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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
312
# of Listings
3
Avg # of Bedrooms
$468
Avg. $ / Sq.Ft.
$1,078,011
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

9 Properties Found. Page 1 of 1.

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.
#MDAA2123314

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!
#MDAA2105526

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!
#MDAA2125880

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!
#MDAA2122672

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.
#MDAA2128032

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!
#MDAA2103890

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.
#MDAA2102850

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!
#MDAA2100630

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.
#MDAA2117604

ANNAPOLIS

1864 MILVALE ROAD

4 Beds

5 Baths

8,119 Sq.Ft.

$5,450,000

MLS#: MDAA2117604

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