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$1,495,000

Welcome to 2005 Saint Stephens Woods Drive, an impressive estate set on a beautiful, private lot in one of Crownsville's most sought-after wooded settings. The home underwent a major remodel, transforming every room and creating a combination of timeless traditional character with thoughtfully modernized living spaces. Designed for both everyday living and memorable entertaining, this expansive home offers an extraordinary combination of generous living spaces, multiple bedroom levels, beautifully updated bathrooms, and seamless connections to the outdoors. The main level welcomes you with an elegant formal living room and dining room, a private library/study, two convenient powder rooms, and a spacious laundry room. At the heart of the home, the kitchen opens to a dramatic great room, creating an inviting gathering space filled with natural light and views of the surrounding landscape. From the great room, step directly onto the rear porch and decks overlooking the private grounds, pond, and mature woods. Upstairs, the primary bedroom is a true retreat, highlighted by an amazing primary bathroom that offers a unique spa-like experience. A second bedroom features its own en-suite bath, while additional bedrooms are thoughtfully served by a Jack-and-Jill bath. A second upper level adds two more bedrooms and a full bath, bringing the home to six bedrooms and offering tremendous flexibility for family, guests, work-from-home spaces, or hobbies. With bathrooms and individual rooms remodeled and upgraded over the years, the home has been continually refreshed to meet today's expectations for comfort, style, and functionality. The finished lower level takes entertaining and recreation to another level. A spacious recreation room provides plenty of room to gather, while a dedicated gym makes staying active convenient at home. A fun turf-lined "soccer" room adds a unique touch for athletes and kids alike, and the lower-level bar creates the perfect setting for game days and casual entertaining. Walk directly from this level to the patio and enjoy even more outdoor living space. A three-car side-entry garage provides abundant parking and storage, while the private lot offers a peaceful backdrop of trees and pond views. With multiple decks and a rear porch, there are countless places to enjoy the beauty and tranquility of the setting. A rare opportunity to enjoy traditional elegance, updated interiors, expansive living spaces, and a private natural setting come together in this distinctive Crownsville home. Schedule your private tour today!

6 Beds ⋅ 6 Baths

Welcome to 2005 Saint Stephens Woods Drive, an impressive estate set on a beautiful, private lot in one of Crownsville's most sought-after wooded settings. The home underwent a major remodel, transforming every room and creating a combination of timeless traditional character with thoughtfully modernized living spaces. Designed for both everyday living and memorable entertaining, this expansive home offers an extraordinary combination of generous living spaces, multiple bedroom levels, beautifully updated bathrooms, and seamless connections to the outdoors. The main level welcomes you with an elegant formal living room and dining room, a private library/study, two convenient powder rooms, and a spacious laundry room. At the heart of the home, the kitchen opens to a dramatic great room, creating an inviting gathering space filled with natural light and views of the surrounding landscape. From the great room, step directly onto the rear porch and decks overlooking the private grounds, pond, and mature woods. Upstairs, the primary bedroom is a true retreat, highlighted by an amazing primary bathroom that offers a unique spa-like experience. A second bedroom features its own en-suite bath, while additional bedrooms are thoughtfully served by a Jack-and-Jill bath. A second upper level adds two more bedrooms and a full bath, bringing the home to six bedrooms and offering tremendous flexibility for family, guests, work-from-home spaces, or hobbies. With bathrooms and individual rooms remodeled and upgraded over the years, the home has been continually refreshed to meet today's expectations for comfort, style, and functionality. The finished lower level takes entertaining and recreation to another level. A spacious recreation room provides plenty of room to gather, while a dedicated gym makes staying active convenient at home. A fun turf-lined "soccer" room adds a unique touch for athletes and kids alike, and the lower-level bar creates the perfect setting for game days and casual entertaining. Walk directly from this level to the patio and enjoy even more outdoor living space. A three-car side-entry garage provides abundant parking and storage, while the private lot offers a peaceful backdrop of trees and pond views. With multiple decks and a rear porch, there are countless places to enjoy the beauty and tranquility of the setting. A rare opportunity to enjoy traditional elegance, updated interiors, expansive living spaces, and a private natural setting come together in this distinctive Crownsville home. Schedule your private tour today!

2005 Saint Stephens Woods Dr, Crownsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4433727171

$1,499,900

Experience luxury, privacy, and exceptional versatility in this stunning 8,600+ total finished sq. ft. home in Crownsville, set on 1.3 private acres surrounded by beautiful natural views. Designed with multi-generational living in mind, the home features two spacious primary suites, including a main-level suite and a second-level primary retreat. Enjoy a custom-designed home theater, full second kitchen, wet bar, 3-car garage, new roof, and whole-house backup generator. With expansive living spaces, premium amenities, and a peaceful private setting, this exceptional property offers the perfect blend of luxury, comfort, and functionality.

6 Beds ⋅ 7 Baths

Experience luxury, privacy, and exceptional versatility in this stunning 8,600+ total finished sq. ft. home in Crownsville, set on 1.3 private acres surrounded by beautiful natural views. Designed with multi-generational living in mind, the home features two spacious primary suites, including a main-level suite and a second-level primary retreat. Enjoy a custom-designed home theater, full second kitchen, wet bar, 3-car garage, new roof, and whole-house backup generator. With expansive living spaces, premium amenities, and a peaceful private setting, this exceptional property offers the perfect blend of luxury, comfort, and functionality.

1178 Gumbottom Rd, Crownsville

Listing courtesy of Invision Realty Inc.. Contact:

$2,349,999

Some Places Witness History. Others Become Part of It. Tucked away on one of Maryland's most historic corridors, 1116 & 1118 Gumbottom Road encompasses nearly 45 acres of history, legend, and possibility. Once a farm and steeped in local lore with ties to Maryland's colonial and Revolutionary-era heritage, this is more than a home—it's a rare opportunity to become part of the American story. Set on a quiet no-through road, the property includes approximately 40 acres plus a separate 5-acre parcel with a 1997 perc test on file (county approval required; buyers to verify). Whether envisioned as a private estate, equestrian retreat, homestead/hobby farm, or multi-generational compound, the possibilities are as expansive as the landscape itself. Rolling pastures, mature trees, ATV trails, and multiple outbuildings—including a barn and former horse corral—create a setting that feels worlds away, yet remains convenient to Annapolis, Baltimore, Washington, D.C., golf courses, marinas, dining, and shopping. The thoughtfully updated farmhouse blends modern comfort with timeless character. Recent improvements include updates to the roof, barn, electrical and plumbing systems, flooring, paint, and bathrooms, preserving the home's charm while making it move-in ready. Inside, six bedrooms and six bathrooms offer exceptional flexibility. The heart of the home is a welcoming kitchen with quartz countertops that opens to a warm family room with exposed beams and a fireplace. A formal dining room, sun-filled office/parlor overlooking magnolia trees, and a main-level primary suite with private entrance, ensuite bath, and sweeping pasture views complete the first floor. Upstairs, three additional bedrooms include a private ensuite and two connected by a charming secret passageway, along with a beautifully renovated full bath. The lower level features a spacious recreation room, workshop, half bath, and direct access to the three-car garage. Outdoors, the lifestyle opportunities are endless. Explore wooded trails, gather around the secluded campsite and fire pit, practice your golf swing, relax by the pool, or simply enjoy the peace and privacy of your own historic countryside retreat. Conveniently located near golf courses, dining, shopping, and boating, this is more than a home—it’s a rare opportunity to enjoy a turnkey property with room to grow. Sale includes the 5-acre parcel known as 1118 Gumbottom Rd.(a previous perc was done in 1997).*Per the county, buyers must verify independently. Agents please see remarks. Rarely does a property offer this combination of acreage, character, history, and future potential. More than a home, this is a legacy property—one that has witnessed generations of Maryland history and is ready for its next chapter.

6 Beds ⋅ 6 Baths

Some Places Witness History. Others Become Part of It. Tucked away on one of Maryland's most historic corridors, 1116 & 1118 Gumbottom Road encompasses nearly 45 acres of history, legend, and possibility. Once a farm and steeped in local lore with ties to Maryland's colonial and Revolutionary-era heritage, this is more than a home—it's a rare opportunity to become part of the American story. Set on a quiet no-through road, the property includes approximately 40 acres plus a separate 5-acre parcel with a 1997 perc test on file (county approval required; buyers to verify). Whether envisioned as a private estate, equestrian retreat, homestead/hobby farm, or multi-generational compound, the possibilities are as expansive as the landscape itself. Rolling pastures, mature trees, ATV trails, and multiple outbuildings—including a barn and former horse corral—create a setting that feels worlds away, yet remains convenient to Annapolis, Baltimore, Washington, D.C., golf courses, marinas, dining, and shopping. The thoughtfully updated farmhouse blends modern comfort with timeless character. Recent improvements include updates to the roof, barn, electrical and plumbing systems, flooring, paint, and bathrooms, preserving the home's charm while making it move-in ready. Inside, six bedrooms and six bathrooms offer exceptional flexibility. The heart of the home is a welcoming kitchen with quartz countertops that opens to a warm family room with exposed beams and a fireplace. A formal dining room, sun-filled office/parlor overlooking magnolia trees, and a main-level primary suite with private entrance, ensuite bath, and sweeping pasture views complete the first floor. Upstairs, three additional bedrooms include a private ensuite and two connected by a charming secret passageway, along with a beautifully renovated full bath. The lower level features a spacious recreation room, workshop, half bath, and direct access to the three-car garage. Outdoors, the lifestyle opportunities are endless. Explore wooded trails, gather around the secluded campsite and fire pit, practice your golf swing, relax by the pool, or simply enjoy the peace and privacy of your own historic countryside retreat. Conveniently located near golf courses, dining, shopping, and boating, this is more than a home—it’s a rare opportunity to enjoy a turnkey property with room to grow. Sale includes the 5-acre parcel known as 1118 Gumbottom Rd.(a previous perc was done in 1997).*Per the county, buyers must verify independently. Agents please see remarks. Rarely does a property offer this combination of acreage, character, history, and future potential. More than a home, this is a legacy property—one that has witnessed generations of Maryland history and is ready for its next chapter.

1116 Gumbottom Rd, Crownsville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767