37

Homes for Sale in 20685

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  • /16

    $499,999

    • 5 Beds
    • 2.5 Baths
    • 3,224 Sq Ft

    1492 Dogwood Cir, Saint Leonard, MD 20685

    Just a short walk to the Beach! This Great Contemporary Home offers 5 Beds/2.5 Baths, an Open Floor plan, Stainless Steel Appliances, Granite Kitchen counters, Hardwood Floors throughout, Spiral Stairs lead up to the Owners Suite and down to the Basement! The Roof was replaced in 2017 w/ 45 yr Architectural shingles, Hot Water heater was replaced 2018, Sewage ejector pump was replaced 2018, and

    Agent Photo

    Vicki Alvey

    RE/MAX One

    (410) 847-7757

    1492 Dogwood Cir, Saint Leonard, MD 20685
  • /2

    $25,000

    • Land
    • 4,791 Sq Ft
    • $227,273 per Acre

    6055 Poplar Rd, Saint Leonard, MD 20685

    Located in the desirable Long Beach community of Saint Leonard, 6055 Poplar offers a peaceful Chesapeake Bay–area lifestyle in Calvert County. The neighborhood is quiet and residential, known for its coastal charm, friendly community feel, and proximity to the water—ideal for a primary residence or weekend retreat. Just a short drive away are local restaurants, seafood spots, and everyday

    Agent Photo

    Kathiuska Ramirez

    Samson Properties

    (410) 888-0102

    6055 Poplar Rd, Saint Leonard, MD 20685
  • /47

    $509,900

    • 5 Beds
    • 3.5 Baths
    • 3,156 Sq Ft

    5817 Magnolia Cir, Saint Leonard, MD 20685

    Look for our OPEN HOUSE this Saturday 12-3 PM.This well established beachfront community with annual events for family and friends awaits you soon! Enjoy visiting this beautiful home as you pull into the expansive driveway after a hard days work! The new steel 2 car garage door with remote will keep you out of the weather too! Enjoy relaxing on your concrete front porch or sun-filled rear

    Agent Photo

    Juan Aranda

    CENTURY 21 New Millennium

    (410) 376-8615

    5817 Magnolia Cir, Saint Leonard, MD 20685
  • /3

    $450,000

    Open House 6/19 Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,511 Sq Ft

    4150 Williams Wharf Rd, Saint Leonard, MD 20685

    4150 Williams Wharf Rd offers a rare opportunity to own a private multi-home retreat property in the heart of sought-after Mid-Calvert County, Maryland. Situated on approximately 3 peaceful acres surrounded by picturesque farmland and scenic Southern Maryland countryside, this unique estate delivers an exceptional blend of privacy, versatility, and lifestyle-focused living.Featuring two

    Agent Photo

    Danielle Sloan

    Samson Properties

    (443) 241-7735

    4150 Williams Wharf Rd, Saint Leonard, MD 20685
  • /34

    $450,000

    • 2 Beds
    • 1.5 Baths
    • 1,288 Sq Ft

    2020 Woods Rd, Saint Leonard, MD 20685

    Beautifully refreshed and full of potential, this charming rambler on basement sits on approximately 1 private acre in the peaceful rural setting of St. Leonard. This property features no HOA, a fully unfinished basement with rough-in for an additional bathroom, and an impressive approximately 75’ x 40’ pole barn ideal for contractors, hobbyists, car enthusiasts, equipment storage, workshop

    Lesa Clark Redfin Corp

    2020 Woods Rd, Saint Leonard, MD 20685
  • /106

    $1,000,000

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    4721 Rock Creek Cir, Saint Leonard, MD 20685

    Nestled amongst the trees with a breathtaking view of the waterfront, this stunning contemporary split-level home offers the perfect escape from the city in under an hour or if you're lucky enough you can call Saint Leonard home year round! The only way to describe the feeling of walking the property is a serene, luxury retreat. Take a deep breath and exhale, this is really your new home!

    Melinda Brown EXP Realty, LLC

    4721 Rock Creek Cir, Saint Leonard, MD 20685
  • /45

    $589,000

    • 5 Beds
    • 3.5 Baths
    • 3,592 Sq Ft

    7425 Mayflower Ct, Saint Leonard, MD 20685

    Spacious colonial nestled in a cul-de-sac the charming and quiet Island Creek Meadow neighborhood in Saint Leonard. Situated on a beautiful wooded one acre lot with ample privacy. Boasting five generously sized bedrooms, including a large primary suite, and three and half baths. Entertain and host with a custom finished basement to include a large living room with theatre style lighting and

    Megan Erickson Berkshire Hathaway HomeServices PenFed Realty

    7425 Mayflower Ct, Saint Leonard, MD 20685
  • /2

    $85,000

    • Land
    • 36,590 Sq Ft
    • $101,190 per Acre

    5675 Arbor Cir, Saint Leonard, MD 20685

    Welcome to 5675 Arbor Circle — your opportunity to claim a slice of Southern Maryland's most coveted waterside community. Tucked among a lush canopy of mature trees in the established Flag Harbor neighborhood of St. Leonard, this beautiful wooded lot offers the perfect setting for your custom-built Chesapeake Bay retreat.Surrounded by nature yet connected to everything that makes coastal

    RJ Soni Northrop Realty

    5675 Arbor Cir, Saint Leonard, MD 20685
  • /53

    $525,000

    $75K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,379 Sq Ft

    1815 Highland Dr, Saint Leonard, MD 20685

    Run!!! Don't Walk!! This exquisite Cape Cod residence, nestled on the Shores of Calvert Beach, offers a harmonious blend of comfort and bay living, perfectly positioned along the banks of the picturesque Chesapeake Bay. With 2,379 square feet of thoughtfully designed living space, this home features four spacious bedrooms and three full bathrooms, ideal for both relaxation and entertaining. Step

    Samuel J Thomas Hyatt & Company Real Estate LLC

    1815 Highland Dr, Saint Leonard, MD 20685
  • /38

    $340,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    6070 Hill Rd, Saint Leonard, MD 20685

    This 3 Bedroom, 1.5 Bath Rambler with an oversized 1-car detached Garage is located on a quiet street in Long Beach on the Bay (a Chesapeake Bay beach community). Hardwood Floors and Ceramic Tile throughout home. Brand new washing machine (3/2026) and hot water heater (spring/2025). In the rear of the home, there are extra outdoor spaces to enjoy your home. A screened-in Porch is off the Dining

    Gail Siegel O'Brien Realty ERA Powered

    6070 Hill Rd, Saint Leonard, MD 20685
  • /29

    $324,900

    $5K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    5457 Bayview Ave, Saint Leonard, MD 20685

    The beach is calling! Step into this charming 3-bedroom, 1-bath home at 5457 Bayview Ave, St. Leonard, MD, completely renovated in a boho-organic modern style. This beachside sanctuary features new LVP floors, a fresh kitchen with butcher block counters, gold hardware/fixtures & new appliances, a luxurious retreat-style bath with sage green custom tile, large vanity & gold accents, new

    Josh Wilbanks Saeculum Real Estate LLC

    5457 Bayview Ave, Saint Leonard, MD 20685
  • /60

    $1,175,000

    • 4 Beds
    • 4 Baths
    • 2,818 Sq Ft

    4005 Lloyd Bowen Rd, Saint Leonard, MD 20685

    Welcome to an extraordinary Southern Living–inspired waterfront bungalow offering a rare blend of tranquility, luxury, and charm in pristine condition. Tucked away on a quiet, secluded road with only three homes, this exceptional property is surrounded by water and bordered by 25 acres of protected, unbuildable land, ensuring lasting privacy and breathtaking natural beauty.Ideally located

    Jeannine Wayson Coldwell Banker Realty

    4005 Lloyd Bowen Rd, Saint Leonard, MD 20685
  • /24

    $290,000

    Open Sat 11AM - 2PM
    • 3 Beds
    • 1 Bath
    • 889 Sq Ft

    1440 Plateau Rd, Saint Leonard, MD 20685

    Welcome home to this inviting rambler nestled in the Long Beach community of St. Leonard. Perfectly situated in a peaceful, established neighborhood, this 3-bedroom, 1-bath home offers comfortable living with modern convenience.Step inside to hardwood floors that flow throughout the main living areas. The living room is anchored by a cozy pellet stove, ideal for relaxing evenings or

    Toni Lowman O'Brien Realty ERA Powered

    1440 Plateau Rd, Saint Leonard, MD 20685
  • /13

    $910,000

    • 2 Beds
    • 1 Bath
    • 1,388 Sq Ft

    4870 Calvert Dr, Saint Leonard, MD 20685

    "DO NOT KNOCK ON DOOR" Tenant occupied Investment opportunity to purchase 2 homes and a lot, along with two commercial buildings. All five properties are being sold together at a discount. Also seller is willing to hold some financing. This listing is for the three residential units. The two commercial are listed together.

    Pattee McInerney Scott McInerney RE/MAX One

    4870 Calvert Dr, Saint Leonard, MD 20685
  • /105

    $969,900

    • 4 Beds
    • 4.5 Baths
    • 4,468 Sq Ft

    7440 Sedwick Ct, Saint Leonard, MD 20685

    STUNNING WATERFRONT! Set on 2.21 private acres along St. Leonard Creek, this exceptional waterfront home offers 4,468 square feet, 4 bedrooms, 4.5 bathrooms, a detached 2-car garage w/ an unfinished storage space above, and a fully finished basement in a setting that feels private, peaceful, and made for everyday luxury. Watch the numerous Bald Eagles and other wildlife and melt away into this

    Mark Frisco CENTURY 21 New Millennium

    7440 Sedwick Ct, Saint Leonard, MD 20685
  • /44

    $1,200,000

    • 4 Beds
    • 5 Baths
    • 3,500 Sq Ft

    2237 Garrity Rd, Saint Leonard, MD 20685

    No HOA. Total square footage of 3520. The house's total sq ft is 2400 with 3 bedrooms and 2.5 baths. A 1120 sq ft apartment with 1 bedroom and 1 bath. The Garage has a 1/2 Bath. The property is in the forest management program for reduced taxes. Tucked along the protected waters of Saint Leonard Creek, this is the kind of property you don’t just visit, you settle into. Deep water, nearly 800 feet

    Dawn Riley Deep Roots Real Estate

    2237 Garrity Rd, Saint Leonard, MD 20685
  • /30

    $450,000

    • 3 Beds
    • 3 Baths
    • 1,600 Sq Ft

    5860 Lilac Cir, Saint Leonard, MD 20685

    This private cedar cottage is situated on a quiet cul-de-sac within view of boats docked at Flag Harbor Yacht Haven. The cottage has two levels with bedrooms and bathrooms on both levels. The kitchen has an open floor plan to the dining area and living room. It has been completely painted inside as well as new luxury vinyl planking (LVP) in place. Use it as your primary residence or your weekend

    Michael McDermitt Long & Foster Real Estate, Inc.

    5860 Lilac Cir, Saint Leonard, MD 20685
  • /9

    $70,000

    • Land
    • 28,314 Sq Ft
    • $107,692 per Acre

    5859 Long Beach Dr, Saint Leonard, MD 20685

    Seize the chance to own a piece of paradise with this stunning .65-acre wooded lot one mile from Flag Harbor Marina on the Chesapeake, an oasis of tranquility. Bring your own builder to build your dream home in this sub division. For example the neighboring lot at 5853 is similar in size and supports a a 2300 SQFT home. The property supports a water hook up costing approximately $5500 as well as

    Christina Elliott The KW Collective

    5859 Long Beach Dr, Saint Leonard, MD 20685
  • /62

    $584,900

    • 4 Beds
    • 3.5 Baths
    • 3,101 Sq Ft

    1035 Kings Creek Dr, Saint Leonard, MD 20685

    Welcome to the lifestyle you’ve been dreaming of in Kings Creek Estates—one of the most desirable communities in St. Leonard, where towering mature trees, top-rated schools, and a genuine sense of community create the perfect backdrop for everyday living. Nestled in the heart of Calvert County, you’ll enjoy easy access to the Chesapeake Bay, Patuxent River, the fossil-rich shores of Calvert

    Jason Donovan RE/MAX Leading Edge

    1035 Kings Creek Dr, Saint Leonard, MD 20685
  • /38

    $335,000

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    1506 Dogwood Rd, Saint Leonard, MD 20685

    Welcome to your beach staycation! This charming rambler offers 2 bedrooms and 1 full bathroom, making it an excellent option for a first-time home buyer, downsizer, or anyone looking for a peaceful retreat near the water. Inside, you'll find a spacious living room filled with natural light, a huge kitchen with plenty of cabinet and storage space, and Chesapeake Bay views from the dining area.

    Tannar Jones Samson Properties

    1506 Dogwood Rd, Saint Leonard, MD 20685
  • /40

    $459,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    405 Ball Rd, Saint Leonard, MD 20685

    If you’ve been searching for peace, privacy, and the freedom to live life your way—this is it.Nestled on nearly 6 acres of beautifully tree-lined land, this 3-bedroom, 2-bath rambler offers the kind of seclusion that’s getting harder and harder to find. No HOA, no noise, no compromises—just quiet country living with room to breathe.Inside, you’ll love the ease of true one-level living,

    Randall Utz EXP Realty, LLC

    405 Ball Rd, Saint Leonard, MD 20685
  • /6

    $633,900

    New Construction
    • 4 Beds
    • 2.5 Baths

    5859 Long Beach Dr, Saint Leonard, MD 20685

    TO BE BUILT NEW CONSTRUCTION. Beautiful lot Co- Marketed with Caruso Homes. This Model is the -----DEERFIELD--- The Deerfield is a four-bedroom floor plan with the option to add an In-Law suite downstairs. Enjoy gathering with family and friends in this open concept home which features a large great room that flows right into the kitchen. A 9-foot island and plenty of counter space will please

    Christina Elliott The KW Collective

    5859 Long Beach Dr, Saint Leonard, MD 20685
  • /17

    $549,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    6041 Hill Rd, Saint Leonard, MD 20685

    Deeded Boat Slip Conveys!! Bayside Living! Bayview new construction only a short walk to the private beach & marina! This 2000sqft 3 Bed 2.5 Bath Colonial with an attached 1.5 Car Garage & an Unfinished Basement, has been designed to Maximize the Views while the .91 acre lot maximizes privacy! The primary bedroom & attached balcony will have substantial views of the Chesapeake Bay! This floorplan

    Mark Frisco CENTURY 21 New Millennium

    6041 Hill Rd, Saint Leonard, MD 20685
  • /2

    $699,900

    • Studio
    • 3,600 Sq Ft

    920 Woods Rd, Saint Leonard, MD 20685

    Dawn Riley Deep Roots Real Estate

    920 Woods Rd, Saint Leonard, MD 20685
  • /40

    $549,700

    $46K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,468 Sq Ft

    5600 Calvin Ct, Saint Leonard, MD 20685

    Discover the perfect blend of country serenity and classic craftsmanship in this stately brick-front Colonial. Situated in the Harbourside community, this home offers a spectacular daily view: a working pasture with horses grazing right outside your window. Backing to private woods, this property is a peaceful retreat for those looking to put their own personal touch on a home with "forever"

    Mike Benton Home Towne Real Estate

    5600 Calvin Ct, Saint Leonard, MD 20685
  • /52

    $625,000

    $170K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,345 Sq Ft

    4200 Henry Ct, Saint Leonard, MD 20685

    | Where Privacy Meets Presence |Some homes make you pause at the door. | This is one of them. |Set on over five acres of mature woodland in Saint Leonard, 4200 Henry Court is a renovated dramatic estate that commands attention from the moment you arrive. The bold double entry doors, brick exterior, and Juliet balcony above the portico signal something exceptional before you ever step

    Shayla Gaskins Long & Foster Real Estate, Inc.

    4200 Henry Ct, Saint Leonard, MD 20685
  • /43

    $375,000

    $5K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 900 Sq Ft

    6815 Marshall Rd, Saint Leonard, MD 20685

    Appointment only :) This charming rambler boasts a perfect starter home with room to grow! Nestled along a peaceful, tree-lined road where neighbors offer fresh-baked bread and farm-fresh eggs, this rare Calvert County gem offers the quintessential country lifestyle on nearly four acres of private land. Finding a flat, usable corner lot of this size is a true rarity in the area, providing an

    Angie Carle Home Sweet Home Real Estate LLC

    6815 Marshall Rd, Saint Leonard, MD 20685
  • /63

    $869,900

    $30K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 5,936 Sq Ft

    1000 Solomon Frazier Ct, Saint Leonard, MD 20685

    Luxury home on 5 private wooded acres in sought-after Calvert County, Maryland with Chesapeake Bay boating access. Bordered by 121 acres of protected community open space, this property offers rare privacy, natural views, and resort-style amenities. The oversized kitchen features solid cherry cabinetry and expansive prep space ideal for entertaining. Main level includes a dramatic second family

    Jeffrey Lewis Berkshire Hathaway HomeServices PenFed Realty

    1000 Solomon Frazier Ct, Saint Leonard, MD 20685
  • /72

    $2,800,000

    • 5 Beds
    • 4.5 Baths
    • 8,191 Sq Ft

    6675 Marshall Rd, Saint Leonard, MD 20685

    Welcome to a breathtaking, unparalleled, retreat in Calvert County, Maryland, where luxury meets nature on a remarkable 103-acre estate. Enter through elegant gates and meander up a breathtaking lane that unfolds to reveal a stunning, picturesque setting and the grand main house, a true masterpiece of modern contemporary design. Spanning over 8,000 square feet, this meticulously updated home

    Greg Beckman Coldwell Banker Realty

    6675 Marshall Rd, Saint Leonard, MD 20685
  • /60

    $649,900

    Coming Soon
    • 3 Beds
    • 3.5 Baths
    • 3,126 Sq Ft

    548 Windmill Dr, Saint Leonard, MD 20685

    Welcome to 548 Windmill Drive, in the desirable community of Parran's Grant. Located in beautiful St. Leonard, this is a place to call home for many years to come! If you're looking for that special, move-in-ready home, well-maintained by the original owners, search no more! The immaculate interior blends seamlessly into the verdant surroundings on this private 1.1 acre flag lot. Tucked just off

    Brooke Matthews RE/MAX One

    548 Windmill Dr, Saint Leonard, MD 20685
  • /2

    $319,900

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    1225 Calvert Beach Rd, Saint Leonard, MD 20685

    Coming Soon! The property will be available for showings on Friday, June 12th.Don't miss this fantastic opportunity to own in the sought-after Calvert Beach community of Southern Maryland! This 3-bedroom, 1-bath rancher sits on an impressive half-acre+ lot and delivers the ease and comfort of single-level living. The spacious backyard offers room to relax, entertain, or garden, while a paved

    Lindsey Burch Samson Properties

    1225 Calvert Beach Rd, Saint Leonard, MD 20685
  • /60

    $539,000

    • 3 Beds
    • 3 Baths
    • 2,046 Sq Ft

    1614 Avenue B, Saint Leonard, MD 20685

    Experience this beautifully renovated, coastal retreat in sought after Calvert Beach, on the Chesapeake Bay. In 2022, the new owners gutted (down to the studs), reconstructed, and redesigned the entire main floor of this three-bedroom, three-bathroom Rambler with full, walk-out Basement. The renovation included all new plumbing, electric, HVAC, and such high-end upgrades as heated floors in two

    Gail Siegel O'Brien Realty ERA Powered

    1614 Avenue B, Saint Leonard, MD 20685
  • /86

    $599,900

    • 4 Beds
    • 3.5 Baths
    • 3,900 Sq Ft

    1824 Oriole Way, Saint Leonard, MD 20685

    Welcome to the crown jewel of Oriole Landing. Perfectly positioned on what many consider the community's most desirable lot, this stunning home sits at the end of a quiet cul-de-sac on nearly an acre of beautifully landscaped property. This extended QBHI Charleston Model has almost 3,900 square feet of thoughtfully designed living space, you'll find the perfect balance of luxury, comfort, and

    Randall Utz EXP Realty, LLC

    1824 Oriole Way, Saint Leonard, MD 20685
  • /69

    $749,500

    • 4 Beds
    • 2.5 Baths
    • 4,924 Sq Ft

    7421 Stone Ct, Saint Leonard, MD 20685

    Custom built colonial with Water Access, Brand New Roof with a Lifetime Shingle Warranty, and an extremely efficient Geothermal HVAC system! Crafted with precision by the original owner, a skilled custom homebuilder, this stately colonial reflects uncompromising quality with no original detail overlooked. Home does need some updating but bones are extremely strong! With 4 bedrooms and 2.5 baths,

    Conor Stueckler Keller Williams Flagship

    7421 Stone Ct, Saint Leonard, MD 20685
  • /2

    $70,000

    • Land
    • 16,117 Sq Ft
    • $189,189 per Acre

    5665 Arbor Cir, Saint Leonard, MD 20685

    Rare opportunity to build your dream home in the sought-after waterside community of Flag Harbor, nestled along the western shore of the Chesapeake Bay in beautiful Calvert County, Maryland. This peaceful lot sits in a serene, established neighborhood where the Bay lifestyle is not just a backdrop — it's a way of life. Enjoy the sights and sounds of the water just steps from your future front

    RJ Soni Northrop Realty

    5665 Arbor Cir, Saint Leonard, MD 20685
  • /45

    $320,000

    $20K PRICE INCREASE
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    5421 Chesapeake Ave, Saint Leonard, MD 20685

    OPEN HOUSE! Sunday, June 7th from 1:30pm-3pm! Come take a look at this NEWLY renovated 3-bedroom, 1-bathroom home in Saint Leonard, MD! This home was just updated with new LVP flooring and fresh paint through-out! The kitchen cabinets and counters were updated, as well! New outlets, switches, and covers were added to brighten her up! A few new lights were put up and smoke detectors have been

    Lindsey Burch Samson Properties

    5421 Chesapeake Ave, Saint Leonard, MD 20685
  • /70

    $875,000

    • 4 Beds
    • 3 Baths
    • 2,298 Sq Ft

    3925 Shamrock Ct, Port Republic, MD 20676

    Welcome to this beautifully maintained waterfront split-foyer home nestled on 1.15 private acres in a sought-after water-access community. Designed for comfort, leisure, and waterfront living, this property offers the perfect blend of indoor charm and outdoor enjoyment. Step inside to find 4 spacious bedrooms and 3 full bathrooms, including a newly finished lower level featuring a cozy propane

    Angela Jewell O'Brien Realty ERA Powered

    3925 Shamrock Ct, Port Republic, MD 20676
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