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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
272
# of Listings
3
Avg # of Bedrooms
$428
Avg. $ / Sq.Ft.
$925,284
Med. List Price

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13 Properties Found. Page 1 of 1.

Don't miss this incredible opportunity to build your dream luxury estate home on this amazing private 3.3 acre homesite with amazing waterviews and privacy. Tucked away back off of your 1/4 mile private driveway which sets the tone as you approach your very own oasis. Come witness our vision and be a part of creating a generational estate that Annapolis rarely sees. The main level boasts soaring 10-foot ceilings, exposed beams, and wide plank floors, creating a spacious and inviting atmosphere. The gourmet kitchen is a chef’s dream, featuring built-in cabinetry, sleek quartz countertops and backsplash, a generous island, double ovens, a gas cooktop, and a walk-in pantry. The kitchen seamlessly flows into the dining area, with large windows and glass doors that frame stunning views of the creek. Step outside to a covered patio, perfect for outdoor entertaining, located just off the dining and family room. Upstairs, the expansive primary suite offers panoramic water views through large windows. The spa-like primary bathroom includes a freestanding tub, oversized shower, water closet, and a walk-in closet. This level also features three additional spacious bedrooms, two full bathrooms, and a convenient laundry room. The finished lower level includes a fifth bedroom, a full bathroom, and a large recreation room, providing plenty of space for guests or family activities. Situated on a private 3.3 acre lot with pristine waterfrontage, this property has the ideal depth for a private pier to accommodate your boat. Experience ultimate privacy, luxury, and waterfront living all in one. Appointments are required for a private showing—please contact the listing agent for details and don’t miss out on this once-in-a-lifetime opportunity!
#MDAA2110220

ANNAPOLIS

1632A WINCHESTER ROAD

5 Beds

4 Baths

5,000 Sq.Ft.

$4,950,000

MLS#: MDAA2110220

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.
#MDAA2120604

ANNAPOLIS

1715 PORTERS HILL ROAD

4 Beds

4 Baths

7,887 Sq.Ft.

$3,995,000

MLS#: MDAA2120604

Coveted West Annapolis Waterfront property with deep water floating dock! Recently updated with fresh paint, refinished floors and new carpeting throughout. Experience elegance and grace in this stunning 4 story home that is sure to captivate. The contemporary architecture and voluminous spaces mixed with traditional finishes and floor plan creates a wonderful combination. Expertly designed and built additions include the glass enclosed lanai with elevator and guest room above in 2006, Living room, 2 car garage and bird's nest with balcony completed in 2009, gourmet Kitchen was expanded and beautifully updated in 2015. Upon entry, the soaring foyer is awe-inspiring and the elegant living room, with built-in bar, sets the tone. With 3 custom bars and multiple gathering areas, this home is perfect for entertaining. The gourmet kitchen is a chef's dream, featuring a large island and top-of-the-line finishes and breakfast nook, which flows seamlessly into the spacious family room with walls of windows overlooking Weems Creek. The adjacent library/den boasts mahogany built-ins and flooring, gas fireplace and views; a perfect place to curl up with a book. This home offers three ensuite bedrooms for ultimate comfort and privacy. The master bedroom is a sanctuary with a vaulted ceiling, custom built-ins, enormous walk in closet for 2 and the best views in the house. Wake up every morning and enjoy the activity on the sparkling waters of the creek and the Severn River. The spacious guest room suite with glass breezeway from the main house boasts an elevator directly into the room, creating a truly private oasis for guests and family. This floor also includes an additional bedroom or theater room with adjacent hall bath; providing flexible living options. The fourth floor features a unique bird's nest with elevator access and a wrap-around deck offering panoramic views of Weems Creek and the Severn River. With three elevators throughout the house, accessibility to all four levels is effortless. The exquisite sunroom with folding glass doors epitomizes indoor/outdoor living. Simply open 2 sides of the room to the outdoors and let the party flow onto the sprawling rear deck. The wrap-around IPE deck and multiple level seating areas are ideal for taking in the incredible views from every vista. The lush landscaping and stone stairs lead to the water's edge and the private pier with deep-water floating dock with multiple slips can accommodate a 50ft yacht. Be sure to not miss the stone patio on the way down; ideal for relaxing as the sun sets. This property truly captures the essence of waterfront living by blending luxury and comfort in an unparalleled setting. Welcome Home!
#MDAA2115056

ANNAPOLIS

411 RIDGELY AVENUE

4 Beds

4 Baths

5,950 Sq.Ft.

$3,950,000

MLS#: MDAA2115056

New on site 4 days ago
Come explore the shores of Bay Ridge. As Annapolis's premiere waterfront community, Bay Ridge boasts an Olympic-sized swimming pool, a marina with 120 slips, and a private clubhouse. Serving as home to the Chesapeake Bay Foundation, this community stewards and embodies all of the finer aspects of living on the Chesapeake. With miles of shoreline, private beaches, and breathtaking views, Bay Ridge has become the preferred place for generations of families to call home. Annual parades, festivals, and community events fill the calendars of the welcoming residents and guests alike. This neighborhood is where everyone wants to call home. Completed in the Fall of 2022, this home has served as a model for Whitehall Building & Company, Annapolis' largest waterfront home builder. Comprising 5k sq. ft. of space under roof, it includes 4k sq. ft. of finished space, an oversized 3-car garage, 5BR, and 5.5 baths. The Elevator, walls of windows, and well-appointed finishes of this luxury residence will appeal to buyers from all generations. Completing this offering is a well-groomed, large .44 acre meticulous yard with WIFI irrigation leading to a new pier and 10k lb remote-controlled boat lift. (See video. Sale includes both 90 and 92 E Lake lots which house is built on)
#MDAA2131926

ANNAPOLIS

90 E LAKE DRIVE

5 Beds

5 Baths

4,204 Sq.Ft.

$3,795,000

MLS#: MDAA2131926

This Murray Hill masterpiece is a 5-bedroom, 4 bathroom home that was originally built in 1913 and underwent a complete custom renovation a few years ago. Situated on a double lot on one of the most desirable streets in Annapolis. It blends formal sophistication with modern luxuries including an elevator! Offering rare private driveway, a two-car garage with separate storage room. Featuring over 7,000 sq ft, state-of-the-art custom kitchen with two dishwashers, first and second floor laundry rooms, electric window blinds, screened-in-porch, a fully fenced yard, irrigation system, mature landscaping, two fireplaces, high ceilings, crown and dental molding, custom cabinetry throughout, two zones of HVAC, full service security system with cameras. Generous primary suite with fireplace, his and hers closets, marble shower and dual vanities. This property is a one of a kind and must see.
#MDAA2130800

ANNAPOLIS

39 SOUTHGATE AVENUE

5 Beds

3 Baths

8,647 Sq.Ft.

$3,750,000

MLS#: MDAA2130800

A rare opportunity at the Annapolis Town Center — two units combined into one stunning residence. This 4-bedroom, 3-bath luxury condo features expansive living spaces, two private balconies, and high-end custom finishes throughout. Enjoy the convenience of four garage parking spaces and two storage units, along with all the premier amenities of GrandView Condominiums. This one-of-a-kind residence showcases true custom design and craftsmanship throughout. All main living spaces and bedrooms feature Provenza hardwood flooring, while custom cabinetry and built-ins are designed by Woodworking by Design. The chef’s kitchen impresses with a dramatic Calacatta Lumanyx waterfall island, full-height backsplash, sparkling black perimeter counters, and seamless integration to a glass-front wine room. Smart-home living is elevated with a full Lutron system (including motorized shades), Sonos sound, and security by Petitbon. Designer stone selections carry into every space, from brushed titanium hearths and fireplace walls to quartz vanities, thresholds, and mosaic details in bathrooms and wine room. Sophisticated finishes, modern automation, and bespoke craftsmanship make this luxury condominium truly one of a kind.
#MDAA2124774

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 405 & 406

4 Beds

3 Baths

3,422 Sq.Ft.

$3,600,000

MLS#: MDAA2124774

Exceptional Waterfront and Beachfront living on Horn Point in coveted Eastport. Launch your kayak or SUP after morning coffee, and watch the sailboat races from your deck, yard, and beach later that day. This elegant charmer is the Perfect place to watch the Blue Angels without leaving home! The home was completely re-built in 2009 (all that remains is the original garage floor) and has been meticulously maintained. Upon your first steps inside, you'll be drawn to spectacular views of the Severn River as you walk through an open floor plan adorned with rich Brazilian hardwood flooring and abundant natural light. The main level offers a great room with a perfectly blended family room, dining area with a gas fireplace, a second sitting area, a gourmet kitchen and private deck. A separate hall leads you to 2 spacious bedrooms and full bath. The gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a generous island perfect for entertaining. Dining and relaxing on your private deck overlooking the yard and beach is steps away from the kitchen. Privately located behind the kitchen the home gym with vaulted ceilings and water views can be converted to a home office, play area, an additional sitting room, and more. The main level laundry room and hallway to the garage also lead you to a bonus work-room attached to the garage. This room could easily become a creative space, painting studio, she-shed, or additional home office. The beautiful floating staircase complements the great room and leads you to the upper level. The primary suite is all about the view! Breathtaking Severn River and Chesapeake Bay- front views and a spa-like bathroom with a jetted tub and walk-in, steam shower. The primary suite would not be complete without a large dressing room with access to a separate home office / sitting room with water views, and private deck. The fourth bedroom with en suite is on the upper level, with a walk in closet and access to attic storage. The exterior is equally impressive, showcasing a yard and private beach on the Severn River. Relax on the balcony or deck, surrounded by lush landscaping and exterior lighting that enhances the ambiance. The property also includes an attached garage with attic storage above it and ample driveway space for convenience. A generator is included and a pier is an option for your buyer. With a prime bayside location, this home offers not just a residence but a lifestyle of luxury and tranquility. Experience the perfect blend of modern amenities and natural beauty, making every day feel like a vacation. Don't miss the opportunity to call this remarkable property your own!
#MDAA2126296

ANNAPOLIS

513 HORN POINT DRIVE

4 Beds

3 Baths

3,236 Sq.Ft.

$3,500,000

MLS#: MDAA2126296

Wake up to Severn River views, not dock maintenance! 812 Coachway is an all-brick waterfront estate in The Downs on the Severn, offering 6 bedrooms, 7 baths, and over 7,500 square feet of refined indoor-outdoor living. Thoughtfully updated to merge timeless architecture with modern luxury, nearly every room frames stunning Severn River views. A two-story foyer leads to the office with custom built-ins, living and dining rooms, and a sunroom that opens to expansive decks and terraces. The gourmet kitchen features quartz counters, stainless steel appliances, induction cooktop, and a bay-window breakfast area flowing seamlessly into the family room with fireplace and full bar. The upper-level primary suite includes a fireplace, brand new spa bathroom with wet room, and a private deck overlooking the water. Four additional bedrooms, multiple updated baths, and an upper-level laundry offer effortless comfort. The walkout lower level is designed for gathering, with a recreation room, wet bar, exercise/guest suite, and direct access to the pool, patios, and fenced yard. Recent upgrades include new composite decks and refreshed landscaping for a resort-like, low-maintenance setting. The Downs is one of Annapolis’s premier waterfront neighborhoods, offering: • Two deep-water marinas with direct Severn River and Chesapeake Bay access • Kayak & paddleboard launch areas • Clubhouse, pool, tennis & pickleball courts • Walking paths and peaceful, nature-rich surroundings Think morning coffee on the water. Paddleboard before brunch. Wine on the deck at sunset. A serene, elevated waterfront lifestyle with a “waterfront yoga deck” feel and true *lock-and-leave* convenience. Boat slips are available at the marina 2 minutes away!
#MDAA2121546

ANNAPOLIS

812 COACHWAY

6 Beds

5 Baths

8,349 Sq.Ft.

$3,499,999

MLS#: MDAA2121546

Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and 2.5 baths it has all the elements needed to enjoy life to the fullest; either as the perfect weekend retreat or permanent residence. The Annapolis area and the surrounding waterways are sure to entertain in every season. The upper level of the home is dedicated to the spacious Primary suite with unique sitting area and expansive roof deck. Take in panoramic views of Spa Creek, Annapolis Harbor and Eastport. An unparalleled vantage point for sunrise coffee or sunset cocktails. The main level offers multiple cozy gathering areas including a formal living room with fireplace, home office and light filled gourmet kitchen with dining area. The kitchen area flows effortlessly into the dining area and out onto the rear deck overlooking Spa Creek. Perfect for gathers of all sizes and dining al fresco. The lower level provides an ideal retreat for family or guests with 2 spacious bedroom a full bath and a cozy family room with fireplace. Head out to the charming covered patio to read a book or sip your evening cocktail or venture out on the water from the private pier. The amazing location is walkable to everything Annapolis has to offer and Spa Creek provides quick access to the Chesapeake Bay and beyond. Welcome Home!
#MDAA2109630

ANNAPOLIS

9 SHIPWRIGHT STREET

3 Beds

2 Baths

2,621 Sq.Ft.

$3,495,000

MLS#: MDAA2109630

New on site 4 days ago
Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't miss your chance to own the last remaining waterfront lot and be in your new home by next boating season in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to work with the builder to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Also listed as just a lot without a house package. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle and opportunity to customize the perfect paradise.
#MDAA2132406

ANNAPOLIS

48A E LAKE DRIVE

4 Beds

3 Baths

4,150 Sq.Ft.

$3,395,000

MLS#: MDAA2132406

1486 Downham Market is the ultimate Annapolis deep-water estate—designed for those who demand luxury, security, and boating excellence. Perfectly positioned at the mouth of Clements Creek—one of the safest hurricane holes on the Severn River—this home pairs architectural brilliance with one of the region’s most coveted waterfront settings. A commanding 180’ pier with three boat slips, 50-amp power, and 11’ MLW welcomes yachts and sport boats alike—Hinckley, Viking, Boston Whaler, Pursuit, or Chris-Craft—this property can handle them all. Reinforced pilings are ready for lifts, making this a boater’s dream with full riparian rights. From here, you’ll be on the Severn and Chesapeake Bay in minutes. Inside, walls of glass frame sweeping water views from nearly every room. Across three levels, the transitional design blends clean lines with warmth: hardwood floors, designer lighting, and soaring ceilings. The chef’s kitchen is fully outfitted with commercial-grade appliances, granite counters, and gas cooking, flowing into multiple living and dining areas anchored by a dramatic two-sided stone fireplace. The primary suite is a true retreat—private sitting room and fireplace, a spa bath with skylight, soaking tub, glass shower, and custom walk-in closet. Additional ensuite and Jack-and-Jill bedrooms provide comfort and privacy for family or guests. The walkout lower level is built for entertaining with a rec room, wet bar, wine storage, gym, fifth bedroom, full bath, and a glass-wrapped sunroom ready for a hot tub retreat. Outdoor living is extraordinary: multi-level decks, panoramic views, and serene waters that stretch toward the Severn and Bay. A brand-new septic system and advanced water treatment with reverse osmosis and UV protection offer peace of mind. Set in the prestigious Downs on the Severn, residents enjoy two marinas, clubhouse, pool, tennis and pickleball, and a close-in location to Annapolis, D.C., and Baltimore. Waterfront estates of this caliber almost never hit the market. 1486 Downham Market is ready now—bring your yacht, bring your lifestyle, and claim your place on the Severn.
#MDAA2119714

ANNAPOLIS

1486 DOWNHAM MARKET

5 Beds

4 Baths

5,260 Sq.Ft.

$3,250,000

MLS#: MDAA2119714

Welcome to 1979 Baltimore Annapolis Blvd — where original charm meets opportunity. Set along one of the Severn River’s most desirable stretches with unobstructed views of the U.S. Naval Academy, this distinctive residence offers 5,522 finished square feet across three levels—seamlessly blending timeless character with a 2015 expansion and thoughtful modern updates. Enjoy a front-row seat to the annual Blue Angels air show right from your own waterfront! The property’s deep-water pier and bulkhead, constructed in 2003, feature a 40,000-lb lift, a 15,000-lb lift, and two 1,500-lb jet ski lifts, accommodating multiple vessels with ease. With 10 feet of water depth and ample dockside parking, it’s an exceptional setup for boating enthusiasts. The main floor of the original home features beautiful hardwood floors, a wood-burning fireplace, a bedroom and full bath, a retro kitchen, and warm gathering spaces that open to a sunroom and screened porch. The 2015 addition introduced a spacious three-car garage, providing exceptional storage and convenience. Upstairs, the original portion of the home offers three bedrooms and a full bath, including a primary suite with a private balcony. The 2015 addition extends the second level with a bright loft and additional bedroom, ideal for a guest suite, home office, or creative space. A rough-in for another bathroom lies beneath the subfloor in the area connecting the original and new sections. Downstairs, the original basement features a laundry area, a rough-in for a utility sink, and a wood-burning fireplace. The newer section is a workshop dream, with soaring ceilings and its own exit to the backyard. Additional features include two Trane HVAC systems and a built-in speaker system. Outside, a built-in BBQ and private dock set the stage for effortless waterfront living—perfect for boating, fishing, or simply soaking in the serenity of life on the Severn with sweeping views of the Naval Academy. With abundant space, a flexible layout, and private water access, 1979 Baltimore Annapolis Blvd is ready to become the next owner’s dream waterfront retreat.
#MDAA2128142

ANNAPOLIS

1979 BALTIMORE ANNAPOLIS BOULEVARD

5 Beds

2 Baths

6,794 Sq.Ft.

$3,200,000

MLS#: MDAA2128142

**Open House - Sunday, Dec 7th, 11 -1 pm** Welcome to 856 St Edmonds Place! Have it all with stunning views from nearly every room, deep water, privacy, and a spacious floorplan for multi generational living! Spectacular custom built waterfront home in the sought after Downs community of Annapolis! Breathtaking views await you from every corner of this updated and well conceived home. Dramatic details throughout highlight the open floorplan and entertaining is a dream! Gourmet Kitchen with high end appliances, light filled formal dining room, soaring ceilings and imposing stone fireplace highlight the gathering room, cozy waterside family room off the kitchen, amazing primary suite with floor to ceiling windows and luxurious bath and oversized closet, two additional bedrooms and a full bath complete the upper level, bright and airy lower level with family room, theater, two additional bedrooms with en suite baths and plenty of storage, enjoy the flexibility of an enormous maintenance free deck and a stunning screened porch, attached two car garage and additional detached one car garage with amazing 1 BR/1Bath updated in law suite/caretaker space, whole house generator, new tram and steps for convenient access to your pier with covered slip, two new boat lifts and jet ski lift nestled perfectly on Brewer Creek with quick access to the Severn River and the Chesapeake Bay! Located close to the community pool and sports courts with an an easy commute to Washington DC, BWI and Baltimore!
#MDAA2105068

ANNAPOLIS

856 ST EDMONDS PLACE

5 Beds

4 Baths

6,595 Sq.Ft.

$3,100,000

MLS#: MDAA2105068

Buyers resources
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