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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

358

# of Listings

3

Avg # of Bedrooms

$482

Avg. $ / Sq.Ft.

$1,113,127

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$1M - $3M

74 Properties Found. Page 1 of 5.

#MDAA2109620

ANNAPOLIS

2762A BON HAVEN LANE

6 Beds

5 Baths

4,400 Sq.Ft.

$2,950,000

MLS#: MDAA2109620

Welcome to 139 Spa Drive – A Stunning Waterfront Craftsman Home on Spa Creek!

Experience the best of coastal-inspired living at this beautifully designed, single-family home located directly on Spa Creek. This exquisite residence offers three fully finished levels, each with expansive walls of windows that flood the home with natural light and showcase breathtaking water views.

The open-concept layout is ideal for both entertaining and everyday living. A gourmet kitchen sits at the heart of the home, complete with custom shaker cabinetry, quartz countertops, a stylish tile backsplash, premium Bosch appliances, and an oversized center island that offers ample seating and storage. The adjacent Great Room features a cozy gas fireplace and opens to a large waterside deck—perfect for enjoying the serene surroundings year-round.

Upstairs, the luxurious primary suite offers a tranquil escape with its own private balcony overlooking Spa Creek, a second gas fireplace, and a spa-like bathroom featuring a double vanity, freestanding soaking tub, frameless glass walk-in shower, and a linen closet. The expansive, under-finished walk-in closet is a blank canvas offering endless potential to perfectly reflect your personal style and become a dream space. Two additional generously sized bedrooms each have their own beautifully appointed en suite bathrooms, and a convenient second-floor laundry room adds everyday ease.

The lower level offers approximately 1,300 square feet of finished living space, including a bright and spacious walk-out family room plumbed for a future wet bar, a full bath, an egress fourth bedroom, and two storage areas. The recreation space opens to a stone patio and professionally landscaped yard—ideal for hosting or relaxing in style.

Built with lasting quality and exceptional craftsmanship, this home features 2x6 framing, Hardie Plank siding with stone accents, Anderson high-efficiency windows, and a durable standing seam metal roof. Inside, you’ll find 9-foot ceilings throughout, solid wood interior doors, engineered hardwood floors, and detailed architectural millwork. Outdoor features include a bluestone front porch and rear patio, a paver driveway, and professionally designed landscaping. The home is equipped with three heating and cooling zones, a propane tank servicing both fireplaces and the kitchen range, and a full-house sprinkler system with recessed heads.

Whether you’re an avid boater or simply cherish the tranquility of waterfront living, this home delivers a rare combination of elegance, comfort, and direct water access. Enjoy your private, fully outfitted 90-foot slip with a 16-foot width, 54-foot finger pier, and 220-foot platform, and a mean low water depth of 4.5 feet—making this an unparalleled waterfront offering.

ANNAPOLIS

139 SPA DRIVE

4 Beds

4 Baths

4,628 Sq.Ft.

$2,900,000

MLS#: MDAA2115180

Jenkins Lane is an extraordinary private estate on deep water, nestled along Whitehall Creek with direct access to the Chesapeake Bay. This exquisite property spans over 5 acres, featuring a tree-lined driveway that leads to the electronic gated entrance. Upon arrival, you'll find a side-entry, oversized two-car garage, offering plenty of additional parking space for guests.
With over 700 feet of bulkheaded waterfront, the property offers a private pier complete with a 10,000-pound boat lift, three slips, water, electric, and 6+ feet of Mean Low Water (MLW) — perfect for boating enthusiasts and waterfront living. The expansive grounds are thoughtfully designed, showcasing a large patio and a waterside saltwater pool, where you can relax while enjoying breathtaking, unobstructed views of the creek, complete with picturesque sunsets that are truly one of a kind.
The recently renovated home embraces an open floor plan, ideal for both casual living and entertaining. The chef’s kitchen is equipped with premium stainless steel appliances, a large island, and plenty of prep space. Just outside, a screened porch offers a serene spot to unwind.
The lower level is perfect for entertaining, featuring a spacious entertainment area, a full wet bar, a wine closet, and a newly updated full bath. Ample storage space ensures that all your belongings have a place.
As an added bonus, this property includes an additional .66-acre potentially buildable lot, further enhancing its value and potential.
This is a rare and special opportunity to own a premier waterfront estate that combines luxury living, extensive outdoor amenities, and endless possibilities.
Motivated seller. Seller will consider and entertain all reasonable offers. This beautiful property is priced well below the appraised value.

ANNAPOLIS

543 JENKINS LANE

4 Beds

3 Baths

2,705 Sq.Ft.

$2,795,000

MLS#: MDAA2098024

This stunning contemporary three-level home on Mill Creek has been completely renovated from top to bottom, seamlessly blending modern design with breathtaking waterfront views. With 375 feet of shoreline, a private deep water pier (7 ft MLW) with boat lift and a sandy beach, this home offers an unparalleled waterfront lifestyle. The meticulous remodel includes but is not limited to new windows, stunning new flooring, upgraded utility systems and updated kitchen and bathrooms, all of which enhanced both form and function throughout the home. The striking exterior features sleek metal-clad siding, accent metal roofing, and expansive windows that flood the interior with natural light while framing panoramic water views. The main level welcomes you with soaring ceilings in the elegant living room, where a dramatic curved wall of windows and a wood-burning fireplace create a warm yet sophisticated ambiance. The open floor plan flows seamlessly from the dining area into the gourmet kitchen, featuring a peninsula and island—both with seating—alongside a casual dining space perfect for everyday meals. A main-level bedroom with windows overlooking the water and a full bath complete this level. Upstairs is dedicated to the primary suite which offers a true retreat with a spa-like ensuite bath, a private rooftop deck, and an open loft-style space ideal for a home office or sitting area. The lower level is designed for relaxation and versatility, with two additional water-view bedrooms, a full bath, and a spacious family room with a wood-burning fireplace and direct access to the backyard and waterfront. A laundry room, tons of storage and a convenient kitchenette make this level perfect for guests or extended stays. Head down to the water’s edge and set out for a day on the water, perfectly located to take advantage of the Chesapeake Bay's best cruising and fishing areas. Attractive destinations such as the Annapolis Harbor, Baltimore's Inner Harbor, St. Michaels, Oxford, and Solomon's Island are only a short cruise away and just minutes from accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

378 FOREST BEACH ROAD

4 Beds

3 Baths

4,122 Sq.Ft.

$2,750,000

MLS#: MDAA2107066

BAY RIDGE WATERFRONT! Great opportunity for a wonderful home with stunning water views of Lake Ogleton in the coveted Bay Ridge community! This 4 bedroom, 4 bath home features vaulted ceilings, screened porch, gourmet Kitchen, spacious bedrooms and private Primary Suite all with beautiful views overlooking Lake Ogleton. The light and bright main level living space is filled with natural light and features an open floor plan joining the kitchen, dining and living space all flowing effortlessly to the expansive waterside screened porch. Spend every night watching the sunset over Lake Ogleton! The 3 bedrooms, 3 baths plus office space on this level provides plenty of room for accommodating family and guests. The spacious Primary bedroom is located on the 3rd floor for added privacy and extraordinary views from the private balcony. The entry level boasts a full bath and the perfect entertaining space with a wet bar, cozy pellet stove, spacious deck, and direct access to the sprawling backyard that flows to the water's edge and to the private deep water dock with 6ft MLW. Enjoy fishing, swimming, kayaking and heading out on the water directly from the fully equipped pier with multiple lifts and slips; perfect for the boating enthusiast! Celebrate the waterfront lifestyle and feel like you are on vacation every day! The sought-after Bay Ridge Community features a community pool with a clubhouse that overlooks the beautiful waters of the Bay, community beaches on both the River and the Bay and a community Marina with a newly renovated clubhouse. Off-the-water activities include enjoying the basketball court, playground, ball fields, common areas and year-round community activities. Walk or ride your bike for miles along the water and enjoy all the benefits of the Bay Ridge lifestyle, there is no other place like it! Located just minutes from downtown Annapolis and Eastport which offer the perfect balance of small-town charm and big world sophistication. 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

68 E LAKE DRIVE

4 Beds

4 Baths

3,010 Sq.Ft.

$2,699,000

MLS#: MDAA2102404

Nestled on Chase Pond along the serene shores of the Chesapeake Bay, 2680 Claibourne Court offers an unparalleled waterfront living experience. This meticulously renovated coastal contemporary-style residence boasts 5 bedrooms, 4 full bathrooms, and seamlessly blends luxury with comfort. Set on a generous 2.62-acre waterfront lot, the property features a private pier with boat lifts and a beach, providing direct access to the bay's tranquil waters. The open-concept sun-bathed main level offers a living room featuring a stone fireplace with gas insert, gourmet chefs eat-in kitchen, dining room, sitting room, a generous bedroom with walk-in closet, a full bath, and rear deck the full length of the first floor. Stunning stairs open from the lower level to the crow’s nest adds a wonderful architectural feature. The second level offers a primary suite with private balcony, beautiful bathroom featuring separate vanities, shower, soaking tub, and ample storage. 3 additional bedrooms, 1 full bath, and a large laundry room complete the second level. The 3rd level offers two additional rooms currently used as office and exercise room. The crow’s nest offers 360 degree striking views. The expansive lower level offers a recreation room, wet bar, full bathroom, mud/gardeners’ room, large 2-car garage, and abundance of storage. A flag-stone patio off the rear is great for entertaining. Outdoor amenities include a private pier with boat lifts, a beach area, and lush, landscaped grounds—perfect for boating enthusiasts and nature lovers. The home also features a whole-house sound system and is elevator-ready for future convenience. Located in the highly desirable Annapolis Roads community, this peaceful retreat is just minutes from downtown Annapolis, offering convenient access to shops, restaurants, and cultural attractions—all in a stunning bayfront setting.

ANNAPOLIS

2680 CLAIBOURNE COURT

5 Beds

4 Baths

3,415 Sq.Ft.

$2,695,000

MLS#: MDAA2111674

Introducing a coastal gem with artistic touches… Nestled by the waterfront, this property offers a luxurious blend of functional design and artisan craftsmanship. With approximately 2,000 sq. ft. of Timbertek decking, relax on the master bedroom's private balcony with soft down-lighting or lounge on the carefully crafted deck seating under the bow window's gentle glow. Walk along durable brick pathways, set on deep concrete foundations, leading to a driveway masterfully designed by Driveway Impressions of Annapolis. Complementing these is a picturesque stone garden and meticulously crafted stone structures by Earth Design. Inside, the radiant Australian Cypress wood floors set the stage. Hand-painted touches by renowned Annapolis artist, Cindy Fletcher Holden, grace the kitchen and living spaces. The kitchen boasts Corian counters, top-tier appliances, and British hand-painted decorative tiles. All exterior wall-mounted lights and door fixtures are crafted from Baldwin's enduring lifetime brass, a testament to the home's commitment to quality. Add in modern conveniences like a powerful generator, and tech-ready provisions, and this residence is both a haven of luxury and a masterpiece of design. Embrace this harmonious blend of comfort, artistry, and coastal living. The mean low water is over 6 feet at the private dock. Incredible views up Lake Ogleton which leads out to eh Severn River and Chesapeake Bay respectively. Adjacent lot that is an approx 0.47 acre waterfront parcel with public sewer can be purchased separately for $400,000 or can be combined with 1011 Dulaney for $2,950.000. Engineering has not been done but the lot could be a fabulous accessory dwelling unit (ADU) for this property or an opportunity to maintain the privacy you already have. More details available upon request. Don’t miss out!

ANNAPOLIS

1011 DULANEY LANE

4 Beds

4 Baths

3,470 Sq.Ft.

$2,600,000

MLS#: MDAA2080722

#MDAA2103110

ANNAPOLIS

2175 CHESAPEAKE HARBOUR DRIVE

4 Beds

4 Baths

2,513 Sq.Ft.

$2,595,000

MLS#: MDAA2103110

Incredible opportunity to own this once in a lifetime property in the heart of Downtown Annapolis! Wonderful and extensive updates including a new grease trap, new grease lines, new sanitary lines, new counter tops, freshly renovated bathrooms and more! The listing is for the building only but the seller is willing to consider all offers!

ANNAPOLIS

81 MAIN STREET

None Beds

None Baths

N/A

$2,450,000

MLS#: MDAA2105176

Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. See potential plans in the pictures and meet the builder to discuss your dream home or bring your own builder. Don't miss your chance to own the last remaining waterfront lot in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle.

ANNAPOLIS

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$2,390,000

MLS#: MDAA2113706

**TEAR DOWN/NEW BUILD PACKAGE** The homesite sits on an elevated 3 acres offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. The proposed Luxury Wye Mills model features an open concept with the convenience of single level living as the primary suite and an additional bedroom with ensuite full bath along with laundry are all on the main level! The gourmet kitchen with an oversized island adjoins the dining room and overlooks a large family room with access via French sliders to a covered porch --- perfect for hosting family and friends! A huge walk-in pantry with coffee bar and a mudroom/powder room off of the garage complete the main level. The upper level features 2 additional bedrooms with ensuite bathrooms and walk-in closets. The basement offers a finished rec area with the option of adding 2 additional bedrooms and a full bathroom and/or finishing additional living space to create the theater room/home gym, etc of your dreams. The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department
requirements, with the final piece being a public water extension along the existing house frontage. The
subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the
legwork to get it to this point will convey. PLEASE NOTE: The existing home does have a moisture issue, and the HVAC system is not currently functioning. Call agent for more info. Documentation for the subdivision
efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed
subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The
home is being sold strictly as-is, where is. Any inspections for buyer's information only. Existing home without new build package listed under MLS#: MDAA2103336.

Builder is offering $10,000 towards options with use of preferred lender and title companies. HARDI-PLANK SIDING IS STANDARD! CO-PERM FINANCING REQUIRED - 100% VA CO-PERM OPTIONS AVAILABLE - BUILDER'S PREFERRED LENDER HAS GREAT RATES & A SPECIAL 5% DOWN NO PMI LOAN PROGRAM FOR BUYERS IN CERTAIN MEDICAL & PROFESSIONAL FIELDS! PLEASE NOTE: Photos are representative of builder's work and show previously completed custom homes with options/upgrades. Buyer must be pre approved for construction to permanent financing before meeting with builder and touring homes that are under construction. Please visit Whitehall Building website for more info. **PLEASE DO NOT SHOW WITHOUT AN APPOINTMENT**

ANNAPOLIS

1634 ORCHARD BEACH ROAD P 269

4 Beds

4 Baths

3,803 Sq.Ft.

$2,350,000

MLS#: MDAA2113364

Built by Captain Beriah Maybury in 1772 and known as the Kings' Arms Tavern, this Historically designated property is a MUST SEE! This Five-Bay wide brick Single Family Home sits on top of a high scored stone foundation. 9.5 foot ceilings illuminated by nearly floor to ceiling windows showcase a lovely Library with built-In Bookcases and a wood burning Fireplace; a Two Room Parlor, also with a wood burning Fireplace; an addition erected possibly as early as the 1830's includes a large Dining Room with high domed ceiling, a kitchen and a small porch. The upstairs 4 Bedrooms, 3 with their own wood burning Fireplace, wood floors, 2 full Baths and laundry provide plenty of room! The partially finished basement, most recently used as a woodworking shop, has a separate street entrance and could possibly be reimagined as additional living space. The long, gated driveway leads to 2 garage spaces and parking for an additional 6 cars and a charming English garden and patio area. Furnace chimney recently relined. This home is being sold AS IS, but has great bones. Bring your own TLC. Call Listing Agent with questions.

ANNAPOLIS

41 CORNHILL STREET

4 Beds

2 Baths

4,404 Sq.Ft.

$2,300,000

MLS#: MDAA2109384

Fabulous waterfront "Deck Home" with heated saltwater pool and unprecedented views across Broad Creek out to the South River. This special residence located in the Southwater Point enclave of waterfront homes offers the perfect elevation to oversee the stunning sunset and water views. The layout of the home is perfectly designed to enjoy the ever changing scenery from almost every room in the home. The well appointed interior boasts painted wood vaulted ceilings, exposed beams and gleaming hardwood floors throughout the main level. The gourmet Kitchen with island flows into the spacious Living room and Dining room with the floor to ceiling brick fireplace as the focal point. A cozy place to gather on a cool winter night! The expansive rear deck or the sun room off the kitchen are ideal for entertaining or relaxing all year long. The Primary bedroom suite on the main level exudes a true sense of peace and serenity with the panoramic water views, access to rear deck and a luxurious spa like bath featuring, double vanities, heated floors, soaking tub, huge walk-in shower and enviable custom closet. Head down the stairs to the lower level walkout with walls of glass and heated floors to enjoy the Family room with additional fireplace, 2 spacious and light-filled bedrooms with shared bath and a fully equipped bar area that is perfect for hosting all the friends and family that are sure to visit! Let the party flow out to the lower level patio and to the refreshing pool with expansive deck or head to the water's edge with easy access via the tram or stairs to the private pier with 2 boat lifts; perfect for the boating enthusiast. The detached 2 car garage completes this amazing property and the ideal location for quickly accessing the South River or Chesapeake Bay by boat, heading by car to Historic Annapolis or hopping on Rt. 50 to get back to Washington, DC., makes this property a must see. Welcome Home!

ANNAPOLIS

2908 SOUTHWATER POINT DRIVE

3 Beds

2 Baths

3,243 Sq.Ft.

$2,245,000

MLS#: MDAA2100378

Exciting Opportunity in Sherwood Forest – Enjoy breathtaking panoramic water vistas of Brewers Pond and Round Bay on the Severn River. Observe Bald Eagles, Herons, and Osprey soaring amidst the stunning backdrop from your water view deck or spacious living room adorned with floor-to-ceiling windows. This elegantly designed home, nestled in the hillside, seamlessly blends modern amenities with the charm of a traditional cottage. Situated on one of the most secluded homesites in Sherwood Forest, ample parking is available for entertaining family and friends. Sherwood Forest is a prestigious gated community comprising 341 residences. Residents enjoy access to a plethora of amenities including a spacious multi-purpose Club House, General Store, 9-Hole Golf Course, 6 Tennis Courts, Marina, Beaches, Swimming Pool, Basketball Court, Bowling Alley, Pickle Ball Courts, Archery Pit, Nature Lab, and a renowned Children’s Summer Camp Program. Numerous fields throughout the neighborhood cater to various sports such as Lacrosse, Soccer, Football, Softball, Volleyball, and Badminton. The surrounding forest boasts over 5 miles of scenic walking and mountain biking trails, with a picturesque 2-mile waterfront loop offering captivating views of the Severn River and Brewers Pond. Golf carts are the preferred mode of transportation within the community. The vibrant social calendar is filled with events including the 3rd of July Fireworks, 4th of July Parade, Summer Dances, 5K Race, Corn Roast, Clam Bake, Tennis and Golf Tournaments, and much more. Holiday festivities cater to both adults and children alike. A one-time $20,000 membership fee to join the Sherwood Forest Club is required as part of your Real Estate Transaction.

ANNAPOLIS

201 NOTTINGHAM HILL

5 Beds

3 Baths

2,353 Sq.Ft.

$2,200,000

MLS#: MDAA2115758

Epping Forest WATERFRONT! Stunning Craftsmen cottage in Epping Forest with captivating water views across Saltworks Creek to the Severn River. Recently updated with new roof, remodeled bathrooms, redesigned upper level with new spacious balcony, new stairs to the new floating dock and much more has been improved on this fabulous property. This highly coveted private gated waterfront community on the Severn River offers the perfect setting to celebrate the Annapolitan lifestyle and the charming 3 bedroom, 2.5 bath home provides all the necessary elements for easy waterfront living. As you walk into the home the tall ceilings and natural light from the walls of windows and doors frame the beautiful setting and highlight the lush landscaping and water views. The stunning wood floors, updated finishes and thoughtful layout create a comfortable and striking interior space. The open floor plan is perfect for entertaining with the Gourmet Kitchen, Dining Area and Living Room with fireplace all seamlessly flowing out to the waterside covered porch; the perfect place to dine al fresco or head a few steps closer to the water to the seating area and roast some marshmallows over a fire pit as you watch the activity of the boats and waterfowl on the Severn River. The upper level boasts 2 bedrooms with shared bath and spacious private balcony off the Primary's bedroom offering breathtaking elevated views and cool summer breezes. The lower level contains a family room, bedroom and full bath for all those extra guests you are sure to have! The recently built deep water floating dock with 50ft boat slip is a boating enthusiast's dream and the dedicated mooring ball that conveys with the property adds additional options for docking. The location provides easy access to explore all of Annapolis's waterways and beyond. Exclusive Epping Forest Gated Community offers fabulous amenities including the clubhouse with waterside bar and grill, deep-water marina, sandy beach, boat ramp, tennis courts, hiking paths plus year-round activities including: July 4th fireworks, Labor and Memorial Day festivities, oyster roast and summer camps. There's so much fun to be had in Epping Forest, great social clubs include the boat club, volleyball leagues, swim team and garden club. Come and enjoy all that Epping has to offer! Conveniently located to access Downtown Annapolis, head over the Bay Bridge to the Eastern shore or jump on Rt. 50 to get back to Washington, D.C. Annapolis living at its best! Epping Forest is a Special Tax District, ($2456.14/yr.) with binding Rules & Regulations. Welcome Home!

ANNAPOLIS

327 RIVERVIEW TRAIL

3 Beds

2 Baths

1,759 Sq.Ft.

$2,150,000

MLS#: MDAA2103222

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