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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

311

# of Listings

3

Avg # of Bedrooms

$439

Avg. $ / Sq.Ft.

$995,619

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

311 Properties Found. Page 5 of 21.

Private Annapolis Estate | 4 Acres | Guest House | In-Law Suite

A truly one-of-a-kind offering, "Pleasant Plains" blends land, character, and lifestyle in a way rarely found so close to downtown Annapolis --- and in the Broadneck School District!

A tree-lined drive leads to the Tudor-inspired main residence with generous living and entertaining spaces, complete with a private in-law suite. And the separate 3-bedroom guest house expands the possibilities—ideal for multi-generational living, extended guests, or an income producing AirB&B.

Opportunities like this—acreage, multiple dwellings, and a timeless setting—are seldom available anywhere in Annapolis. All just minutes to Historic Downtown, the U.S. Naval Academy, and within 30 milies Washington, DC and Baltimore.

1677 Pleasant Plains is more than a property—it’s a retreat, a gathering place, and a lifestyle unlike anything else on the market.

ANNAPOLIS

1677 PLEASANT PLAINS ROAD

6 Beds

3 Baths

6,955 Sq.Ft.

$1,350,000

MLS#: MDAA2123996

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

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15 right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!!

ANNAPOLIS

1836 CHERRY ROAD

None Beds

None Baths

3.92 acres

$1,300,000

MLS#: MDAA2126556

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!!

ANNAPOLIS

1814 PLEASANT PLAINS ROAD

5 Beds

2 Baths

1,919 Sq.Ft.

$1,300,000

MLS#: MDAA2126554

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek water frontage and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!!

ANNAPOLIS

1814 & 1836 PLEASANT PLAINS & CHERRY ROAD

5 Beds

2 Baths

1,919 Sq.Ft.

$1,300,000

MLS#: MDAA2124862

New on site 2 days ago

#MDAA2130366

ANNAPOLIS

45 E LAKE DRIVE

None Beds

None Baths

0.45 acres

$1,299,900

MLS#: MDAA2130366

Amazing NEW CONSTRUCTION is now complete! Experience luxury living in this beautifully crafted new home, located in the amenity-rich waterfront community of Arundel on the Bay. Enjoy some partial water views and exceptional design throughout. This quality-built residence features wide-plank hardwood floors, gorgeous, detailed trim work throughout and a thoughtfully designed open-concept layout. The gourmet kitchen boasts contemporary quartz countertops, GE Café appliances including a gas range, microwave drawer, stainless farm sink, center island,and stylish brushed bronze fixtures and lighting! A dedicated office on the main level provides the perfect work-from-home space or 4th bedroom area! The spacious owner's suite offers vaulted ceilings, a custom walk-in closet, and a spa-inspired bath. An additional ensuite bedroom provides comfort and privacy for guests or family. Main garage level has the opportunity for ANOTHER full bath (has rough in) and either another bedroom or large recreational room! Gorgeous TimberTech Decking w/contemporary rails runs entire length of home! Fall in love with everything it has to offer! Be sure to see the pier and playground area a few blocks down the road! Custom builder C.A.Desimone

ANNAPOLIS

3506 ROCKWAY AVENUE

4 Beds

3 Baths

3,576 Sq.Ft.

$1,299,000

MLS#: MDAA2117330

PRICE REDUCED! 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.

$1,299,000

MLS#: MDAA2117898

***PRICE DROP****
Experience classic architecture and modern livability in this 6,500+ sq ft Koch-built Colonial in the desirable Colonial Manor community. Bright, open interiors, high ceilings, and beautifully landscaped outdoor spaces make this home ideal for both everyday comfort and elegant entertaining.

Car enthusiasts will love the attached three-car garage – oversized, with soaring ceilings high enough to accommodate a car lift, abundant storage capacity, and space that could serve as a small workshop if one parking bay is repurposed. It’s a true standout among homes in the neighborhood.

The main level offers a grand two-story foyer with Waterford lighting, a private office, formal living and dining rooms, a light-filled sunroom, and a spacious kitchen with center island, stainless appliances, and casual dining area open to the large family room with a wood-burning fireplace. The laundry and powder room are conveniently located near the garage entry.
Upstairs, the expansive primary suite feels like a retreat, with a sitting room, dual walk-in closets, and a spa-style bath offering an oversized soaking tub, double vanity, and separate shower. Four additional generously sized bedrooms share Jack-and-Jill baths, providing each with direct access to a full bathroom.

The finished lower level – nearly 2,000 sq ft – includes a potential sixth bedroom (currently used as an entertainment room) and a full bath with multi-head shower. The expansive open area offers endless possibilities for recreation, media, or fitness, and already includes rough-in plumbing for a future full wet bar. Two large unfinished areas provide excellent utility and storage options, along with additional storage beneath the central staircase. With walk-out access to the rear patio, this level is ready to be customized into the ultimate entertaining or multi-purpose space.

Freshly painted inside and out within the past three years, the home also includes updated lighting, new shutters and window treatments, plantation shutters through the main level, newer washer, dryer, dishwasher, and a water softener. Additionally, Seller is offering 1-year home warranty with AHS.

Set on a beautifully landscaped lot with a two-tiered entertaining patio and in-ground irrigation, this residence combines space, craftsmanship, and location – just minutes to Downtown Annapolis, Broadneck schools, Route 50, and BWI.

ANNAPOLIS

1405 COLONIAL MANOR COURT

6 Beds

4 Baths

6,522 Sq.Ft.

$1,291,000

MLS#: MDAA2127750

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.

$1,250,000

MLS#: MDAA2121406

None

ANNAPOLIS

32 EAST STREET

3 Beds

2 Baths

2,940 Sq.Ft.

$1,200,000

MLS#: MDAA2128006

Beautifully Appointed Eastport Home. Conveniently located in the heart of Eastport, Annapolis, this newer home offers the perfect blend of style, comfort, and walkability. Set on a premium corner lot, the property features a desirable detached garage and wonderful curb appeal. The main level showcases an open floor plan anchored by a gourmet kitchen with granite countertops, stainless steel appliances, and custom cabinetry with crown molding. A private office provides the perfect space for working from home, while the formal dining room is ideal for hosting dinners. The sitting room across from the office offers an inviting retreat—perfect for curling up with your favorite book or simply unwinding in comfort. A spacious family room with a gas fireplace is the perfect gathering space, complemented by a full bathroom for added convenience. Gleaming wood floors run throughout, tying the spaces together with warmth and elegance, while a wet bar and expansive deck extend the home’s entertaining potential outdoors. Upstairs, the luxurious primary suite boasts a sitting area and spa-like bath, offering a private retreat at the end of the day. Two additional ample-sized bedrooms and another full bathroom provide comfort and flexibility for family or guests, while the conveniently located upper-level laundry makes everyday living a breeze. An unfinished basement with rough in could be finished with a recreation room, bedroom and a full bathroom. Endless possibilities. With easy access to Eastport’s vibrant restaurants and just a short walk to downtown Annapolis, this home is a must-see for those seeking both convenience and elegance.

ANNAPOLIS

412 JEFFERSON STREET

3 Beds

3 Baths

4,006 Sq.Ft.

$1,199,900

MLS#: MDAA2127072

Welcome to this waterfront ranch home in the highly sought-after community of Bon Haven, situated on over an acre of serene land along the beautiful South River. This renovated gem, complete with a new private pier and boat access, offers an idyllic lifestyle for water enthusiasts and nature lovers alike. This property is back on the market due to financing falling through for the buyer!

As you arrive, you'll be greeted by an expansive front yard and a spacious driveway leading to the front porch. Step inside to discover the warmth of beautifully renewed hardwood floors that flow seamlessly throughout the main living areas.

The living room features a charming wood-burning fireplace with a custom marble mantle, creating a cozy focal point as well as a large picture windows offering lots of natural light! From here, enter the oversized family room, complete with another wood-burning fireplace, custom wood mantle, and direct access to the backyard, water views, and pier. This space also connects to the attached two-car garage.

The renovated eat-in kitchen boasts custom cabinetry, granite countertops, and new LVP flooring. Natural light filters through the newly installed Roman shades, adding a touch of elegance to this functional space.

Down the hallway, you'll find the private primary suite with an en-suite bathroom and a walk-in closet. Two additional generously sized bedrooms and a large hall bathroom provide ample space for family or guests.

The lower level offers a substantial unfinished basement, laundry room, separate room for home gym or office and lots of storage space - all ready for customization to suit your recreational needs.

Recent updates include:

*Remodeled kitchen
*New HVAC system
*Water heater and water softening system
*Privacy fencing
*Fresh paint and updated flooring
*Newly built private pier
*The property also includes a charming chalet/boat house and a tram, both sold in "as-is" condition.

Enjoy endless water activities on the South River, including power boating, canoeing, kayaking, personal watercraft, sailing, waterskiing, swimming, and fishing.

All that's left to do is move in and embrace the beauty of waterfront living. Don’t miss your chance to tour this incredible property and experience the charm of all four seasons on the South River!

ANNAPOLIS

2762 BON HAVEN LANE

3 Beds

2 Baths

3,134 Sq.Ft.

$1,199,000

MLS#: MDAA2101278

#MDAA2127360

ANNAPOLIS

301 UNITY LANE

5 Beds

5 Baths

7,616 Sq.Ft.

$1,197,000

MLS#: MDAA2127360

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