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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

296

# of Listings

3

Avg # of Bedrooms

$470

Avg. $ / Sq.Ft.

$1,067,632

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

296 Properties Found. Page 4 of 20.

FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views with this rare opportunity to own an exquisite penthouse at the GrandView in Annapolis Town Center. Perched atop the prestigious 12th floor, this sprawling residence stands as one of the most coveted penthouses, offering panoramic views that stretch for miles, complemented by two expansive balconies that provide front-row seats to the vibrant holiday events and outdoor venues of the Town Center.

Step inside to discover a world of refined elegance, where light cascades through oversized windows, illuminating the dramatic 11-foot ceilings that stretch overhead, creating an atmosphere of open, airy sophistication. This penthouse boasts an expansive layout, featuring three private ensuite bedrooms, each a serene retreat of comfort and luxury. A large den offers flexibility for your lifestyle, whether as a home office, media room, or additional guest space, ensuring this home meets your every need. Newly installed 2-Zone HVAC system, new tankless water heater, and new washer and dryer.

The heart of this home is the open floor plan, seamlessly connecting living spaces with Brazilian cherry hardwood and ceramic tile floors underfoot, exuding warmth and timeless elegance. The gourmet kitchen is a chef's dream, outfitted with high-end appliances, sumptuous granite countertops, and a massive kitchen island, making it perfect for hosting gatherings or savoring quiet moments over coffee.

GrandView isn’t just a residence; it’s a community that offers a true sense of belonging. Residents enjoy exclusive access to a rooftop sky lounge and pool, an outdoor kitchen, a state-of-the-art fitness center, and a club/party room, all designed to foster a lifestyle not just of luxury, but of wellness and social connectivity. The addition of a professionally managed concierge staff ensures every day is lived with ease, convenience, and security.

Situated in the heart of Annapolis, GrandView places you just a stroll away from the finest dining, Whole Foods, Target, Life Time Fitness Club, banking, and boutique shopping. Historic downtown Annapolis, the US Naval Academy, Anne Arundel Medical Center, and Annapolis Mall are mere minutes away, making this a dream location for commuters with quick access to Route 50 and 97.

Seize this unmatched opportunity to indulge in refined urban living at its most sophisticated. Schedule your showing today and take the first step into a life filled with luxury, comfort, and breathtaking beauty in this unparalleled penthouse residence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1210

3 Beds

3 Baths

3,520 Sq.Ft.

$1,750,000

MLS#: MDAA2103424

Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Maryland. This home will feature a perfect blend of classic Eastport and luxury coastal craftsman design. Permitting is complete. This expansive 3600 +/- (approx. 850 unfinished) sq. foot home will offer 4 bedrooms and 3 baths with an open floor plan concept. Truly an entertainer’s dream with hardwood floors, high ceilings, impressive millwork and trim, walk-in closets, beautiful gourmet kitchen, large rooms with multiple dining and gathering areas, and a fully finished basement. The second level of the home offers three bedrooms including the owner’s suite. The suite features a fireplace and master bath with dual vanity, frameless glass shower and soaking tub. The builder did not leave anything out, by placing an office or bedroom on the main level and washer and dryer on the second floor for convenience. The exterior of the home will include a charming front porch, back deck for hosting seasonal barbecues, and ample green space in the rear. A landscaping package is included, as well as 3 off-street parking spaces. Walkability to downtown Annapolis including premier restaurants, shopping, yacht clubs, water activities, and more... Take advantage of this rare opportunity to purchase Eastport new construction. The delivery delivery is summer 2025.

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,700,000

MLS#: MDAA2032362

Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This exceptional 4-bedroom, 4-bathroom home is perfectly situated on the shores offering unique views of the Chesapeake Bay and Oyster Creek from nearly every room. Step inside to discover the open design, highlighting a gourmet kitchen designed for both beauty and function, featuring granite countertops, stainless steel appliances, and breakfast bar. The open-concept living and dining areas flow easily out to the multi-level waterfront decking, ideal for entertaining or simply enjoying the peaceful surroundings. The luxury primary suite is a true sanctuary, complete with a private waterfront deck, spa-like bathroom featuring a walk-in shower, soaking tub, and a generous walk-in closet. The third-level living space includes a full bath and offers endless possibilities—perfect as a media room, guest suite, or home office with elevated views.
Outside, a private pier with a 20,000 lb boat lift invites you to explore the water with ease. Whether you're boating, fishing, or just soaking in the serene creekfront setting, this property offers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own a slice of waterfront paradise on Oyster Creek. Property is in a Special Tax District. - $2,274.75 annually.

ANNAPOLIS

3300 SHORE DRIVE

4 Beds

4 Baths

2,798 Sq.Ft.

$1,650,000

MLS#: MDAA2116986

#MDAA2120636

ANNAPOLIS

3126 PORT WAY

4 Beds

3 Baths

3,892 Sq.Ft.

$1,630,000

MLS#: MDAA2120636

Spectacular Water View Home nestled at the tip of Eastport Peninsula between Spa Creek, Back Creek and the Severn River in the premiere gated community of Chesapeake Landing, with onsite Yacht Club and pool memberships available. 21 Chesapeake Landing embodies the epitome of Eastport’s waterfront lifestyle. The Maritime Republic of Eastport is a vibrant waterfront community deeply rooted in both sailboat racing and pleasure boating traditions. Residents treasure the walkable lifestyle, with more than 50 restaurants, pubs, boutique shops, and historic City Dock and Downtown Annapolis just steps away. This immaculately-maintained home has been thoughtfully designed with meticulous, high-level upgrades, resulting in a seamless blend of elegance, comfort, and timeless design. A private in-law, guest suite or
entertainment room on the ground level adds to the homes versatility. On the main level, expansive sliding glass doors open onto one of three decks; an ideal setting for savoring water views, or simply relaxing with evening libations. It’s also a front-row seat for the 4th of July, New Year’s Eve fireworks displays and the annual Blue Angels Airshow. The daily parade of sail and power boats, regattas, navy vessels and pirate ships is a spectacular bonus that makes this home truly unique. At the heart of the home is a spectacular chef’s kitchen: An oversized center island invites casual gatherings, while custom cabinetry, complete with artful display nooks, add depth and functionality. Sleek stainless-steel appliances pair beautifully with the honed-granite countertops, to provide ample prep space for the most discerning gourmet. A private deck just off the kitchen is perfectly positioned for effortless outdoor grilling. The open-concept layout is both flexible and inviting. Island seating flows naturally into the adjacent dining area, which overlooks the living room and captures water views beyond. Rich, gleaming hardwood floors span the main, bedroom, and loft levels, adding warmth and sophistication throughout. The living room is a true retreat, enhanced by 9-foot ceilings and a gas fireplace that adds instant ambiance with the flip of a switch. Upstairs, wake up to enjoys water views of Annapolis Harbor and the Severn River. The graciously sized owner’s suite welcomes you with dramatic vaulted ceilings and abundant natural light. The recently renovated spa-inspired ensuite bath is a sanctuary in itself, featuring a glass-enclosed shower and soaking tub that doubles as a steam room complete with folding chairs for relaxation and the therapeutic benefits of a sauna. Dual vanities, high-end fixtures, and generous storage, all finished in calming, modern tones complete the experience. Two additional bedrooms offer versatility and comfort; ideal for guests, family, or as a dedicated art studio, home gym, or private home office. The ground-level living space adds even more flexibility. Featuring its’ own paver patio and private entrance, a full bath and a custom kitchenette—including a refrigerator, sink, microwave, built-in storage and neutral tile flooring. This area can be completely closed off from the rest of the home, making it a perfect in-law suite, private guest quarters or family entertainment area. Additional amenities include a one-car garage, an extra driveway parking space, a large paver patio, and the freedom to lock, leave, and travel with peace of mind. Outside your front door, the Eastport lifestyle unfolds. Take a leisurely stroll to local waterfront restaurants, pubs, and boutique shops. Catch a water taxi to historic downtown Annapolis, or launch your kayak or paddleboard from nearby Horn Point Beach Park. Eastport offers the charm of a coastal village with the energy of a thriving maritime hub, just across Spa Creek from the U.S. Naval Academy and all the culture, history, and amenities of downtown Annapolis! Don't Miss The Opportunity to Make This Your Home!

ANNAPOLIS

21 CHESAPEAKE LANDING

4 Beds

3 Baths

2,232 Sq.Ft.

$1,599,000

MLS#: MDAA2117644

Welcome Home to 3529 Chrisland Drive! This beautifully upgraded 5-bedroom, 4-bathroom is located in the highly desired neighborhood of Annapolis Cove, only minutes from downtown Annapolis. Enjoy stunning views of the water from all aspects of your new home. A gourmet open kitchen, family room, formal dining room, formal living room, sunroom, private office and half bath offer amazing living spaces on the first floor. A fully screened in porch off the living room, exterior porch and gazebo off the kitchen offer relaxing views of the water morning and night. The third floor includes a large primary bedroom and updated on suite, three additional bedrooms and a full bathroom. The fully finished walkout basement offers a full bedroom, full bathroom with room for a game room/media room and a home gym. Life in Annapolis Cove offers access to parks, a playground, basketball courts and the option to join the waterfront Bay Ridge Pool and secure a slip in the private community marina. This is a must-see home that won't last, schedule your showing today and don't miss out on the opportunity to own this beautiful home!

ANNAPOLIS

3259 CHRISLAND DRIVE

5 Beds

3 Baths

4,583 Sq.Ft.

$1,550,000

MLS#: MDAA2118272

A Rare Find in the Heart of Eastport! Built in 2006 with timeless Eastport charm, this beautifully maintained home offers the perfect blend of traditional style and modern convenience. Enjoy off-street parking for 2 cars and a host of high-end features throughout. Step inside to discover hardwood flooring on all 3 levels, radiant floor heat, and zoned heating and cooling – including a private AC control in the primary suite. The spacious layout includes three full baths with stone tile details, a whirlpool tub and 2-person shower in the primary bath, and a soaking tub in the guest bath.
The primary bedroom features skylights with rain sensors and remote-controlled shades, as well as his and hers closets. Enjoy a full-size washer & dryer on the second floor. The large 3rd level loft can be used as a 4th bedroom. On the main level there is a pantry/mudroom, separate side entry leads you to step to the unfinished basement with 8' ceilings. Designed with safety and comfort in mind, this home includes ceiling sprinklers on all levels, enhanced fire-rated walls, and a top-rated corner for a wood stove. Outdoor living is just as impressive with rain gardens in the front and back, Leaf Filter gutter guards, outdoor water and electric access, and dimmable lighting on the front porch as well as inside kitchen/dining areas. Additional highlights: Updated interior paint throughout (2024); New refrigerator (2024); dishwasher (2023); and microwave with stove exhaust (2025). Security system with front door camera. Included in the fenced rear yard is a permanent exclusive 5’ rear easement for added privacy.
Enjoy the best of Eastport living in a home designed for comfort, efficiency, and peace of mind.

ANNAPOLIS

541 SECOND STREET

4 Beds

3 Baths

2,341 Sq.Ft.

$1,499,000

MLS#: MDAA2114340

#MDAA2051918

ANNAPOLIS

2644 CLAIBOURNE ROAD

6 Beds

4 Baths

3,702 Sq.Ft.

$1,484,000

MLS#: MDAA2051918

#MDAA2116952

ANNAPOLIS

1028 SANDPIPER LANE

3 Beds

2 Baths

2,552 Sq.Ft.

$1,450,000

MLS#: MDAA2116952

Enchanting Craftsman-Style Waterfront Retreat in Epping Forest

Tucked away in the prestigious gated community of Epping Forest, this beautifully renovated Craftsman-style home offers a rare opportunity to enjoy serene waterfront living with a private deep-water pier on Clements Creek, just off the Severn River. Complete with a 12,000 lb boat lift and a private sandy beach, it’s a dream for boating enthusiasts and nature lovers alike. From this peaceful sanctuary, you’ll have direct access to all of Annapolis’s waterways—and beyond.

Expertly positioned on a perfectly elevated 0.39-acre lot, this elegant 4-bedroom, 4-bath residence offers over 3,000 square feet of refined living space spread across three thoughtfully designed levels. Embraced by tranquil wooded surroundings, the home reveals seasonal vistas—lush, leafy treetops in summer, transitioning to sweeping water views in winter, with captivating glimpses throughout the year.

A graceful stone stairway with sleek cable railing ascends to the front entrance, framed by lush landscaping and the soothing sounds of nature. This harmonious blend of architecture and setting creates a serene, private retreat—yet it remains just moments from the conveniences of modern living.

Inside, the open floor plan and abundant natural light highlight the home’s craftsmanship and thoughtful design. The kitchen, dining area, and living room with fireplace seamlessly connect to a screened-in porch and a spacious deck—ideal for al fresco dining and enjoying the tranquil surroundings.

The main level includes a bedroom and full bath, perfect for one-level living. Upstairs, a spacious landing with soaring ceilings leads to two ensuite bedrooms, including the luxurious primary suite with a private balcony, treetop vistas, and a spa-like bath featuring dual vanities and a walk-in tiled shower.

The versatile lower level offers a cozy family room with fireplace, an additional bedroom and full bath, a home office or bonus room, generous storage, and a private patio—perfect for guests or multi-generational living.

Residents of Epping Forest enjoy an unparalleled lifestyle with access to a waterfront clubhouse and bar, deep-water marina, sandy beach, boat ramp, tennis courts, hiking trails, and a full calendar of community events including fireworks, oyster roasts, holiday festivals, and summer camps. Active social groups like the boat club, volleyball leagues, swim team, and garden club offer something for everyone.
Annapolis, known as the "Sailing Capital of America," boasts one of the longest and most vibrant boating seasons on the East Coast—extending well into the fall, when the waterways are framed by dynamic foliage and crisp, golden light.
Conveniently located just minutes from Downtown Annapolis, the Bay Bridge, and major routes to Washington, D.C., this home is the perfect blend of relaxation, recreation, and accessibility.

ANNAPOLIS

357 OVERLOOK TRAIL

4 Beds

4 Baths

3,070 Sq.Ft.

$1,398,000

MLS#: MDAA2121406

Make an appointment to visit our show home! This listing is for an End Unit at the standard price, however, Sturbridge Homes is offering a generous pre-construction incentive package for early buyers, including: $40,000 in closing cost credit, $30,000 in options and upgrades, including a hot tub installed on the rooftop terrace, No upcharge for end units (-$25,000), a one-year membership to Lifetime Fitness. Submit your deposit now to lock in current pricing and have the ability to customize your home! Sales Center appointments are available now. A sample of the builder's work nearby is available to tour.
Welcome to Towne Row - A community of 18 Luxury Townhomes in the Annapolis Town Center Corridor.
A Towne Row home is superior in every way. The craftsmanship and expansive spaces are apparent immediately. Notice the contemporary exterior, rooftop terrace for entertaining and stargazing, and two-car garage. Savor the spacious kitchen and luxurious owner's suite, privately situated on its own level, and the high-end materials and fixtures throughout. Live graciously and vertically on four generous levels, whisked up and down by your private elevator. This is Towne Row, your haven, your showplace, your new home. It's like none other in Annapolis. Features include: 3,100 Square Feet of Living Space, 3 Bedrooms + Den, 3 Full Baths, 2 Half Baths, Expansive Gourmet Kitchen With Walk-out Deck, Private Elevator, Elegant, Spacious Owner's Suite on Its Own Level, Quartz Countertops Throughout, Four Levels of Finished Living Space, Rooftop Deck With Space for Hot Tub, Two-car Garage, Energy Star & LEED Gold Certified

Location, location, location. Living at Towne Row puts you in the heart of the bustling Annapolis Town Center corridor. You have instant access to an array of upscale and casual restaurants, boutiques and shops, favorite grocery stores, sophisticated fashion and home goods retailers, fitness clubs, movie theaters, and essential services. Plus, you'll be minutes from the Annapolis historic district, endless waterways, nearby marinas, and a short drive to Baltimore and Washington, D.C. It's luxury living and convenience beyond compare.

Lot dimensions, floor plans, and square footage figures are approximate. Architectural renderings are samples only and may not reflect the exact product. Sellew Rd. has not been built and may not appear on some mapping apps.

ANNAPOLIS

208 SELLEW ROAD

3 Beds

3 Baths

3,100 Sq.Ft.

$1,375,000

MLS#: MDAA2119308

Move-in ready new construction from acclaimed local builder, Sturbridge Homes. This spectacular home offers over 5,000 square feet of finished space in the heart of Annapolis's Homewood neighborhood, close to all of the entertainment and enjoyment available in our historic town. Located near the new Annapolis Public Library, Maryland Hall, Annapolis Town Center, and the Naval Academy Stadium, this home is situated for you to enjoy the best of in-town life, yet relax in a tree-lined neighborhood environment.
This home is excellently upgraded with 9-foot ceilings on all three levels, quartz countertops, ceramic tile, stainless appliances, and hardwood flooring throughout the 1st floor, owner’s suite, and stair/hallways. The primary suite is a luxurious oasis with plenty of space to enjoy, a huge customizable walk-in closet, and a spectacular multi-head walk-in shower. The lower level features a separate entrance, a bedroom and a full bathroom, and a large wet bar with a beverage refrigerator, making it perfect for entertaining guests, caregiving, or multi-generational living. The builder has included many thoughtful touches, like decorative moulding, wood closet and pantry shelving, and a mudroom bench and organizer. The front porch is a perfect spot to savor your morning coffee, and the backyard offers endless possibilities. The home comes with a $15,000 closing cost credit (conditions apply), a $10,000 credit toward closet customization, a package of smart home features, and a 10-year limited warranty. Enjoy the low-maintenance lifestyle of a new construction home for many years to come!

ANNAPOLIS

9 RUSTY RED DR

5 Beds

4 Baths

5,464 Sq.Ft.

$1,375,000

MLS#: MDAA2117898

Make an appointment to visit the showroom! Welcome to Towne Row - A community of 18 Luxury Townhomes in the Annapolis Town Center Corridor.
A Towne Row home is superior in every way. The craftsmanship and expansive spaces are apparent immediately. Notice the contemporary exterior, rooftop terrace for entertaining and stargazing, and two-car garage. Savor the spacious kitchen and luxurious owner's suite, privately situated on its own level, and the high-end materials and fixtures throughout. Live graciously and vertically on four generous levels, whisked up and down by your private elevator. This is Towne Row, your haven, your showplace, your new home. It's like none other in Annapolis. Features include: 3,100 Square Feet of Living Space, 3 Bedrooms + Den, 3 Full Baths, 2 Half Baths , Expansive Gourmet Kitchen With Walk-out Deck, Private Elevator, Elegant, Spacious Owner's Suite on Its Own Level, Quartz Countertops Throughout, Four Levels of Finished Living Space, Rooftop Deck With Space for Hot Tub, Two-car Garage, Energy Star & LEED Gold Certified

Location, location, location. Living at Towne Row puts you in the heart of the bustling Annapolis Town Center corridor. You have instant access to an array of upscale and casual restaurants, boutiques and shops, favorite grocery stores, sophisticated fashion and home goods retailers, fitness clubs, movie theaters, and essential services. Plus, you'll be minutes from the Annapolis historic district, endless waterways, nearby marinas, and a short drive to Baltimore and Washington, D.C. It's luxury living and convenience beyond compare.
A 5 % deposit reserves your new home! Sturbridge Homes is offering a generous pre-construction incentive package for early buyers, including: $40,000 in closing cost credit, $30,000 in options and upgrades, including a hot tub installed on the rooftop terrace, no upcharge for end units, a one-year membership to Lifetime Fitness. Get in on these specials now, lock in current pricing, and have the ability to customize your home! Conditions apply. Sales Center appointments are available now. A sample of the builder's work nearby is available to tour.
Lot dimensions, floor plans, and square footage figures are approximate. Architectural renderings are samples only and may not reflect the exact product. The Riva Road address is for reference/GPS ease only. Once the community road is constructed, it will be called "Sellew Rd."

ANNAPOLIS

2555 RIVA ROAD

3 Beds

3 Baths

3,100 Sq.Ft.

$1,350,000

MLS#: MDAA2113932

Back on the Market!

Escape to your own private Estate. 6100+ sqf of finished space with 2.2 acres of land in the most desirable location of Annapolis. 6 Bedrooms, 4.5 Bathrooms, with > 1000sqf for Master Suite. Two Fireplaces. Move-in condition. Potential for subdivision (check with engineer/county).

A stone's throw to downtown without the city taxes. Across from B&A bike Trail & WWII Memorial. Direct access to Rt50 without any stoplights! BroadneckHS/Severn RiverMS/ArnoldES. Agent Owner.

BRING YOUR OFFERS. All reasonable offers will be considered. Also open to reasonable allowance for prefered cosmetic updates to be completed prior to closing.

Open to Owner Financing or leasing it at $6500/month.

Property is now vacant on combo . Agent Owner.

ANNAPOLIS

1707 RITCHIE HIGHWAY

6 Beds

4 Baths

6,196 Sq.Ft.

$1,325,000

MLS#: MDAA2095284

#MDAA2124850

ANNAPOLIS

45 E LAKE DRIVE

None Beds

None Baths

0.45 acres

$1,299,900

MLS#: MDAA2124850

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