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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
310
# of Listings
3
Avg # of Bedrooms
$440
Avg. $ / Sq.Ft.
$995,893
Med. List Price

Browse Annapolis Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

310 Properties Found. Page 17 of 21.

Welcome to the sought-after community of Cape St. Claire! This lot is being offered as an addition to a home for sale. Please contact the county for possible development.
#MDAA2116560

ANNAPOLIS

1167 GREEN HOLLY DRIVE

None Beds

None Baths

0.21 acres

$160,000

MLS#: MDAA2116560

BUSINESS SALE ONLY- Fantastic opportunity to own this turnkey and well established restaurant in the heart of downtown Annapolis. Approximately 1500SF with 20 dine-in seat capacity. Fully equipped kitchen ready for any menu. Downtown Annapolis boasts a vibrant and diverse restaurant scene, seamlessly blending historic charm with modern culinary offerings. This location has excellent visibility on the popular Main St. Beer & Wine license available. Landlord approval of new tenant is required. Showings by appointment only.
#MDAA2105548

ANNAPOLIS

138 MAIN STREET

None Beds

None Baths

N/A

$150,000

MLS#: MDAA2105548

Level lot, 2017 perc evaluation indicated a possible home up to a 2,500 sq ft . Buyer to verify all information.
#MDAA455886

ANNAPOLIS

1012 CARRS ROAD

None Beds

None Baths

0.16 acres

$98,000

MLS#: MDAA455886

Welcome to 1848 Milvale located in the Saint Margarets area of Annapolis. As you enter the home you are struck by the beautiful wide views of Mill Creek, the open floor plan, and architectural details. The dining room and living room have gorgeous coffered ceilings, cherry hardwood floors, extensive millwork, floor-to-ceiling windows, and French doors that overlook the saltwater pool, spa, and creek. The kitchen offers a huge central island, wolf range, and custom cabinetry. Off the kitchen is the family room... it's striking with its vaulted barrel ceiling, custom built-ins, bar area, gas fireplace, and curved bank of windows centering again on the views of Mill Creek. The home has 2 main-floor bedroom suites with attached baths. The waterside bedroom has a poolside door and views of the creek while the front bedroom has serene views of the cornfields across the road facing East. One of the architectural highlights of the home is the stairwell tower with its impressive wide girth access to two distinct upper-level areas. Flooded with light, the high ceiling with clerestory windows first lands at the hall library-study. This cozy nook opens to a multi-purpose suite that can be used as a 3rd bedroom, a nursery, a 2nd family room, or an often-needed teen hangout area. The tower takes a turn to the left and accesses the primary bedroom and adjoining waterside office. The primary bedroom provides his and her walk-in closets, a huge spa bath with a soaking tub, heated floors, a walk-in shower, and laundry. Off of the primary bedroom is a handsome office with custom cabinets, a gas fireplace, and a deck to enjoy your morning coffee or a sunset cocktail. The lower level is the fifth-bedroom suite. This room is both the seller's workout room and wine cellar. The utility room has a wash sink, great for gardening, and houses the water treatment systems and 2 Geo-Thermal systems. The home has beautiful hardscaping with irrigation, and a rock garden water feature in the front of the home, and in the back, there is 148 ft of water frontage with a handsome Belgium stone seawall. The pier is "like new" with 2 slips, a 15,000 lb. boat lift, and 8 MLW. The pier is in a NO WAKE ZONE on weekends .. Located on one of the most sought-after roads in Annapolis and known for its privacy and country-like living, Milvale Road winds along the banks of Mill Creek in Saint Margarets surrounded by farmland and corn fields. A perfect place to unwind and enjoy the best sunsets around! Available from December 1, 2024-June 1, 2025
#MDAA2074056

ANNAPOLIS

1848 MILVALE ROAD

5 Beds

5 Baths

5,855 Sq.Ft.

$25,000

MLS#: MDAA2074056

Severn River Luxury Estate – 6-Month Furnished Rental in Annapolis. Available Fall 2025 through Spring 2026. Escape the chill of northern winters and enjoy the temperate beauty of the Mid-Atlantic from this luxurious waterfront estate in Annapolis, Maryland. Overlooking the Severn River and the iconic U.S. Naval Academy, this elegant retreat offers the perfect blend of relaxation, recreation, and refined living. Set on a private property with sweeping water views, this fully furnished home is ideal for a six-month stay, whether you're working remotely, entertaining guests, or simply recharging in a stunning setting. Enjoy pickleball on your private court, sunset walks along the water, dinners in downtown Annapolis just minutes away, or quiet mornings on one of the home's multiple verandas. Inside, you’ll find: * A grand formal dining room * Gourmet kitchen with top-of-the-line appliances, walk-in pantry, and dining area * Main-level office and cozy two-sided fireplace in family room * Multiple living and family rooms, including a club/game room over the garage * Private pier, in-ground pool, and outdoor entertaining space The second level features a luxurious primary suite with spa-like bath, water views, and a private veranda. Additional ensuite bedrooms and a spacious bonus room with balcony provide plenty of flexibility for guests, office space, or relaxation. A third-floor bedroom suite with sitting area and bath offers even more space and privacy, while the finished basement includes a bedroom, full bath, workout room, rec room, and walk-out access to the backyard. This is not just a rental—it’s a seasonal lifestyle upgrade in one of the East Coast’s most scenic and storied towns. Live well. Entertain often. Relax deeply. Welcome to your seasonal waterfront escape.
#MDAA2119338

ANNAPOLIS

1932 CARROLLTON ROAD

8 Beds

8 Baths

9,315 Sq.Ft.

$23,000

MLS#: MDAA2119338

Listed Lease Rate is ONLY for Option to purchase and reflects proposed amount for equivalent mortgage payment with owner financing. Final/other lease amount to be negotiated based on terms, and credit worthiness directly with owner. 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. Potential Owner Financing at $6500/month. Specific terms to be negotiated. Property is now vacant on combo . Agent Owner.
#MDAA2110450

ANNAPOLIS

1707 GOVERNOR RITCHIE HIGHWAY

6 Beds

4 Baths

6,196 Sq.Ft.

$6,500

MLS#: MDAA2110450

Experience waterfront living in this exceptional 5 bedroom, 4 1/2 bath home, perfectly positioned to capture breathtaking panoramic views of the South River and unforgettable sunsets. Designed for comfort and style, this residence features an open-concept layout with a spacious living room highlighted by a stone wood-burning fireplace. The kitchen boasts a very large granite island with seating. The sitting area just off of the living room is the perfect place to reflect while taking in the sparkling water views. The primary suite offers a luxurious escape with a spa-inspired bath and stunning river views. Two bedrooms and 1 1/2 bath on the main level are perfect for overnight guests. Spacious finished lower level with full bath, fireplace and walk out to waterside decking perfect to extend entertaining outdoors. A protected private pier with deep water, multiple slips, and a jet ski lift invites endless waterfront adventures. The dock can accommodate a sailboat at the end of the pier or the big slip. This South River waterfront is truly one-of-a-kind. Property is available furnished or unfurnished. Landlord will consider including all utilities and furnishings for $7500 per month.
#MDAA2129844

ANNAPOLIS

125 ISLAND VIEW DRIVE

5 Beds

4 Baths

3,105 Sq.Ft.

$6,500

MLS#: MDAA2129844

Amazing waterfront residence on the Chesapeake Bay with almost 360 degree water views of the Chesapeake Bay, Fishing Creek, and South River. Enjoy a quiet and friendly neighborhood with private beaches and a pier for your boat across the street. Never hassle with bay bridge traffic and enjoy a unique location which is 5 miles to downtown Annapolis, 5 minutes to major retail and restaurants, and a 45 minute drive to downtown Baltimore and Washington DC. The open floor plan provides a great room with cathedral ceilings, hardwood floors, an updated gourmet kitchen, a dining area, and a wood burning fireplace all with panoramic bay views of the bay bride and Thomas Point Light House. A deck off the great room provides a perfect spot to enjoy the bay breeze, to watch the water life of the Chesapeake, and to see spectacular sights of the stars and moon over the bay at night. Up a few steps, you will find the large master bedroom with en-suite bath, large walk-in closet, and views of Fishing Creek through large windows. 2 additional bedrooms, a 2nd full bath, and laundry closet complete this level. Ground level foyer, 2-car attached garage, and storage shed complete the property. 2+ year lease preferred. See agent notes for Tenant responsibility.
#MDAA2117630

ANNAPOLIS

3563 NARRAGANSETT AVENUE

3 Beds

2 Baths

2,082 Sq.Ft.

$6,000

MLS#: MDAA2117630

Discover the magic of life on the water with this enchanting storybook home nestled along the serene Severn River. Breathtaking panoramic river views from nearly every room. Spacious light-filled living areas with timeless architectural charm. Lush landscaped gardens for outdoor entertaining. Wake up to the gentle sound of the river, sip morning coffee as sailboats drift by, and enjoy evenings with spectacular sunsets. Enter on the stoned and tree lined road that opens to a high bluff overlooking the Severn River. The perfect home for the discerning tenant. Hardwood floors and elegant finishes throughout. Open floor plan with a first-floor master, gourmet kitchen, enclosed porch, fireplace, and breathtaking views. Lower level boasts a private guest suite, family room and ample storage. Upper level houses 2 generously sized bedrooms that share a Jack-and-Jill bath. Privacy abounds with the spacious outdoor patio and expansive yard - all cared for by the landlord's contractor. Your only job is to enjoy this magnificent location. Close to the B&A bike trail and easy access to downtown Annapolis and major roadways.
#MDAA2116104

ANNAPOLIS

5 WAVELAND FARMS ROAD

4 Beds

3 Baths

3,273 Sq.Ft.

$6,000

MLS#: MDAA2116104

Experience the best of coastal Maryland living in this beautifully updated single-family home, nestled on a serene half-acre lot just minutes from the marina. Featuring four spacious bedrooms, two and a half baths, and three finished levels, this home offers both comfort and flexibility for today’s lifestyle. Step inside to a bright, open layout highlighted by a gorgeous modern kitchen—complete with Calacatta quartz countertops, stainless steel appliances, and a navy-and-white cabinetry design that’s both timeless and bold. The inviting dining and living areas flow seamlessly to a large rear deck, perfect for morning coffee or evening gatherings around the custom fire pit under the stars. Upstairs, unwind in the primary suite with its private deck, walk-in closet, and spa-inspired bath. Convenience meets function with an upstairs laundry room, while the lower level adds extra space for a gym, home office, or media room. Outside, you’ll find ample driveway parking, no HOA restrictions, and the bonus of being offered fully furnished***—making this property truly move-in ready. Whether you’re looking for a weekend retreat or a full-time coastal residence, this Annapolis gem captures the charm of Chesapeake Bay living in every detail.
#MDAA2127670

ANNAPOLIS

920 OLD ANNAPOLIS NECK ROAD

4 Beds

2 Baths

2,552 Sq.Ft.

$4,998

MLS#: MDAA2127670

BEAUTIFUL COLONIAL HOME ON QUIET CUL DE SAC, SURROUNDED BY 34 LUXURY HOMES. THIS HOME HAS BEEN METICULOUSLY MAINTAINED. GOURMET KITCHEN. SUNROOM. MASTER BEDROOM WITH SPACIOUS EN SUITE BATH. OFFICE. 2 FAMILY ROOMS, 1 WITH GAS FIREPLACE. FORMAL DINING ROOM. HUGE STORAGE ROOM WITH SHELVING INCLUDED. 2 CAR GARAGE. BEAUTIFUL PATIO. ENTERTAINERS DELIGHT! AVAILABLE DECEMBER 1, 2025!
#MDAA2129808

ANNAPOLIS

612 SAMANTHA COURT

4 Beds

2 Baths

4,592 Sq.Ft.

$4,900

MLS#: MDAA2129808

***Tenant Occupied 24 hour notice on all showings****Welcome to 106 Annapolis St. in sought after West Annapolis. This Hammond Wilson designed luxury Penthouse Unit is a one-of-a-kind rental option in a sought after Annapolis location. The 2 bedrooms PLUS Den/3rd Bedroom is loaded with high end finishes. Bright custom Kitchen features Quartz countertops, KitchenAid Stainless Steel Appliances. Open floor plan, wide plank hardwood floors throughout the unit. Primary bedroom with ensuite bathroom, porcelain tile and dual vanity. Unit has 2 different balconies that overlook Annapolis St. Rent includes 2 parking spaces in garage below building. Building has an elevator or use the stairs. Unbeatable location, right in the heart of West Annapolis. Shops, restaurants (RAR Chessie's Wharf, Evelyn's and Ingrano), coffee and Ice Cream shop just steps outside the front door. Close to USNA & Stadium walk to Downtown and easy access to Rt. 50. Pets on Case by Case. Available 11/7/25
#MDAA2127104

ANNAPOLIS

106 ANNAPOLIS STREET 203

2 Beds

2 Baths

1,406 Sq.Ft.

$4,600

MLS#: MDAA2127104

Views of the Great Chesapeake Bay come with this updated and upgraded Oyster Creek waterfront. Shared pier with a large boat slip, community beach and boat ramp for easy water access to the Bay. No smoking house and no pets allowed.
#MDAA2113692

ANNAPOLIS

1330 WASHINGTON DRIVE

3 Beds

2 Baths

1,584 Sq.Ft.

$4,500

MLS#: MDAA2113692

Welcome to Eastport! This exquisitely restored 1945 Cape Cod boasts modern amenities, four bedrooms, and two full bathrooms. Available with lovely antique furnishings to sleep up to 8 people. The expansive, fenced backyard boasts a deck and patio. You'll love the charm, the glorious gardens, and the proximity to all that Annapolis has to offer. Walk to restaurants, shops, and yacht clubs! This is the iconic Eastport experience you've been dreaming of. Welcome home!
#MDAA2128478

ANNAPOLIS

922 JACKSON STREET

4 Beds

2 Baths

2,184 Sq.Ft.

$4,500

MLS#: MDAA2128478

Nestled in the charming Boucher Place community, this exquisite end-of-row townhouse offers a luxurious lifestyle defined by elegance and comfort. Built in 2011, this carriage house-style residence boasts a sophisticated blend of modern design and timeless appeal, making it the perfect sanctuary for those who appreciate the finer things in life. As you approach the property, you are greeted by beautifully maintained sidewalks and inviting street lights that illuminate the path to your new home. The cement siding not only enhances the aesthetic appeal but also ensures durability and low maintenance, allowing you to spend more time enjoying your luxurious surroundings. Step inside to discover a spacious 1,800 square feet of thoughtfully designed living space. This home features three generously sized bedrooms and three and a half bathrooms, providing ample room for relaxation and privacy. The warm ambiance is complemented by a cozy gas fireplace, perfect for creating a welcoming atmosphere during cooler months. The heart of the home is the gourmet kitchen, equipped with high-end stainless steel appliances, including a built-in microwave, dishwasher, and electric stove. Whether you are a culinary enthusiast or prefer casual dining, this kitchen is designed to inspire. The open layout seamlessly connects the kitchen to the living area, making it an ideal space for entertaining or enjoying quiet evenings at home. Additional highlights include a partially furnished interior that exudes style and comfort, along with a convenient detached garage that offers two spaces for your vehicles. The property also includes essential amenities such as common area maintenance, parking, and trash removal, ensuring a hassle-free living experience. Available for lease starting November 15, 2025, with flexible terms ranging from six to eighteen months, this residence invites you to embrace a lifestyle of luxury and convenience. Experience the perfect blend of modern living and classic charm in this exceptional townhouse, where every detail has been meticulously crafted to create a true sense of home. Don't miss the opportunity to make this exquisite property your own.
#MDAA2129406

ANNAPOLIS

19 BOUCHER PLACE

3 Beds

3 Baths

1,800 Sq.Ft.

$4,500

MLS#: MDAA2129406

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