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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

290

# of Listings

3

Avg # of Bedrooms

$449

Avg. $ / Sq.Ft.

$1,030,216

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

290 Properties Found. Page 7 of 20.

#MDAA2122046

ANNAPOLIS

1755 ROBINHOOD ROAD

3 Beds

2 Baths

1,558 Sq.Ft.

$824,900

MLS#: MDAA2122046

#MDAA2121246

ANNAPOLIS

1583 KESWICK PLACE

5 Beds

4 Baths

5,530 Sq.Ft.

$800,000

MLS#: MDAA2121246

Welcome to this exquisite home nestled conveniently close to downtown Annapolis and Eastport. This former four bedroom model home with 2 car garage is most likely the largest house in Ambridge on a corner lot. The home has been freshly painted and carpeted and is situated on a nice corner lot in this premier community with downtown Annapolis in one direction and Quiet Waters Park in the other. Features include over 3,500 square feet on all three levels and 2,400 + finished square feet on first and second level. (The two car garage is not included in the 3,500 square feet.) Floor plans are attached. Sunny open floor plan featuring large kitchen with white cabinetry, granite and pantry, plus stainless steel refrigerator (8/2023, $2,400). Family room has wood burning fireplace and custom built-in cabinetry. Dining room also has custom built-in cabinetry with bump out window and newer chandelier. Hardwood throughout first level. Two level foyer. Large upper level features an open sitting area with skylight leading to four bedrooms including primary bedroom and bath. Fully unfinished lower level offers 1,100 square feet and awaits your finishing touches. Will sell some furniture upon request. Easy access to commuting routes to Baltimore, Washington D.C., and/or Fort Meade. Newer HVAC system (2021), irrigation system, and security system. Owner Agent. There is no sign on the property. MDAA2123566 is the for lease listing for this property.

ANNAPOLIS

919 BERWICK DRIVE

4 Beds

2 Baths

3,346 Sq.Ft.

$799,900

MLS#: MDAA2123438

Luxurious penthouse condo with tons of natural light and views overlooking the fountain and plaza! 1285 square feet of living space encompassing a spacious Living room with fireplace, Kitchen with granite counters and plenty of cabinet space and 2 spacious bedrooms with ensuite baths. Every room boasts views and sliding doors onto a juliet balcony, perfect for letting in the fresh air and the cool evening breeze. Neutral finishes throughout and recently new refrigerator (1.5 years old) and HVAC unit (2 years old) creates peace of mind and a move-in ready blank canvas. Simplify your life with easy lock and go living. Fabulous 24/7 live concierge services, secure and monitored building, designated parking space and storage area. Even bills are streamlined since most utilities are included in the monthly condo fee. Enjoy the plethora of amenities that the Residences at Park Place provides including outdoor pool, courtyard for entertaining and grilling, hot tub, dog park, party room with billiards table, fitness room and many social activities. Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. Traveling or commuting is just as convenient by easily 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

5 PARK PLACE 722

2 Beds

2 Baths

1,285 Sq.Ft.

$799,000

MLS#: MDAA2112456

Priced to Sell: Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community: Welcome to 3117 Port Way, a beautifully updated home nestled in the highly desirable Anchorage Waterfront community of Annapolis. This spacious 5-bedroom, 3-bathroom residence offers approximately 2,400 square feet of open-concept living space on a 0.34-acre lot, complete with a partially fenced backyard and invisible fence, ideal for pets or added privacy. This move-in-ready property combines modern comfort, thoughtful upgrades, and premium waterfront community living—an absolute gem in Annapolis!

Step inside to discover a bright and airy layout enhanced by large windows that invite abundant natural light and offer tranquil views of the mature landscape. The modern kitchen is a chef’s delight, featuring quartz countertops, a gas range, white cabinetry, skylights, and stainless-steel appliances. Additional highlights include a 1-car garage, generous living and dining areas, and thoughtful updates throughout.

The primary bedroom features its own en-suite bathroom, providing a private retreat within the home where you fall asleep hearing the horns of ships anchored on the Chesapeake Bay. The family room offers a cozy ambiance with a wood-burning fireplace and a rough-in for gas conversion, flanked by custom wall built-ins—perfect for displaying books, décor, or media. Throughout the upstairs bedrooms, primary bath, and lower-level bedrooms, you’ll find professionally installed solid wooden doors, adding a refined and durable touch. A laundry chute conveniently located in the hallway bathroom leads to a well-equipped laundry room with ample storage space and an adjacent separate utility room for added organization.

The main level boasts gleaming hardwood floors, seamlessly connecting the living, dining, and kitchen areas in a cohesive open-plan layout. Comfort meets efficiency with a high-efficiency cooling system and hydronic gas heating for year-round comfort. Additional upgrades include a water treatment system with softener, a whole-house central vacuum system, and a gas generator.
A new roof was installed in April 2025, adding value and durability, while the spacious backyard provides the perfect setting for entertaining, relaxing, or enjoying outdoor activities.

Located in the highly sought-after Anchorage Waterfront community, residents enjoy exceptional amenities with an HOA fee of just $118/month, which includes access to a boat slip, marina, boat ramp, community pool, rack for kayaks and paddle boards and a half basketball court. Don’t miss the chance to own this hidden gem in one of Annapolis’s most coveted neighborhoods.

ANNAPOLIS

3117 PORT WAY

5 Beds

3 Baths

2,288 Sq.Ft.

$797,000

MLS#: MDAA2116652

Cape St. John in Annapolis, MD is a welcoming, family-oriented waterfront community known for its friendly neighbors and strong sense of togetherness. Nestled along the South River, residents enjoy exclusive access to a private beach, community pier, boat launch, and kayak racks—perfect for outdoor enthusiasts and families alike. With a voluntary HOA, the community maintains its charm without pressure, and neighbors are always quick to lend a hand or share a smile. It’s the kind of place where people know each other by name, and lifelong friendships are made.
Beautifully maintained and freshly painted, this 3-bedroom, 2.5-bath water-privileged home offers a perfect blend of comfort, style, and outdoor living. Highlights include a stunning in-ground pool, expansive wood decking, and a private fenced yard backing to mature trees for added privacy and seasonal water views of the beautiful South river.
The updated eat-in kitchen features granite countertops, a tile backsplash, and newly installed LVP flooring that flows seamlessly into the vaulted dining room with skylights. Just steps away, the spacious recreation room showcases a unique custom wood stove from Denmark—ideal for cozy gatherings.
Enjoy year-round living in the large, tiled sunroom, complete with vaulted ceilings, skylights, and three sliding doors that open directly to the poolside deck—perfect for entertaining.
The main-level laundry/mudroom has been thoughtfully updated with crown molding, beadboard, new cabinetry, counters, sink, ceramic tile flooring, and a stackable washer/dryer. This space also offers direct access to the pool area for added convenience.
Upstairs, the primary suite boasts cathedral ceilings, a walk-in closet, en-suite bath, and a comfortable sitting area. Two additional bedrooms and a full bath, along with newer carpeting, complete the upper level.
Additional features include a one-car garage, circular paver driveway, boat storage pad, and a powered shed/workshop.
Recent Upgrades:New roof, Gutters and Gutter Guards (2022), Freshly painted and repaired exterior(2022), LVP flooring throughout main level(2022), New carpeting (2022), HVAC (2020), Pool pump house (2018), New high end custom pool cover(2022), Landscape lighting (2022)

ANNAPOLIS

253 CAPE SAINT JOHN ROAD

3 Beds

2 Baths

1,878 Sq.Ft.

$795,000

MLS#: MDAA2123540

**💜💜💜💜💜💜💜💜💜💜💜💜💜💜💜** OPEN HOUSE, Sunday, August 24th from 1pm to 3pm. **Luxury Living with all the Bells & Whistles! This Gorgeous Move-in-Ready 4-Finished level, End of Group Townhome Features 3-4 Bedrooms, 3-Full Bathrooms, 1-Half Bath; Two (2) Car rear load Garage with High Grade Epoxy Flooring and Custom bi-level Stone Accent Walls; Ample Storage, PLUS a Tesla charger! **Main Level is the Front Door and Garage Entry into a Cozy Family Room which features a Full Bathroom, as well as Additional Storage area. **2nd Level features a Spacious Open Floor Plan - Great for Entertaining! This Gourmet Kitchen provides Unparalleled Convenience Combined with Casual Comfort and Elegance. Plenty of Counter space with a Kitchen Island and Breakfast Bar; Sep Coffee/Bar Nook, PLUS a Walk-in Pantry and half bath! *Stainless Steel Appliances; Refrigerator with Water Filtration system; Soft Close Cabinetry. **Ascend to Your Owner's Suite for Ultimate Convenience of your daily routine. Deluxe Bathroom, Sep Water Closet, and a Huge Walk-in Closet; **Two (2) additional well-appointed Bedrooms offering Comfort and Privacy. Both rooms feature 9' Ceilings. **Shared Hall Bathroom. **Sep Laundry area; Sep Hall Linen Closet. **Venture to the 4th level (use as a 4th Bedroom or make this area a Personal Gym, Home Office, Serene Retreat) and Enjoy Evenings Under the Stars! Watch the Blue Angels Fly Over as well as July 4th Fireworks! **For a little down time, enjoy Sitting outside under your Covered Front Porch and soak in all the Peaceful surroundings! **Added Perks: Added a 'Flo by Moen' device which monitors water pressure, temperature, flow rate in real-time, plus offers features like leak detection and alerts. **Energy Star Certified Appliances; and Custom Window Blinds; and a Ring System ********************** Call Me for Details about GRANT Funds up to $10,000 towards Buyer's Closing Costs as well as the CHiP loan program (ZERO down payment with NO Mortgage Insurance). **BUT WAIT THERE'S MORE!! ........ FHLB monies are back for a LIMITED TIME….with higher amounts to HELP Buyers! This Program Offers $17,500 in funds to Buyer's -OR- $20,000 for buyers that are Community Partners (defined as buyers employed in or retired from any of the following professions: enforcement officers, educators, health care workers, firefighters, other first responders; veterans and active duty-military or their surviving spouse). Check out the FHLB Workforce Housing Plus+ Program which Offers $15,000 to any Buyer! **Click on the Movie icon next to the photos to Navigate through all Levels of this Gorgeous Home!

ANNAPOLIS

113 TREBLIS WAY

4 Beds

3 Baths

2,348 Sq.Ft.

$779,500

MLS#: MDAA2118974

Chic Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5-bath condo in the sought-after Acton's Landing community. Perfectly situated on the street level for effortless access, this unit combines convenience with luxury. The open-concept layout features a generous living space, a large kitchen with a center island, breakfast bar, and plenty of storage—ideal for a weekend getaway or everyday living. The separate den offers a perfect work-from-home setup or cozy retreat.
The primary suite is a true haven, complete with a spa-inspired bath featuring a soaking tub, walk-in shower, and ample closet space. Enjoy easy access to the building’s parking garage just steps from your door. Community amenities include a fitness center, gym, party room, library, and more. Located just a short stroll from the water taxi and the vibrant shops, dining, and charm of historic downtown Annapolis—this is city living at its best. Don’t miss your chance to own in one of Annapolis’ most desirable communities!

ANNAPOLIS

66 FRANKLIN STREET 20

1 Beds

1 Baths

1,342 Sq.Ft.

$775,000

MLS#: MDAA2120238

Time for a Lifestyle Upgrade — Welcome to GrandView at Annapolis Town Center! Step into elegance with this spectacular "Everest" model on the 6th floor — a rare opportunity to own one of the most coveted floorplans in the building. This stunning, move-in-ready home shows like a designer model and boasts an array of luxurious upgrades designed for both comfort and style. Enjoy two spacious primary suites, a guest powder room, and a versatile office/den ideal for remote work or quiet relaxation. The open-concept living and dining area features soaring 10-foot ceilings, gleaming hardwood floors throughout (no carpet!) and custom lighting that create a sophisticated, yet warm atmosphere. The gourmet kitchen is a chef’s dream, equipped with granite countertops, high-end KitchenAid black stainless steel appliances, and rich cabinetry. Additional highlights include a large laundry room, large closets for optimal organization, a newer HVAC system, and a private balcony overlooking the vibrant boulevard — the perfect spot to enjoy a glass of wine and live music during the center’s summer concerts. Located on the highly sought-after retail side of the building, you’ll enjoy a true urban vibe with direct access to the best of Annapolis Town Center — Whole Foods, Target, top-rated restaurants, cafes, and boutique shops, all just steps from your door. GrandView amenities include: two assigned garage parking spaces, concierge service, state-of-the-art fitness center, rooftop pool with panoramic views and secure entry and elegant common spaces. Just minutes to Historic Downtown Annapolis, the Annapolis Mall, Anne Arundel Medical Center, and with easy access to Route 50 and I-97 for commuting to D.C. or Baltimore. Experience elevated living at GrandView — this is a MUST-SEE unit!

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 606

2 Beds

2 Baths

1,682 Sq.Ft.

$755,000

MLS#: MDAA2111666

Tucked away on a peaceful cul-de-sac in the desirable Georgetown Grove community, this beautifully maintained three-level waterfront home offers the perfect blend of privacy, comfort and convenience. Set on the largest lot in the neighborhood, the property abuts onto the headwaters of Back Creek. A picturesque, wooded lot surrounds the home and provides a blanket of greenery during the summer season. Stunning views of Back Creek and its boats are enjoyed the rest of the year. A protected wetland bird sanctuary is situated just behind the home, attracting blue herons, hawks, and an abundance of wildlife. The community also provides kayak and paddleboard access to the creek, affording you incredible views of boats and marinas, and the Chesapeake Bay.

The home features an open concept living and dining area, a dramatic two-story vaulted ceiling, and a wall of feature windows that frame lush landscaping and provide abundant natural light. The kitchen features white cabinetry, granite countertops, pantry storage, and a sunlit table area overlooking the deck, trees and creek. Just beyond, the family room offers a cozy retreat with a fireplace and a triple-panel sliding glass door that leads to the multi-tiered entertainment deck, ideal for outdoor gatherings and peaceful relaxation. Upstairs, the primary suite includes two closets, a separate vanity area, and a spacious en suite bath with double vanity, soaking tub, and separate shower. Two additional bedrooms, one with a cathedral ceiling, share an updated full bath. The spacious, finished lower-level walkout provides a functional space that includes a large cedar closet, full bath with steam shower, and walk-out access to a stone patio surrounded by trees and a water view. If needed, this large space could serve as an in-law suite or rental unit.

The property also offers a rare opportunity to experience the waterfront while living in the heart of Annapolis. Downtown historic Annapolis, the Naval Academy, Eastport, marinas, restaurants, grocery shopping and commuter routes to Washington DC are all just minutes away. Quiet Waters Park is a short walking/biking distance, providing family recreation, summer concert series, educational events, and watercraft rentals. A local marina, grocery store and restaurants are all within walking distance.

Enjoy gracious living in this private Georgetown Grove home, along with a vibrant lifestyle that comes with living in the heart of Annapolis.

ANNAPOLIS

39 WINDWHISPER LANE

3 Beds

3 Baths

3,193 Sq.Ft.

$750,000

MLS#: MDAA2114986

Amazing opportunity to own a beautiful parcel of land on desirable Shot Town Road area where large estates abound. Build a sprawling estate or subdivision potential giving three smaller estates.

ANNAPOLIS

SHOT TOWN ROAD

None Beds

None Baths

7.83 acres

$750,000

MLS#: MDAA2113200

Don't miss this incredible opportunity to own a charming 5 bedroom (3 in main house, 2 in apartment) ranch-style home in the highly sought-after Parkwood community in Annapolis. Tucked away at the end of a private road and backing to the serene woods and Back Creek, this property offers a unique sense of privacy and tranquility with rental opportunity. The Parkwood community is a water-privileged haven, featuring a marina with a pier, multiple docks, and a convenient waitlist system for boat slips. You'll have front-row seats to exciting events like the Blue Angels and fireworks shows, all while being just steps away from the vibrant Eastport neighborhood and a short distance to the historic Downtown Annapolis, offering shopping, dining, entertainment, and the renowned Naval Academy. This sprawling home provides main-level living at its finest, with two well-designed additions that add extra space and versatility. The attached garage is a dream, accommodating up to four vehicles and boasting a recently updated apartment on the upper level. This apartment includes a great room, 2 bedrooms, a kitchen, and a full bath, making it an ideal in-law/guest suite, a haven for midshipmen, or a rental. Inside the main home, you'll find a cozy living room with crown molding and a brick-accented fireplace, creating the perfect gathering spot. The kitchen offers upgraded stone counters, a tile backsplash, slate flooring, and a convenient breakfast table space. The adjacent dining room features a built-in cabinet and buffet, adding convenience to your dining experiences. A wonderful family room addition is flooded with natural light through its beautiful windows, creating an inviting area for entertaining and hosting holiday gatherings. The primary bedroom boasts an en-suite bath, while two additional bedrooms and a full bath round out the living quarters. The breezeway between the house and garage is a versatile space that can serve as a recreation room or provide extra storage. This house is also equipped with a storage shed and Generac generator. With the perfect blend of comfort, convenience, and opportunity in one of Annapolis's most desirable communities, don’t miss this opportunity to make this house your home. Property Updates: Carpet, paint, HVAC, baths upgraded, electric panel box, family room windows, kitchen backsplash, apartment updates, and more!

ANNAPOLIS

3 PARK LANE

5 Beds

3 Baths

3,235 Sq.Ft.

$750,000

MLS#: MDAA2096836

Commercially zoned C-1 pad site available adjacent to McDonald's and Wendy's. Just shy of 1 acre. Public Utilities. Great visibility from Rt. 50. Build your office building, a restaurant, retail center, mixed use building, residential apts or condos over ground floor commercial, etc. See documents section for more information.

ANNAPOLIS

1440 WHITEHALL ROAD

None Beds

None Baths

0.92 acres

$749,900

MLS#: MDAA2018250

1.485 acre RLD zoned parcel/ lot available adjacent to McDonald's, Wendy's. Potential uses include daycare, veterinarian, assisted living, club, group home, kennel, plant nursery, produce stand, etc. All utilities are available. Easy access on and off of Rt. 50. Refer to documents section.

ANNAPOLIS

1444 WHITEHALL ROAD

None Beds

None Baths

1.49 acres

$749,900

MLS#: MDAA2018258

Welcome to 303 Riding Ridge, Located in the Very Desirable Hunt Meadows neighborhood.
This Well Cared for ONE OWNER home is Move In Ready, and Includes Many Desirable Upgrades
Main Level Entrance features Easy Care Upgraded Luxury Vinyl flooring leading to Living Room with
Large Easy Clean Tilt Sash Thermal Windows,
Separate Dining Area featuring Oak Hardwood Floors, Overhead Lighting, and Tilt Sash Thermal
Windows
Eat In Kitchen features Easy Care Upgraded Luxury Vinyl flooring, Stainless steel appliances, Beautiful
Granite Countertop, Pantry storage, and under counter lighting
Convenient Powder room Includes Easy Care Luxury Vinyl Flooring, and newer toilet
A few steps away is the expansive sunken family room with beautiful custom oak hardwood floors,
Large Tilt Sash Thermal windows with view of private wooded lot,
Ceiling fan, AND Raised Hearth Brick wood burning fireplace. ALSO Home Includes Natural Gas, for
future conversion to a gas fireplace, Or Gas Cooktop stove in the kitchen
Moving to the Third Level you will find ( 2 ) nice size bedrooms with good size closets, easy care tilt sash
Thermal Windows and Ceiling fan in First bedroom. The ensuite primary bedroom features a ceiling fan,
large closet with hidden lighting, Easy Care tilt sash Thermal Windows overlooking
rear wooded private yard, and newer bath with marble counterop and shower walls.
The Finished Lower Level includes a cedar closest, Bonus Room which can be a 4th

Bedroom as has a
closet and escape window, OR private office for those times when working from home is necessary..
The Highlight of the lower level is a Movie room to keep the family entertained with their favorite movie.
Bose Surround Sound system and Sony stereo equipment included.
Finally the Lower Level also has a wonderful Insulated floored crawlspace for storage, and a utility room
with Included washer and Dryer
The quiet cul-de-sac lot features trees for privacy ( No Homes can be built behind lot )
with beautiful autumn views, from expansive dual level decks ( great for entertaining, grilling out, or
enjoying a propane firepit )
AND if you need additional back yard space, the rear yard can be cleared, as property line is
APPROXIMATELY 48’ from rear of den ( See plot survey )
The included amenities of Hunt Meadows include an oversize pool, toddler pool, tennis courts,
a reserve-able pavilion, perfect for hosting family and friend gatherings.
Stroll along walking path and sidewalks, or take advantage of the nearby pathway, connecting directly
to the beautiful Quiet Waters park along the scenic South river.
The Convenient location of this beautiful home is close to downtown Annapolis, and an easy commute to
DC or Baltimore.

ANNAPOLIS

303 RIDING RIDGE ROAD

4 Beds

2 Baths

2,238 Sq.Ft.

$749,500

MLS#: MDAA2121348

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