13,215

Hollywood, MD Homes

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  • /75

    $725,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 5,268 Sq Ft

    22985 Sheffield Ct, Hollywood, MD 20636

    Welcome to 22985 Sheffield Ct in Hollywood, MD—featuring the highly sought-after Pendleton A Model on just under 1 acre, a thoughtfully designed home that blends functionality with everyday comfort. The main level offers a well-executed floor plan with 9’ ceilings and oversized 6’ windows, creating bright, open living spaces throughout. Enjoy a spacious living room, formal dining area, and an

    Conor Loughran CENTURY 21 New Millennium

    22985 Sheffield Ct, Hollywood, MD 20636
  • /55

    $525,000

    Sold May 19, 2025

    23141 Grey Squirrel Ln, California, MD 20619

    • 4 Beds
    • 3.5 Baths
    • 3,286 Sq Ft
    • Built 1992

    Last Sold Summary

    • $160/SF
    • 7 Days On Market

    Current Estimated Value $546,664

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    23141 Grey Squirrel Ln, California, MD 20619
    • /14

      Est $175,198

      Not Listed For Sale

      23243 White Birch Ct, California, MD 20619

      • 1 Bed
      • 1 Bath
      • 759 Sq Ft
      • Built 1986
      23243 White Birch Ct, California, MD 20619

      Last Sold Summary

      • $231/SF
      • 1 Day On Market
      • Last Sold Price $175,000
      • May 31, 2024

      Last Listing Agent John Gatton Century 21 New Millennium

  • /26

    $329,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    44143 Plowmans Ln Unit B, California, MD 20619

    To Be Built – THE NASSAU COVEDon’t miss this incredible opportunity to build the Nassau Cove—a stunning villa in the desirable Wildewood Village 55+ community in California, Maryland. The Nassau Cove truly lives up to its name. Enter this attached home through the one-car garage and step right into the gorgeous gourmet kitchen. Its large center island overlooks both the inviting great room

    Erica Stevenson NVR, INC.

    44143 Plowmans Ln Unit B, California, MD 20619
  • /55

    $430,000

    Sold Mar 11, 2026

    23084 Vanda Way, California, MD 20619

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • Built 2021

    Last Sold Summary

    • $195/SF
    • 4 Days On Market

    Current Estimated Value $427,444

    Last Listing Agent Edward Tully RE/MAX One

    23084 Vanda Way, California, MD 20619
    • /41

      Est $217,516

      Not Listed For Sale

      23241 Rosewood Ct, California, MD 20619

      • 2 Beds
      • 1.5 Baths
      • 936 Sq Ft
      • Built 1990
      23241 Rosewood Ct, California, MD 20619

      Last Sold Summary

      • 1% Below List Price
      • $235/SF
      • 4 Days On Market
      • Last Sold Price $220,000
      • Jun 28, 2024

      Last Listing Agent Robin Errington Century 21 New Millennium

  • /22

    $300,000

    • Land
    • 1.51 Acres
    • $198,675 per Acre

    41708 Fenwick St, Leonardtown, MD 20650

    Discover a rare opportunity to create your dream home just moments from the charm and culture of Leonardtown Historic Art District. Ideally situated within walking distance to local shops, dining, the scenic Leonardtown Wharf, and the United States Postal Service. This property offers the perfect balance of privacy and community living. Conveniently located within walking distance of highly rated

    Tig Wright Redfin Corp

    41708 Fenwick St, Leonardtown, MD 20650
  • /105

    $690,000

    Sold Mar 31, 2026

    41438 Silver Charm Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft
    • Built 2010

    Last Sold Summary

    • $165/SF
    • 5 Days On Market

    Current Estimated Value $686,906

    Last Listing Agent Heather Foster RE/MAX One

    41438 Silver Charm Ct, Leonardtown, MD 20650
    • /2

      Est $174,257

      Not Listed For Sale

      44710 Beechwood Ct, California, MD 20619

      • 1 Bed
      • 1 Bath
      • 759 Sq Ft
      • Built 1983
      44710 Beechwood Ct, California, MD 20619

      Last Sold Summary

      • 16% Above List Price
      • $198/SF
      • Last Sold Price $150,000
      • Apr 29, 2024

      Last Listing Agent datacorrect BrightMLS Non Subscribing Office

  • /77

    $715,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 4,385 Sq Ft

    41389 Holiday Ct, Leonardtown, MD 20650

    Welcome to 41389 Holiday Court, a stunning QBH Sotterley model located in the highly sought-after QBH community of Leonard’s Grant! Perfectly positioned on a desirable corner lot, this beautifully maintained 5-bedroom, 3.5-bath home offers the ideal blend of space, functionality, and thoughtful upgrades throughout. Step inside to find gorgeous hardwood floors flowing through the main level,

    Laura Bernth RE/MAX One

    41389 Holiday Ct, Leonardtown, MD 20650
  • /23

    $315,000

    Sold Feb 17, 2026

    41886 Stephen Young Ct, Hollywood, MD 20636

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1996

    Last Sold Summary

    • $312/SF
    • 82 Days On Market

    Current Estimated Value $315,874

    Last Listing Agent Terri Hamrick O'Brien Realty ERA Powered

    41886 Stephen Young Ct, Hollywood, MD 20636
    • /21

      Est $225,784

      Not Listed For Sale

      44790 Locust Ridge Ct, California, MD 20619

      • 2 Beds
      • 1.5 Baths
      • 936 Sq Ft
      • Built 1992
      44790 Locust Ridge Ct, California, MD 20619

      Last Sold Summary

      • 10% Above List Price
      • $219/SF
      • 14 Days On Market
      • Last Sold Price $205,000
      • Sep 01, 2023

      Last Listing Agent Maria Thorpe Coldwell Banker Premier

  • /2

    $539,900

    Coming Soon
    • 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
  • /80

    $517,000

    Sold Aug 26, 2025

    23371 Hosta Ln, California, MD 20619

    • 4 Beds
    • 3.5 Baths
    • 2,990 Sq Ft
    • Built 2006

    Last Sold Summary

    • $173/SF
    • 79 Days On Market

    Current Estimated Value $529,181

    Last Listing Agent Katy Galloway Century 21 Redwood Realty

    23371 Hosta Ln, California, MD 20619
    • /34

      Est $330,255

      Not Listed For Sale

      43183 Riverside Dr, Hollywood, MD 20636

      • 2 Beds
      • 1 Bath
      • 1,271 Sq Ft
      • Built 1955
      43183 Riverside Dr, Hollywood, MD 20636

      Last Sold Summary

      • 7% Above List Price
      • $242/SF
      • 97 Days On Market
      • Last Sold Price $308,000
      • Feb 07, 2024

      Last Listing Agent Amy Scott OE Realty

  • /2

    $605,000

    Coming Soon
    • 4 Beds
    • 4.5 Baths
    • 4,280 Sq Ft

    43675 Wild Iris St, California, MD 20619

    WELCOME TO 43675 WILD IRIS STREET. THIS SPACIOUS HOME FEATURES AN OPEN FLOOR PLAN WITH HUGE ROOMS AND A GREAT FLOW THROUGHOUT. YOU'LL ENTER ON THE COVERED PORCH TO AN INVITING FOYER WITH A FORMAL DINING ROOM AND A LIVING ROOM/OFFICE ON EITHER SIDE. NEXT YOU'LL NOTICE THE GENEROUS FAMILY ROOM WHICH FLOWS TO THE BREAKFAST AREA AND AMAZING KITCHEN WITH OVERSIZED ISLAND AND AMPLE CABINET AND COUNTER

    Jennifer Mullennix CENTURY 21 New Millennium

    43675 Wild Iris St, California, MD 20619
  • /30

    $290,000

    Sold Jul 21, 2025

    23520 F D R Blvd Unit 403, California, MD 20619

    • 2 Beds
    • 2 Baths
    • 1,236 Sq Ft
    • Built 2013

    Last Sold Summary

    • $235/SF
    • 21 Days On Market

    Current Estimated Value $290,528

    Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

    23520 F D R Blvd Unit 403, California, MD 20619
    • /44

      Est $349,458

      Not Listed For Sale

      26356 Pleasant Ct, Hollywood, MD 20636

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 1972
      26356 Pleasant Ct, Hollywood, MD 20636

      Last Sold Summary

      • 8% Above List Price
      • $191/SF
      • 12 Days On Market
      • Last Sold Price $324,900
      • Sep 01, 2023

      Last Listing Agent Sandy Fullerton RE/MAX

  • /54

    $459,900

    • 4 Beds
    • 2 Baths
    • 1,676 Sq Ft

    43902 Yellow Wood Way, California, MD 20619

    Welcome home to this beautifully maintained rambler with an open floor plan, ideally situated on a quiet cul-de-sac and landscaped corner lot. Offering 4 bedrooms and 2 full baths, this home features heated ceramic tile flooring in the bathrooms for added comfort and luxury. The spacious family room boasts cathedral ceilings and a cozy gas fireplace, flowing seamlessly into the large kitchen with

    Erika Yowell EXP Realty, LLC

    43902 Yellow Wood Way, California, MD 20619
  • /71

    $545,000

    Sold May 30, 2025

    23242 Windflower Way, California, MD 20619

    • 4 Beds
    • 3.5 Baths
    • 2,737 Sq Ft
    • Built 2011

    Last Sold Summary

    • $199/SF
    • 15 Days On Market

    Current Estimated Value $551,282

    Last Listing Agent Laura Bernth RE/MAX One

    23242 Windflower Way, California, MD 20619
    • /27

      Est $217,182

      Not Listed For Sale

      44693 White Oak Ct Unit 513, California, MD 20619

      • 2 Beds
      • 1.5 Baths
      • 936 Sq Ft
      • Built 1982
      44693 White Oak Ct Unit 513, California, MD 20619

      Last Sold Summary

      • 1% Below List Price
      • $235/SF
      • 3 Days On Market
      • Last Sold Price $220,000
      • Dec 05, 2024

      Last Listing Agent Erika Yowell EXP Realty, LLC

  • /48

    $420,000

    • 3 Beds
    • 3.5 Baths
    • 2,183 Sq Ft

    44088 Eucalyptus Way, California, MD 20619

    Welcome to this beautifully maintained 3-level townhome in desirable Wildewood. Built in 2021 and lovingly cared for by its original owner, this home offers over 2,100 square feet of comfortable living. With 3 bedrooms, 3 full bathrooms, and 1 half bath, the layout is thoughtfully designed for both everyday living and easy entertaining. The main level is filled with natural light thanks to

    Melissa Rodriguez RE/MAX One

    44088 Eucalyptus Way, California, MD 20619
  • /36

    $420,000

    Sold Oct 16, 2025

    23125 Winterberry Ln, California, MD 20619

    • 3 Beds
    • 2 Baths
    • 1,523 Sq Ft
    • Built 1998

    Last Sold Summary

    • $276/SF
    • 28 Days On Market

    Current Estimated Value $424,423

    Last Listing Agent Jan Kleponis O'Brien Realty ERA Powered

    23125 Winterberry Ln, California, MD 20619
    • /11

      Est $213,950

      Not Listed For Sale

      23140 Cobblestone Ln Unit 303, California, MD 20619

      • 2 Beds
      • 2 Baths
      • 1,299 Sq Ft
      • Built 1995
      23140 Cobblestone Ln Unit 303, California, MD 20619

      Last Sold Summary

      • 13% Above List Price
      • $146/SF
      • 44 Days On Market
      • Last Sold Price $189,900
      • Jun 13, 2024

      Last Listing Agent Pennie Platt Home Towne Real Estate

  • /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 Redwood Realty

    0 Cedar Lane Rd, Leonardtown, MD 20650
  • /39

    $615,000

    Sold Feb 09, 2026

    43248 Waverly Ct, Hollywood, MD 20636

    • 4 Beds
    • 4 Baths
    • 4,495 Sq Ft
    • Built 2006

    Last Sold Summary

    • $137/SF
    • 50 Days On Market

    Current Estimated Value $624,256

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    43248 Waverly Ct, Hollywood, MD 20636
    • /22

      Est $176,409

      Not Listed For Sale

      23240 Chestnut Oak Ct Unit 1045, California, MD 20619

      • 1 Bed
      • 1 Bath
      • 759 Sq Ft
      • Built 1988
      23240 Chestnut Oak Ct Unit 1045, California, MD 20619

      Last Sold Summary

      • 2% Below List Price
      • $237/SF
      • 10 Days On Market
      • Last Sold Price $180,000
      • Jun 14, 2024

      Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

  • /46

    $489,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 132 TO BE BUILT 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

    Laura Bernth RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
  • /17

    $226,000

    Sold Jun 24, 2025

    44708 Beechwood Ct Unit 617, California, MD 20619

    • 2 Beds
    • 1.5 Baths
    • 936 Sq Ft
    • Built 1983

    Last Sold Summary

    • $241/SF
    • 21 Days On Market

    Current Estimated Value $225,880

    Last Listing Agent Bradley Franzen/Retired Franzen Realtors, Inc.

    44708 Beechwood Ct Unit 617, California, MD 20619
    • /18

      Est $206,930

      Not Listed For Sale

      23140 Cobblestone Ln Unit 308, California, MD 20619

      • 2 Beds
      • 2 Baths
      • 1,185 Sq Ft
      • Built 1995
      23140 Cobblestone Ln Unit 308, California, MD 20619

      Last Sold Summary

      • 9% Above List Price
      • $160/SF
      • 1 Day On Market
      • Last Sold Price $189,950
      • Aug 01, 2023

      Last Listing Agent Bryan Clarke RE/MAX

  • /56

    $899,900

    $60K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,408 Sq Ft

    44760 Joy Chapel Rd, Hollywood, MD 20636

    Hollywood waterfront on Cuckold Creek—custom-built, one-owner home offering space, quality, and beautiful water views. The main level features hardwood floors throughout, a primary bedroom with full bath, and a well-appointed kitchen with granite countertops and custom cabinetry, open to the breakfast area and family room with a gas fireplace. A bright sunroom overlooks the creek and provides

    Carol Kalmus-Choporis Century 21 Redwood Realty

    44760 Joy Chapel Rd, Hollywood, MD 20636
  • /2

    $650,000

    Sold Mar 23, 2026

    24502 Half Pone Point Rd, Hollywood, MD 20636

    • Land
    • 33,105 Sq Ft
    • $855,263 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    24502 Half Pone Point Rd, Hollywood, MD 20636
    • /27

      Est $218,257

      Not Listed For Sale

      44790 Locust Ridge Ct, California, MD 20619

      • 2 Beds
      • 1.5 Baths
      • 936 Sq Ft
      • Built 1992
      44790 Locust Ridge Ct, California, MD 20619

      Last Sold Summary

      • 12% Above List Price
      • $208/SF
      • 4 Days On Market
      • Last Sold Price $195,000
      • Jul 11, 2023

      Last Listing Agent Farrah Fuchs Redfin Corp

  • /56

    $450,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,313 Sq Ft

    23256 Oak Crest Ln, California, MD 20619

    Nestled on a quiet side street in Wildewood, this meticulously-maintained Colonial has been lovingly updated! A recent roof, siding, gutters, water heater, and 1-year-old HVAC system, will bring peace-of-mind for years to come. Cross the welcoming front porch, and head into this comfortable 2,300+ sq ft, 4 bedroom, 2.5 bath home. The updated kitchen features attractive custom cabinets w/

    Andrew Shemeta CENTURY 21 New Millennium

    23256 Oak Crest Ln, California, MD 20619
  • /30

    $340,000

    Sold Nov 18, 2025

    23450 Dahlia Cir, California, MD 20619

    • 2 Beds
    • 4 Baths
    • 2,022 Sq Ft
    • Built 2006

    Last Sold Summary

    • $168/SF
    • 3 Days On Market

    Current Estimated Value $340,050

    Last Listing Agent Derek Tenney Atlantic Southern Realty INC

    23450 Dahlia Cir, California, MD 20619
    • /25

      Est $221,090

      Not Listed For Sale

      23242 Chestnut Oak Ct, California, MD 20619

      • 2 Beds
      • 1.5 Baths
      • 936 Sq Ft
      • Built 1988
      23242 Chestnut Oak Ct, California, MD 20619

      Last Sold Summary

      • $236/SF
      • 2 Days On Market
      • Last Sold Price $221,000
      • Apr 28, 2025

      Last Listing Agent Brian Mayer Real Broker, LLC

  • /30

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650

    *** PENDING *** Homesite 159 Oakley D1 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, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural

    Laura Bernth RE/MAX One

    Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650
  • /7

    $9,999

    Sold Jul 18, 2025

    26819 Valley Cir, Mechanicsville, MD 20659

    • Land
    • 40,075 Sq Ft
    • $10,868 per Acre

    Last Sold Summary

    • 255 Days On Market

    Current Estimated Value $127,667

    Last Listing Agent Bryce Jenifer Keller Williams Legacy

    26819 Valley Cir, Mechanicsville, MD 20659
    • /16

      Est $214,286

      Not Listed For Sale

      23242 Chestnut Oak Ct Unit 1051, California, MD 20619

      • 2 Beds
      • 1.5 Baths
      • 936 Sq Ft
      • Built 1988
      23242 Chestnut Oak Ct Unit 1051, California, MD 20619

      Last Sold Summary

      • 7% Above List Price
      • $214/SF
      • 7 Days On Market
      • Last Sold Price $200,000
      • May 02, 2024

      Last Listing Agent Connie Fitzgerald RE/MAX

  • /42

    $479,900

    New Construction 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

Showing Results 321 - 360, Page 9 of 18

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