Refine Search
Map
Sort by
$950,000
5 Beds ⋅ 4 Baths
Tucked away on 1.39 private acres with approximately 530 feet of waterfront, this exceptional retreat offers sweeping water views, spectacular sunsets, and direct access just around the bend from the Potomac River. A rare opportunity for boating enthusiasts, the property features a substantial pier with multiple deep-water slips, boat lift, electric, and excellent crabbing and fishing right from your backyard. The spacious home offers over 4,700 square feet with 5 bedrooms and 4 full baths, including multiple main-level bedrooms and flexible living spaces designed to capture the waterfront setting. Large windows frame serene water views throughout, while expansive indoor and outdoor entertaining areas create the perfect setting for gatherings, weekend escapes, or full-time waterfront living. Originally built in 1974 the property includes a waterside workshop/boathouse, generous parking, and beautifully maintained grounds with mature trees and a gently sloping lawn to the water’s edge. Whether you are looking for a peaceful private residence, a weekend retreat, or the ultimate boating lifestyle, this Southern Maryland waterfront property delivers an unmatched setting

20535 Golden Thompson Rd, Avenue

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$435,900
3 Beds ⋅ 4 Baths
Beautiful Colonial home move in ready for a fresh start! As you enter the foyer, the hardwood floors lead you through the main living areas of the home including the formal dining room, formal living room and family room off kitchen. The kitchen includes stainless appliances, gas stove and plenty of cabinets. The open concept kitchen and family room areas are perfect for entertaining and hosting gatherings. A breakfast area complete with a coffee bar will appeal to your inner barista! Doors open to the back deck so get the grill for ready for summer cookouts and enjoy the level back yard for your next corn hole tournament. The upper level of the home has a primary bedroom, walk in closet and en suite with soaking tub, dual sinks and tile floors. Two additional bedrooms and full bathroom in the hallway are great for guests and company. The finished basement has a rec room, full bathroom, and additional room that can be used as a den/office/guest area. The driveway provides for ample parking and a one car garage. Close to schools, shopping, and area amenities. Easy access to route 235 for those driving to areas north and south. Close to PAX Naval Air Station. Schedule your online appointment today.

45525 Sunflower St, Great Mills

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$449,900
3 Beds ⋅ 4 Baths
Located in the highly desirable Wildewood Community, this spacious single-family home sits on a large corner lot and features a 2-car side-load garage. Offering 3 bedrooms plus an additional versatile room that is ideal for a home office, study, or optional 4th bedroom - this home provides flexibility to suit your needs. The inviting vestibule entry offers a practical buffer from the elements and a welcoming first impression. The open kitchen is equipped with white cabinetry, granite countertops, and a generously sized walk-in pantry with ample shelving. Enjoy outdoor living on the deck just off the main living area. The family room features a cozy wood-burning fireplace, perfect for relaxing evenings. Upstairs, the primary suite includes multiple closets and a private en suite bath with a soaking tub, dual vanities, and a separate shower. Two additional bedrooms are well-proportioned and share convenient access to additional bathroom. The basement offers a partially finished area ideal for recreation or additional living space, along with a storage room and a full bathroom that includes a washer and dryer. A well-rounded home combining space, functionality, and a sought-after location. Close to schools, restaurants, and shopping. Minutes to PAX NAS! Schedule your showing today!

23294 Holly Hill Ln, California

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$375,000
3 Beds ⋅ 2 Baths
--------------------------- SELLER OFFERING CLOSING HELP- CONTACT FOR DETAILS-------------------------- PRICED TO SELL MANY RECENT UPDATES INCLUDING ROOF AND NEW HVAC 1200 Sq foot unfinished basement offers potential investment WELCOME TO SAINT MARY’S BEACH! Nestled on a beautifully wooded 0.78-acre lot on a quiet cul-de-sac, 26864 Oak Ridge Drive in Mechanicsville, Maryland offers tremendous potential and the perfect blend of privacy, convenience, and Southern Maryland lifestyle living. Surrounded by mature hardwoods and peaceful natural scenery, this well-maintained property provides a relaxing retreat while remaining conveniently located to many of the area’s major destinations. The spacious main level offers approximately 1,782 square feet of living space featuring 3 bedrooms, 2 full bathrooms, an open floor plan, and a comfortable sitting room located just off the dining area, creating an inviting atmosphere for entertaining and everyday living. Natural light fills the home while the thoughtful layout provides both comfort and functionality. The lower level features a convenient walk-out basement offering an additional 1,296 square feet with tremendous expansion possibilities including room for a large family room, additional bedrooms, a full bathroom, home office, recreation area, or guest accommodations. Total potential living space is approximately 3,078 square feet. In addition to the main residence, the property also includes a separate cottage/outbuilding offering endless possibilities for storage, workshop space, hobby area, studio, or future creative use — left entirely to your imagination. Located within the desirable Saint Mary’s Beach community, the property is only 1.3 miles from Route 235 via Sandgates Road and slightly more than one mile from local waterfront favorites including Sandgates Inn, Seabreeze Restaurant and Tiki Bar, and beautiful Snow Hill Park situated along the scenic Patuxent River offering boating, fishing, kayaking, hiking, picnicking, and waterfront recreation. Commuters will appreciate the property’s convenient proximity to Park & Ride commuter lots with access toward Washington D.C. and surrounding employment centers. The home is also within reasonable commuting distance to Naval Air Station Patuxent River, making it an excellent option for military personnel, government contractors, and civilian employees seeking a peaceful lifestyle outside the busier metro areas. Nearby schools serving the area include Mechanicsville Elementary School, Margaret Brent Middle School, and Chopticon High School. Enjoy the charm of country living while remaining close to shopping, dining, recreation, waterfront parks, and commuter routes. This is a rare opportunity to own a beautiful property with exceptional potential in one of Southern Maryland’s most scenic and established communities.

26864 N Oak Ridge Dr, Mechanicsville

Listing courtesy of Samson Properties. Contact: 7033788810
$244,900
3 Beds ⋅ 2 Baths

21730 Gambier Pl, Lexington Park

Listing courtesy of RE/MAX One. Contact: 4437718009
$534,900
4 Beds ⋅ 3 Baths
This brand-new home blends the latest construction techniques with timeless old-world craftsmanship. Featuring high-efficiency systems and appliances throughout, it sits in a well-established waterfront community and offers beautiful water views. Just a short stroll away, you'll find multiple river accesses complete with a pier and boat launch. The community is golf cart friendly, and the home's lot includes state-of-the-art stormwater management systems for peace of mind. Inside, high-grade vinyl flooring greets you with elegant cove molding, pocket doors, ceiling fans, and a whole-home sprinkler system. The kitchen is conveniently located just off the garage for easy unloading. The first floor boasts a spacious dining room, living room, and family room—ideal for entertaining guests or hosting large holiday gatherings. Up the handsome wood staircase, you’ll discover generously sized bedrooms, a convenient laundry room, and stylish tile bathrooms. The impressive owner’s suite offers a private bath, abundant closet space, and serene views of Trent Creek. Every bedroom includes ceiling fans for added comfort. Be the first to live in this exceptional new construction home. Perfectly located and thoughtfully designed, it’s ready for you to make it your own. Contact me today for a private showing!

29725 Bruce Rd, Mechanicsville

Listing courtesy of Action Real Estate Services, Inc.. Contact:

$699,900
2 Beds ⋅ 3 Baths
Enjoy panoramic sunset views with waterfrontage on both the Potomac River and Calvert Creek. Lovingly owned by the original local family for over 50 years, this solid all-brick home offers timeless charm with replacement windows and a durable metal roof. The spacious, functional kitchen features abundant cabinetry, making it ideal for preparing meals and hosting family gatherings. Situated on 2 private acres, the property boasts approximately 200 feet of riprap shoreline on the Potomac River and more than 800 feet of frontage on Calvert Creek. This exceptional waterfront setting provides convenient access to nearby restaurants and marinas by both boat and car. Spend your days boating, crabbing, oyster harvesting, and fishing right from your own property while taking in the incredible waterfront views and sunsets.

48724 Curleys Rd, Ridge

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$375,000
3 Beds ⋅ 1 Baths
3 bedroom, 1 bathroom home tucked away on a peaceful, secluded 3+ acre lot! This home features upgrades throughout, including a kitchen with white shaker cabinets. Enjoy the privacy, outdoor space, and quiet setting, plus a storage shed for extra convenience. A great opportunity for anyone looking for a private retreat with room to spread out.

38330 Hatchet Thicket Rd, Avenue

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636
$339,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully renovated home in the heart of Hollywood! Completely updated in 2024, this move-in ready property blends modern finishes with timeless charm and offers the perfect mix of comfort, style, and convenience. From the moment you arrive, you’ll appreciate the fresh exterior appeal and thoughtfully redesigned interior spaces. Inside, the home features a bright and open layout with updated flooring, modern fixtures, refreshed kitchen and baths, and stylish finishes throughout. The fully renovated kitchen offers contemporary cabinetry, upgraded countertops, and newer appliances, making it ideal for both everyday living and entertaining. Spacious living areas and comfortable bedrooms provide flexibility for families, guests, or a home office setup. Enjoy peace of mind knowing the major updates were completed in 2024, giving the next owner the feel of a nearly new home without the wait. Conveniently located near shopping, dining, schools, and Patuxent River Naval Air Station, this property offers easy access to all that Southern Maryland has to offer while still maintaining a quiet residential feel. Don’t miss your opportunity to own this turnkey renovated home at 25263 Sotterley Road!

25263 Sotterley Rd, Hollywood

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$375,000
4 Beds ⋅ 2 Baths
Rambler on nearly 5 private acres - bring your vision! Discover the ease of one-level living nestled in the heart of Mechanicsville. Offering 4 bedrooms and 2 bathrooms, this property provides plenty of space both inside and out. Enjoy the peace and privacy of the expansive lot, where you can relax, listen to the birds, and truly unwind. Detached garage included for additional storage, hobbies, or workshop space. Conveniently located near local parks, shopping, and commuter routes, this home offers the perfect mix of rural charm and everyday convenience. This property is ready for your vision and presents an excellent opportunity to build instant equity. With some updates and improvements, the potential here is incredible. Whether you're looking for room to spread out, create your dream homestead, or simply enjoy peaceful country living, this property offers endless possibilities. Photos have been staged by AI.

27020 Cat Creek Rd, Mechanicsville

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636
$1,749,000
3 Beds ⋅ 4 Baths
Welcome to this stunning custom waterfront home, situated high on Half Pone Point, offering elegant living on the St. Mary’s side of the Patuxent River. Built in 2014, this well-maintained property features quality workmanship throughout its approximately 4,500 square feet of above-grade living space. The bright and open interior features a first-floor owner's suite, spacious secondary bedrooms upstairs, and a large upper-level craft/media room. The main level offers 9' ceilings, hardwood floors, a dedicated office, dining room, and an inviting family room with a coffered ceiling, adjacent to a tile-floored sunroom to capture coastal scenery all year, complete with an indoor porch swing. The main-level primary suite boasts elegant tray ceilings and three expansive walk-in closets. The spa-like primary bath features a heated floor, a separate walk-in shower, dual vanities, a private water closet, and a luxurious two-person whirlpool tub, with convenient direct access to the spacious laundry room. The chef-inspired gourmet kitchen features stunning granite counters, custom 42" cabinetry, and a full suite of professional stainless steel appliances. Culinary enthusiasts will appreciate the gas cooktop with a dedicated pot filler and the large corner pantry. Transition seamlessly to the unparalleled outdoor oasis, designed for grand entertaining. The 14x20 composite deck features sleek glass railing panels for unobstructed views and a retractable awning for shade. Below, a hardscape patio defines a comfortable conversation area centered around a remote-controlled gas fire pit—ideal for enjoying cool coastal evenings. This is the epitome of coastal living, defined by exceptional waterfront amenities: 100 feet of private Patuxent River frontage, complete with a 290-foot pier and boat lift, providing effortless deep-water access to the Chesapeake Bay and stunning, direct views of the iconic Solomons Island Bridge. Ample storage and flex space abound, including an oversized 3-car garage, a dedicated RV pad, and a 16x10 Amish-built shed. The unfinished walk-up basement offers vast potential, complete with built-in shelving, a workbench, a convenient half bath, and an exterior entrance. Modern systems ensure year-round comfort and peace of mind, including a dual-zone HVAC system (heat pump with gas furnace backup) and a ready-to-use home generator. Built for enduring resilience and convenience, the home features durable HardiePlank siding and 30-year Timberline architectural shingles. Short commute to NAS Pax River, home of the US Naval Test Pilot School. Embrace the Southern Maryland lifestyle with immediate access to recreational boating, fishing, and crabbing. Explore nearby historic towns—Solomons, St. Mary’s City, and Leonardtown—offering fine dining, seasonal concerts, and festivals. It's your turn to claim this luxury retreat and coastal charm, entertaining friends and family along the picturesque shores of the Patuxent River.

24814 Half Pone Point Rd, Hollywood

Listing courtesy of RE/MAX One. Contact: 4437718009
$1,100,000
3 Beds ⋅ 3 Baths
Want to live near your business?! This beautiful and classic 3 bedroom, 2 and half bathroom rancher has well-maintained curb appeal and the interior to match, beginning with the flower bed enriched porch. From the front door you are greeted with a spacious living room great for relaxing and enjoying the view from the large picturesque windows. This area also includes a separate kitchen/dining room area that blends well for entertaining. The kitchen's focal point is its large island with a solid brass footrest. From the kitchen you are led to the 1.49 acre backyard with a patio area to enjoy nature. The main area of the home also has a home office, family room and pub-style game room; all can be transformed to fit your lifestyle! The laundry room includes a 3-year-old washer and dryer, powder room and build-in ironing board. On the other end of home there is a full bathroom, along with two bedrooms and a true primary suite. This primary suite is guaranteed to provide you your very own private oasis! Enter into its personal hallway that leads to a generous bedroom with two walk-in closets. The bathroom includes a double sink countertop, a soaker tub and a separate walk-in shower. It doesn't stop there! The suite extends to its very own sunroom full of windows and has a separate heating and cooling system. AS AN ADDED BONUS: This property includes a Commercial shop with ample parking space. The shop consists of a very sizable workshop area with a bay door, lobby and office areas, storage room and two restrooms. Due to the lack of use for a few years, it will need your TLC and vision. This building was originally the home of Smith's Repair. Recognized by St Mary's County Economic Development for six decades of service this would be a great location to bring your business. On the land there is also a shed with a sink as well as a 2-car garage. Perks: All structures have a new roof (2025), all building have electricity. This property is being sold As-Is. Preferred title company is Cardinal Title. Professional photos coming soon.

20098 Piney Point Rd, Callaway

Listing courtesy of Samson Properties. Contact: 2407246550
$499,000
5 Beds ⋅ 3 Baths
Discover the potential of this rare dual-property opportunity at 19745 Three Notch Rd! Whether you're searching for a multi-generational living setup, an investment opportunity, or the perfect blend of homeownership and passive income, this unique offering delivers endless possibilities. The main residence features a spacious 3-bedroom, 2 full bath rambler with a versatile bonus room—perfect for a home office, playroom, or guest space. Enjoy comfortable one-level living with ample space both inside and out. Tucked directly behind the main home at 19722 Teddy Way, you'll find a separate 2-bedroom, 1 full bath trailer offering privacy and flexibility for extended family, guests, or rental income potential. Live in one property while generating passive income from the other, or maximize your investment by utilizing both residences. Conveniently located close to shopping, restaurants, schools, and commuter routes, this is a truly unique opportunity you won’t want to miss!

19745 Three Notch Rd, Lexington Park

Listing courtesy of Infinitas Realty Group. Contact: 2409252224
$505,000
5 Beds ⋅ 3 Baths
Welcome to 37681 Asher Road in Mechanicsville, Maryland—a charming and well-maintained property offering comfort, space, and privacy in a peaceful Southern Maryland setting. Situated on a spacious lot, this home provides the perfect balance of quiet country living while still being conveniently located near shopping, dining, and commuter routes. Inside, you’ll find a functional and inviting layout with generous living spaces, abundant natural light, and comfortable bedrooms designed for everyday living. The home offers a warm and welcoming atmosphere, ideal for both relaxing and entertaining. The exterior features ample yard space, perfect for outdoor activities, gatherings, or simply enjoying the surrounding nature. Whether you're looking for a primary residence or a place to escape the hustle and bustle, this property delivers flexibility and charm. Don’t miss the opportunity to own a home in the desirable Mechanicsville area—schedule your showing today!

37681 Asher Rd, Mechanicsville

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$649,900
5 Beds ⋅ 2 Baths
Welcome to your waterfront escape on the point of St. George Island, where the Potomac River meets the Chesapeake Bay. This home was built by the local Amish community for this family. This rare offering features 154 feet of riprapped shoreline, delivering sweeping water views and front-row seats to breathtaking sunrises, passing boats, and endless coastal serenity. The main home offers 4 bedrooms and 1.5 baths, with water views from both the kitchen and living room, creating a daily backdrop that never gets old. The updated kitchen features granite countertops and an eat-in area, perfect for casual dining while overlooking the water. A wraparound screened porch invites you to relax, entertain, and enjoy the bay breeze in every season. For boating enthusiasts, the property is fully equipped with a private pier, electric, and boat lift, making it easy to get out on the water at a moment’s notice. Additional features include: Detached garage with apartment above and full bath – ideal for guests, rental income, or private workspace Carport and shed for added storage and functionality New HVAC systems in both the main home and garage Public sewer recently installed (approx. $48,000 investment) Deep well .36-acre lot with mature fruit trees Whether you're looking for a full-time residence, weekend retreat, or income-producing opportunity, this property offers the perfect blend of waterfront living, versatility, and long-term value. Opportunities like this—on the point, with this much frontage—don’t come around often.

16104 Piney Point Rd, Piney Point

Listing courtesy of Samson Properties. Contact: 4439757555
$384,900
3 Beds ⋅ 2 Baths
The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the MLS. You may use the disclosure language below in lieu of the MLS task requirements issued through RESNET. Disclosure language must be entered in the Agent Private Remarks. If spacing is an issue, you may attach an Offer Instruction document to the MLS along with the First Look Notice of Interest document. No offers will be reviewed unless a buyer has submitted a First Look Notice to you. At a minimum, the first 3 sentences below as italicized should be entered to the Agent Private Remarks section of the MLS with further instruction to read the offer instructions attached in the MLS document section. An Offer Instruction document is attached for your convenience. If using this document insert the Seller’s name per the listing letter and add the RESNET offer fee and offer link from the RESNET MLS tasks prior to loading the document to the MLS. Charming and beautifully updated brick rancher located in the heart of Leonardtown! This single-level home offers 3 bedrooms and 1.5 bathrooms, making it ideal for easy, comfortable living. Recently remodeled, the property features fresh updates throughout, blending classic charm with modern touches. Enjoy a spacious, level lot perfect for outdoor entertaining, gardening, or simply relaxing. The solid brick construction provides timeless curb appeal and durability, while the interior improvements make this home move-in ready. Conveniently located near local shopping, dining, and amenities, this is a great opportunity to own a well maintained home in a desirable area. Don’t miss it!

42249 Saint Johns Rd, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005
$325,000
5 Beds ⋅ 2 Baths
Welcome to this spacious home set on a large lot, offering sought-after features including energy-efficient solar panels. This split-foyer design includes an attached garage and is ideally located for an easy commute to Pax River, with convenient access to shopping and dining. Featuring 5 bedrooms and 2 bathrooms, this home provides plenty of space for comfortable living. Come take a tour today!

45706 Belvoir Rd, Great Mills

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636
$340,000
3 Beds ⋅ 2 Baths
JUST REDUCED!! This home is located in the tucked-away community of Longview Beach at 36797 Ricardo Drive, Bushwood, Maryland, and is currently priced at $340,000.00. Sitting on 10,500 sf. is just under 1/4 acre. This recently updated home with great features for winter is the perfect location for the summer. A new metal roof with lighting rods was installed in 2019, including upgrading installation in the attic/ceiling and exterior walls. Home features a renovated eat-in kitchen with custom cabinets, a large kitchen counter area for breakfast, and new lighting that opens into the family room. The kitchen has access to the rear yard, and a covered carport or front porch area completes the living space. This gem is awaiting a new owner to enjoy all the benefits of just a short a quiet haven for all nature lovers to sip your morning coffee and watch the wildlife that passes by. In the early morning, you can take a walk down less than half a mile to the shoreline for some early morning fishing, drop your boat at the pier, or just enjoy the view of the Potomac River. The home is located From Drive Time 1hour and 42 minutes from Washington, DC From King George, Virginia, Drive time 45 Minutes From Annapolis, MD, the Drive time is 1 hour and 48 minutes

36797 S Ricardo Dr, Bushwood

Listing courtesy of Smart Realty, LLC. Contact: 3012525515
$314,990
3 Beds ⋅ 1 Baths
BUYER GOT COLD FEET. Their loss is your gain. Welcome to this fully renovated home offering a rare combination of modern upgrades, extra space, and a flexible layout that works for today’s buyers. Whether you’re a first-time buyer or looking for a strong investment, this property stands out with major systems already taken care of and thoughtful improvements throughout. The home has been updated from top to bottom, including a new HVAC system, new roof, new well pump and pressure tank, and a brand-new septic system that has been perc’d and permitted, with installation scheduled prior to settlement. Inside, you’ll find a remodeled kitchen and bathroom with clean, modern finishes that make the space feel move-in ready from day one. The work has already been done so you can move in without worrying about costly updates. The flat, usable lot provides space to enjoy the outdoors, entertain, or expand your vision. Two sheds convey with the sale, including one that is insulated with electric, making it a great option for a home office, workshop, or additional storage. Sale will include adjacent lot at no additional costs, total acreage is over 3/4 acres. Commuters will appreciate being just 20 minutes to NAS Patuxent River and only 5 minutes from Webster Field, making it a practical choice for professionals who want more space without sacrificing convenience. With its updates, extra space, and versatile setup, this property offers a lot of opportunity in one package. This one you won’t want to miss. Hurry, this place won’t last! UPDATE: Septic Mound system complete! Appraised over $340k.

49725 Fresh Pond Neck Rd, Scotland

Listing courtesy of NextHome Envision. Contact: 3018816398
$849,900
4 Beds ⋅ 2 Baths
**A Rare Opportunity: Quintessential Waterfront Charm with Deep-Water Access on the Patuxent River** Welcome to 23690 West Patuxent Beach Road, California, Maryland 20619—a property that perfectly captures the essence of waterfront living. This charming original home, built in 1900, offers approximately 700 feet of waterfront and features commanding views of Kingston Creek and/or the Patuxent River from every room. Meticulously updated in 2021, the home has benefited from significant improvements including updated electric, well, septic, roof, and HVAC systems, ensuring comfortable living while preserving its timeless appeal. The property is being offered furnished and is already generating income, with numerous Airbnb rentals reserved for 2026. Enjoy immediate boat access with a valuable deep-water dock on-site. Whether enjoyed as-is or treated as an ideal canvas to create your masterpiece, this property is truly lovely and unique. **The Ultimate Private Waterfront Compound** For an unparalleled family compound opportunity, this listing may be combined with the adjacent property at **23680 West Patuxent Beach Road**. Purchased as a package, you would own a private, four-acre peninsula boasting a total of 1,000 feet of waterfront and a deep-water dock. The adjacent property, 23680, features a newly constructed custom home built in 2022 by Caruso, offering modern luxury, a grand master suite, a chef's kitchen, a gas fireplace, volume ceilings, 5 bedrooms, and 2.5 baths. Water views are available from every room in both residences. This unique pairing allows you to live in one home and rent or sell the other. Both properties are sold furnished and have existing Airbnb bookings for 2026. The entire private compound is located just five minutes from the shops and restaurants at Solomon’s Island. This once-in-a-lifetime opportunity is proudly offered individually or combined with the adjacent home as a compound.

23690 W Patuxent Beach Rd, California

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535
$399,000
3 Beds ⋅ 2 Baths
Fully renovated. Move-in ready. Prime downtown location. Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value. Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of the home. Outside, enjoy a fully fenced yard surrounding the property — perfect for pets, gatherings, or private outdoor living. The detached two-car garage adds both convenience and versatility, offering space for vehicles, storage, or even a workshop. All the hard work has been done — just move in and enjoy. Located to downtown shops, dining, and local attractions, this home combines lifestyle, location, and value in one compelling package. Homes like this don’t last — schedule your showing before it’s gone.

41620 Church St, Leonardtown

Listing courtesy of Evergreen Properties. Contact:

$125,000
2 Beds ⋅ 1 Baths
Pending release: Big Price cut AS-IS – Investor Special in Waterfront Community! Welcome to 22845 Pleasant Ln, Bushwood, MD 20618 — a prime opportunity for investors or buyers with vision. Situated on a spacious double lot (Lots 19 & 20 totaling approximately half an acre), this property offers incredible potential for expansion, renovation, or future value growth. The home is being sold AS-IS, but key essentials are already in place — running water, a new heater, and functional systems throughout. A new A/C unit was installed at the rear of the home, adding to the property's upside. Located just approximately 1,000 feet from the water, this home is part of a desirable waterfront community, making it an excellent option for a starter home, vacation retreat, or investment project. With ample lot size and room to grow, this is a great buy with endless possibilities. Bring your ideas and transform this property into something truly special!

22845 Pleasant Ln, Bushwood

Listing courtesy of Goodridge Real Estate. Contact: 3016333892
$399,000
4 Beds ⋅ 3 Baths
Beautifully Updated Home!!! Just Minutes from NAS Patuxent River! Welcome to this beautifully maintained 4-bedroom, 2.5-bath home in the desirable Essex South community. Offering approximately 1,776 square feet of thoughtfully designed living space, this move in ready property combines comfort, convenience, and everyday functionality. Step inside to discover updated finishes, spacious living areas, and a versatile floor plan designed for modern living.Thoughtfully designed with spacious bedrooms throughout, this home offers exceptional comfort and flexibility for modern living. The well appointed kitchen flows seamlessly into the main living spaces including the main level bedroom ideal for guests, multi generational living, or a private home office. creating an inviting atmosphere for entertaining and everyday life. Outside, you'll appreciate the home's attractive curb appeal and welcoming front yard, while the manageable backyard offers a low maintenance outdoor space perfect for relaxing without spending weekends on yard work. Located just minutes from NAS Patuxent River, this home is an exceptional opportunity for military personnel, government contractors, and commuters seeking a quick drive to work. Enjoy easy access to shopping, restaurants, parks, schools, and all that St. Mary's County has to offer. 100% financing may be available for qualified buyers. Seller is also willing to negotiate select furnishings with an acceptable offer.

21314 S Essex Dr, Lexington Park

Listing courtesy of RE/MAX One. Contact: 4105356291
$769,900
4 Beds ⋅ 2 Baths
Waterfront property on Saint George Island - Original owners are offering this rare opportunity to own a beautifully maintained waterfront home on sought-after St. George Island. Situated on a combined 1.4-acre parcel that includes both the waterfront lot and house lot. This property offers serene views, and direct access to St. George's Creek via a private pier with easy access by boat to ST. Mary's River, the Chesapeake Bay & the Potomac River! Home features: 4 bedrooms, 2 bathrooms. Spacious open floor plan with 9' ceilings. Great room ideal for entertaining. Bright kitchen with breakfast bar and new appliances. Charming front porch with stunning water views. Heat pump with oil backup (2022). Gas hot water heater (2016), well pump (2020), whole house generator (2022) ensures comfort during outages. Waterfront and Outdoor Amenities: Private pier with decking & stringers replaced in 2021. Water at pier; conduit installed for future electric. Perfect for boating, fishing , or enjoying tranquil sunsets over the water. Close proximity by car or boat to several local restaurants. Outbuildings & workshop space: 40' X 24' garage/shop with finished walls and 3 garage doors, 12 x 24 car port, 18' X 12' workshop with second story and built-in workbench 10'X20', & a shed for additional storage. This property offers a unique blend of waterfront living, workshop space and peaceful island charm - all under the care of its original owners. Whether you're looking for a full-time residence, weekend escape, or retirement retreat, this is a must-see!

16460 Sayre Point Ln, Piney Point

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$335,000
3 Beds ⋅ 1 Baths
3BR / 1B Rambler on an acre of land w/garage (storage), Detached carport and outbuildings. Paved driveway just off Hollywood/Leonardtown Road. Hardwood floors throughout Living Room, Hall and bedrooms. Level rear yard bordered by trees. Oil Furnace, water heater, utility sink and washer hook-up are located in the (walk-in) storage area under the home.

24040 Hollywood Rd, Hollywood

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500
$379,900
3 Beds ⋅ 3 Baths
Nestled in a peaceful Southern Maryland setting, this private property offers the perfect blend of space, serenity, and convenience. Surrounded by open farmland, the home provides a quiet retreat while still being just minutes from St. Mary’s College. Major system updates offer true peace of mind, including a new roof, updated septic and well, replacement windows, and an upgraded heating system. With these big-ticket items already completed, the next owner can focus on personal touches and cosmetic improvements rather than costly upgrades. The home features durable vinyl siding and beautiful original hardwood floors, adding both character and long-term value. Inside, you’ll find a spacious layout with 3 bedrooms and 2 bathrooms, along with 3 additional rooms in the basement and a bathroom. Currently generating $3,250 per month in rental income, this property presents a strong investment opportunity with immediate cash flow. Whether you are looking to expand your portfolio or create your own private retreat, this property offers incredible potential in a sought-after Southern Maryland location.

16320 Point Lookout Rd, Saint Marys City

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636
$729,900
6 Beds ⋅ 3 Baths
Are you finding yourself longing for a peace and quiet that only life on the water can bring? Come home to stargazing without light pollution, dinner on the patio watching osprey, herons and geese in the creek. Spend your weekends boating, fishing, crabbing on the pier or taking long walks with both water and farm views. Invite your friends and family because this home has 6 bedrooms and 3 bathrooms with a floorplan perfect for a multi family living situation or even a vacation rental. The first floor living room is both cozy with the fireplace and also fun with the bar area and room to dance or game. You'll love the natural light coming into the kitchen with expansive windows bringing the creek views as close as you can get without stepping outside. So much granite counter space especially with the mobile island, newer appliances, an undermount sink, appliance garage and desk space might just make this your favorite room of the house. Whether you're having elaborate formal meals or casual fare, the dining room seats as many as you want and a fireplace and amazing views to top it off. Completing the main level are 2 spacious bedrooms, a full bath and laundry room with a 2nd shower. You'll also appreciate the side entrance of the home that open to a large entryway currently used as a library that can double as an office with access to the 2nd level leading to another primary bedroom, ensuite bathroom with soaking tub and separate shower. Plus 3 additional bedrooms, 3rd full bath and common space where you'll discover the spiral staircase taking you back to the lower living room. Plenty of parking with 2 paved driveways, a sideload attached garage and 2nd single car garage/shed plus another shed for storage. The covered front porch brings you panoramic views of a farm and woods where wildlife roam. The side and backyard have unobstructed views of St. Jerome Creek where you can dock your boat or launch your kayak with easy quick access to the Chesapeake Bay. Ridge is just far enough away from the hustle and bustle but still close enough to shopping and commuting. Locally you'll enjoy the waterfront restaurants, farmstands and state park. Just a few minutes to historic St. Marys City and St. Marys College.

49716 Airedele Rd, Ridge

Listing courtesy of RE/MAX One. Contact: 4105356291
$925,000
3 Beds ⋅ 3 Baths
This well-maintained, three-story Waterfront home on Tanners Creek offers a spacious and versatile layout. Three levels of living space including 3 bedroom 3 bath. The main level features 2 bedrooms, 1 full bathroom, a living room, a kitchen, and a dining area. The upper level includes a primary bedroom with a full bath, while the lower level offers a kitchenette with a large pantry, a family room, and 1 full bath. Both the main and lower levels have been freshly painted. All three levels have exterior access to each level of the home with large deck areas for maximum water views. A spiral staircase connects all three levels, adding charm and character. The home and detached garage have recently been power washed, and the pier was rebuilt in 1993. Situated across the street on a separate lot, the impressive garage spans over 2,500 sq ft across two climate-controlled levels and provides ample parking. Garage door openers were installed in 2007. A shed in the backyard conveys with the property, and French doors were added to the lower level in 2008. The generator, purchased in 2009, is also included. Square footage is based on tax records and may not be accurate. The home sits on a 0.20-acre lot and features large decks on both the main and upper levels, as well as a screened-in porch ideal for summer gatherings. A new oil tank was installed in 2019, and the heating/AC system was replaced in September 2018. The septic system was pumped in March 2025. This sale includes four separate lots with separate tax id #'s which will be provided in disclosures. Please note: the property is located in a flood zone, and two TDRs (Transferable Development Rights) do not convey with the sale but may be negotiable. Less than 1/2 mile to Point Lookout State Park; Check out video tour

14623 C Way Dr, Scotland

Listing courtesy of NOVA Brokers, LLC.. Contact:

$495,000
4 Beds ⋅ 2 Baths
One level living with waterfront views are ready for you to move right in! This one story home includes 4 bedrooms and 2 full bathrooms. The home was renovated in 2016. As you enter the home, the open concept kitchen and main living area are perfect for hosting gatherings or entertaining. The kitchen has quartz counters, upgraded cabinets, stainless appliances, tile backsplash, upgraded lighting, dining area, and hardwood floors. Enjoy views of St. George's Creek from the main living area or sit on the expansive front porch and enjoy a cup of coffee or evening cocktail. The bedrooms are spacious and include a full bath located in the hallway. As you leave the main living area, the step down family room with wood burning fireplace provide a cozy feel and space to relax. Doors open to the back patio complete with built in brick barbeque, large yard, barns, shed, and fenced yard. The primary suite has hardwood floors and a large walk in closet. The primary bathroom creates a spa like feel with the claw foot soaking tub, updated cabinets and walk in shower. Close to area restaurants, historic St. George's Island, and other area sites and amenities. Schedule your online appointment today.

44939 Shore Dr, Tall Timbers

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$1,050,000
3 Beds ⋅ 2 Baths
Beautifully maintained rambler on a spacious lot along St. Patrick’s Creek in the sought-after Olen Mattingly neighborhood—offering true one-level living with no steps. This custom-built home features 3 large bedrooms and 2 full baths, with an open-concept floor plan designed to maximize natural light and scenic creek views. Breathtaking water views pour through large windows in the living room, dining room, and primary suite—creating a bright and serene atmosphere throughout the home. The kitchen is equipped with granite countertops, stainless steel appliances, and custom cabinetry, flowing seamlessly into the main living and dining areas—perfect for everyday living and entertaining. Hardwood and tile flooring run throughout, adding both style and durability. Enjoy the expansive backyard with direct creek frontage—ideal for outdoor recreation, relaxing, or hosting gatherings. A covered patio and large rear deck provide the perfect spaces to unwind or entertain while taking in the peaceful surroundings. A standout feature is the 40'x32' detached garage with a 12' lean-to across the entire back—offering exceptional space for vehicles, boats, storage, or a workshop. Move-in ready and just in time for summer—don’t miss this opportunity for easy, waterfront living.

38150 Boatman Ln, Avenue

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005