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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
316
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,071,137
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

316 Properties Found. Page 18 of 22.

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

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

Welcome Home to Annapolis Experience the coastal charm and vibrant lifestyle of Maryland’s Chesapeake Bay—where boating, sailing, and sunsets on the water are part of everyday life. Nestled within a highly sought-after school district, this light-filled beach-style chalet perfectly blends modern updates with the warmth of a true retreat. Step through the inviting entryway into a bright, open floor plan. The main-level flex room offers endless possibilities—ideal for a home office, fitness studio, or game lounge. The beautifully remodeled kitchen showcases stunning Calacatta quartz countertops, a navy-and-white cabinetry duo, and stainless-steel appliances. Designed for both family gatherings and weekend entertaining, the kitchen flows seamlessly into the dining area and out onto a spacious deck overlooking more than half an acre of private, tree-lined yard—perfect for cookouts, bonfires, and starlit evenings by the outdoor fireplace. When it’s time to unwind, retreat to four oversized bedrooms offering plenty of room to relax and recharge. From its thoughtful design to its serene setting, this Annapolis home captures everything you’ve been searching for in your next chapter. Schedule your private tour today and come see why life is better by the Bay.
#MDAA2127670

ANNAPOLIS

920 OLD ANNAPOLIS NECK ROAD

4 Beds

2 Baths

2,552 Sq.Ft.

$5,550

MLS#: MDAA2127670

***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

Experience your own piece of paradise. Enjoy this fully furnished, well appointed home in a river front community. 4 bedrooms 3 baths close to the end of a quiet street. See the South River from your front yard and second floor kitchen deck. Close to Maryland's state capital, commuter routes and plenty of restaurants and shopping.
#MDAA2125248

ANNAPOLIS

122 BAY VIEW DRIVE

4 Beds

3 Baths

2,200 Sq.Ft.

$4,300

MLS#: MDAA2125248

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. 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, new garbage disposal, and security system. Owner Agent. There is no sign on the property. Listing MDAA2123438 is the Sale listing for this property.
#MDAA2123566

ANNAPOLIS

919 BERWICK DRIVE

4 Beds

2 Baths

2,292 Sq.Ft.

$4,200

MLS#: MDAA2123566

Charming corner lot home for rent on the coveted Eastport Horn Point peninsula in Annapolis, MD. This cozy residence features 4 bedrooms and 2 fully renovated baths, separate dining and front entry sunporch which provides a comfortable living space for its occupants. With a small but efficient kitchen, rear deck, and mini split air and heating with natural gas radiator heat backup, and unfinished basement, this home offers convenience and comfort in a most desirable location near downtown and Eastport eateries! Don't miss out on the opportunity to make this lovely house your new home. Small pets considered on a case-by-case basis with additional monthly pet rent. This is a non-smoking unit. No groups please.
#MDAA2127894

ANNAPOLIS

530 FIRST STREET

4 Beds

2 Baths

1,200 Sq.Ft.

$4,150

MLS#: MDAA2127894

Absolutely Gorgeous Historic Annapolis home , full of the charm and style yet completely restored with all of the modern conveniences . Close to everything 1 block from main street.....City Dock, Bar, Restaurants...... across from City Hall, Close to spa creek ..... Come sit back and enjoy the Annapolis life style. Pets allowed with non refundable pet fee of $250 per Pet and $50 a month pet rent per pet Parking permits are required now by the city. Must apply for them https://www.annapolisparking.com/ or through a specific webpage https://www.annapolis.gov/1824/New-Residents
#MDAA2116374

ANNAPOLIS

151 DUKE OF GLOUCESTER STREET

4 Beds

3 Baths

1,990 Sq.Ft.

$4,100

MLS#: MDAA2116374

Feel like you're on vacation every day at home in this beautiful 3 bedroom, 2 bathroom, 1370 SF condo at Severn House in Eastport. Enjoy watching sailboats from your couch or relaxing at the community waterfront pool. Love your spacious water view balcony, perfect for entertaining friends. The living room opens to the dining room and balcony, providing a lovely flow for gatherings. With 3 bedrooms, you have the flexibility for an office or extra guest room. You'll appreciate the convenience of a full-size washer and dryer in your condo. The community offers a pool, boat slips, and park-like grounds, creating a serene environment. The owner covers monthly condo fees and provides a 2 parking spaces with guest parking available on a first-come, first-serve basis up to 10 days at a time. Owner is able to leave some furniture if tenant requests. Please note, Severn House does not permit pets. The owner is open to a 12-36 month lease, which is available online, and the condo can be ready for you by November 1. No Smoking. Welcome to your New Home! Check out our video tour too!
#MDAA2128924

ANNAPOLIS

772 FAIRVIEW AVENUE C 772 C

3 Beds

2 Baths

1,370 Sq.Ft.

$4,000

MLS#: MDAA2128924

697 Giddings, 3 levels of Modern luxury in the heart of West Annapolis. Designed by Hammond Wilson Architects and built by Bayview Builders. This townhome is loaded with high end finishes. Custom kitchen with Quartz Countertops, stainless steel top of the line appliances. The lower level has a full bath and rec room that could be used as a 3rd bedroom. Open modern floor plan with hardwood floors throughout. Pella Double-Pane windows which helps keeps the street noise to a minimum. French doors lead to a nice sized patio perfect for any outdoor activity. Shops and restaurants right outside your front door. Restaurants include InGrano, (fine dining), Chessies Wharf by RAR Brewing, Evelyn's Cafe, Bean Rush Coffee shop and Always Ice Cream. Walkable to downtown, Naval Academy and stadium. Water access 5 blocks away. Easy access to RT 50/97. Pets case by case, rent includes 2 parking spot. Electric car charging available.
#MDAA2128808

ANNAPOLIS

697 GIDDINGS AVENUE

2 Beds

2 Baths

1,523 Sq.Ft.

$4,000

MLS#: MDAA2128808

One of the largest homes in Atlantis features 5 bedrooms and 4 1/2 baths!!! Over 3000 sq ft with finished basement and 1 car garage. Access to Tot Lot and larger kid playground. Access to the community pier for fishing, crabbing, and kayaking. Community does bi-weekly food trucks. 4 kayaks will be left at the house for tenants to use. The pier access is a 5 min walk, 1 street over. Pets are considered case by case. Pet rent $25 per month. No groups please. Minimum credit score 675.
#MDAA2128710

ANNAPOLIS

946 AQUA COURT

5 Beds

4 Baths

N/A

$3,850

MLS#: MDAA2128710

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