13,157

Hollywood, MD Homes

Section Image
    • 44570 River Otter Dr, California, MD 20619
      44570 River Otter Dr, California, MD 20619
      44570 River Otter Dr, California, MD 20619
      /32

      Est $369,352 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,068 Sq Ft

      44570 River Otter Dr, California, MD 20619

      44570 River Otter Dr, California, MD 20619
  • 44224 Pine Creek Ln, California, MD 20619
    44224 Pine Creek Ln, California, MD 20619
    44224 Pine Creek Ln, California, MD 20619
    /56

    $449,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft

    44224 Pine Creek Ln, California, MD 20619

    Nestled at the end of a tranquil cul-de-sac in the desirable Wildewood community, this beautifully updated Rambler offers the perfect blend of comfort, style, and convenience. Featuring new flooring throughout, fresh interior paint, and a brand-new HVAC system, this 1,861-square-foot home is truly move-in ready.Inside, you’ll find three spacious bedrooms and two well-appointed baths, along

    Erika Yowell EXP Realty, LLC

    44224 Pine Creek Ln, California, MD 20619
  • 20575 Peaches Hide A Way, Hollywood, MD 20636
    20575 Peaches Hide A Way, Hollywood, MD 20636
    20575 Peaches Hide A Way, Hollywood, MD 20636
    /5

    $140,000 Sold Feb 28, 2025

    20575 Peaches Hide A Way, Hollywood, MD 20636

    • Land
    • 5.25 Acres
    • $26,667 per Acre

    Last Sold Summary

    • 66 Days On Market

    Current Estimated Value $138,500

    Last Listing Agent Michael Hunter Real Broker, LLC

    20575 Peaches Hide A Way, Hollywood, MD 20636
    • 44321 Ocelot Way, California, MD 20619
      44321 Ocelot Way, California, MD 20619
      44321 Ocelot Way, California, MD 20619
      /33

      Est $367,102 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,068 Sq Ft

      44321 Ocelot Way, California, MD 20619

      44321 Ocelot Way, California, MD 20619
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    /79

    $639,000 Under Contract

    • 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
  • 24665 E Montiego Rd, Hollywood, MD 20636
    24665 E Montiego Rd, Hollywood, MD 20636
    24665 E Montiego Rd, Hollywood, MD 20636
    /30

    $366,000 Sold Feb 24, 2025

    24665 E Montiego Rd, Hollywood, MD 20636

    • 5 Beds
    • 3 Baths
    • 2,006 Sq Ft
    • Built 1974

    Last Sold Summary

    • $182/SF
    • 56 Days On Market

    Current Estimated Value $367,790

    Last Listing Agent James Barnes EXP Realty, LLC

    24665 E Montiego Rd, Hollywood, MD 20636
    • 44241 Beaver Creek Dr, California, MD 20619
      44241 Beaver Creek Dr, California, MD 20619
      44241 Beaver Creek Dr, California, MD 20619
      /52

      Est $384,102 Not Listed For Sale

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

      44241 Beaver Creek Dr, California, MD 20619

      44241 Beaver Creek Dr, California, MD 20619
  • 43447 Drum Cliff Rd, Hollywood, MD 20636
    43447 Drum Cliff Rd, Hollywood, MD 20636
    43447 Drum Cliff Rd, Hollywood, MD 20636
    /31

    $665,000

    • 3 Beds
    • 2 Baths
    • 3,684 Sq Ft

    43447 Drum Cliff Rd, Hollywood, MD 20636

    Welcome to your private retreat at 43447 Drum Cliff Rd! This charming 3-bedroom, 2-bath home sits on 3 scenic acres in the heart of Hollywood, offering the perfect mix of peace, privacy, and modern updates. Inside, you'll find brand new carpet in the upstairs bedrooms, real tile in the kitchen, and bamboo hardwood flooring in the dining area. A new French door opens to a brand new back deck,

    Mack Davis Douglas Realty, LLC

    43447 Drum Cliff Rd, Hollywood, MD 20636
  • 24415 Fwd Dr, Hollywood, MD 20636
    24415 Fwd Dr, Hollywood, MD 20636
    24415 Fwd Dr, Hollywood, MD 20636
    /82

    $699,000 Sold Sep 12, 2025

    24415 Fwd Dr, Hollywood, MD 20636

    • 4 Beds
    • 4 Baths
    • 3,771 Sq Ft
    • Built 2017

    Last Sold Summary

    • $185/SF
    • 50 Days On Market

    Current Estimated Value $697,360

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    24415 Fwd Dr, Hollywood, MD 20636
    • 41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      /39

      Est $631,435 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,993 Sq Ft

      41419 Whimsical Ct, Leonardtown, MD 20650

      41419 Whimsical Ct, Leonardtown, MD 20650
  • 24991 Briscoe Rd, Hollywood, MD 20636
    24991 Briscoe Rd, Hollywood, MD 20636
    24991 Briscoe Rd, Hollywood, MD 20636
    /130

    $1,250,000 Pending

    • 3 Beds
    • 3 Baths
    • 3,747 Sq Ft

    24991 Briscoe Rd, Hollywood, MD 20636

    Experience the epitome of waterfront living at this exceptional property nestled along Spring Cove in the coveted Cuckold Creek of the Patuxent River. Meticulously maintained, this home boasts an extensive bulkhead that frames the shoreline, a wraparound pier, a private covered boat lift, and deep, protected waters, offering unrivaled access for aquatic adventures. Entertain your friends and

    Mark Posey Greenmark Real Estate

    24991 Briscoe Rd, Hollywood, MD 20636
  • 23075 Hollywood Rd, Leonardtown, MD 20650
    23075 Hollywood Rd, Leonardtown, MD 20650
    23075 Hollywood Rd, Leonardtown, MD 20650
    /82

    $574,000 Sold Jul 24, 2025

    23075 Hollywood Rd, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 3,238 Sq Ft
    • Built 1942

    Last Sold Summary

    • $177/SF
    • 55 Days On Market

    Current Estimated Value $573,664

    Last Listing Agent Katy Galloway CENTURY 21 New Millennium

    23075 Hollywood Rd, Leonardtown, MD 20650
    • 23024 Thornbury Dr, Hollywood, MD 20636
      23024 Thornbury Dr, Hollywood, MD 20636
      23024 Thornbury Dr, Hollywood, MD 20636
      /30

      Est $730,834 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,872 Sq Ft

      23024 Thornbury Dr, Hollywood, MD 20636

      23024 Thornbury Dr, Hollywood, MD 20636
  • 43135 Goldsborough Place, Hollywood, MD 20636
    43135 Goldsborough Place, Hollywood, MD 20636
    43135 Goldsborough Place, Hollywood, MD 20636
    /5

    $90,000 Under Contract

    • Land
    • 2.78 Acres
    • $32,374 per Acre

    43135 Goldsborough Place, Hollywood, MD 20636

    2.78 acres with recorded and approved perc plat. Property surrounded by local protected lands. Ready for you to contact your engineer and start your building permits.Per the St. Mary's County Health Dept. 43135 Goldsborough Place already has a sewage reserve area with satisfactory percs that was approved in 2006 that can still be utilized.The perc test provided is from 2006 and was used

    Patrick Dugan O'Brien Realty ERA Powered

    43135 Goldsborough Place, Hollywood, MD 20636
  • 42264 Ridge Rd, Mechanicsville, MD 20659
    42264 Ridge Rd, Mechanicsville, MD 20659
    42264 Ridge Rd, Mechanicsville, MD 20659
    /33

    $195,000 Sold Oct 10, 2025

    42264 Ridge Rd, Mechanicsville, MD 20659

    • 3 Beds
    • 2 Baths
    • 2,020 Sq Ft
    • Built 1950

    Last Sold Summary

    • $97/SF
    • 106 Days On Market

    Current Estimated Value $254,072

    Last Listing Agent Heidi Heiderman Samson Properties

    42264 Ridge Rd, Mechanicsville, MD 20659
    • 24278 Half Pone Point Rd, Hollywood, MD 20636
      24278 Half Pone Point Rd, Hollywood, MD 20636
      24278 Half Pone Point Rd, Hollywood, MD 20636
      /69

      Est $1,657,591 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 5,548 Sq Ft

      24278 Half Pone Point Rd, Hollywood, MD 20636

      24278 Half Pone Point Rd, Hollywood, MD 20636
  • 0 Cedar Lane Rd, Leonardtown, MD 20650
    0 Cedar Lane Rd, Leonardtown, MD 20650
    0 Cedar Lane Rd, Leonardtown, MD 20650
    /17

    $3,800,000 Pending

    • Land
    • 52.18 Acres
    • $72,825 per Acre

    0 Cedar Lane Rd, Leonardtown, MD 20650

    This property offers the perfect blend of rural charm and convenient access to urban amenities. With the potential for annexation into the town of Leonardtown, there are exciting development possibilities on the horizon. Don't miss this unique opportunity!

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    0 Cedar Lane Rd, Leonardtown, MD 20650
  • 26369 Jones Wharf Rd, Hollywood, MD 20636
    26369 Jones Wharf Rd, Hollywood, MD 20636
    26369 Jones Wharf Rd, Hollywood, MD 20636
    /26

    $330,000 Sold Dec 29, 2025

    26369 Jones Wharf Rd, Hollywood, MD 20636

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1994

    Last Sold Summary

    • $344/SF
    • 41 Days On Market

    Last Listing Agent Diane Fenwick RE/MAX One

    26369 Jones Wharf Rd, Hollywood, MD 20636
    • 23107 Poppy Way, California, MD 20619
      23107 Poppy Way, California, MD 20619
      23107 Poppy Way, California, MD 20619
      /28

      Est $475,969 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,020 Sq Ft

      23107 Poppy Way, California, MD 20619

      23107 Poppy Way, California, MD 20619
  • 42470 Helen Ct, Hollywood, MD 20636
    42470 Helen Ct, Hollywood, MD 20636
    42470 Helen Ct, Hollywood, MD 20636
    /14

    $399,999

    • 6 Beds
    • 2.5 Baths
    • 1,716 Sq Ft

    42470 Helen Ct, Hollywood, MD 20636

    Classic two-story Colonial located on a quiet cul-de-sac in the desirable Gillens Grove community of Hollywood, MD. Offering approximately 1,716 square feet, this home features 3 bedrooms & 3 bathrooms and sits on a generous 37,343 sq ft lot, providing ample space and privacy. Conveniently located near schools, shopping, and commuter routes.

    Norman Domingo XRealty.NET LLC

    42470 Helen Ct, Hollywood, MD 20636
  • 44222 Beaver Creek Dr, California, MD 20619
    44222 Beaver Creek Dr, California, MD 20619
    44222 Beaver Creek Dr, California, MD 20619
    /32

    $365,000 Sold Jun 20, 2025

    44222 Beaver Creek Dr, California, MD 20619

    • 4 Beds
    • 2.5 Baths
    • 2,110 Sq Ft
    • Built 2011

    Last Sold Summary

    • $173/SF
    • 0 Days On Market

    Current Estimated Value $366,629

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    44222 Beaver Creek Dr, California, MD 20619
    • 41474 Affirmed Way, Leonardtown, MD 20650
      41474 Affirmed Way, Leonardtown, MD 20650
      41474 Affirmed Way, Leonardtown, MD 20650
      /76

      Est $663,122 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,050 Sq Ft

      41474 Affirmed Way, Leonardtown, MD 20650

      41474 Affirmed Way, Leonardtown, MD 20650
  • 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
  • 22950 Wintergreen Ln, California, MD 20619
    22950 Wintergreen Ln, California, MD 20619
    22950 Wintergreen Ln, California, MD 20619
    /49

    $490,000 Sold Sep 02, 2025

    22950 Wintergreen Ln, California, MD 20619

    • 4 Beds
    • 3.5 Baths
    • 3,087 Sq Ft
    • Built 1994

    Last Sold Summary

    • $159/SF
    • 78 Days On Market

    Current Estimated Value $490,911

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    22950 Wintergreen Ln, California, MD 20619
    • 43535 Abis St, Hollywood, MD 20636
      43535 Abis St, Hollywood, MD 20636
      43535 Abis St, Hollywood, MD 20636
      /93

      Est $650,140 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,478 Sq Ft

      43535 Abis St, Hollywood, MD 20636

      43535 Abis St, Hollywood, MD 20636
  • 44180 Beaver Creek Dr, California, MD 20619
    44180 Beaver Creek Dr, California, MD 20619
    44180 Beaver Creek Dr, California, MD 20619
    /23

    $364,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,056 Sq Ft

    44180 Beaver Creek Dr, California, MD 20619

    Beautiful and well-maintained 3 bedroom 2.5 bath townhome with over 2,050 finished sq. ft. Open main level with spacious living room, dining area, and a kitchen offering ample cabinetry, pantry, stainless steel appliances, and gas stove. Master Bedroom features two walk-in closets and a private bath with soaking tub, separate shower, and dual vanities. Upstairs laundry room for your convenience.

    DJ Brady EXP Realty, LLC

    44180 Beaver Creek Dr, California, MD 20619
  • 24415 Lakeland Dr, Hollywood, MD 20636
    24415 Lakeland Dr, Hollywood, MD 20636
    24415 Lakeland Dr, Hollywood, MD 20636
    /37

    $385,000 Sold May 26, 2025

    24415 Lakeland Dr, Hollywood, MD 20636

    • 3 Beds
    • 1 Bath
    • 1,212 Sq Ft
    • Built 1964

    Last Sold Summary

    • $318/SF
    • 43 Days On Market

    Current Estimated Value $373,970

    Last Listing Agent Gloria Abell Coldwell Banker Premier

    24415 Lakeland Dr, Hollywood, MD 20636
    • 43651 Wild Iris St, California, MD 20619
      43651 Wild Iris St, California, MD 20619
      43651 Wild Iris St, California, MD 20619
      /28

      Est $531,321 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,388 Sq Ft

      43651 Wild Iris St, California, MD 20619

      43651 Wild Iris St, California, MD 20619
  • Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
    /42

    $479,900 Pending

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

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650

    ***UNDER CONTRACT*** Unit 137 Oakley D1New 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, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural

    Laura Bernth RE/MAX One

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
  • 41403 Heritage Ln, Leonardtown, MD 20650
    41403 Heritage Ln, Leonardtown, MD 20650
    41403 Heritage Ln, Leonardtown, MD 20650
    /53

    $605,000 Sold May 16, 2025

    41403 Heritage Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft
    • Built 2016

    Last Sold Summary

    • $181/SF
    • 6 Days On Market

    Current Estimated Value $603,213

    Last Listing Agent Wanda White CENTURY 21 New Millennium

    41403 Heritage Ln, Leonardtown, MD 20650
    • 24406 Broad Creek Dr, Hollywood, MD 20636
      24406 Broad Creek Dr, Hollywood, MD 20636
      24406 Broad Creek Dr, Hollywood, MD 20636
      /67

      Est $670,642 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 5,128 Sq Ft

      24406 Broad Creek Dr, Hollywood, MD 20636

      24406 Broad Creek Dr, Hollywood, MD 20636
  • 23773 Meredith Ct, Hollywood, MD 20636
    23773 Meredith Ct, Hollywood, MD 20636
    23773 Meredith Ct, Hollywood, MD 20636
    /72

    $640,000 Pre-Foreclosure

    • 3 Beds
    • 2.5 Baths
    • 3,478 Sq Ft

    23773 Meredith Ct, Hollywood, MD 20636

    Spacious home in desirable Hollywood location. (Abell's Ridge) The main level greets you with hardwood flooring in the Foyer. Large owners suite with two walk in closets. The owner's full bath features tile flooring, a double jetted soaking tub, separate shower.Four car garage with work area of garage heated. New HVAC in 2023. Fireplace has wood stove insert. Unfinished basement . Over 7

    Gloria Abell Coldwell Banker Premier

    23773 Meredith Ct, Hollywood, MD 20636
  • 24334 Daphne Dr, Hollywood, MD 20636
    24334 Daphne Dr, Hollywood, MD 20636
    24334 Daphne Dr, Hollywood, MD 20636
    /59

    $620,000 Sold Oct 30, 2025

    24334 Daphne Dr, Hollywood, MD 20636

    • 4 Beds
    • 3.5 Baths
    • 3,605 Sq Ft
    • Built 2017

    Last Sold Summary

    • $172/SF

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    24334 Daphne Dr, Hollywood, MD 20636
    • 24412 Broad Creek Dr, Hollywood, MD 20636
      24412 Broad Creek Dr, Hollywood, MD 20636
      24412 Broad Creek Dr, Hollywood, MD 20636
      /47

      Est $546,297 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,588 Sq Ft

      24412 Broad Creek Dr, Hollywood, MD 20636

      24412 Broad Creek Dr, Hollywood, MD 20636
  • 23146 Hollins Way, Hollywood, MD 20636
    23146 Hollins Way, Hollywood, MD 20636
    23146 Hollins Way, Hollywood, MD 20636
    /72

    $649,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 4,094 Sq Ft

    23146 Hollins Way, Hollywood, MD 20636

    Welcome to this spacious and beautifully maintained home featuring 4 bedrooms and 3.5 bathrooms, perfectly designed for both everyday living and entertaining. A charming front porch welcomes you into the home, setting the tone for its warm and inviting atmosphere. The heart of the home is a large kitchen that opens into a bright and airy great room, creating the perfect gathering space for family

    Steven Carroll Berkshire Hathaway HomeServices PenFed Realty

    23146 Hollins Way, Hollywood, MD 20636
  • 23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, Leonardtown, MD 20650
    /48

    $469,900 Sold Sep 18, 2025

    23664 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    23664 Dragonfly Ln, Leonardtown, MD 20650
    • 24418 Broad Creek Dr, Hollywood, MD 20636
      24418 Broad Creek Dr, Hollywood, MD 20636
      24418 Broad Creek Dr, Hollywood, MD 20636
      /30

      Est $556,247 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,148 Sq Ft

      24418 Broad Creek Dr, Hollywood, MD 20636

      24418 Broad Creek Dr, Hollywood, MD 20636
  • 45216 Clarkes Landing Rd, Hollywood, MD 20636
    45216 Clarkes Landing Rd, Hollywood, MD 20636
    45216 Clarkes Landing Rd, Hollywood, MD 20636
    /81

    $1,775,000 Pending

    • 6 Beds
    • 5.5 Baths
    • 6,646 Sq Ft

    45216 Clarkes Landing Rd, Hollywood, MD 20636

    VERY PRIVATE POINT of land with all-brick sprawling residence was designed to take full advantage of the waterfront lifestyle at this unique site. Cuckold Creek is highly sought after for boating and watersports, depth of water, surrounding value. This point has a unique private beach, a deep water private pier, and a beautiful elevation. Catch your own blue crabs at the pier and have summer crab

    Chris McNelis Berkshire Hathaway HomeServices PenFed Realty

    45216 Clarkes Landing Rd, Hollywood, MD 20636
  • 44017 Swift Fox Dr, California, MD 20619
    44017 Swift Fox Dr, California, MD 20619
    44017 Swift Fox Dr, California, MD 20619
    /54

    $380,000 Sold Sep 24, 2025

    44017 Swift Fox Dr, California, MD 20619

    • 3 Beds
    • 2.5 Baths
    • 2,082 Sq Ft
    • Built 2011

    Last Sold Summary

    • $183/SF
    • 6 Days On Market

    Current Estimated Value $378,209

    Last Listing Agent Diana Washabaugh CENTURY 21 New Millennium

    44017 Swift Fox Dr, California, MD 20619
    • 22905 Camden Ct, Hollywood, MD 20636
      22905 Camden Ct, Hollywood, MD 20636
      22905 Camden Ct, Hollywood, MD 20636
      /72

      Est $772,787 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 5,425 Sq Ft

      22905 Camden Ct, Hollywood, MD 20636

      22905 Camden Ct, Hollywood, MD 20636

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