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Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.

One of the most popular communities provided by Maryland Sandbox

274

# of Listings

3

Avg # of Bedrooms

$510

Avg. $ / Sq.Ft.

$1,357,507

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

274 Properties Found. Page 1 of 19.

A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and sophistication.

Set on just under a half acre of level waterfront, the property showcases one of the most complete private pier systems in the area: a heavily built main pier, two floating docks, and three boat lifts (16,000lb, 8,000lb, and 2,500lb), plus lighting, water, 30/50-amp shore power, Tide Slide moorings, and 6' MLW at the 70' T-head. A charming boathouse and waterside deck capture the magic of Spa Creek from morning to sunset.

Outdoor living is exceptional. A stunning 40' x 20' PebbleTec saltwater pool—rebuilt in 2024—anchors a series of Ipe decks and natural stone patios and decks designed for effortless entertaining. The outdoor kitchen with piped natural gas grill, refrigerator, and sink extends gatherings well into the warm months, while covered and uncovered spaces offer year-round enjoyment.

The exterior speaks to enduring quality with Carderock stone foundations, mahogany trim and ceilings, Loewen windows, Canadian cedar siding, copper gutters and flashings, and custom mahogany entry doors. A detached heated and cooled two-car garage includes a beautifully finished upper level with kitchenette, laundry, living/sleeping area, and private bath—ideal for guests or an au pair.

Inside, the home is defined by warm natural luxury featuring a stunning barrel vaulted mahogany ceiling with cove lighting. Additional curated details include: mahogany doors, black bronze hardware, 5" Cumaru flooring, custom cabinetry, and extensive millwork throughout. The chef’s kitchen features Sub-Zero and Wolf appliances with granite and soapstone surfaces. The main level Primary suite with inspiring view of pool and waterfront provides convenience and options for aging in place. The lower-level recreation spaces provide a relaxed retreat with a private bedroom suite, family room, wet bar, gym and full laundry room. An abundance of thoughtful design is presented throughout the home with multiple wet bars, radiant heated tile floors in five bathrooms and the main-level bar, and four separate laundry areas.

Less than half a mile from Church Circle, this residence delivers the rare ability to live on the water while enjoying the full walk-everywhere lifestyle of historic Annapolis. This is Spa Creek living at its finest: sophisticated, effortless, and undeniably special. Welcome Home!

ANNAPOLIS

5 FRANKLIN STREET

5 Beds

6 Baths

5,993 Sq.Ft.

$12,500,000

MLS#: MDAA2143556

Absolutely one of the finest waterfront offerings in the City of Annapolis. Ideally situated on Spa Creek, this exceptional property boasts sweeping water views and showcases the Annapolis skyline, creating a waterfront lifestyle with a myriad of opportunities for boating, kayaking, and entertaining. Enjoy direct water access with the ability to travel by boat to City Dock, local restaurants, and ice cream destinations—an unmatched Annapolis waterfront lifestyle. A prime vantage point for the Blue Angels, fireworks, and the annual boat parade further confirms the setting.
Set within an exclusive enclave of three prominent homes, the residence features a waterside heated saltwater pool, deep-water pier, and a spacious Ipe deck designed for outdoor living. The grounds are beautifully landscaped with lush boxwoods and specimen plantings, creating a private and serene setting.
Architecturally distinctive and extensively updated, the home showcases high-end renovations by Pyramid Builders. A dramatic marble foyer, floor-to-ceiling windows, and solid wood doors enhance the home’s refined design. The gourmet kitchen is top-of-the-line, featuring Sub-Zero refrigeration, a white 6-burner Viking cooktop, high-gloss Premier cabinetry, Neolith porcelain countertops known for their heat and stain resistance, designer lighting, and a striking floating staircase. A custom bar with a marble countertop is perfectly positioned for entertaining.
Offering 4–5 bedrooms, 5 full and 1 half baths, including a desirable first-floor bedroom, the home also features stained black oak flooring throughout. A two-car garage with ample driveway parking provides convenience for residents and guests alike.

ANNAPOLIS

8 SPA VIEW CIRCLE

4 Beds

5 Baths

6,061 Sq.Ft.

$12,500,000

MLS#: MDAA2143164

Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining.

Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors.
Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026.
The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems.
This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!

ANNAPOLIS

3285 HARNESS CREEK ROAD

6 Beds

7 Baths

10,745 Sq.Ft.

$11,650,000

MLS#: MDAA2142870

New on site today

None

ANNAPOLIS

2035 MAIDSTONE FARM ROAD

5 Beds

6 Baths

7,105 Sq.Ft.

$8,750,000

MLS#: MDAA2130456

Perfectly positioned along the waterfront in the prestigious Murray Hill neighborhood of Annapolis, this extraordinary estate represents a rare opportunity to own a fully reimagined luxury residence where privacy, walkability, boating lifestyle, and architectural sophistication converge in one of the East Coast’s most coveted waterfront settings. RenownedBohan Contracting has been extensively renovating the home since October 2025. The home has not been lived in since completion, offering an exceptionally rare “like-new” experience where every finish, appliance, system, and curated detail remains untouched. Set on an unusually expansive waterfront lot for downtown Annapolis standards, the property delivers a sense of scale and privacy that is nearly impossible to replicate within Murray Hill. Mature landscaping, multiple outdoor living spaces, Brazilian Ipe decking, and panoramic water views create a setting that feels worlds away while remaining just moments from the energy and charm of downtown Annapolis. Designed for the discerning buyer seeking a refined waterfront retreat, the residence effortlessly balances elevated entertaining with relaxed coastal living. Whether arriving by boat after a day on the Chesapeake Bay, hosting sunset gatherings overlooking Spa Creek, or enjoying peaceful mornings watching sailboats drift by, the home was designed around an experience. Inside, timeless design and modern luxury unfold at every turn. The fully reimagined chef’s kitchen rivals those found in premier custom estates, anchored by a complete JennAir Noir appliance suite including a 48-inch dual-fuel range with double ovens, professional refrigeration, dual integrated dishwashers, multiple beverage centers, built-in ice maker, and a butler's pantry designed as both a prep and entertaining space. Custom Schrock “Trademark” maple cabinetry, designer-selected Waterworks fixtures, Calacatta Miraggio Cielo quartz with dramatic waterfall detailing, and layered architectural lighting elevate the space into a true showpiece. Throughout the residence, every finish was intentionally selected to create warmth, sophistication, and understated luxury. Wide-plank white oak flooring, custom white oak ceiling beams, Restoration Hardware lighting, Baldwin hardware, integrated Sonos audio throughout the home, Lutron lighting controls, custom plaster fireplaces, upgraded insulation for sound attenuation, and CAT6 wiring provide the seamless blend of craftsmanship and modern infrastructure expected at this caliber of home. The primary suite serves as a private sanctuary, complete with custom built-ins, boutique-style California Closets systems, integrated laundry, and a bespoke fireplace designed to create an atmosphere reminiscent of a luxury waterfront hotel suite. Every secondary space continues the same level of thoughtful execution and design continuity rarely achieved in residential renovations. Outside, the waterfront experience becomes truly exceptional. A private pier with electric, boat lift, paver stone extended driveway, refinished gates, and oversized outdoor entertaining areas creates a lifestyle tailored for effortless luxury. The property’s unique positioning offers both protected water access and breathtaking views while maintaining an uncommon sense of seclusion in the heart of Annapolis. Located just minutes from Downtown Annapolis, the United States Naval Academy, award-winning restaurants, yacht clubs, boutique shopping, and private aviation access, this home is ideally suited for the executive or entrepreneur seeking an uncompromising second home or primary waterfront residence within easy reach of Washington D.C., Northern Virginia, Philadelphia, and New York. The ability to enjoy a true luxury waterfront lifestyle with boating access, walkability, privacy, and substantial land all within one of Annapolis’ most prestigious neighborhoods is extraordinarily rare.

ANNAPOLIS

11 S ACTON PLACE

4 Beds

3 Baths

3,658 Sq.Ft.

$7,999,000

MLS#: MDAA2144478

This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection dancing across the water and spilling into a home designed to embrace the view at every turn. This extraordinary residence is both a private retreat and an entertainer’s dream, with expansive balconies and roof decks on every level, making indoor/outdoor living a breeze. Inside, soaring ceilings and walls of glass frame the ever-changing views like a living masterpiece, while the grand chef’s kitchen, stone-floored sunroom, and elegant dining spaces invite gatherings large and small. The primary suite is an entire level of indulgence, complete with soaring ceilings, a fireplace, spa-like bath, wet bar, expansive dressing room, laundry, and its own private balcony for starlit evenings. Additional ensuite bedrooms and a guest suite with kitchenette ensure comfort for family and friends, while the lower level—with wine cellar, kitchenette, and direct access to the pool—extends the living space to the outdoors. With a sandy beach and two private piers, one tucked into Crouches Cove and the other stretching into the Severn river, this estate offers not just a home but a lifestyle of breathtaking vistas on the water, boating adventures at your doorstep, and the unmatched beauty of Annapolis waterfront living. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis, convenient to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., the location provides the very best this region has to offer in a 30-mile radius. If you are looking for a truly special property with EPIC water views, resort like amenities and a great private setting, this is the property you have been waiting for. Welcome Home!

ANNAPOLIS

125 S WINCHESTER ROAD

5 Beds

5 Baths

11,269 Sq.Ft.

$7,500,000

MLS#: MDAA2132598

Escape to another world with this striking French modern waterfront estate. Exquisitely sited on a premium and private 4.15 acre lot with 600 feet of impressively rip-rapped water frontage, coveted waterfront pool, tennis court and picturesque views of the serene waters of Whitehall Creek. This ultra-luxe 9,000+ square-foot, 7 bedroom, 5.5 bathroom custom built home has been completely renovated. It is evident from the moment you walk in the front door that no expense was spared with this stunning home. Curated with premium quality, top of the line materials, combined with the tranquil views, exquisite design, and top-tier finishes, 1524 Cedar Lane Farm Road is truly one-of-a-kind and showcases unparalleled craftsmanship. The property both inside and out is an absolute entertainer's dream. The lush lawn and landscaping gracefully extends to the water's edge and leads to the well-appointed multi-slip IPE pier with boat lifts, 2 jet ski lifts, upgraded power, water and great lighting including underwater LED fishing lights. Inside, this stunning home boasts an awe-inspiring Great Room with soaring ceilings, architectural beams, and panoramic water views and features brushed Teak hardwood flooring, renovated high-end gourmet Kitchen with marble counters, 10 burner Wolf range, 5 fireplaces, Restoration Hardware lighting, renovated bathrooms throughout and much more! Fall asleep to captivating, sweeping views from the Primary's suite, enjoy watching the early morning wildlife activity on the water. Located on Whitehall Creek which flows out to Whitehall Bay and beyond to the Chesapeake Bay, you are perfectly located to take advantage of the Bay's best cruising and fishing areas. Attractive destinations such as the Annapolis Harbor, Baltimore's Inner Harbor, St. Michaels, Oxford, and Solomon's Island are only a short cruise away and just minutes from accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

1524 CEDAR LANE FARM ROAD

7 Beds

5 Baths

9,024 Sq.Ft.

$6,995,000

MLS#: MDAA2131054

Standing proudly along the South River, just minutes from downtown Annapolis and the open waters of the Chesapeake Bay, this custom-built 2015 shingle-style residence captures the essence of refined waterfront living with a seamless balance of elegance, comfort, and connection to the outdoors. Thoughtfully designed and bathed in natural light, the home is positioned to take full advantage of its spectacular, ever-changing views, while an energy-efficient geothermal system provides exceptional year-round comfort and sustainability.

The main level is anchored by a beautifully appointed primary suite, offering a private retreat with a custom-designed closet and a spa-inspired bath. A soaking tub perfectly positioned to overlook the pool and waterfront creates a serene daily ritual, complemented by a walk-in shower and refined finishes throughout. The living spaces flow effortlessly from the kitchen to the dining area and living room, creating an inviting setting for both intimate gatherings and larger-scale entertaining, all enhanced by walls of windows that frame the surrounding landscape and water views from every room

Upstairs, two ensuite bedrooms each enjoy sweeping views of the South River, along with private balconies that invite quiet mornings and sunset reflections. The home’s thoughtful layout ensures both privacy and connection, with each space designed to highlight the remarkable setting.

Outdoors, the experience is equally compelling. The inviting waterside pool and multiple stone patios serve as the centerpiece for summer living, surrounded by impeccable, professionally curated landscaping that enhances both beauty and privacy. At the water’s edge, a charming auxiliary structure offers endless flexibility, ideal as a studio, creative retreat, or convenient storage for waterfront essentials.

With 219 feet of shoreline and just under an acre of beautifully sited land, this exceptional waterfront setting is designed for those who truly embrace life on the water. A private deep-water, multi-slip pier equipped with two boat lifts makes it effortless to head out at a moment’s notice, whether for an early morning cruise, an afternoon of fishing and watersports, or a sunset run along the South River into the open expanse of the Chesapeake Bay. From leisurely days spent boating and exploring nearby coves to hosting friends dockside or simply enjoying the ever-changing views, this property offers a seamless connection to a lifestyle defined by freedom, adventure, and the enduring appeal of waterfront living.

Set within the sought-after Wild Rose Shores community on Ferry Point, this exceptional property delivers a rare combination of newer construction, thoughtful design, and an elevated waterfront lifestyle in one of the Annapolis area’s most desirable settings. Welcome Home!

ANNAPOLIS

411 FERRY POINT ROAD

3 Beds

3 Baths

3,287 Sq.Ft.

$6,725,000

MLS#: MDAA2143624

Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career.

Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a suitcase and begin enjoying the Annapolis waterfront lifestyle from day one.

The unrivaled architectural detail, exquisitely curated finishes, and sweeping views across Spa Creek elevate this residence into a class of its own. Privately positioned at the end of a quiet street within one of downtown’s most coveted waterfront enclaves, this 3-bedroom, 3.5-bath retreat is equally suited as an elegant weekend escape or a full-time residence.

Dramatic Palladian windows bathe the interiors in natural light while perfectly framing the ever-changing harbor views. At the heart of the home, the gourmet kitchen—appointed with custom cabinetry, premium appliances, and a striking designer hood—flows seamlessly into both the formal living room and inviting family room, each enhanced by a gas fireplace and captivating water vistas. A main-level secondary primary suite offers comfort and flexibility for guests of all generations.

Upstairs, the extraordinary waterside primary suite features vaulted ceilings, walls of glass, a gas fireplace, spa-inspired bath with soaking tub, and a custom dressing room with center island. A private balcony provides the ideal perch for sunrise coffee or sunset reflections overlooking Spa Creek, Annapolis Harbor, and Eastport.

Designed for effortless waterfront living, two deep-water piers with approximately 9 feet of MLW accommodate substantial vessels, with immediate access to the Severn River, the Chesapeake Bay, and beyond. Walkable to the shops, restaurants, and charm of downtown, this rare offering delivers convenience, privacy, elegance, and ease in one remarkable package. Welcome Home!

ANNAPOLIS

1 SHIPWRIGHT HARBOR

3 Beds

3 Baths

3,108 Sq.Ft.

$5,898,000

MLS#: MDAA2132250

Prime location at the intersection of Route2/Solomons Island Rd and MD-450/West St. 100% Leased! Building was recently fully remodeled to include New Glass, New Facade, New Elevator, New HVAC and New Lobbies. 120 free surface parking spaces (4/1,000 ratio). Easy access to Routes 50 and 97.

ANNAPOLIS

2024 WEST STREET

None Beds

None Baths

34,573 Sq.Ft.

$5,850,000

MLS#: MDAA2131116

Set on 4.5 picturesque acres along the Severn River, this exceptional Tudor–French Country estate blends timeless architecture with refined craftsmanship just minutes from downtown Annapolis. Panoramic river views define the property, complemented by a detached two-car garage with private guest quarters featuring a kitchenette and full bath. Outdoor living is equally compelling, with a fire pit, boathouse for convenient dockside storage, and a private pier equipped with a 20,000 lb boat lift—ideal for embracing true waterfront living. Access the dock via a scenic path and stairs or by private tram. Inside, light-filled interiors capture sweeping water views and flow effortlessly through a thoughtfully designed floor plan suited for both everyday living and elegant entertaining. A dramatic curved staircase anchors the foyer, leading to a main level that includes a gourmet kitchen, living room with a gas fireplace, bar, office, mudroom, two powder rooms, and a formal dining room. The chef’s kitchen is outfitted with a 6+ burner Wolf range, hammered copper sinks, dual dishwashers, expansive prep space, and a generous pantry. The living area opens to a spacious deck, perfect for waterfront gatherings. Upstairs, the primary suite offers a private retreat with its own balcony, wet bar, two walk-in closets, dual vanities, and a walk-in shower. This level also includes flexible bonus space, two additional bedrooms, a full bath, and a laundry room. The lower level expands the living space with two additional bedrooms, two full baths, a family room with fireplace and bar, and a game room—all with easy outdoor access and continued river views. All levels of this home can be accessed by an elevator. Some of the well executed details in this home include wooden beams, arched doorways, curved walls, extensive stone work, intricate iron work, dramatic light fixtures, walnut flooring, dramatic built-ins and the highest level of craftsmanship and execution. A rare opportunity to own a meticulously crafted waterfront retreat that seamlessly combines old-world charm with modern luxury.

ANNAPOLIS

1716 SEVERN FOREST DRIVE

5 Beds

4 Baths

6,573 Sq.Ft.

$5,775,000

MLS#: MDAA2139364

Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715-1717 Porters Hill Road is a unique heritage property with over a century of history. Set on a 2.96 acre lot with 429 ft of waterfrontage, the property is comprised of two separate parcels and includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 8+ ft water depth and can accommodate a large vessel as well as an assortment of smaller boats. The tram makes access to the water effortless, and the entire property enjoys exceptional privacy. Steeped in its storied past yet thoughtfully updated for modern living, this retreat captures the perfect balance of historic charm and casual elegance. The heart of the main home is a sunlit great room with original log walls and quarried stone fireplace, a vaulted ceiling, and expansive windows which frame water views at every turn. An adjoining den, with separate entrance option, is a perfect place to relax. This could easily become another main level bedroom with ensuite bathroom. The kitchen is striking under its vaulted ceiling accented by exposed beams. The custom cabinetry and generous island give the space so much functionality while maintaining the artisanal character. The kitchen opens to the dining area overlooking the water. Step outside and you’re embraced by nature: multiple porches and decks overlook lush, manicured grounds that lead down to the water’s edge. The main-level primary suite is a true sanctuary, designed for privacy and tranquility. The bedroom, with a vaulted ceiling, has a screened porch overlooking the water. Two expansive walk-in closets offer custom organization systems that would make a clothing connoisseur smile. The spa-like bathroom gets lots of natural light from the windows that frame the water, and the freestanding soaking tub is situated to enjoy this view. A dual-sink vanity, heated floors, and generous walk-in shower with a built-in bench make getting ready feel effortless and luxurious. A dedicated laundry area just off the hallway makes day-to-day living very easy. Part of the primary suite is a gracious office with gas fireplace and outdoor access. This is a totally flexible space: install a wall of bookshelves and you’d have a lovely library. Upstairs, there are two generously sized bedrooms. One has water views and a waterside balcony; the other overlooks the lush landscaping out front. There is a hall bathroom. A separate guest bedroom suite above the garage, complete with its own living area and luxe bathroom, is ideal for visiting friends and family who desire more privacy. The second home, on the 1717 lot, offers a contemporary setting with clean lines and spacious deck. The dramatic two-story family room facing the kitchen means tons of natural light for the entire house. The main level has a bedroom and full bathroom, and there are two more bedrooms upstairs that share a hall bath. The walk-out lower level features a rec room and a large utility/storage area.

The Historical Context: Originally built in the 1880s, the log house on 1715 was one of three identical structures used as hunting lodges. It is the only one that remains. The construction of the log house is one of great craftmanship, including sizing each log to be approximately the same diameter as others. It's amazing that 1715-1717 has such easy access to downtown Annapolis by car or boat, and for those who commute to DC or Baltimore, Route 50 is less than 10 minutes. This incredible heritage property, encompassing almost three acres, two dwellings and a deep-water pier with boathouse, is the ultimate Annapolis retreat.

ANNAPOLIS

17151717 PORTERS HILL RD

7 Beds

5 Baths

7,500 Sq.Ft.

$4,950,000

MLS#: MDAA2139184

Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715 Porters Hill Road is a unique heritage property with over a century of history. Set on a 1.7 acre lot with 265 ft of waterfrontage, the property includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 7+ ft water depth and can accommodate a large vessel as well as an assortment of smaller boats. The tram makes access to the water effortless, and the entire property enjoys an exceptional privacy.
Steeped in its storied past yet thoughtfully updated for modern living, this retreat captures the perfect balance of historic charm and casual elegance. The heart of the home is a sunlit great room with original log walls and quarried stone fireplace, a vaulted ceiling, and expansive windows which frame water views at every turn. An adjoining den, with separate entrance option, is a perfect place to relax. This could easily become another main level bedroom with ensuite bathroom. The kitchen is striking under its vaulted ceiling accented by exposed beams. The custom cabinetry, GE Monogram stainless steel appliances and generous island give the space so much functionality while maintaining the artisanal character. The kitchen opens to the dining area overlooking the water. The table is anchored by a craftsman-style light fixture, and the entire first and second floors have beautiful wood floors. Step outside and you’re embraced by nature: multiple porches and decks overlook lush, manicured grounds that lead down to the water’s edge.
The main-level primary suite is a true sanctuary, designed for privacy and tranquility. The bedroom, with a vaulted ceiling, has a screened porch overlooking the water. Two expansive walk-in closets offer custom organization systems that would make a clothing connoisseur smile. The spa-like bathroom gets lots of natural light from the windows that frame the water, and the freestanding soaking tub is situated to enjoy this view. A dual-sink vanity, heated floors, generous walk-in shower with a built-in bench, and a spacious cosmetic area with dedicated seating make getting ready feel effortless and luxurious. A dedicated laundry area just off the hallway makes day-to-day living very easy. Part of the primary suite is a gracious office with gas fireplace and outdoor access. This is a totally flexible space: install a wall of bookshelves and you’d have a lovely library.
Upstairs, there are two generously sized bedrooms. One has water views and a waterside balcony; the other overlooks the lush landscaping out front. There is a hall bathroom. A separate guest bedroom suite above the garage, complete with its own living area and luxe bathroom, is ideal for visiting friends and family who desire more privacy. The Historical Context: Originally built in the 1880s, this log house was one of three identical structures used as hunting lodges. It is the only one that remains. The construction of the log house is one of great craftmanship, including sizing each log to be approximately the same diameter as others. Lore has it that around the turn of the 20th century, the Naval academy wanted to acquire more land by the academy and traded this peninsula for land across from College Creek. The Naval Academy superintendent, Admiral David Porter, could be where the name Porter’s Hill derived from. In the 1920’s, the Whitehead family – three brothers known for running bootleg liquor to Baltimore and Washington during Prohibition — used the property as a place to entertain and stop on the way to Baltimore. In the 1940s, the brothers’ exploits caught up with them, and the State of Maryland confiscated the Porters Hill peninsula. Through a unique trade involving the Jones family’s gravel pit (now the site of the 895 Tunnel), this private waterfront enclave found its next chapter.

ANNAPOLIS

1715 PORTERS HILL ROAD

4 Beds

4 Baths

6,594 Sq.Ft.

$3,950,000

MLS#: MDAA2142344

New on site 1 day ago

A truly exceptional historic residence is now being offered for sale in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa 1830 residence masterfully restored and refined in collaboration with renowned Hammond Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic 3-story brick home seamlessly blends timeless architectural beauty with sophisticated modern livability. Spanning over 5,400 square feet, the residence offers an extraordinary combination of elegance, scale, and versatility with 6 bedrooms, 5 bathrooms, and beautifully curated living spaces throughout. Rich period details, soaring ceilings, and remarkable craftsmanship define the interiors, while a dramatic 3-story brick fireplace serves as a stunning architectural focal point. Thoughtful renovations honor the home’s storied history while elevating it with refined finishes and modern functionality. Equally captivating are the home’s enchanting outdoor spaces, where beautifully manicured grounds, lush landscaping, vibrant flower beds, and a serene koi pond create a private garden retreat rarely found in downtown Annapolis. Set on a prime 7,324 square foot lot along one of the city’s most coveted historic streets, the property offers an atmosphere of tranquility and timeless elegance just moments from the waterfront and bustling downtown scene. Whether envisioned as a luxurious private residence, multi-generational living arrangement, or exceptional investment opportunity, this remarkable property offers an unmatched lifestyle surrounded by boutique shopping, acclaimed waterfront dining, art galleries, historic landmarks, and the unmistakable charm of Annapolis Harbor. Elegant, iconic, and rich with history, 16 Maryland Avenue represents downtown Annapolis living at its absolute finest.

ANNAPOLIS

16 MARYLAND AVENUE

6 Beds

5 Baths

4,474 Sq.Ft.

$3,849,000

MLS#: MDAA2142212

TO-BE-BUILT home by Mueller Homes, a highly regarded local builder, is prepared to construct the proposed 3 or 4 bedroom, 4-bath home designed for connection and comfort. Tucked into the charming waterfront community of Bay Ridge in Anne Arundel County, this thoughtfully designed coastal home blends classic seaside character with modern livability—perfectly scaled for relaxed, everyday life. The first floor offers an easy, open flow anchored by a spacious kitchen, seamlessly connecting to a dining area and living room. A versatile home office provides flexibility as a potential guest bedroom, while a well-appointed mudroom and dedicated laundry room keep the home organized and functional. Upstairs, the second-floor features three generously sized bedrooms, each complete with its own ensuite bathroom and walk-in closet. The layout also allows for a potential fourth bedroom configuration if desired.

This .22 acre lot has been in the same family for the past 58 years and is coming to market for the first time. With 57 feet of waterfrontage on the sparkling shores of Lake Ogleton, the possibilities are endless for building the waterfront home of your dreams! This property is priced to sell quickly, at $361,000 below the tax assessed value! The sought-after Bay Ridge Community features a plethora of amenities, including a community pool with a clubhouse that overlooks the beautiful waters of the Bay, community beaches on both the River and the Bay, and a community Marina with a newly renovated clubhouse. Off-the-water activities include enjoying the basketball court, playground, ball fields, pickleball courts, common areas, and year-round community activities. Walk or ride your bike for miles along the water and enjoy all the benefits of the Bay Ridge lifestyle. There is no other place like it! Located just minutes from downtown Annapolis and Eastport, which offer the perfect balance of small-town charm and big world sophistication. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97, which provides direct access to Baltimore, BWI, Ft. Meade/NSA, and Washington, DC, or head over the Bay Bridge to the Eastern Shore for a quick beach vacation.

ANNAPOLIS

48 E LAKE DRIVE

4 Beds

4 Baths

3,000 Sq.Ft.

$3,788,000

MLS#: MDAA2142464

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