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Leonardtown MD Real Estate & Homes for Sale

53 Properties Found

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$649,000

21897 Fairway Drive Leonardtown, MD 20650

MLS: MDSM2022878 Photos
Beds:
5
Baths:
3.00
Sq.Ft.:
3,664
Status:
Active
MLS#:
MDSM2022878
Type:
Residential
Subdivision:
Breton Bay Landing
Lot size:
0.98 Acres
Year built:
1997
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Infinitas Realty Group 240-925-2224
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ADDITIONAL INFORMATION

Custom-Built Beauty Overlooking Breton Bay Golf Course! ? Welcome to 21897 Fairway Drive, Leonardtown, MD—a stunning 5-bedroom, 2.5-bath custom-built home in the desirable Breton Bay community. This home is in impeccable condition with numerous upgrades—simply move right in and start enjoying luxury living! ? Main Level Highlights: 9 ft. ceilings with elegant crown molding throughout Gleaming hardwood & tile flooring Gourmet kitchen with granite countertops & stainless steel appliances Family room with a charming brick/gas fireplace, perfect for cozy gatherings Custom window treatments throughout the home ?? Owner’s Suite Retreat: Spacious sitting area for ultimate relaxation Two walk-in closets Luxurious en-suite bath with upscale finishes ? Outdoor & Community Perks: Breathtaking golf course views right from your backyard Access to optional community amenities: golf, pool, and tennis memberships available Short walk to the community beach park featuring a pier, picnic area, and tot lot

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$669,900

23534 Belmar Drive Leonardtown, MD 20650

MLS: MDSM2022692 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,738
Status:
Active
MLS#:
MDSM2022692
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2008
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

PRICE REDUCTION! Discover unparalleled luxury at 23534 Belmar Drive, an extraordinary residence nestled in the prestigious Leonard’s Grant neighborhood of Leonardtown, MD. This impressive home boasts over 5,000 square feet of refined living space, seamlessly blending comfort, style, and modern functionality in one of St. Mary’s County’s most sought-after communities. Step inside to experience a bright, open-concept floor plan filled with natural light and high-end finishes. This home features five generously sized bedrooms and 3.5 meticulously appointed baths, providing ample space for family living and entertaining guests. Recent high-quality upgrades ensure lasting performance and efficiency, including brand-new HVAC systems installed in 2023 and 2024, a state-of-the-art tankless water heater (2024), and a sump pump with battery backup for added peace of mind. Low-cost solar panels enhance energy efficiency, reducing utility costs while allowing the local electricity provider to pay you. The fully finished basement offers a premium surround sound system, perfect for movie nights, game days, or simply enjoying your favorite music. A screened-in back porch provides a peaceful retreat where you can sip morning coffee or unwind in the evenings under the stars. Living in Leonard’s Grant means enjoying top-tier neighborhood amenities, including a sparkling community pool, a clubhouse, basketball and tennis courts, and sidewalk-lined streets, playgrounds, and walking trails. The home is conveniently located just minutes from shopping, dining, and historic downtown Leonardtown, with a short commute to NAS Patuxent River (less than 20 minutes). Whether you seek a peaceful retreat or a dynamic space for entertaining, this home offers the perfect blend of luxury, modern amenities, and community charm. Don’t miss this rare opportunity—schedule your private tour today and experience all that 23534 Belmar Drive has to offer!

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$645,000

41443 Whimsical Court Leonardtown, MD 20650

MLS: MDSM2023194 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,400
Status:
Active
MLS#:
MDSM2023194
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.26 Acres
Year built:
2010
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to this beautifully updated 5-bedroom, 3.5-bath Colonial home, offering the perfect blend of modern updates and classic charm. Step inside to find refinished hardwood floors, fresh paint, and new carpet throughout, creating a bright and inviting atmosphere. The heart of the home extends outdoors, where you'll discover a serene, tree-lined backyard with an incredible outdoor living space. Enjoy your morning coffee in the screened-in composite patio, host summer cookouts on the grilling patio, or unwind under the stars on the paver patio with a cozy fire pit. There's even a large outdoor shed for extra storage. With ample space, a fantastic layout, and stunning outdoor features, this home is ready to impress.

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$449,900

40905 Knight Road Leonardtown, MD 20650

MLS: MDSM2023050 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
1,820
Status:
Active
MLS#:
MDSM2023050
Type:
Residential
Subdivision:
Breton Bay Estates
Lot size:
0.52 Acres
Year built:
1980
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

Welcome to 40905 Knight Road in beautiful Leonardtown, Maryland! This inviting home offers a perfect mix of comfort and practicality, featuring three spacious bedrooms and 2.5 baths—ideal for entertaining or everyday living. Sitting on a generous half-acre lot, the property provides plenty of space to enjoy the outdoors. The fenced backyard is perfect for gatherings, and the large patio and fire pit create a cozy spot to relax with family and friends. Inside, recent upgrades make life even more comfortable. A newly installed HVAC system ensures year-round climate control, while a new water pressure tank keeps everything running smoothly. Located in the highly sought-after Breton Bay community, this home offers a warm neighborhood feel just minutes from the golf club, complete with a bar, restaurant, and pool—only about two minutes from your doorstep. You'll enjoy convenient access to local schools, shopping, and dining, all while savoring the peaceful, relaxed setting.

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$460,000

40827 Lake And Breton View Drive Leonardtown, MD 20650

MLS: MDSM2023068 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
2,524
Status:
Active
MLS#:
MDSM2023068
Type:
Residential
Subdivision:
Breton Bay
Lot size:
0.67 Acres
Year built:
1969
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Have you been searching for a home with the PERFECT Water Views!! Without; the Water view price?? This home may be what your heart Desires!! Walk your kayaks right down the SAME block to the community beach access spot. The "walking beach" as they call it. This home has water views from BOTH levels. There are wood burning stoves on BOTH levels. The main beach access with playground and pavilion are also an easy walk from this home. Not to mention the incredible screened in porch and deck that exist here. If you like being outdoors and comfortable, this home was made for you. The fully fenced and private yard are additional benefits too. This home has a very spacious layout and has plenty of opportunity for you to make it your own. The civic association is an optional buy in, no mandatory HOA here! Don't miss your opportunity to own a great home, on a great lot with ALL of the extra's and of course: the VIEWS!!!!

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$635,000

23348 Lindsay Drive Leonardtown, MD 20650

MLS: MDSM2022602 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,540
Status:
Active
MLS#:
MDSM2022602
Type:
Residential
Subdivision:
Clark's Rest Phase 1
Lot size:
0.15 Acres
Year built:
2022
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Fairfax Realty Premier 301-439-9500
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ADDITIONAL INFORMATION

Welcome to 23348 Lindsay Drive — where space, style, and comfort come together in the heart of Leonardtown’s sought-after Clark’s Rest community. This nearly new 5-bedroom, 4-bath home offers over 3,500 sq ft of beautifully designed living space with thoughtful upgrades and a flexible floor plan perfect for modern living. Step inside to a sun-drenched open layout featuring luxury vinyl plank flooring, a spacious family room, and a gourmet kitchen with granite countertops, a large center island, and a walk-in pantry. A first-floor bedroom and full bath are ideal for guests or multigenerational living. Upstairs, find four generously sized bedrooms — each with a walk-in closet — and a serene primary suite with dual vanities and a tiled shower. The partially finished basement offers even more room to grow with space for a rec room, home gym, or office. Enjoy community amenities including a pool, clubhouse, playgrounds, tennis courts, and walking trails — all just minutes from downtown Leonardtown, shopping, restaurants, and top-rated schools. Freshly priced to sell — this is your opportunity to own a move-in-ready home in one of Leonardtown’s most desirable neighborhoods.

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$455,000

41925 Nazareth Court Leonardtown, MD 20650

MLS: MDSM2022948 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,512
Status:
Active
MLS#:
MDSM2022948
Type:
Residential
Subdivision:
Academy Hills
Lot size:
0.27 Acres
Year built:
2005
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

DESIRED SCHOOL DISTRICT, SUBDIVISION & TOWN! 3 LEVELS of SPACIOUS LIVING! This beautiful Colonial home is nestled in the highly sought-after Academy Hill subdivision of Historic Leonardtown. Sitting on an end lot that backs to trees on .27 acres, it boasts a fenced backyard with a durable 2-year-old vinyl privacy fence —an ideal setting for privacy and entertaining on your deck. The three-level layout includes a walk-out basement, approximately 85% finished, with an unfinished storage room for added functionality. The large attached two-car garage comes equipped with a convenient utility sink. The main level features stunning exotic Brazilian cherry hardwood floors, complemented by neutral paint, stainless steel appliances, a 5-year-old HVAC system, and a spacious open-concept layout. A kitchen island, pantry, and ample cabinets provide functionality and style. Additional highlights include double-hung windows, French glass doors, 6-panel wood doors, wainscoting, ceramic tile flooring, and a mix of 2-year-old carpeted areas in the spacious upstairs bedrooms and the basement. The primary bedroom features a walk-in closet and a luxurious en suite bathroom with double sinks, a soaking tub, and a separate shower. This home is ideally located, a few minutes from the highly-rated Duke Elementary, Leonardtown Middle & Leonardtown High Schools, just a short walk to the College of Southern Maryland (w/Pool!), MedStar St. Mary’s Hospital, and the charming, vibrant, Leonardtown Square, offering a free town trolley (no need for an UBER!) - which comes to this neighborhood, boutique shops, dining, and year-round events. It's proximity to Public Boat Launch Ramps, Golf Courses, Marinas, NAS Pax River, Solomons Island, MIR/Buds Creek, and the vibrant California shopping and dining district makes it an ideal hub. Just South of Washington DC, and Annapolis. The surrounding area is rich in history and culture, offering fishing, boating, crabbing, oystering, farms, wineries, nature trails, beaches, parks, scenic back roads, Amish and Menonite Farm Fresh Stands & Home Crafted Products, and SO MUCH MORE. Situated just 60 miles south of Washington, D.C., and 50 miles from National Harbor, this property perfectly blends modern comforts and historic charm. Make it your dream home today! ***THE FIRST SET OF PHOTOS (STAGED) ARE FROM THE PREVIOUS LISTING - with permission. Defer to the CURRENT listing photos for current lighting fixtures, and other details that have been swapped out/changed.*****

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$695,000

23055 Town Run Drive Leonardtown, MD 20650

MLS: MDSM2022446 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
4,019
Status:
Active
MLS#:
MDSM2022446
Type:
Residential
Subdivision:
Meadows At Town Run
Lot size:
0.17 Acres
Year built:
2021
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Stunning Clarke Model by Quality Built Homes Located in the desirable Meadows at Town Run, this 4-bedroom, 3.5-bath home offers over 4,000 square feet of living space, including a finished lower level. Built in 2021, this home is just a few years old and has been meticulously maintained. Enjoy a prime location with Duke Elementary and the library within walking distance, Downtown Leonardtown just 5 minutes away, and Leonardtown Junior and High Schools a short 10-minute drive. Inside, the home features upgraded birch engineered flooring throughout the main level and second-floor hallway, as well as hardwood stairs to both the upper and lower levels. Crown molding throughout adds an elegant touch. The spacious family room, complete with a coffered ceiling, flows into the kitchen and breakfast nook. The kitchen is well-appointed with painted white cabinets, granite countertops, stainless steel appliances, and crown molding. A formal dining room with extra windows and detailed trim provides a bright and inviting space. The private office, enclosed with glass French doors, offers a quiet work-from-home setup. Upstairs, the primary suite features an angle tray ceiling, two walk-in closets, and a private en suite with a corner soaking tub, granite-topped vanities, and a spa inspired 4.5'x7' tiled shower, that includes two shower heads, a seat, a ledge, and two recessed lights. Three additional bedrooms and a full bath with quartz countertops and 2nd floor laundry complete the upper level. The finished lower level provides extra space for a recreation room, home gym, or media area. Outdoor features include a maintenance-free deck and stamped concrete patio, perfect for relaxing or entertaining. The home sits on a corner lot with a rear-entry garage, enhancing curb appeal. Meadows at Town Run offers a welcoming community feel with convenient access to schools, shopping, and dining. Schedule your showing today!

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$449,900

22362 Armstrong Drive Leonardtown, MD 20650

MLS: MDSM2023036 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,028
Status:
Active
MLS#:
MDSM2023036
Type:
Residential
Subdivision:
Society Hill
Lot size:
1.06 Acres
Year built:
1973
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Charming Home with a Rare Double Lot in Society Hill, Leonardtown, MD Nestled in the desirable Society Hill neighborhood of Leonardtown, this one-of-a-kind property offers a rare opportunity with its expansive double lot—a true gem in the community. While the home retains a timeless charm, it presents an exciting chance to add your personal touch and modern updates. Inside, you'll find character-filled spaces, including spacious living areas, and an inviting layout that exudes warmth. The home’s unique charm shines through in its craftsmanship, offering a perfect blend of nostalgia and potential. The large lot provides endless possibilities—expand the home, create an outdoor oasis, or enjoy the extra space for recreation and entertaining. The entire home generator will ensure your lights are on even when the power is out. Located just minutes from downtown Leonardtown, you'll have easy access to local shops, restaurants, and waterfront attractions. If you're looking for a home with personality, history, and room to grow, this is your chance to make it your own!

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$985,000

22855 White Swan Way Leonardtown, MD 20650

MLS: MDSM2022826 Photos
Beds:
5
Baths:
6.00
Sq.Ft.:
6,762
Status:
Active
MLS#:
MDSM2022826
Type:
Residential
Subdivision:
Avenmar
Lot size:
3.59 Acres
Year built:
2001
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: KW Metro Center 703-535-3610
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ADDITIONAL INFORMATION

Move right in.....this home is a showstopper....better than new! Tucked away on 3.59 acres, everything has been upgraded. Main level offers stunning hardwood flooring throughout, great room with 2 story ceilings and walls of windows letting nature and light in. Formal living room with custom, built-in bar and formal dining make this an exceptional home for entertaining and large gatherings. Kitchen for the gourmet cook offers natural quartzite stone counters, butlers pantry, coffee bar, beverage fridge, stainless appliances and top of the line Viking range. The beautiful sunroom at the far end of the home is perfect for an in-home office or to curl up with a good book. Fully finished, walk-out basement is a whole new world! Work-out room, wet bar/kitchen, media room, 2 large storage rooms, full bath and you can even stroll out to enjoy a dip in the hot tub. The private master suite on the upper level offers a built-in vanity area, custom bath w/ natural quartzite stone counters and built-in his & hers closets. Enjoy the amenities of the Avenmar Community; pool, dock and kayak storage, tennis courts, tot lot and club house.

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$649,900

41536 Fairwood Court Leonardtown, MD 20650

MLS: MDSM2022852 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
3,080
Status:
Active
MLS#:
MDSM2022852
Type:
Residential
Subdivision:
Clark's Rest
Lot size:
0.15 Acres
Year built:
2024
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

PRICE IMPROVEMENT! This home is less than 2 years young in the sought after, planned Clarks Rest community! Four (4) Bedrooms, Three (3) Full Baths, Powder Room Main Floor, and Two (2) Car Garage with EV Charger. When you enter the Two Story Foyer, you'll be welcome to the Formal Living Room on the right with the Formal Dining Room to the left and open to the Family Room with Gas Fireplace. Large Gourmet Kitchen opens to the Morning Room and Family Room with upgraded Cabinets, Appliances, Tiled Backsplash and Quart Countertops. Walk down the Gallery, past the center staircase and you enter the Library, perfect for a Home Office or Playroom. Upstairs you'll find the oversized , Deluxe Owner's Suite/Bath which includes Dual Walk-in Closets, 5'x5' Tiled Shower w/Dual Showerheads, Separate, Tiled Corner Soaking Tub, Private Water Closet and Separate Vanities. Three (3) secondary bedrooms also found on the second floor with one (1) having it's own Private Bath, and two (2) sharing the Hall Bath. The Unfinished Basement has a three (3) piece bath rough-in ready to finish with a Walk-Out Exit to a spacious, level backyard. Upgraded lighting and ceiling fans throughout the home along with luxury vinyl plank flooring/staircase.

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$424,900

39880 Lady Baltimore Avenue Leonardtown, MD 20650

MLS: MDSM2022524 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,348
Status:
Active
MLS#:
MDSM2022524
Type:
Residential
Subdivision:
St Clements Woods
Lot size:
0.46 Acres
Year built:
1994
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Infinitas Realty Group 240-925-2224
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ADDITIONAL INFORMATION

Introducing this beautiful 3 Bedroom 2 Full Bath Rambler in Leonardtown. Some updates in this beautiful home include new vinyl flooring throughout, the Roof was replaced in 2019, the appliances are less than 2 years old, the Heat Pump was replaced in 2020, and much much more!This home features a huge pantry in the kitchen, a huge laundry room with even more cabinets for storage, a beautiful living room with a wood stove, a huge dining room with a cathedral ceiling, and the master bedroom has a walk-in closet!! A true summer paradise awaits you out the back door. Cool off this hot summer in the pool! The pool liner and pump were just replaced 2 years ago. Tons of space for entertaining guests at the tiki bar or on the covered deck! The backyard is fully fenced in with vinyl fencing!

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$450,000

20798 Waterside Drive Leonardtown, MD 20650

MLS: MDSM2022922 Photos
Beds:
2
Baths:
1.00
Sq.Ft.:
1,018
Status:
Active
MLS#:
MDSM2022922
Type:
Residential
Subdivision:
Brubachers
Lot size:
0.18 Acres
Year built:
1950
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX Closers 301-472-4422
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ADDITIONAL INFORMATION

Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiast’s paradise. Enjoy the sights and sounds of ospreys, fish, and abundant wildlife right from your doorstep. Key features include: ? Approximate water depth: 2.5 ft at low tide, 4.5 ft at high tide ? Seawall refurbished in 2020 for added shoreline protection ? Private pier with an electric boat lift—perfect for boating adventures Don’t miss this rare chance to own a piece of paradise with endless potential. Whether you’re looking for an investment, vacation retreat, or future dream home, this waterfront gem is a must-see!

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$615,000

23617 Belmar Drive Leonardtown, MD 20650

MLS: MDSM2022962 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
2,870
Status:
Active
MLS#:
MDSM2022962
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2011
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to this beautifully maintained Colonial home, perfectly situated on a lovely lot! Featuring 5 bedrooms and 3.5 baths, this open and airy home boasts fresh, light-colored paint throughout, creating a bright and inviting atmosphere. The heart of the home is the gourmet kitchen, complete with granite countertops, a gas stovetop, and a huge pantry—perfect for cooking and entertaining. The expansive primary suite is a true retreat, offering a luxurious en-suite bathroom with dual sinks, a massive walk-in shower, and a relaxing corner soaking tub. Enjoy the outdoors in the charming backyard, complete with a spacious deck and raised garden beds—ideal for gatherings or quiet evenings.

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$799,900

41115 Paw Paw Hollow Lane Leonardtown, MD 20650

MLS: MDSM2022526 Photos
Beds:
4
Baths:
6.00
Sq.Ft.:
6,116
Status:
Active
MLS#:
MDSM2022526
Type:
Residential
Subdivision:
Paw Paw Hollow
Lot size:
1.8 Acres
Year built:
1997
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

72 hour kick-out clause in place. Offers still being accepted. Stunning Brick Front Colonial in Paw Paw Hollow - 1.8 Acres of Private Luxury Welcome to this well maintained and beautifully designed brick front Colonial in the highly sought-after Paw Paw Hollow. This spacious 4-bedroom, 5.5-bathroom home offers over 5,000 square feet of living space on a generous 1.8-acre lot, providing the perfect blend of comfort, elegance, and privacy. Main Level Features Include: Inviting formal living and dining rooms, perfect for entertaining. Expansive two-story family room with plenty of natural light. Chef's kitchen with a center island, ample cabinetry, and modern appliances. Convenient main level bedroom and full bath for guests or in-laws. Upper Level Features: 3 large bedrooms with 3 full baths for ultimate comfort and privacy. A cozy den for reading or office space or use as upper level play room. Lower Level Features: Spacious finished basement with a rec room and additional family room, ideal for recreation and relaxation. Full bath for added convenience. Additional Features: Enjoy year-round fitness with your own indoor exercise pool. Attached garage and 3-car carport, offering plenty of parking and plus attached heated storage area with garage door.. Paved circular driveway ensures ease of access and adds curb appeal. Beautifully landscaped yard with a private outdoor patio, perfect for outdoor living and relaxation. Has inground sprinkler system and invisible fence to help keep your furry friends from wandering off. This home has been wonderfully maintained inside and out, offering the ideal combination of luxury and comfort in a private, serene setting. Don't miss out on this exceptional property. Schedule your private tour today!

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$20,000,000

19700 Mulberry Fields Road Leonardtown, MD 20650

MLS: MDSM2022614 Photos
Beds:
6
Baths:
5.00
Sq.Ft.:
13,458
Status:
Active
MLS#:
MDSM2022614
Type:
Residential
Subdivision:
Leonardtown
Lot size:
490.17 Acres
Year built:
1755
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Long & Foster Real Estate, Inc. 202-483-6300
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ADDITIONAL INFORMATION

Welcome to Historic Mulberry Fields, situated on just under 500 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south façade, the magnificent mile-long “Avenue Field,” lined with trees stretching to the Potomac River provides a breathtaking panoramic view downhill to the white sandy riverbank. The interior of the manor house is of simple and educated taste. The grand center hall and the 2 front (south) rooms (the great room and dining room) have walls of rectangular raised panels to the ceiling, making it one of the most completely paneled 18th-century houses in Maryland. Throughout the house, many original moldings, doors, and mantels are intact. Air conditioning and heating were added to all rooms. The owners retained an architectural firm and have plans - approved by the Historic Trust - for a renovation that would enlarge the kitchen, the bathrooms and adding another wing to the house on the west side. Flanking each side of the north entrance are 2 historic dependencies, both similar in design. Each is of brick, 2-story in height. They were placed symmetrically north of the mansion, forming a rectangular court with the Kitchen Garden, Bowling Green and Orchard separated by a row of large boxwoods. These buildings were used as service buildings with the East dependency as “The Kitchen” and the West dependency as the “The Weaving House.” These structures were used to house slaves, such as cooks, stable hands, waiters, and housekeepers who were tasked with running the household and gave the mansion and outbuildings the appearance of a busy village. “The Kitchen” has been remodeled and now serves as a guest cottage, while the “Weaving House” retains its original historic riven clapboard partition walls, floors, doors, and hardware. Next to the 2 dependencies flanking the Manor House are numerous other historic buildings, such as the “Dairy” and the “Meat/Smoke House” (both east of the Manor House). Other historic buildings include a Carriage House, a Garage/Tool Shed, an Art Studio, a Pole Barn, a Horse and Cattle Barn, a Tobacco Barn, a remodeled Sheep Barn, 2 Equipment Barns, a Farmhouse, and an old dwelling that could be remodeled and turned into a rental unit. Several buildings were added in the 1930s. These include 6 occupied rental units, incl. 3 units in what was previously the Sheep Barn, a 4-BR Farmhouse, a 1-BR Cottage in the renovated “Kitchen" and a 1-BR Trailer. Taken together, these currently produce an income of $70,000. Add'l income is provided by leasing the fields for farming and from the U.S. Navy that keeps a navigation signal on the Potomac River. More income can be obtained by renovating some of the existing buildings. With that Mulberry Fields could have a total of twelve rental units. Mulberry Fields was added to the National Registry of Historic Places in 1973. The Maryland Historical Trust Deed of Easement ALLOWS LIMITED INDUSTRIAL OR COMMERCIAL activities to be conducted at Mulberry Fields if the external appearances of its buildings are not altered (please ask for more info). Owners of Mulberry Fields must abide by a Conservation Easement, a Historical Preservation Easement, and three Rd Easements. Appr. 100 acres of land is leased out for farming and 300 acres is forest. This unique historic property is close to Leonardtown, Lexington Park and Solomon’s Island with numerous historic sites, wineries, antique shops, art galleries and restaurants, Deerfield Airport (private jet) as well as St. Mary’s County Regional Airport. 1h15 min drive to Washington DC and its major airports - Dulles Int’l Airport, and Reagan Nat’l Airport. MORE IN-DEPTH HISTORY AVAILABLE UPON REQUEST.

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$375,000

20959 Redgate Lane Leonardtown, MD 20650

MLS: MDSM2022416 Photos
Beds:
3
Baths:
1.00
Sq.Ft.:
1,026
Status:
Active
MLS#:
MDSM2022416
Type:
Residential
Subdivision:
St Marys
Lot size:
2.02 Acres
Year built:
1961
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Keller Williams Legacy 443-660-9229
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ADDITIONAL INFORMATION

A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This single-family ranch-style home features 3 bedrooms and 1 bathroom. Built in 1961, it offers approximately 1,026 square feet of living space and is situated on a 2.02-acre lot. This home also includes a detached garage with space for two vehicles. For investors, the property's sizable lot and ranch-style design may offer potential for renovation or expansion. The absence of a homeowner’s association (HOA) could also provide additional flexibility for property modifications. Nearby schools include Piney Point Elementary School, Leonardtown Middle School, and Leonardtown High School. For more information or to schedule a viewing, please contact the listing agent, Greg Jones, at Keller Williams Legacy.

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$699,900

23773 Meredith Court Leonardtown, MD 20650

MLS: MDSM2022554 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
3,478
Status:
Active
MLS#:
MDSM2022554
Type:
Residential
Subdivision:
Abells Ridge
Lot size:
7.02 Acres
Year built:
1997
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Coldwell Banker Jay Lilly Real Estate 301-863-0300
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ADDITIONAL INFORMATION

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 acres. This property consists of two lots. You can build a family members house right next door. Owner is still working on clean out and some minor repairs and painting. Seller prefers we use CLA title to close. Professional Pictures to come.

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$535,000

25365 Point Lookout Road Leonardtown, MD 20650

MLS: MDSM2022468 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,952
Status:
Active
MLS#:
MDSM2022468
Type:
Residential
Subdivision:
Leonardtown
Lot size:
0.36 Acres
Year built:
1936
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Unique property : Residential AND Commercial !!! Both are presently rented. The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both units. Showings by appointments only.

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$650,000

22626 Chickadee Lane Leonardtown, MD 20650

MLS: MDSM2022382 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
2,948
Status:
Active
MLS#:
MDSM2022382
Type:
Residential
Subdivision:
Avenmar
Lot size:
2 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: JPAR Real Estate Professionals 301-684-4895
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ADDITIONAL INFORMATION

PRICE REDUCED!! Welcome to your new home in the lovely Avenmar Community! Upon entering your new home you’re greeted by a stunningly adorned 2 story foyer. As you make your way around the lower level you will find a formal living and dining room with a timeless trim work design and new LVP installed in 2022. Walking into the kitchen you have an open concept flowing seamlessly into your family room where you will find a gas fireplace to keep you and your family cozy all winter long. As you go out the back door to your beautiful stamped concrete patio that was made for entertaining and you’ll find a walkway to your outdoor fire pit and be able to take in the views of your wooded 2 acre lot. Heading back inside and moving upstairs you’ll find 4 large bedrooms. The primary suite is a true escape with a walk in closet that provides an abundance of room and en-suite bathroom featuring a separate toilet room and a large soaking tub perfect for relaxing after a long day! You can have peace at mind with a new roof installed in 2023, sump pump with battery back up (2022), washing machine (2024), dryer (2023). Other upgrades are the main level LVP (2022) and the stamped concrete patio was done in 2023. Community amenities are abound, with access to a clubhouse, tennis and volleyball courts, an equestrian center, scenic walking paths, and a community pier on Breton Bay with a kayak launch. Immerse yourself in the convenience of living just moments from Breton Bay Golf Club and the lively Leonardtown square. You’ll be able to find fine dining, pubs, charming shops and more that are all locally owned and operated, giving you a sense of true community!

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$675,000

41810 Chelsey Faye Lane Leonardtown, MD 20650

MLS: MDSM2021276 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
2,650
Status:
Active
MLS#:
MDSM2021276
Type:
Residential
Subdivision:
None Available
Lot size:
0.58 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: JPAR Real Estate Professionals 301-684-4895
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ADDITIONAL INFORMATION

Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional quality by Graham & Co Custom Creations. Building a custom home allows you to choose between the standard home on a crawl space or opt for a basement foundation for an additional cost, giving you the opportunity to personalize this beautiful dwelling to your exact needs. If there is some other details you want to add or change you have the ability to do so! Don’t miss this opportunity to own a truly unique home that combines style, functionality, and future potential.

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$1,635,000

Address not provided Leonardtown, MD 20650

MLS: MDSM2021304 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
2,130
Status:
Active
MLS#:
MDSM2021304
Type:
Residential
Subdivision:
Bayside
Lot size:
48.9 Acres
Year built:
1951
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Haley Family Realty 301-686-0545
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ADDITIONAL INFORMATION

Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The house is well-kept with 4 Bedrooms and 2 Baths; a place-to-relax front porch; the master bedroom and the laundry room (washer and dryer included) are on the entry level. Also, a foundation for a 3,000+ square-foot house has been started near the water and has the electric meter installed. A pier on the farm is on the protected Cecil Creek where boaters and non-boaters can enjoy the tranquility and hours of fishing, crabbing, and just enjoying life. If it's hunting you want, many deer, turkeys, ducks and other waterfowls have been sighted on this sportsman's paradise. A 24-Hour Appointment Notice is necessary for all showings. To show/view the house, call the Listing Agent who will schedule an appointment for/with you.

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$530,000

41815 Chelsey Faye Leonardtown, MD 20650

MLS: MDSM2016780 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,627
Status:
Active
MLS#:
MDSM2016780
Type:
Residential
Subdivision:
None Available
Lot size:
0.84 Acres
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: JPAR Real Estate Professionals 301-684-4895
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ADDITIONAL INFORMATION

Warm, charming with style on CHELSEY FAYE. The Chelsey Model Home is a modestly sized one story design that is loaded with all the necessities. Beautiful white siding and stained timber accents are perfect material choices for the farmhouse style. Offering an open main level with one large space for living and dining. The family room has a high ceiling. Enjoy the cozy ambiance of this home with a warming fireplace. The owner's suite is private & separate from the other bedrooms. Perfect for relaxation & tranquility. The owner's bath features a large shower and ample closet space. Bedroom three is a flexible space that doubles as a work space. The optional upper level adds another sleeping space and a large bonus room. The bonus room can be utilized as simple storage or finished for a recreation or exercise room; the choice is yours! Graham & Co Custom Builder. Board and Batten is optional. Custom Build- floor plan can be modified. New Construction Home to Be Built. Custom Builder. Second story is optional

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$831,025

Wathen Road Leonardtown, MD 20650

MLS: MDSM2016354 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,700
Status:
Active
MLS#:
MDSM2016354
Type:
Residential
Subdivision:
None Available
Lot size:
7.5 Acres
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Amber & Company Real Estate 240-224-8005
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ADDITIONAL INFORMATION

NEW CONSTRUCTION TO BE BUILT. This stunning 7.5-acre lot is co-marketed with Caruso Homes, featuring the impressive DEERFIELD model—a four-bedroom floor plan with the option to include a convenient In-Law suite on the main level. Embrace the joy of gathering with loved ones in this thoughtfully designed open-concept home, highlighted by a spacious great room seamlessly connected to the kitchen. The kitchen boasts a 9-foot island, and ample counter space, pleasing any chef, while the formal dining room provides an elegant space for family meals. The second floor showcases a generously sized owner's suite with an ensuite bath and his-and-her walk-in closets. Three additional bedrooms, a hall bath, and a well-placed laundry room complete the upper level. For those seeking additional living space, an optional third floor offers a loft and full bath. Customize your home with various options and upgrades to reflect your unique style. Prospective buyers have the flexibility to choose from Caruso's range of models that suit the lot, with prices varying accordingly. Please note that the provided photos are courtesy of the Builder and may depict optional features and upgrades not included in the base price. Final square footage is approximate and will be determined with the selection of final options. Any upgrades or custom changes will incur additional costs. Images shown are of proposed models and do not represent the final appearance of the house and yard settings. Prices are subject to change without notice and are dependent on chosen elevations and options. The displayed price includes the Base House Price, the Lot, and the Estimated Lot Finishing Cost only. The builder tie-in is non-exclusive, providing buyers with flexibility and choice in their home-building journey.

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$859,900

40533 Breton Knolls Ct Leonardtown, MD 20650

MLS: MDSM2015098 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2015098
Type:
Residential
Subdivision:
None Available
Lot size:
1.87 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX Realty Group 301-843-5100
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ADDITIONAL INFORMATION

TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spanning 4,058 square feet of luxury living. As you step inside, you are greeted by an open layout that radiates warmth and spaciousness. The heart of the home, a two-story family room with fireplace, is bathed in natural light, creating an inviting atmosphere for entertaining and relaxation. Cook gourmet meals in the chef-inspired kitchen, featuring 42" custom-designed cabinets, granite countertops, and a generous island, making it a hub of creativity and connectivity. There's also a convenient mudroom connecting the garage and kitchen, simplifying the task of unloading groceries. The first level boasts a large two-car garage, a beautiful hardwood-floored foyer leading to the main staircase, a formal living room with a bay window, and a spacious formal dining room. This design provides the option of an in-law suite or a study with an attached bathroom, catering to the needs of a growing family or those who work from home. Additionally, a sunroom off the kitchen offers a tranquil space to enjoy the beauty of every season. On the second floor, the king-sized master suite is a sanctuary, featuring a seating area, dual walk-in closets, and a master bath that is nothing short of luxurious. The master bath includes ceramic tile flooring, a custom tile shower, a soaking tub, and dual vanities. This is a space dedicated to unwinding and pampering yourself. The second floor also hosts three more generously sized bedrooms, each with its own walk-in closet. With two of the bedrooms sharing a Jack and Jill bathroom, providing comfort and convenience for family and guests alike. Enjoy the incredible location, only 8 min from downtown Leonardtown, easy access to 243, and minutes from Brenton Bay! Your home is more than a building; it's an expression of your unique personality and lifestyle. With Litz Custom Homes, your vision becomes a reality, and 40533 Breton Knolls Court is your canvas. Embrace the opportunity to design your perfect living space and experience the joys of true customization. This is not just a house; it's your future home, waiting to be sculpted into your personal masterpiece. Please note that the images of the house are for illustration purposes only, finishes are upgrades and will be priced separately.

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.


Leonardtown Real Estate

Leonardtown is located in Maryland. Leonardtown, Maryland has a population of 4,445. Leonardtown is more family-centric than the surrounding county with 66.19% of the households containing married families with children. The county average for households married with children is 35.05%.

The median household income in Leonardtown, Maryland is $126,472. The median household income for the surrounding county is $102,859 compared to the national median of $69,021. The median age of people living in Leonardtown is 32.3 years.

Leonardtown Weather

The average high temperature in July is 87.8 degrees, with an average low temperature in January of 28.4 degrees. The average rainfall is approximately 45.5 inches per year, with 14.3 inches of snow per year.

Leonardtown Map

Leonardtown Real Estate Market Conditions

  • Median sales price

    $511,500
    12.7%
    change since last quarter

  • # Active listings

    72
    30-day change

Leonardtown Schools and Demographics

Education near Leonardtown, MD

City County
High School Graduates 86.69 91.67
College Degree - 2 year 4.14 7.83
College Degree - 4 year 43.83 33.03
Graduate Degree 20.41 11.79
Expenditures per Student 15,242 15,242
Students per Teacher 15.9 15.9

Elementary Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Benjamin Banneker Elementary School PK - 05 683 15 20656
Evergreen Elementary School PK - 05 795 19.3 20619
George Washington Carver Elementary School PK - 05 644 17 20634
Greenview Knolls Elementary School PK - 05 408 17.9 20634
Leonardtown Elementary School PK - 05 789 18.6 20650
Piney Point Elementary School PK - 05 529 18.7 20690

Middle Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Leonardtown Middle School 06 - 08 933 15.9 20650

High Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Great Mills High School 09 - 12 1,549 17.8 20634
Leonardtown High School 09 - 12 1,831 20.8 20650

Ungraded Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Dr. James A. Forrest Career and Technology Center UG - UG 0 0 20650
St. Mary's County Evening High UG - UG 0 20650

Demographics near Leonardtown, MD

City County
Neighborhood Type Small town
Population 4,445 113,209
Population Density 1,169 316
Median Age 32.3 36.7
People per Household 2.8 2.8
Median Household Income 126,472 102,859
Average Income per Capita 41,923 44,208

Real estate near Leonardtown

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