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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

314

# of Listings

3

Avg # of Bedrooms

$468

Avg. $ / Sq.Ft.

$1,079,019

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

314 Properties Found. Page 1 of 21.

Experience sweeping waterfront vistas and unforgettable sunsets from this never-lived-in, newly completed luxury estate on 1.04 acres along the protected waters of Aberdeen Creek.
Designed by Hammond Wilson Architects and built by the award-winning Pyramid Builders, this custom residence was conceived to celebrate its extraordinary waterfront setting, where southwest sunsets reflect beautifully across the creek each evening.
With nearly 380 feet of shoreline, the property features a 125-foot private pier with 6’ MLW at mid-dock and 10’ at the end, plus three boat slips with water, electric, and lighting. A floating dock and rare boathouse with traveler hoist and lift provide both convenience and character—amenities seldom found today.
The grounds, envisioned by acclaimed landscape architects Campion Hruby, showcase an artful balance of natural beauty and elegant design. Lush plantings, custom stonework, fountains, and thoughtfully crafted hardscapes enhance the sense of arrival and frame breathtaking views at every turn.
Outdoor living spaces are designed for seamless enjoyment of the water. A heated saltwater pool with Ipe decking is accented by fountains and counter-current swim jets for both leisure and exercise, appearing to spill toward the creek. A Bluestone patio with gas fire pit, hot tub, and a screened porch with retractable NanaWall glass doors extend the living space outdoors, while the outdoor kitchen makes entertaining effortless. Whether relaxing by the pool, dining alfresco, or gathering around the fire, every experience is enriched by the waterfront setting.
Inside, interiors by Erin Page Pitts continue the theme of light and openness. English white oak floors, expansive windows, and carefully placed rooms ensure the water is always in view. The chef’s kitchen features Wolf appliances, dual islands, and a catering pantry, while a 1,200-bottle wine cellar offers sophistication for collectors.
Smart home technology provides modern comfort with Ketra lighting that mirrors natural light, Sonos surround sound, and custom AV throughout. Geothermal heating and cooling, NuCedar siding, and a 50-year architectural roof speak to efficiency and longevity. Car enthusiasts will appreciate the two-car attached garage with climate-controlled storage and a detached three-car garage with flex space and half bath.
This pristine, never-occupied waterfront estate embodies the pinnacle of Annapolis living—where world-class architecture, craftsmanship, exquisite landscaping, and endless water views combine to create a rare opportunity for waterfront living at its finest. Please DO NOT drive down private road without an appointment.

ANNAPOLIS

3182 HARNESS CREEK ROAD

4 Beds

5 Baths

7,845 Sq.Ft.

$11,500,000

MLS#: MDAA2123314

Rare opportunity for a true legacy property on the Severn River! Built by Pilli Custom Homes, this home is a masterpiece of craftsmanship. Wake up every morning to the everchanging scenery out your windows, step out onto your private balcony with a freshly brewed coffee from your in-room coffee bar, feeling the gentle river breeze as you watch sailboats drift by. Make your way down via the elevator or stairs to the heart of the home —a gourmet kitchen designed for both function and beauty. A commercial-grade stove, oversized island, high end appliances and butler’s pantry set the stage for memorable meals, whether it’s a casual breakfast in the sunlit dining area or a feast prepared for guests. The open floor plan ensures that no moment is spent away from the home’s most stunning feature—its endless panoramic water views. Mid-morning calls for a stroll, tram or ATV ride down to your private beach, toes in the sand, as the water laps gently at the shore. Perhaps it’s time for a boat ride. Your commercial-sized pier, equipped with multiple lifts and slips, makes it effortless to set out for an afternoon on the water. The land lovers can take an easy walk into Annapolis or stay closer to home and lounge by the heated saltwater pool, where the sound of the waves blends with the laughter of loved ones. A distinguished home office showcases exquisite woodwork, built-ins, and a double-sided fireplace; a great place to catch up on some work if you can take your eyes off the mesmerizing views. As the day winds down, retreat to one of the many cozy sitting rooms including the stunning sitting room with walls of windows, a perfect hideaway overlooking the pool and river, ideal for a quiet moment with a book or a glass of wine. In the cooler months, the home's fireplaces—found in the living room, family room, office, and even the primary bath—offer warmth and ambiance. Evening entertainment takes shape in the lower-level London pub bar, where friends gather for a game of billiards or a lively conversation. A family movie night in the spacious den, a midnight swim under the stars. The possibilities are endless in a home designed for both grand entertaining and peaceful retreat. As night falls, retreat to the primary suite, a true sanctuary with a private balcony, a fireplace flickering in the background, and a spa-like bath where a deep soaking tub and towel-warming drawers create the perfect end to a perfect day. At 1900 Carrollton Road, every day feels like a dream—a life immersed in luxury, comfort, and the beauty of the Severn River. This is more than a home; it’s a legacy. Welcome Home!

ANNAPOLIS

1900 CARROLLTON ROAD

7 Beds

6 Baths

13,165 Sq.Ft.

$8,995,000

MLS#: MDAA2105526

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.

$8,750,000

MLS#: MDAA2125880

Enjoy Luxury Living on Spa Creek. This is the perfect property for those who seek a serene backdrop to an extraordinary life. With exclusivity and serenity, the Penthouse with 2 guest suites at South Annapolis Yacht Centre Residences combines premier waterfront living with spectacular design that is both timeless and modern. Enjoy breathtaking views of Spa Creek, the Annapolis Harbor and the historic skyline of downtown Annapolis from almost every room and the multiple exterior decks. This property encompasses the stunning Penthouse condo with 3 bedrooms, 2.5 baths and includes 2 guest suites with full baths on the ground level. The guest suites feature waterviews, expansive exterior deck, walls of windows and open floor plans. The suites could be adjoined or used in whatever manner suits your needs. Currently utilized as a gym and a lounge/office space. A balanced combination of clean, modern materials invites natural light to flow through each of the 3 units and the curated finishes are exquisite including polished Cristallo Quartzite slabs in the gourmet kitchen with integrated sink and stunning Waterworks faucet, La Cornue Chateau range with custom hood, marble slabs and vanities in bathrooms, exquisite custom tile, and top of the line Toto toilets just to name a few. The South Annapolis Yacht Centre provides an elegant boutique lifestyle in a marina village setting comprised of 11 Residences and a full-service marina. SAYC is part of the rich Annapolis maritime heritage with 74 new deep water slips (12ft MLW+) to accommodate boats up to 140ft, extensive electrical supply options, waterfront boardwalk, travel lift & direct access to essential marine services. Enjoy the Eastport Lifestyle. Stroll the artful and nautical streets to amenities like; restaurants, pubs and street-end parks. Not to mention you are merely steps away from downtown Annapolis and Naval Academy attractions. Each Residence features waterfront decks & terraces, the perfect outdoor setting for dining al fresco and enjoying glorious sunsets over Spa Creek. Truly an ideal setting for watching the Blue Angels, 4th of July fireworks and the Parade of Lights. Absolutely the best Annapolis has to offer! From this location, you are close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. The historic 18th-century seaport town of Annapolis, Maryland is America's sailing capital. Annapolis offers the perfect balance of small-town charm and big world sophistication. Come home to your Haven! The South Annapolis Yacht Center is located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft.Meade/NSA and Washington, DC. Welcome Home!

ANNAPOLIS

287 STATE STREET 3

3 Beds

4 Baths

4,702 Sq.Ft.

$7,950,000

MLS#: MDAA2122672

Custom built and beautifully sited on Spa Creek, this waterfront residence offers over 5,000 square feet of above-ground living space with 6–8’ MLW, private pier with 10,000 lb boat lift and sweeping water views of Spa Creek. A gracious front hallway entrance with a curved staircase sets the tone for the home’s elegant design and inviting flow. The main level features hardwood floors, recessed lighting, and water views from nearly every room. The living room includes built-in bookcases and a wood-burning fireplace, while the family room—located off the kitchen—offers a second wood-burning fireplace and access to the expansive IPE deck with pergola. The dining room overlooks Spa Creek, and the custom kitchen features white cabinetry, refinished granite countertops, Thermador appliances, and a large island with gas cooktop.
Upstairs, the spacious primary suite includes cathedral ceilings, a gas fireplace, soaking tub, walk-in closet, and an adjoining office/flex space with private waterfront balcony. Additional highlights include a guest suite with balcony, third-floor studio/office, and separate in-law or nanny quarters with full bath, kitchenette, and private entrance. A large mudroom with multiple closets, laundry area, and half bath connects to the oversized two-car garage.
Recent upgrades include an architectural-grade roof (2023), resurfaced Dryvit exterior (2023), two new hot water heaters (2025), encapsulated crawl spaces (2025), new smoke detectors (2025), and a whole-house generator. Exceptional waterfront living just minutes from downtown Annapolis.

ANNAPOLIS

117 SPA VIEW AVENUE

5 Beds

4 Baths

6,050 Sq.Ft.

$6,995,000

MLS#: MDAA2128032

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#: MDAA2103890

South Annapolis Yacht Center is located on Spa Creek overlooking the beautiful skyline of Historic Annapolis. This award winning residence features an elegant interior design that brings the feel of the adjoining waterway into the living area. Patrick Sutton thoughtfully did the interior design and Bret Anderson of Pyramid Builders constructed this magical 3 bedroom, 3 bath waterfront residence. A bright open floor plan, perfect for entertaining, connects to the wrap around deck overlooking the water. The kitchen features a six burner La Cornue range with matching hood, Sub-Zero refrigerator with custom freezer draws, wine cooler and a large luxe marble center island all overlooking the water. The Primary Suite enjoys beautiful views of Spa Creek & Annapolis, a large dressing room with rosewood cabinets and a luxurious spa like bath. The Primary suite walls are fully upholstered with a wool herringbone material and braided leather trim giving the space a warm comfortable feel. There are 2 additional ensuite bedrooms with one doubling as a den/in home office. There are 2 gas fireplaces, one in the main living area and one on the waterfront deck. There is a rented 1 car garage (across the street, $700/mo) and a storage unit in the lower level of the building. Access to this fabulous residence is via an elevator that opens directly into the unit. Enjoy watching the Christmas Boat Parade, Commissioning Week Blue Angels Show and the 4th of July Fireworks from the waterfront deck. The adjoining world class marina not only is a perfect spot to keep your boat but a great view to watch some of the most beautiful yachts on the East Coast. The prime Spa Creek location, the quality of construction and the award winning interior design puts this property in a league of its own. CHECK OUT THE 3D FLOOR PLAN.

ANNAPOLIS

287 STATE STREET 2

3 Beds

3 Baths

2,949 Sq.Ft.

$5,950,000

MLS#: MDAA2102850

Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by renowned local architect as the culmination of an award winning career. The unsurpassed attention to architectural details, exquisitely curated finishes and breathtaking views of Spa Creek places this trophy home in a league of its own. Tucked away at the end of a quiet street in a premier residential enclave on the banks of Spa creek, this 3 bedroom 3.5 bath is the perfect weekend getaway or forever home. Awe- inspiring palladian windows flood the rooms with natural light and frame the ever-changing water and harbor views. Enjoy entertaining from the gourmet kitchen with custom cabinetry, high end appliances, and beautiful range hood; located in the center of the home the kitchen flows easily into the formal living room and family room both with gas fireplaces and water views. The main level secondary primary suite provides options for friends and family of all ages. Upstairs the spectacular waterside Primary suite boasts vaulted ceilings, floor to ceiling windows, gas fireplace, spa-like bath with soaking tub and custom closet with center island. Relax every morning and evening from the private balcony while enjoying the panoramic views of Spa Creek, Annapolis Harbor, and Eastport. The 2 deep water piers with 9ft MLW can accommodate boats of all sizes and the location provides quick access from Spa Creek out to the Severn River, Chesapeake Bay and beyond. Walkable to everything Annapolis has to offer this truly unique property offers the complete package: convenience, security, beauty and comfort. Welcome Home!

ANNAPOLIS

1 SHIPWRIGHT HARBOR

3 Beds

3 Baths

3,108 Sq.Ft.

$5,898,000

MLS#: MDAA2100630

A Rare Opportunity on Milvale Road and Mill Creek.
This exceptional waterfront property, crafted by renowned builder Lynbrook Homes and thoughtfully designed by architect Vince Green, offers a rare blend of luxury and serenity. The open-concept floor plan is designed to maximize the sweeping, panoramic views of Mill Creek, with western exposure providing breathtaking sunsets year-round.
Spanning three beautifully finished levels, the home is connected by an elevator and showcases designer touches throughout. The gourmet kitchen is a chef’s dream—outfitted with top-tier appliances and ideal for both grand entertaining and intimate gatherings.
The luxurious primary suite is a private retreat, featuring a spa-like bath with a soaking tub, oversized shower, and dual walk-in closets.
Outside, the 250-foot shoreline is secured by a new seawall (2021), while the private pier is a true highlight for boaters: four slips, a 12,000-pound boat lift, three jet ski lifts, and an impressive 8 feet of mean low water depth. Other important features include, Geothermal heating and cooling, propane fireplaces, state of the art water treatment system, 50 KW generator and additional lot across the street.
More than a home, this is a private resort-style sanctuary—designed for those who demand the very best in waterfront living.

ANNAPOLIS

1864 MILVALE ROAD

4 Beds

5 Baths

8,119 Sq.Ft.

$5,450,000

MLS#: MDAA2117604

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!

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.

ANNAPOLIS

1715 PORTERS HILL ROAD

4 Beds

4 Baths

7,887 Sq.Ft.

$3,995,000

MLS#: MDAA2120604

New on site 1 day ago

A new standard of waterfront living unfolds at the South Annapolis Yacht Centre, a boutique enclave of just eleven luxury residences rising along the edge of Spa Creek where Eastport’s maritime heritage meets modern design. Set within this celebrated marina village, Residence #4 is a rare two-level duplex that captures the beauty of the water and the energy of downtown Annapolis from every vantage point.
The residence blends architectural precision with coastal ease. The main level welcomes guests through an elegant entry hall leading to a great room featuring gorgeous wood floors, ample seating around a gas fireplace, a huge island with Quartzite counter, and incredible views down and across Spa Creek. The door to the waterfront deck folds back to create a seamless transition between inside and out; even in colder weather, the number of windows and the size of the doors bring the views of the city’s spires in full focus. The chef’s kitchen includes a double Wolf range and Sub-Zero refrigerator with custom freezer drawers, and there’s plenty of room for multiple chefs to work together! The floor plan also includes an office area with powder room, and the owners installed a beautiful bar with beverage refrigerator and ice machine. The spacious bedroom suite offers a luxurious ensuite bath, and the large walk-in closet has a full-size washer and dryer.
Descend via the private elevator to the lower level, where a second bedroom suite opens to an enchanting waterside deck. There’s a spa-inspired bathroom, walk-in closet, and wet bar with mini-fridge, creating a self-contained sanctuary ideal for visiting friends or family.
Every element of the home reflects the craftsmanship and intent that define the South Annapolis Yacht Centre—an award-winning waterfront community designed by ABS Architects and constructed by Pyramid Builders. The property integrates modern architecture with the rhythms of marina life, offering 74 deep-water slips, a private boardwalk, and access to the full-service marina’s amenities.
Anchored in Eastport’s vibrant waterfront district, the South Annapolis Yacht Centre celebrates the best of Chesapeake Bay living — where sailing heritage, walkable streets, and panoramic water views converge into an atmosphere of understated elegance. 289 State Street, Residence #4 offers more than a home; it offers a lifestyle defined by craftsmanship, connection, and the timeless allure of Annapolis.

ANNAPOLIS

289 STATE STREET 4

2 Beds

2 Baths

1,938 Sq.Ft.

$3,975,000

MLS#: MDAA2129042

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!

ANNAPOLIS

411 RIDGELY AVENUE

4 Beds

4 Baths

5,950 Sq.Ft.

$3,950,000

MLS#: MDAA2115056

Life will never be the same. This slick and sleek coastal contemporary is beautifully designed for optimal waterfront living. With six bedrooms (FIVE ensuites), six full baths and one half bath, waterviews are visible from nearly all living spaces and bedrooms (and three bathrooms, to be fair). Witness the walls of windows on the first level, facing the Chesapeake Bay to the East and Severn River to the Northwest; one will never be bored with the marvelously incessant theatre of watercraft and nature. Enjoy morning coffee out on the open air patio, down at the pier, or in the large, screened porch. If weather is uncooperative, stretch out in the massive open living area, or retreat to one of two second floor water-facing rooms (one perfect for sitting room/office) to take in a new perspective. This home was fully renovated in 2017, sporting gorgeous custom light cherry 5" wood floors on the first and second level and showcasing unique custom, open staircases with black cable handrail system. There are two primary bedroom ensuites; one on the first floor featuring concrete shower floor, bathroom floor and cast concrete countertop. With generous, custom closets and oversized windows featured in each room, both residents and guests are guaranteed to render a five star rating for their stay and experience. This property is one block from 70 acres of walking trails and two blocks from the community beach, playground, picnic pavilion and firepit.

ANNAPOLIS

2514 LYON DRIVE

6 Beds

6 Baths

6,776 Sq.Ft.

$3,850,000

MLS#: MDAA2115858

Chesapeake Bay Cottage with Unmatched Views in Prestigious Bay Ridge. Welcome to Bay Ridge—Annapolis’ most coveted waterfront community—where charm, history, and lifestyle come together. This storybook cottage offers one of the best Chesapeake Bay views and frontages in the neighborhood, with a sandy beach just steps from your front door. Featuring 4 bedrooms and 2 bathrooms, this home exudes coastal charm and comfort. The main level includes two bedrooms, a dining room, a welcoming family room with beamed ceilings and a cozy fireplace, and a separate living room with its own fireplace—perfect for gatherings with family and friends while enjoying the warmth and character of this timeless home. Upstairs, you’ll find a spacious primary bedroom, an additional bedroom, a full bathroom, and a conveniently located laundry area. The home also includes a cellar with a third fireplace, providing excellent storage and additional potential. An expansive yard completes the setting, ideal for entertaining, gardening, or simply relaxing while soaking in the breathtaking water views. Life in Bay Ridge is truly one-of-a-kind. The community boasts world-class amenities including a bayfront pool, deep-water marina, clubhouse, sandy beaches, playgrounds, basketball and pickleball courts, and an active social calendar with year-round neighborhood events. All of this is located just minutes from downtown Annapolis, Eastport, the Naval Academy, and the area’s best dining, shopping, and entertainment. Whether you’re looking for a weekend retreat or a full-time waterfront lifestyle, this cottage offers an incredible opportunity to own a piece of paradise in one of the Chesapeake Bay’s most prestigious enclaves.

ANNAPOLIS

88 RIVER DRIVE

4 Beds

2 Baths

2,799 Sq.Ft.

$3,750,000

MLS#: MDAA2124844

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8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

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BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

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