13,129

Hollywood, MD Homes

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  • /45

    $345,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    44317 Ocelot Way, California, MD 20619

    Welcome to this spacious end-unit townhouse located just minutes from Patuxent River Naval Air Station. This home offers 4 bedrooms and 3.5 bathrooms across more than 2,000 square feet of living space. The entry level includes a private bedroom with a full bath, ideal for guests, extended family, or roommates. The main level features an open floor plan with a bright living room, dining area, and

    Ben Garner Cummings & Co. Realtors

    44317 Ocelot Way, California, MD 20619
  • /25

    $400,000 Sold Aug 15, 2025

    • 1,450 Sq Ft
    • $276/SF
    • 3 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1972

    23888 Hollywood Rd, Leonardtown, MD 20650

    Modern Charm Meets Country! Welcome to your private retreat in the heart of Leonardtown! This completely updated 4-bedroom, 2-bath rambler sits on 1.3 acres of peace and privacy—tucked off the road and surrounded by nature. Inside, you'll fall in love with the wide-open layout, fresh neutral tones, and stunning luxury vinyl flooring that flows seamlessly throughout.The

    Mark Frisco CENTURY 21 New Millennium

    23888 Hollywood Rd, Leonardtown, MD 20650
    • /55

      Est $556,710 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,546 Sq Ft

      23285 Joanne Dr, Leonardtown, MD 20650

      23285 Joanne Dr, Leonardtown, MD 20650
  • /24

    $280,000 Under Contract

    • 4 Beds
    • 1 Bath
    • 1,360 Sq Ft

    22466 Benswood Rd, California, MD 20619

    Welcome to 22466 Benswood Road California, MD. This charming Cape Cod has 4 bedrooms, 1 full bath and sits on a full Acre of land in an excellent location. A wonderful investment opportunity awaits as this property longs to be restored to its full potential. Recent upgrades include a new BAT septic system installed in 2021, A new well pump and pressure tank (2021), new hot water heater (2024),

    Chelsey Bennett EXP Realty, LLC

    22466 Benswood Rd, California, MD 20619
  • /30

    $181,000 Sold Aug 14, 2025

    • 759 Sq Ft
    • $238/SF
    • 5 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1988

    23254 Chestnut Oak Ct, California, MD 20619

    Affordable Convenience! Why pay rent? Move right into this 1-bedroom, 1-bath condo! Updated flooring, bath, and kitchen counter. Nice size living room/dining area with sliding door to patio. Patio looks out on woods/trees. Spacious bedroom and closet. Updated vanity & lighting in the bath w/ tub-shower. Big storage closet, and in-unit laundry. Newer HVAC. Reserved parking. Wildewood amenities -

    Andrew Shemeta CENTURY 21 New Millennium

    23254 Chestnut Oak Ct, California, MD 20619
    • /83

      Est $768,017 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 4,791 Sq Ft

      23326 Pembrook Dr, Hollywood, MD 20636

      23326 Pembrook Dr, Hollywood, MD 20636
  • /50

    $685,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,642 Sq Ft

    23098 Town Run Dr, Leonardtown, MD 20650

    Built in 2022, this stunning QBH Adelina floor plan shows like brand new, complete with every feature you would want if you designed it yourself. Thoughtful upgrades and stylish finishes flow throughout, making this home truly move-in ready. The main level features a 4 ft rear extension, gorgeous LVP flooring, and timeless trim details including crown molding, shadow boxes, and a full front door

    Delaney Burgess RE/MAX United Real Estate

    23098 Town Run Dr, Leonardtown, MD 20650
  • /113

    $638,000 Sold Aug 12, 2025

    • 6,311 Sq Ft
    • $101/SF
    • 86 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2005

    23275 Jenifer Ct, Leonardtown, MD 20650

    Welcome to this three-level home located in the Single Tree community, just a short walk from vibrant downtown. Boasting over 6,700 square feet of beautifully designed living space, this home offers 6 bedrooms, 4.5 bathrooms, and a thoughtfully crafted layout perfect for both everyday living and entertaining.The main level features gleaming hardwood floors, a soaring two-story family room

    Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
    • /21

      Est $316,313 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,609 Sq Ft

      44049 Fieldstone Way, California, MD 20619

      44049 Fieldstone Way, California, MD 20619
  • /80

    $499,900 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 3,041 Sq Ft

    23320 Calla Way, California, MD 20619

    Welcome to this stunning Colonial home featuring 3 bedrooms, 3 full baths, and 1 half bath. The main level boasts an open-concept design with distinct spaces for a family room, dining room, and breakfast nook—perfect for both entertaining and everyday living. The kitchen is a standout with stainless appliances beautiful granite countertops that combine style and durability. Throughout the home,

    Teresa Dove RE/MAX Realty Group

    23320 Calla Way, California, MD 20619
  • /30

    $350,000 Sold Aug 12, 2025

    • 1,104 Sq Ft
    • $317/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    25060 Pinto Dr, Hollywood, MD 20636

    Welcome to 25060 Pinto Drive a charming 3-bedroom, 2-bath rancher offering easy one-level living in a peaceful neighborhood setting. This well-maintained home features a spacious living room filled with natural light, a functional kitchen with plenty of cabinet space, and a cozy dining area perfect for gathering with friends and family.The primary suite includes its own private bath,

    Katherine Dean RE/MAX One

    25060 Pinto Dr, Hollywood, MD 20636
    • /10

      Est $220,304 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,658 Sq Ft

      44861 Hickory Landing Way, Hollywood, MD 20636

      44861 Hickory Landing Way, 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
  • /59

    $525,000 Sold Aug 08, 2025

    • 2,024 Sq Ft
    • $259/SF
    • 22 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1987

    24950 Morgan Rd, Hollywood, MD 20636

    Welcome to your own private oasis! This home boasts five beds and three full baths, along with many custom upgrades to include a new HVAC system installed four years ago. Plenty of space for entertaining, to include a large patio with screened-in sitting area, with heater; perfect for any season. The first oversized garage includes plumbing, electrical and a wet bar. The second garage has

    Amy Scott OE Realty

    24950 Morgan Rd, Hollywood, MD 20636
    • /32

      Est $441,138 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft

      23331 White Elm Ct, California, MD 20619

      23331 White Elm Ct, California, MD 20619
  • /42

    $309,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,628 Sq Ft

    44059 Fieldstone Way, California, MD 20619

    Price Improvement! Make this home your own with $15k in price-drop savings! You'll find easy living in this Wildewood Retirement Village duplex. Enjoy a moment on the welcoming front porch before heading into this freshly painted, 3-bedroom, 2 bath home. Brand new luxury vinyl plank flooring greets you in the foyer and leads through the spacious vaulted-ceiling living room, dining room, kitchen

    Andrew Shemeta CENTURY 21 New Millennium

    44059 Fieldstone Way, California, MD 20619
  • /48

    $659,900 Sold Aug 08, 2025

    • 4,924 Sq Ft
    • $134/SF
    • 26 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2003

    23273 Nicholson St, Hollywood, MD 20636

    Live Large in Leonardtown! This remarkable 4-bedroom, 4-bath home in the coveted Forrest Farm community is your golden opportunity to own a slice of Southern Maryland paradise. Set on nearly 2.5 acres of serene, tree-lined land, this home is a rare find.Step inside and be wowed by brand new SS appliances, NEW LVP & carpet, soaring vaulted ceilings, fresh paint throughout, and a thoughtful

    Mary Helen Wiley Daly RE/MAX One

    23273 Nicholson St, Hollywood, MD 20636
    • /46

      Est $364,365 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,350 Sq Ft

      23296 By the Mill Rd, California, MD 20619

      23296 By the Mill Rd, California, MD 20619
  • /27

    $350,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    24675 Blackistone Rd, Hollywood, MD 20636

    FABULOUS ONE LEVEL LIVING WITH RAMP TO THE FRONT DOOR***3 BEDROOM***2 BATH RAMBLER***DOUBLE HUNG WINDOWS***LARGE EAT-IN KITCHEN***HARDWOOD FLOORS***FRESHLY PAINTED***UPDATED BEST AVAILABLE TECHNOLOGY SEPTIC***2 CAR DETACHED GARAGE***SUN ROOM PORCH***WORKSHOP***1 CAR CARPORT***UPDATED WELL***GENERATOR***METICULOUSLY MAINTAINED LAWN***PANTRY***HEAT PUMP WITH OIL BACK UP***FRONT DOOR RAMP***UPDATED

    Candide Rayle CENTURY 21 New Millennium

    24675 Blackistone Rd, Hollywood, MD 20636
  • /53

    $325,000 Sold Aug 08, 2025

    • 1,680 Sq Ft
    • $193/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1940

    27149 Barton St, Mechanicsville, MD 20659

    Discover the perfect blend of charm and modern updates in this beautifully renovated home situated on a spacious double lot. All major renovations completed just 5 years ago! Roof, siding, heat pump, water heater, porch, kitchen, bathrooms, etc. Enter the door to a cozy screened in porch... perfect for peaceful mornings! Head in the main door to an entryway and family room with vinyl wood

    Cheryl Bare CENTURY 21 New Millennium

    27149 Barton St, Mechanicsville, MD 20659
    • /31

      Est $282,899 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft

      27064 Cape Saint Marys Dr, Mechanicsville, MD 20659

      27064 Cape Saint Marys Dr, Mechanicsville, MD 20659
  • /2

    $1,740,000 Under Contract

    • Land
    • 3.85 Acres
    • $451,948 per Acre

    25845 Point Lookout Rd, Leonardtown, MD 20650

    This listing is 3.85 acres of a total 6-acre commercial property in Leonardtown, Maryland. Don't miss the chance to invest in this thriving and picturesque community. Whether you're looking to create a retail haven, upscale office space, or a dining destination, this property has all the ingredients for success. With its size and location near Patuxent Naval Air Station, this property is a blank

    Anne Davis CENTURY 21 Commercial New Millennium

    25845 Point Lookout Rd, Leonardtown, MD 20650
  • /52

    $620,000 Sold Aug 08, 2025

    • 4,867 Sq Ft
    • $127/SF
    • 41 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2018

    45189 Woodhaven Dr, California, MD 20619

    Welcome to The Woods at Myrtle Point, a highly desirable neighborhood offering this exceptional home with immediate occupancy available. This spacious residence features 5 bedrooms and 3.5 baths, encompassing a generous 4,861 square feet of elegant living space designed for comfort and functionality.The home boasts a versatile private office or study, perfect for work or quiet retreat.

    Lisa Riggleman RE/MAX One

    45189 Woodhaven Dr, California, MD 20619
    • /71

      Est $414,141 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,773 Sq Ft

      22935 Abell St, Leonardtown, MD 20650

      22935 Abell St, Leonardtown, MD 20650
  • /10

    $255,000

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

    24984 Forrest Cove Way, Hollywood, MD 20636

    3 bedroom 2 bath detached single family home situated on a beautiful private lot (1.49 acre). HUD MAKES NO REPAIRS. HUD CASE#241-765957). EQUAL HOUSING OPPORTUNITY. GROUND RENT/HOA/CONDO FEES/FF Fees if any to be verified by purchaser. All offers submitted to HUDHOMESTORE for bid status and availability visit HUDHOMESTORE.

    Christopher White Classic Select Inc

    24984 Forrest Cove Way, Hollywood, MD 20636
  • /59

    $435,000 Sold Aug 07, 2025

    • 2,306 Sq Ft
    • $189/SF
    • 3 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2017

    23265 Lindsay Dr, Leonardtown, MD 20650

    Welcome Home to this stunning 3 Bedroom, 3.5 Bath Townhome in the vibrant community of Clarks Rest in the heart of Leonardtown! Step inside this bright and open floorplan featuring 9 foot ceilings and gleaming hardwood floors throughout the main level. The dining room moves effortlessly to the well-appointed kitchen boasting gourmet Stainless Steel appliances, granite countertops, a large

    Wayne & Christine Floyd RE/MAX Realty Group

    23265 Lindsay Dr, Leonardtown, MD 20650
    • /50

      Est $557,367 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,156 Sq Ft

      44950 Blackistone Cir, Hollywood, MD 20636

      44950 Blackistone Cir, Hollywood, MD 20636
  • /37

    $369,900

    • 3 Beds
    • 1.5 Baths
    • 1,626 Sq Ft

    24313 Mervell Dean Rd, Hollywood, MD 20636

    TAKE ADVANTAGE OF THE PRICE REDUCTION FOR THIS HIDDEN GEM!! Are you interested in fine living with a bit of seclusion? This fully renovated, all brick, custom-built, late 1950s era home could be your dream home! Featuring 3 bedrooms, a brick fireplace, and separate living and dining rooms, the property includes central air, brand new water heater and furnace, and newer kitchen cabinetry. Bonus

    Suzette Hampton Samson Properties

    24313 Mervell Dean Rd, Hollywood, MD 20636
  • /108

    $670,000 Sold Aug 01, 2025

    • 3,203 Sq Ft
    • $209/SF
    • 10 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    25983 Chaffee Ct, Mechanicsville, MD 20659

    This phenomenal property is back on the market! Welcome to this stunning home at 25983 Chaffee Court, where comfort, style, and functionality meet! This immaculate 4-bedroom, 3.5-bathroom residence boasts a wealth of luxurious features, including a spacious 2-car garage with overhead service, and an impressive finished basement that offers both a bar and a small workshop for all your hobby or

    John Gatton CENTURY 21 New Millennium

    25983 Chaffee Ct, Mechanicsville, MD 20659
    • /47

      Est $814,129 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,533 Sq Ft

      24602 Blackistone Rd, Hollywood, MD 20636

      24602 Blackistone Rd, Hollywood, MD 20636
  • /24

    $249,900

    • 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
  • /55

    $800,000 Sold Jul 31, 2025

    • 2,232 Sq Ft
    • $358/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1974

    24611 Greenview Dr, Hollywood, MD 20636

    Waterfront Escape on Cuckold Creek – 4 Bed, 2.5 Bath on 1.03 Acres in Hollywood, MDTucked away on a quiet peninsula along Cuckold Creek, this 2,232 sq ft 4-bedroom, 2.5-bath waterfront retreat offers the perfect blend of tranquility, functionality, and outdoor living—set on 1.03 acres with your own private pier w/ synthetic decking, sandy shoreline, and incredible sunset

    Mark Frisco CENTURY 21 New Millennium

    24611 Greenview Dr, Hollywood, MD 20636
    • /10

      Est $260,262 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      25260 Vista Rd, Hollywood, MD 20636

      25260 Vista Rd, Hollywood, MD 20636
  • /29

    $387,000 Sold Jul 31, 2025

    • 2,165 Sq Ft
    • $179/SF
    • 3 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2019

    22958 Mountain Laurel Ln, California, MD 20619

    Welcome to 22958 Mountain Laurel Ln — the perfect place for your family to grow and thrive! This spacious 3-bedroom, 3.5-bath townhome offers over three levels of beautifully designed living space. Every bedroom has its own dedicated bath! The heart of the home is the gourmet kitchen with a gas cooktop, double wall ovens, and a large island where homework, snacks, and family dinners all come

    Michelle Camaioni RE/MAX One

    22958 Mountain Laurel Ln, California, MD 20619
    • /46

      Est $694,145 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,628 Sq Ft

      22902 S Pembrook Dr, Hollywood, MD 20636

      22902 S Pembrook Dr, Hollywood, MD 20636
  • /72

    $449,900 Sold Jul 31, 2025

    • 2,379 Sq Ft
    • $189/SF
    • 12 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2022

    41554 Briarwood Cir, Leonardtown, MD 20650

    Location is key.... Not just in Leonardtown, but in the community itself. Through every window of the rear of this house is the picturesque setting of the wooded tree line and abundant privacy, not often found in Townhome living. This home is tucked back from main road on an open green in front and woods in the rear. Upgrades to this home from original build include: Premium COREtec Pro Plus

    Wayne & Christine Floyd RE/MAX Realty Group

    41554 Briarwood Cir, Leonardtown, MD 20650
    • /22

      Est $278,770 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,274 Sq Ft

      25263 Sotterley Rd, Hollywood, MD 20636

      25263 Sotterley Rd, Hollywood, MD 20636
  • /41

    $479,900 Sold Jul 31, 2025

    • 2,330 Sq Ft
    • $206/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    41997 Loker Ct, Leonardtown, MD 20650

    Boast in the benefit of this cul-de-sac home on the outskirts of town that backs to a farm but with the closeness and convenience of being so close to area schools, restaurants, stores, and hospital. This home is ready for you to make it your own. The backyard privacy with deck and patio are great for enjoying the nature sounds. Large shed to keep the tools needed to keep the beautiful lawn

    Jimmy Hayden RE/MAX Realty Group

    41997 Loker Ct, Leonardtown, MD 20650
    • /36

      Est $517,164 Not Listed For Sale

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

      23276 Daffodil Dr, California, MD 20619

      23276 Daffodil Dr, California, MD 20619
  • /75

    $566,000 Sold Jul 31, 2025

    • 2,988 Sq Ft
    • $189/SF
    • 10 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2014

    45214 Woodhaven Dr, California, MD 20619

    Step into the lifestyle you’ve been dreaming of in this stunning home, perfectly situated in the highly sought-after community of Myrtle Point.Move-in ready and competitively priced, this home checks all the boxes—you’ve found the one!They say the kitchen is the heart of the home, and this one delivers with an expansive island that’s ideal for entertaining, gathering with loved ones,

    Jessica Raley CENTURY 21 New Millennium

    45214 Woodhaven Dr, California, MD 20619

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