Saint Leonard Homes with Colonial Style

Saint Leonard Homes with Colonial Style

Welcome to Saint Leonard, Maryland—a hidden gem nestled in the heart of Calvert County! This charming waterfront community boasts a rich history and a serene lifestyle, making it an ideal destination for anyone looking to settle down in a picturesque environment. With its proximity to the Chesapeake Bay, residents enjoy breathtaking views and a plethora of outdoor activities, from boating and fishing to hiking along scenic trails.

Saint Leonard is renowned for its warm, welcoming atmosphere and tight-knit community. The area is characterized by its Colonial-style homes, which exude timeless elegance and charm. These stunning residences often feature classic architectural details such as symmetrical facades, gabled roofs, and inviting front porches that beckon you to sit back and enjoy the surroundings. Each home tells a story, reflecting the rich heritage of the region while providing modern comforts and conveniences.

Beyond the beautiful homes, Saint Leonard offers a vibrant local culture with quaint shops, delightful eateries, and community events that bring neighbors together. The nearby Calvert Cliffs State Park is a must-visit, where you can explore fossil hunting, enjoy picnics, or simply take in the natural beauty of the area.

Whether you’re searching for a family home or a peaceful retreat, Saint Leonard’s Colonial-style residences provide a perfect blend of history and modern living. Embrace the charm of this enchanting community and discover the ideal place to call home in Saint Leonard, Maryland!

Newest Saint Leonard Homes with Colonial Style

5 Beds ⋅ 5 Baths

MOTIVATED SELLER- Offering buyer credit of $20,000 with acceptable offer. Nestled in the serene community of St. Leonard Shores, this charming Colonial home offers a perfect blend of comfort and peace. Built in 1988, this residence boasts a generous 3,979 square feet of living space. Step inside to discover beautiful wood oak floors, an open floor plan connecting the kitchen, with upgraded granite countertops, to the family room, making it an ideal space for gatherings. Enjoy cozy evenings by one of the two brick fireplaces. The home also features a formal dining room, perfect for hosting dinner parties, and a spacious living area that invites relaxation. The primary suite offers an en suite bathroom while the additional 4 bedrooms provide ample space for guests. The partially finished walkout basement includes a bar and presents endless possibilities for customization, whether you envision a recreation room, additional bedrooms, or a personal gym. Outside, the property spans 2.39 acres, providing a private, partially fenced, and secluded oasis surrounded by trees. Enjoy the outdoors on the expansive deck, perfect for summer barbecues or quiet evenings under the stars. A large newly renovated shed provides excellent outdoor storage. In addition this home comes with several improvements including a new fiberglass shingle roof (2024), a new septic system (2023), new hot water heater and oil tank, and a whole house back up generator powered by an underground propane tank. Seller is also including a 1 year 2-10 home warranty. The community amenities include a boat ramp, picnic area, and pier/dock, making it easy to embrace the waterfront lifestyle along the Patuxent River and Saint Leonard Creek. This property is more than just a house; it's a place to create lasting memories.

1151 Thompson Ct, Saint Leonard

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990

4 Beds ⋅ 4 Baths

Professional photos coming Aug 8th. VA assumable mortgage at 2.625%! Welcome to 1054 Kings Creek Dr., Saint Leonard, MD 20685 — a beautifully maintained Colonial in the sought-after Kings Creek Estates community, offering nearly 3,200 finished square feet, major recent capital improvements, and a private, wooded setting on more than one-half acre. Thoughtfully maintained, this home offers the ideal combination of generous living space, modern mechanical upgrades, and the privacy today's buyers are seeking. The inviting main level features hardwood floors; a spacious family room with a gas fireplace; formal dining room; dedicated home office, and an updated kitchen with granite countertops, stainless steel appliances, pantry, breakfast area, and recessed lighting. Upstairs, the spacious primary suite offers a walk-in closet, double vanity, soaking tub, and separate shower. The three additional bedrooms provide comfortable accommodations for family and guests. The finished walkout basement significantly expands the home's versatility with a large recreation room, media room, fifth bedroom or flexible bonus space, full bathroom, and abundant storage — ideal for multigenerational living, long-term guests, a home gym, hobby space, or remote work. Major capital improvements provide exceptional value and peace of mind, including a new roof (2018), dual HVAC systems replaced in 2024 and 2025, basement flooring (2022), kitchen sliding glass door (2022), washer and dryer (2023), and a newer refrigerator, helping reduce future maintenance costs while making this home truly move-in ready. The outdoor living is equally impressive with a covered front porch, spacious rear deck, fenced back yard, mature trees, oversized two-car garage, and a storage shed. Situated on a private lot backing to trees, the property offers the perfect balance of peaceful surroundings and everyday convenience. Enjoy easy access to many of Southern Maryland's premier attractions, including: Solomons Island, Calvert Cliffs State Park, Flag Ponds Nature Park, Jefferson Patterson Park & Museum, Chesapeake Bay beaches, local marinas, shopping, restaurants, wineries, breweries, and public boat ramps. Enjoy endless opportunities for boating, fishing, hiking, waterfront dining, and year-round outdoor recreation. Commuters will appreciate the convenient location, approximately 20 miles to NAS Patuxent River, 37 miles to Joint Base Andrews, 42 miles to Annapolis, and 48 miles to Washington, DC, making this an exceptional choice for military personnel, government employees, and anyone seeking more space while remaining connected to major employment centers. Offering nearly 3,200 finished square feet, including a walkout basement, dedicated home office, oversized two-car garage, major capital improvements, and a private wooded setting in one of Calvert County's most desirable neighborhoods, 1054 Kings Creek Dr. presents a rare opportunity to own a move-in-ready home that perfectly combines space, comfort, quality, and location.

1054 Kings Creek, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4105356291

4 Beds ⋅ 5 Baths

No HOA. Total square footage of 3520. The house's total sq ft is 2400 with 3 bedrooms and 2.5 baths. A 1120 sq ft apartment with 1 bedroom and 1 bath. The Garage has a 1/2 Bath. The property is in the forest management program for reduced taxes. Tucked along the protected waters of Saint Leonard Creek, this is the kind of property you don’t just visit, you settle into. Deep water, nearly 800 feet of riprapped shoreline, and over 6 private acres set the stage for a true waterfront lifestyle. The creek opens easily to the Patuxent River. Many people say the Best Crabs in Maryland are found in St. Leonard Creek, and this pier is a place to find them! The pier is built for serious water use. New Trex decking gives it a clean, low-maintenance finish. A covered boathouse, multiple slips, floating dock, dock shed, and room to move make this ideal for boaters who want everything in one place. Whether it’s fishing at sunrise or heading out for a cruise, this setup is ready. The 6.24 acres, five of which are in a Maryland Forestry Program, has many tall pines, poplar, and other trees , making this property secluded and private. A large three-car garage built in 2017 topped by a spacious apartment with a bedroom and a full kitchen. On the main level of the garage there's a half-bath, built-in shelving, 3 massive bays, making it functional for hobbies and storage. This opens up options. Live in the apartment while building your dream home, or use it as a private guest space. The main home has been well cared for over the years and offers a solid foundation for someone ready to make it their own and was renovated in ‘97. You can move in now and update at your own pace without pressure. The large gunite swimming pool was redone in the summer of 2024 . Recently installed was a new automatic pool cover. Additional outbuildings include a machine shed and a smaller shed, giving you room for equipment, projects, or expansion of how you use the land. Location matters here, too. You are minutes to Broomes Island, Solomons Island, and local marinas. Easy access to Route 4 keeps commuting to Prince Frederick, Annapolis, DC, or Pax River within reach while still feeling completely removed once you are home. This is not just a house on the water. It is space, shoreline, and flexibility. Use it as it stands, reimagine it over time, or build something entirely new. Properties like this do not come along often, especially with this kind of frontage and deep water access.

2237 Garrity Rd, Saint Leonard

Listing courtesy of Deep Roots Real Estate. Contact: 4439676687

4 Beds ⋅ 3 Baths

Welcome home to this spacious 4-bedroom, 2.5-bath home, situated on over an acre, offering a traditional floor plan designed for comfortable living and effortless entertaining. The main level features a formal living room, dining room, and a welcoming family room, providing plenty of space for gatherings both large and small. The kitchen flows seamlessly into the living areas, creating a functional layout for everyday living. Step outside to the deck, perfect for relaxing, grilling, or enjoying the private backyard setting. The unfinished basement offers a blank canvas with endless potential for additional living space, a home gym, workshop, or storage. Combining classic charm, generous living areas, and privacy, this home is ready for its next owner to make it their own.

5335 Majesty Ln, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

4 Beds ⋅ 4 Baths

Some homes make you pause at the door. This is one of them. || Renovated in 2025, this custom built home is Set on 5+ wooded acres offering privacy, presence, and over 6,000 sq ft of beautifully updated living space. 4 bedroom, 3.5 bath estate features a soaring two story foyer, dramatic staircase, cathedral ceilings, hardwood floors, and a light filled great room designed for everyday comfort and entertaining. || The flexible layout includes a main level in law suite with full bath, a dedicated home office with wooded views, multiple living areas, and three fireplaces throughout. Upstairs, the owner’s suite feels like a private retreat with its own fireplace, spa bath, generous proportions, and elevated views of the surrounding tree line. || The finished walkout basement adds even more room to live, gather, and unwind with flexible space, a built in sauna!!!, and direct access to the lower patio. Outside, the rear deck, patio, and mature woods create the kind of quiet privacy buyers hope to find but rarely do. || Close to shopping, dining, entertainment, hospital access, and approximately 25 miles to NAS Patuxent River via MD 4, this home delivers space, privacy, and convenience in one unforgettable setting.

4200 Henry Ct, Saint Leonard

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

4 Beds ⋅ 4 Baths

Welcome home to 4585 Mattapany Road, where peaceful country living meets everyday convenience. Nestled on nearly 1.5 private acres in the desirable Woodhaven community, this beautifully maintained Colonial offers approximately 3,300+ finished square feet of thoughtfully designed living space across three finished levels. The main level features formal living and dining rooms, a welcoming family room with a cozy fireplace, and a generously sized eat-in kitchen with upgraded stainless steel appliances. Whether you’re entertaining friends or enjoying a quiet evening at home, the thoughtfully designed floor plan offers comfortable spaces for every occasion. The inviting covered front porch is the perfect place to enjoy your morning coffee while taking in the peaceful surroundings, while the expansive rear deck overlooks the private backyard—a wonderful setting for entertaining and making lasting memories. Upstairs, you’ll find four generously sized, light-filled bright bedrooms, all featuring beautiful hardwood flooring. The spacious primary suite offers a walk-in closet and an en-suite bath with a double vanity, soaking tub, and separate shower. A full hall bath and a conveniently located upper-level laundry room complete the second floor. The fully finished walk-out lower level offers exceptional flexibility with a spacious recreation room featuring high quality surround sound, a full bath, a wet bar with cabinetry and countertop space, and an oversized bonus room. Whether you need additional space for extended family, visitors, a home office, media room, fitness area, or hobbies, this versatile level adapts beautifully to your lifestyle. Let your imagination run wild! Recent improvements include a new roof (2020), upgraded stainless steel kitchen appliances, a newer washer and dryer, and additional mechanical updates, providing added peace of mind for years to come. Surrounded by mature trees, the property offers exceptional privacy and a peaceful setting to enjoy nature. The attached two-car garage and expansive driveway provide parking for at least 8 or more vehicles, making it ideal for entertaining, multiple drivers, boats, trailers, or recreational vehicles. Conveniently located just minutes from shopping, dining, schools, Solomons Island, and Patuxent River Naval Air Station, with an easy commute to Joint Base Andrews, Washington, D.C. and Annapolis this move-in-ready home offers the perfect balance of privacy and convenience. Discover the space, flexibility, and tranquility that make 4585 Mattapany Road a wonderful place to call home.

4585 Mattapany Rd, Saint Leonard

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

4 Beds ⋅ 3 Baths

The original owner / contractor incorporated upgrades in the construction valued at $250,000 over lesser choices for his forever home. Custom built colonial with Water Access, Brand New Roof with a transferable Lifetime Shingle Warranty, and an extremely efficient Geothermal HVAC system! Crafted with precision by the original owner, a skilled custom homebuilder, this stately colonial reflects uncompromising quality with no original detail overlooked. With 4 bedrooms and 2.5 baths, situated on a corner lot with 3.5 acres, this beautiful property offers an incredible blend of privacy and nature. Complete with access to the St. Leonard creek, this home is nestled in a close-knit community with frequent neighborhood parties and wine tasting events. Enjoy the convenient access to the community boat ramp (right across the street!), boat slips, pier, and picnic area are also just steps away. The perfect home for water enthusiasts, nature lovers, and those who appreciate the builders commitment to quality. A double wide foundation is one of the many material upgrades to ensure lasting stability for generations to come! The geothermal HVAC system provides incredible efficient heating and cooling, combined with Anderson windows, solid wood 6 panel doors, and the show stopping oak spiral staircase to highlight the craftsmanship and attention to detail. Attached two car garage and the detached garage give you, the new owners, plenty of parking and storage options, or the potential for a separate home office or workshop. The main level showcases beautiful hardwood floors, elegant crown molding, a formal living room, dining room, home office, and a sunlit family room leading to the patio area and and backyard. Enjoy entertaining family and friends on the back patio and deck, in the park-like setting, with the beautiful flowering trees, serene nature and privacy this home offers. The gourmet kitchen impresses with plenty of space, stainless steel appliances, granite countertops, ample cabinetry, and eat-in kitchen. On the upper level, you'll find the expansive primary suite, with a sitting room (perfect for a secondary office, nursery, or dressing room!), and not one, but two walk-in closets. Three more generously sized bedrooms and a full bath complete the upper level. The finished basement provides a versatile space for a recreation room or guest suite area, with a rough-in for a future bathroom and tons of storage.

7421 Stone Ct, Saint Leonard

Listing courtesy of Keller Williams Flagship. Contact:

4 Beds ⋅ 4 Baths

Enjoy peace of mind from the start with a new roof (2021) and HVAC system (2022), recently serviced and ready for its new owners. Located in the sought-after Mutual Elementary School district, this beautifully maintained 4-bedroom, 3.5-bath home offers the perfect blend of comfort, space, and privacy. Nestled on a private 1-acre lot surrounded by mature trees, you’ll enjoy a peaceful setting while remaining just minutes from shopping, dining, parks, and everyday conveniences, and only 20 minutes from beautiful Solomons Island. The main level features plank flooring and a welcoming family room with a wood stove, creating the perfect spot to gather on cooler evenings. Sliding glass doors lead to the backyard, seamlessly connecting indoor and outdoor living. The kitchen offers table space and a bay window overlooking the scenic rear yard. An additional room provides flexibility and can serve as a formal dining room, home office, playroom, or additional living space. The mostly finished lower level adds valuable living space and includes a full bathroom, making it ideal for entertaining, guests, a home gym, or recreation area. Additional unfinished basement space and a floored attic provide excellent storage options, while a French drain system offers added peace of mind. Upstairs, the spacious owner’s suite features a walk-in closet and dual vanities. Three additional bedrooms and another full bath provide plenty of room for family and guests. Outside, enjoy the privacy of the tree-lined backyard from the large patio, perfect for entertaining, grilling, or simply relaxing. An oversized side-entry two-car garage with abundant shelving and a large storage shed offer plenty of room for vehicles, tools, and hobbies. The outdoor patio set, featuring an oblong table and six chairs, conveys with the property, along with the children’s play equipment, making it easy to start enjoying the outdoor space from day one.

1155 Scenic Way, Saint Leonard

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

3 Beds ⋅ 4 Baths

Welcome to 548 Windmill Drive, in the desirable community of Parran's Grant. Located in beautiful St. Leonard, this is a place to call home for many years to come! If you're looking for that special, move-in-ready home, well-maintained by the original owners, search no more! The immaculate interior blends seamlessly into the verdant surroundings on this private 1.1 acre flag lot. Tucked just off the main drive, it enjoys a quiet and peaceful setting while remaining part of an established neighborhood. The main floor is arranged for easy entertaining and good flow between spaces, featuring durable hardwood and tile floors, custom window treatments, and fresh, neutral walls throughout. The kitchen is a retreat in itself, complete with granite counters, quality custom cabinets, and views from the sink and breakfast area that will draw you outside to the elevated deck and screened gazebo. Hardwood stairs lead to a charming upper level, tastefully appointed, with a ceiling fan in each bedroom. The finished basement offers a recreation room/FR, ample storage, a bonus room, and a full bath, with walkout to the tranquil fully-fenced backyard, shed, stacked stone firepit, and attractive landscaping. The paved driveway includes an additional pad for storing an RV/boat. This Calvert County location affords a healthy, wholesome lifestyle, in a rural setting surrounded by farmland and bordered by the Chesapeake Bay. Nearby Chesapeake Bounty offers a trove of locally grown farm-to-table foods and seafood from local watermen. Flag Ponds Nature Park is a short drive, offering plenty of hiking trails and a sandy bayfront beach. Also nearby: Jefferson Patterson Park, Perigeaux Winery, Running Hare Vineyard. If a boat slip/boat launch is needed, Flag Harbor Marina and Boatyard is just 4 mi. away. Shopping, restaurants, and amenities are easily accessed via a 10-minute drive to Prince Frederick and a 20-minute drive to Solomons, and over the Patuxent River to St. Mary's County. Although you won't want to leave your lovely new home, you may need to commute to work. This location makes commuting easy: NAS Patuxent River is 20 miles away, and Joint Base Andrews, DC, and Annapolis are also within commuting distance.

548 Windmill Dr, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4437718009

5 Beds ⋅ 4 Baths

As a special surprise the sellers have ordered new vinyl, single hung, thermal pane windows and screens from Thompson Creek! Installation to follow soon. New photos to follow. Come out and see all the quality features this exceptionally spacious colonial has for the next lucky buyer. New windows help maximize energy efficiency along with the secure gas fired back-up power generator. This will ensure you never loose power. This well established beachfront community with annual events for family and friends awaits you soon! Enjoy visiting this beautiful home as you pull into the expansive driveway after a hard days work! The new steel 2 car garage door with remote will keep you out of the weather too! Enjoy relaxing on your concrete front porch or sun-filled rear deck with stairs. As you enter the home after a hard days work, enjoy gleaming hardwood flooring throughout the entry foyer, living, dining and family room. The expansive kitchen has a brand new range/oven as well as stainless steel appliances and generous center island for fun and gatherings to come! The second floor boasts 4 bedrooms with generous room sizes. An owners suite offers a large walk-in closet and ensuite with separate corner soaking tub & shower. The three additional bedrooms enjoy large sun filled windows. Heading to the lower level has wonderful flex space, perfect for home gym, office, recreation room or even as separate living area with a 5th bedroom & kitchenette. A covered rear entry includes a double French door. The well maintained yard and exterior is perfect for fun times to come. The paved drive was expanded for recreation vehicles, boat or extra cars for family & guests. No formal HOA lets you enjoy the flexibility with a non-mandatory civic association with a voluntary small annual fee. Come and enjoy the beach and all recreational fun to come. Never worry about power outages with the Generac 24kw whole house generator supported by two new 120 gallon propane tanks. Four exterior mounted cameras and security system will convey.

5817 Magnolia Cir, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

3 Beds ⋅ 3 Baths

Deeded Boat Slip Conveys!! Bayside Living! Bayview new construction only a short walk to the private beach & marina! This 2000sqft 3 Bed 2.5 Bath Colonial with an attached 1.5 Car Garage & an Unfinished Basement, has been designed to Maximize the Views while the .91 acre lot maximizes privacy! The primary bedroom & attached balcony will have substantial views of the Chesapeake Bay! This floorplan has been designed to give buyers the open concept they have been looking for along with good sized bedrooms to boot. Oversized 1.5 Car Garage is perfect for storing your car and having a workshop! Engineering is already complete shortening the wait time! Call to discuss standard features/upgrades! It's hard to find new construction w/ Water Access, a Deeded Boat Slip and Bay Views under $600k!!! Reach out now to be in your new home by Early 2027! Inquire ASAP Before this opportunity is GONE!

6041 Hill Rd, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

4 Beds ⋅ 3 Baths

TO BE BUILT NEW CONSTRUCTION. Beautiful lot Co- Marketed with Caruso Homes. This Model is the -----DEERFIELD--- The Deerfield is a four-bedroom floor plan with the option to add an In-Law suite downstairs. Enjoy gathering with family and friends in this open concept home which features a large great room that flows right into the kitchen. A 9-foot island and plenty of counter space will please the chef and a formal dining room is perfect for serving up family meals. Upstairs, the large owner's suite offers an ensuite bath with his and her walk-in closets. Three additional bedrooms, a hall bath and a convenient laundry room complete the second floor. An optional third floor provides a loft and full bath for additional living space. Plenty of options and upgrades are available to personalize this home and make it your own! --- Buyer may choose any of Caruso’s models that will fit on the lot, prices will vary. Photos are provided by the Builder. Photos and tours may display optional features and upgrades that are not included in the price. Final sq footage are approx. and will be finalized with final options. Upgrade options and custom changes are at an additional cost. Pictures shown are of proposed models and do not reflect the final appearance of the house and yard settings. All prices are subject to change without notice. Purchase price varies by chosen elevations and options. The price shown includes the Base House Price, The Lot and the Estimated Lot Finishing Cost Only. Builder tie-in is non-exclusive. Associated Land listing #MDCA2013614.

5859 Long Beach Dr, Saint Leonard

Listing courtesy of The KW Collective. Contact: 4435741600

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