Last Sold Summary

      • 1% Above List Price
      • $199/SF
      • 26 Days On Market
      • Last Sold Price $325,000
      • Dec 30, 2024

      Last Listing Agent Chris Norris Topside Realty

  • /87

    $949,900

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,466 Sq Ft

    44731 Smiths Nursery Rd, Hollywood, MD 20636

    Deep water Colonial on desirable Cuckold Creek! Enjoy water views, and waterfront living, in this charming 4-bedroom, 3-bath home. Have your coffee as you watch the morning sun shimmer on the water, and then end the day on the back deck for a glorious sunset. Situated on the protected waters of Forrest Landing Cove, you can head down to the dock for a relaxing paddle or gentle sail. Minutes from

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 205-2737

    44731 Smiths Nursery Rd, Hollywood, MD 20636
  • /2

    $900

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    44759 Woodlake Ct Unit 728, California, MD 20619

    44759 Woodlake Ct Unit 728, California, MD 20619
  • /34

    $420,000

    Sold Apr 24, 2026

    23459 Sugar Pine Ln, California, MD 20619

    • 3 Beds
    • 4 Baths
    • 2,148 Sq Ft
    • Built 2022

    Last Sold Summary

    • $196/SF
    • 12 Days On Market

    Current Estimated Value $418,732

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    23459 Sugar Pine Ln, California, MD 20619
    • /22

      Est $302,631

      Not Listed For Sale

      23520 F D R Blvd Unit 308, California, MD 20619

      • 2 Beds
      • 2 Baths
      • 1,470 Sq Ft
      • Built 2013
      23520 F D R Blvd Unit 308, California, MD 20619

      Last Sold Summary

      • 4% Above List Price
      • $197/SF
      • 6 Days On Market
      • Last Sold Price $290,000
      • Oct 03, 2024

      Last Listing Agent Brooke Matthews RE/MAX

  • /64

    $635,000

    • 5 Beds
    • 3 Baths
    • 3,030 Sq Ft

    41585 Austin Ct, Leonardtown, MD 20650

    Welcome to the completely unforgettable curb appeal of this home situated in the only culdesac of custom homes in the Estates at Singletree! Loved and beautifully maintained from the start by its current owners, they have personally curated, creative florals that surround this Southern Living traditional build, all the way to the perimeters of the property which provide abundant blueberries,

    Drema Ballengee-grunst EXP Realty, LLC

    41585 Austin Ct, Leonardtown, MD 20650
  • /6

    $2,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Condo for Rent

    23580 F D R Blvd Unit 404, California, MD 20619

    This 2 bedroom condo has an open floor plan. It includes updated appliances ,a spacious kitchen with breakfast bar and a private balcony. The master bedroom has a sitting area and full bath. Ideally located near the Base, shopping and restaurants. Top floor unit, no one above for peace of mind. Currently tenant OCCUPIED.

    Ron Leonard Leonard Realty, Inc.

    23580 F D R Blvd Unit 404, California, MD 20619
  • /81

    $599,000

    Sold Jul 21, 2025

    43706 Sweetbay St, California, MD 20619

    • 5 Beds
    • 4.5 Baths
    • 4,050 Sq Ft
    • Built 2016

    Last Sold Summary

    • $148/SF
    • 10 Days On Market

    Current Estimated Value $619,228

    Last Listing Agent Anissa Hutchins CENTURY 21 New Millennium

    43706 Sweetbay St, California, MD 20619
    • /78

      Est $609,028

      Not Listed For Sale

      23618 Placid Hill Place, California, MD 20619

      • 5 Beds
      • 3.5 Baths
      • 4,052 Sq Ft
      • Built 2010
      23618 Placid Hill Place, California, MD 20619

      Last Sold Summary

      • 6% Above List Price
      • $142/SF
      • 85 Days On Market
      • Last Sold Price $575,900
      • Dec 30, 2024

      Last Listing Agent Marizel Brewington JPAR Real Estate Professionals

  • /45

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650

    ***Available Now*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - 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

    Laura Bernth RE/MAX One

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
  • /14

    $2,300 Per Month

    • 3 Beds
    • 3.5 Baths
    • 1,698 Sq Ft
    • Townhouse for Rent

    43719 Winterberry Way, California, MD 20619

    AVAILABLE - THIS home leaves nothing else to be desired! Immaculately kept, and waiting for you to move right on in! Commute to work? Work from home? This home is centrally located to accommodate either! Close to Naval Air Station Patuxent River (NAS Pax River) and Solomons Island. With this home, take the stress (and cost) out of moving because it features No Security Deposit! (This home is

    43719 Winterberry Way, California, MD 20619
  • /108

    $534,000

    Sold May 01, 2026

    23380 Verbena Ln, California, MD 20619

    • 4 Beds
    • 4.5 Baths
    • 4,080 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $131/SF
    • 24 Days On Market

    Current Estimated Value $541,944

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    23380 Verbena Ln, California, MD 20619
    • /9

      Not Listed For Sale

      44743 Smiths Nursery Rd, Hollywood, MD 20636

      44743 Smiths Nursery Rd, Hollywood, MD 20636

      Last Sold Summary

      • 58 Days On Market
      • Last Sold Price $200,000
      • Mar 06, 2024

      Last Listing Agent Carl Franzen Franzen Realtors, Inc.

  • /34

    $449,900

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

    Lot 134 - 23685 Weeping Willow Way, Leonardtown, MD 20650

    ***PENDING***** Homesite # 134 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 one-car garage and an entry-level flex space that includes built-in cubbies

    Laura Bernth RE/MAX One

    Lot 134 - 23685 Weeping Willow Way, Leonardtown, MD 20650
  • /64

    $3,250 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,230 Sq Ft
    • House for Rent

    23259 Windflower Way, California, MD 20619

    Discover the charm of this delightful Colonial-style home nestled in the conveniently located community of Primrose Park at Wildewood. It features a 4 bedrooms, 3.5 bathroom, open concept floorpan with beautiful hardwood floors and a living room fireplace. Upstairs 3 bedrooms have walk in closets and laundry is located on 2nd floor near the bedrooms. The fully finished basement offers additional

    Mary-Blake Summerlin CENTURY 21 New Millennium

    23259 Windflower Way, California, MD 20619
  • /18

    $232,500

    Sold Sep 04, 2025

    44693 White Oak Ct, California, MD 20619

    • 2 Beds
    • 1.5 Baths
    • 936 Sq Ft
    • Built 1982

    Last Sold Summary

    • $248/SF
    • 13 Days On Market

    Current Estimated Value $231,122

    Last Listing Agent Lindsey Burch Samson Properties

    44693 White Oak Ct, California, MD 20619
    • /36

      Est $349,001

      Not Listed For Sale

      23926 Hollywood Rd, Hollywood, MD 20636

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1945
      23926 Hollywood Rd, Hollywood, MD 20636

      Last Sold Summary

      • 4% Below List Price
      • $317/SF
      • 103 Days On Market
      • Last Sold Price $364,900
      • Aug 19, 2024

      Last Listing Agent C. Brandon Harrington PAX Real Estate

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