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$1,495,000
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
$3,100,000
3 Beds ⋅ 4 Baths
Set within the gated waterfront enclave of Bayberry Hill, this distinctive waterfront residence with waterside pool offers an exceptional combination of architectural character, wooded privacy, and sweeping water views. Tucked beneath a mature tree canopy, the property feels wonderfully secluded while opening dramatically toward the water, creating a peaceful retreat designed around the Annapolis waterfront lifestyle. A picturesque approach leads through lush landscaping, pond with water feature and across a charming footbridge to the inviting entrance. Inside, soaring wood-clad ceilings, skylights, expansive windows, and impressive stonework create a warm, contemporary aesthetic. The dramatic great room is anchored by a striking floor-to-ceiling stone fireplace, while walls of glass throughout the home bring the surrounding natural beauty indoors. Multiple living spaces offer exceptional versatility for everyday living and entertaining. A glass-enclosed waterside family room adjacent to the gourmet kitchen captures beautiful views and opens to the expansive deck, creating a seamless connection between indoors and out. A beautifully designed wine cellar with custom wood storage, stone accents, and a tasting area adds another distinctive element. The spacious primary suite is a private retreat with vaulted ceilings, a sitting area, dedicated workspace, private side patio and access to the waterside deck. The spa-inspired bath features dual vanities, an oversized soaking tub positioned beneath windows overlooking the water, and a large walk-in shower. The lower level is designed for entertaining with a spacious recreation and game room featuring a fireplace, custom finishes, and sliding doors opening directly to the poolside deck and hot tub. Two bedrooms with ensuite baths, large closets and spectacular pool and water views create an ideal getaway for family or guests. Outside, a series of decks and terraces cascade toward the shoreline, offering multiple places to relax and take in the views. The waterside swimming pool is surrounded by a generous deck beneath the mature trees, while a separate hot tub provides another peaceful vantage point. At the shoreline, a private pier with multiple slips and boat lifts provides effortless access for boating, paddling, and days on the water. Bayberry Hill offers the privacy of a gated waterfront community with water access and tennis/pickleball courts, all within convenient reach of Downtown Annapolis, BWI, major commuting routes, and Washington, D.C. A truly distinctive waterfront retreat where architecture, privacy, and the natural landscape come together beautifully. Welcome Home!

1304 Saint Pauls Way, Crownsville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,499,900
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:

$1,695,000
5 Beds ⋅ 5 Baths
Welcome to an extraordinary opportunity to create your dream home on a private 2.86-acre estate-style homesite in Crownsville, perfectly positioned for those seeking privacy and tranquility without sacrificing convenience to Annapolis, Baltimore, Washington, D.C., and Northern Virginia. To be built by Whitehall Building & Co., this exceptional custom residence is designed for luxury, flexibility, and today’s multigenerational lifestyle. Offering five bedrooms and expansive living space, this home is ideal for a large family, extended family, frequent guests, or anyone who simply wants room to spread out. The main level features a stunning open-concept kitchen, dining, and family room, creating an effortless flow for everyday living and entertaining. The gourmet chef’s kitchen showcases quartz countertops, custom cabinetry, stainless steel appliances, and a large center island designed to be the heart of the home. A private main-level ensuite bedroom provides exceptional flexibility for guests, in-laws, an au pair, or multigenerational living, while the dedicated main-level office is perfectly suited for today’s work-from-home lifestyle. Upstairs, the luxurious primary suite offers generous walk-in closets and a spa-inspired bath designed as a private retreat. Three additional bedrooms include a Jack-and-Jill bath between two bedrooms and a private ensuite for the third, along with the convenience of an upper-level laundry room. The lower level expands the possibilities with a large recreation room included and optional flex space, sixth bedroom, full bath, home theater, gym, playroom, wine room, second family room, or whatever best suits your lifestyle. An oversized two-car garage with the option to expand to accommodate up to four vehicles, providing exceptional flexibility for cars, recreational equipment, and storage. Outside, the nearly three-acre homesite offers the privacy and space rarely found this close to Annapolis, with ample room for a resort-style pool, expansive patios, outdoor kitchen, firepit, gardens, or other outdoor living spaces. Surrounded by natural beauty and close to preserved parks and trails, Crownsville offers a peaceful estate setting while remaining exceptionally convenient to the region’s major employment centers, shopping, dining, recreation, and transportation corridors. Enjoy the best of both worlds, the privacy of your own luxury estate and easy access to the Chesapeake Bay, downtown Annapolis, Baltimore, Washington, D.C., and Northern Virginia. This is more than a new construction home, it is an opportunity to build the lifestyle you've been searching for. Private. Sophisticated. Flexible. Timeless.

916 A Woodward Ln, Crownsville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,350,000
5 Beds ⋅ 5 Baths
Welcome home to 503 Teak Road, an exceptional estate set on nearly one acre (0.97) of beautifully maintained grounds in a quiet, sought-after neighborhood. Mature landscaping and thoughtfully designed hardscaping create a striking first impression, setting the stage for a home that seamlessly blends timeless elegance with everyday comfort. Many recent upgrades including a new roof ensure years of worry free ownership. Inside, a soaring two-story foyer welcomes you into the main level, where a dramatic floor-to-ceiling stacked-stone wood-burning fireplace serves as the centerpiece of the living room. Designed for both entertaining and daily living, the thoughtfully planned layout includes a well-appointed kitchen with a sunny breakfast area, a butler's pantry connecting to the formal dining room, a dedicated laundry room, and two private offices—one of which can easily serve as a main-level bedroom. A spacious three-car garage, with ample additional parking, provides exceptional convenience. Outdoor living is equally inviting. Relax on the expansive paver patio, harvest fresh herbs from the kitchen garden, and enjoy added peace of mind with the whole-house backup generator. A 10' x 16' garden shed, nestled among the mature trees, provides generous storage for tools and outdoor equipment. Upstairs, the private, primary suite offers a peaceful retreat complete with a spacious en-suite bath and two large walk-in closets. Five of the six bedrooms in this home are en-suite with walk-in closets. The finished lower level is designed for entertaining and relaxation, featuring a spacious family room with a gas fireplace, a bar and game room, a dedicated media room, a wine cellar, and guest bedroom with a full bath. Ample storage and utility space ensure everything has its place. Water privileged lifestyle: Community amenities, available through the voluntary HOA—include a pier, gazebo, boat ramp, and beach with access to the Severn River. Enjoy weekends on the water, fishing, swimming and boating, with nearby marinas adding even more convenience. With quick access to Annapolis, Baltimore, Washington, D.C., BWI Airport, Fort Meade, and beyond, this is luxury living at its finest—quietly positioned, elegantly appointed, and perfectly connected.

503 Teak Rd, Crownsville

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

$1,250,000
4 Beds ⋅ 4 Baths
This is the one you have been waiting for! Totally new and renovated from top to bottom this contemporary four levelshouse is your private daily getaway from all the daily hustle and bustle. Located on over two wooded acres but only a few minutes from Annapolis and the Chesapeake Bay, short distance to either Baltimore or DC, it is strategically located. The master bedroom on the main level also features a loft perfect for a home office or studyand accessible only by a spiral staircase. The master bathroom is striking with a soaking tub and a large walk- in shower. The centerpiece of this home is the new large kitchen with a beautiful island overlooking the gorgeous family room with recessed lights and 13 skylights! The new rear deck is one of a kind, just the overall size will be a pleasant surprise, a great place to chill out and enjoy nature or just hang out with friends and neighbors.

1185 Harbor Oak Dr, Crownsville

Listing courtesy of Excel Realty. Contact:

$1,275,000
4 Beds ⋅ 2 Baths
A boater's dream on the Severn River with a price reduction to $1,275,000. Open house this Saturday 8/15, from 11am to 1pm. Welcome to waterfront living at its finest! This stunning 4-bedroom, 2-bath raised rancher is perfectly positioned on a wide stretch of the Severn River, offering breathtaking water views from both the main living areas and the lower-level recreation room. Soaring vaulted ceilings in the living and dining rooms create an open, airy ambiance, while the rec room — complete with a wet bar — is the perfect place to unwind after a day on the water. The pier is a true showpiece, featuring a large landing and two covered boat slips with brand-new roofs — one accommodating vessels 40+ feet and a second equipped with a boat lift for smaller crafts. Additional pier upgrades include updated dock lighting, added electrical outlets, and water service directly to the dock, plus 60 feet of new rip-rap rocks protecting the waterline. Inside, no detail has been overlooked. The fully renovated kitchen and bathrooms shine alongside new hardwood floors in the kitchen, dining, and living areas. All-new windows, exterior and sliding glass doors with electric blinds, and updated interior and exterior lighting complete the transformation. The new roof, fresh siding, gutters, and downspouts ensure worry-free ownership for years to come. Outdoor living is equally impressive — enjoy the new custom paver walkway leading to your firepit overlooking the highly desirable Severn River. Spacious two car garage is heated with 240v electric car charging hook-up. Multiple outbuildings provide excellent storage for all your tools and boating equipment. Ideally located in close proximity to Historic Annapolis while also offering an easy commute to both Baltimore and Washington, DC — this is the waterfront lifestyle you've been waiting for.

1164 Oak View Dr, Crownsville

Listing courtesy of Curtis Real Estate Company. Contact:

$1,375,000
4 Beds ⋅ 4 Baths
Perched on the Severn River, 928 Waterview Drive is a well-maintained waterfront home in the desirable community of Arden on the Severn. Set on a one-third acre lot with a level waterside yard and a convenient tram to the private, multi-slip deepwater pier, this residence invites you to embrace the very best of coastal living. So many boating options, with water depth that can accommodate a sailboat. The home offers over 3,000 square feet of thoughtfully designed living space across three stories. The main level’s open floor plan offers an easy flow between rooms and lots of natural light, while the fireplace in the family room adds a coziness to the space. The spacious kitchen overlooks the waterside deck and opens into the formal dining room. There is casual dining at the breakfast bar, and there's also space for a kitchen table facing the water. The adjoining family room has water views and provides access to the lovely three-season room. Hardwood floors are found in the dining room and family room. Upstairs, a generous primary suite impresses with cathedral ceiling and ample closet space. The ensuite primary bathroom offers dual sinks, walk-in shower and soaking tub. Two additional bedrooms upstairs are generously sized and share a bathroom. The fully finished, walk-out lower level adds exceptional versatility, complete with a recreation room, an additional bedroom, and a full bath — wonderful for guests or multigenerational living. Step out to a shaded, waterside patio from the rec room. An attached two-car garage and ample deck and patio spaces complete this wonderful property. New architectural shingle roof installed July, 2026, and new hot water heater installed April, 2026. Arden on the Severn is a beloved waterfront community, where residents enjoy beaches, boat ramps, a dinghy dock, a covered pavilion, picnic areas, and playgrounds.

928 Waterview Dr, Crownsville

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

$2,349,999
As America celebrates its 250th Anniversary, few properties offer the chance to own a tangible connection to the past. Nestled along one of Maryland's most historic corridors, 1116 & 1118 Gumbottom Road encompasses nearly 45 acres of history, legend, and possibility. Once a horse 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, 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. 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. Sale includes the separate 5-acre parcel known as 1118 Gumbottom Road. A perc test was completed in 1997; buyers are responsible for independently verifying all development potential with Anne Arundel County. 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 this 5-acre parcel known as 1118 Gumbottom Rd. 1116 Gumbottom has 39.96 acres.

1118 Gumbottom Rd, Crownsville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$2,349,999
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