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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
384
# of Listings
3
Avg # of Bedrooms
$475
Avg. $ / Sq.Ft.
$1,072,947
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

384 Properties Found. Page 15 of 26.

Sellers prefer Original Title & Escrow, LLC. Welcome to this beautifully maintained corner ranch in Eastport, MD, with easy access to Downtown Annapolis. No HOA fees! The bathrooms have been remodeled, and the appliances are stainless steel. This home offers two levels of comfortable living space, with three bedrooms and a full bathroom on the upper level, and the same living space in the basement, featuring hardwood floors and an open-concept kitchen. Outside, enjoy a private and beautiful deck, perfect for family cookouts and entertaining. A spacious driveway provides ample parking. The HVAC system has been recently upgraded (1.5 years old). Don’t miss this incredible opportunity—schedule your visit today! Home Inspection is for informational purposes only. “AS IS”
#MDAA2105934

ANNAPOLIS

201 JANWALL STREET

6 Beds

2 Baths

2,039 Sq.Ft.

$550,000

MLS#: MDAA2105934

Charming colonial in water-privileged Hillsmere Estates! This well-maintained 4BR/1.5BA home has great bones and plenty of potential. Enjoy an updated kitchen with a cozy fireplace, hardwood floors, and a main-level bonus room that could be converted to a 5th bedroom. The existing half bath on the main level could become a full, and the spacious primary suite offers room to add a second bath. Two upper bedrooms have newer mini-split systems, in addition to the main HVAC. Outside, you’ll find a fenced yard and oversized garage. The walk-up unfinished basement adds even more space to expand. All this plus community water access, beach, and pier on the South River!
#MDAA2110028

ANNAPOLIS

508 HARBOR DRIVE

4 Beds

1 Baths

1,620 Sq.Ft.

$550,000

MLS#: MDAA2110028

New on site 2 days ago
New Phase at Element at Mill Creek! Building B, The Banyan, is already half-sold, featuring lounge areas, party room, 2-story clubroom, upper & lower terraces, and more! Start your exciting new chapter in this amenity-rich 55+ community located minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. This extraordinary home with private balcony overlooks lush permanent forest retention and showcases gorgeous design upgrades throughout. True chefs kitchen, closet space galore, reserved parking included. Tour this stunning unit and this building's impeccable amenities today!
#MDAA2115846

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 309

2 Beds

2 Baths

1,210 Sq.Ft.

$549,955

MLS#: MDAA2115846

It starts with a feeling. Maybe it’s the hush of the trees as you turn down the quiet street. Or the way the air softens near the Bay—carrying just a hint of salt, sun, and something slower. Tucked away on a generous 12,500 sq ft double lot, this fully renovated 3-bedroom, 2-bath retreat in Arundel-on-the-Bay isn’t just a house—it’s where your next chapter begins. The kind where weekends stretch a little longer, mornings feel a little lighter, and coming home feels like a deep breath out. Inside, the home flows with ease. Natural light spills across fresh finishes. A cozy wood-burning fireplace anchors the heart of the living space. The kitchen is as functional as it is beautiful—ready for impromptu pasta nights, wine with friends, or solo mornings with coffee and silence. But it’s the enclosed patio where life slows down. Wrapped in windows and light, with a sliding door that opens to a wide backyard and a peek of the Bay beyond, this is where you’ll find yourself most often—book in hand, bare feet on the floor, the day unfolding slowly. And beyond your own backyard, a neighborhood that feels like a hidden coastal village. In Arundel-on-the-Bay and Oyster Harbor, community isn’t just a word—it’s a lifestyle. From sunrise to sunset, you’ll often find plenty of friendly faces and happy tails soaking up the sunshine and shoreline spirit in this , launching kayaks into the Bay, or heading down to the private beach to watch the sunset melt into the water. It's a place where salty breezes, friendly faces, and happy tails are part of the everyday scenery. With access to Oyster Creek, Fishing Creek, and the Chesapeake Bay, there’s always something to discover. Take advantage of multiple marinas, community boat ramps, Newport Pier (with slips on a first-come basis), playgrounds, basketball courts, kayak/SUP storage, picnic areas, and walking trails that wind through nature and shoreline. And for dog lovers, Quiet Waters Park—with its popular dog beach and scenic trails—is just a short drive away. And when it’s time to reconnect with city energy, you’re only minutes from historic downtown Annapolis, and with easy access to Route 50, I-97, BWI, and the Eastern Shore, you’re never far from wherever life takes you. But chances are… you won’t want to leave. Because some homes aren’t just about square footage or finishes. Some homes are about how they make you feel. And this one? This one feels like peace. Welcome home.
#MDAA2111546

ANNAPOLIS

1302 MYRTLE AVENUE

3 Beds

2 Baths

1,664 Sq.Ft.

$549,900

MLS#: MDAA2111546

Welcome to your new home! This fabulous single-family home is situated on a spacious .35 acre lot, offering privacy and tranquility less than 10 minutes from downtown Annapolis. The home underwent an extensive renovation in 2021. Key Features: Patio enclosure for extra square footage, a brand-new kitchen, fresh paint, and wall-to-wall hardwood floors. A dormer was built on the back of the house to create a luxurious master bathroom upstairs. The fully fenced rear yard offers privacy and security, with a spacious patio perfect for grilling and relaxing. The HVAC system is only 4 years old, and the crawl space was encapsulated in 2021. New windows throughout the house ensure energy efficiency and comfort. This is a 10! Agents warmly welcome! Not a showingtime listing- call LA
#MDAA2108786

ANNAPOLIS

1032 FOREST HILLS AVENUE

3 Beds

2 Baths

N/A

$549,900

MLS#: MDAA2108786

Ideal Eastport living! This sweet one-bedroom “lock and leave” is steps from the water, features a breathtaking rooftop deck and pool, and is walkable to shops and restaurants. Fully updated with new Pella windows and designer touches ... this corner, fifth-floor unit is bright and cheery with sweeping views of Spa Creek and the Annapolis skyline. The USNA dome, and St. Mary’s steeple are the backdrop for sailboats and yachts navigating up and down the creek. This turnkey elevator top-floor condo features an updated kitchen with new quartz countertops, tile backsplash, stainless appliances, and new cabinets for ample storage. The galley kitchen feels spacious and light as it overlooks the defined dining and open living area. The spacious living room features a window seat with a view that is the perfect perch for guests or a quiet moment with a glass of Sancerre. New luxury vinyl floors flow throughout while tasteful paint colors offer a warm inviting coastal feel. The bedroom features a large closet, and there is additional storage in unit hallway. While laundry is not in the unit, it is available from the shared hallway. With all assessments paid, the reconstructed rooftop deck is also accessible right outside the front door of the unit and offers a gorgeous newly resurfaced pool and space for viewing all the keystone Annapolis events...Blue Angels, July 4 fireworks, Parade of Lights, and New Year’s Eve fireworks. You’ll have the best seat in the house! In warm weather you will have a private oasis for swimming, relaxing, or entertaining. Your 5x5x8 storage cage on the main level provides space for overflow items. An assigned premium parking space has been paid for by the current owner through the end of 2025. Currently the refashioned community marina area has boat slips available; ask for further information. Furniture is negotiable. This is a secured building with a key and call system so you can admit guests from your unit. Fully turnkey with quality updates, #501 has been called “the best in the building” because of its light, location, and vantage point. You will be steps from yacht clubs and marinas, or an evening stroll over the Spa Creek Bridge...a truly magical weekend respite or a great place to call home!
#MDAA2114978

ANNAPOLIS

316 BURNSIDE STREET 501

1 Beds

1 Baths

705 Sq.Ft.

$549,000

MLS#: MDAA2114978

WOW! Dean Street in Annapolis. 5 minute walk to City Dock and all it has to offer. 2- 1 bedroom apartments. Separate meters. Tenants pay all utilities. Upstairs apartment renovated in the past 2 months to include new paint, LTV in hall , kitchen, and bathroom. New carpet with upgraded padding. Nice open floor plan. First floor apartment has access to fenced back yard. Front porch is a great place to relax on warm summer evenings! Property is well maintained. Excellent rental history.
#MDAA2105134

ANNAPOLIS

25 DEAN STREET

2 Beds

2 Baths

1,112 Sq.Ft.

$549,000

MLS#: MDAA2105134

WOW! Dean Street in Annapolis. 5 minute walk to City Dock and all it has to offer. 2- 1 bedroom apartments. Separate meters. Tenants pay all utilities. Upstairs apartment renovated in the past 2 months to include new paint, LTV in hall , kitchen, and bathroom. New carpet with upgraded padding. Nice open floor plan. First floor apartment has access to fenced back yard. Front porch is a great place to relax on warm summer evenings! Property is well maintained. Excellent rental history.
#MDAA2103894

ANNAPOLIS

25 DEAN

2 Beds

None Baths

1,200 Sq.Ft.

$549,000

MLS#: MDAA2103894

Welcome Home to 901 Chesterfield Road!! This Beautifully updated Single family home located in Annapolis has the space you need to create a life you desire. Boasting an array of sleek finishes throughout this 5 Bedroom, 3 Bathroom home has so much to offer!! The main level offers an open concept layout featuring spacious living room, dining area, 3 entry level bedrooms, 2 full bathrooms, and sunroom. The kitchen boasts S/S appliances, white shaker cabinets, Quartz counters and MORE! All bathrooms have been updated with new ceramic tile, and all new bathroom fixtures! The basement has been fully finished to include 2 additional bedrooms, 3rd full bathroom, and utility room. Off street private parkin and SO MUCH MORE!! Book your private showing today before its gone!!
#MDAA2103668

ANNAPOLIS

901 CHESTERFIELD ROAD

5 Beds

3 Baths

2,457 Sq.Ft.

$540,000

MLS#: MDAA2103668

WOW! Nestled along the Chesapeake Bay, this waterfront residence offers views of the community marina and the open water beyond. Situated in the sought-after gated community of The Village of Chesapeake Harbour, this beautifully updated two-bedroom, two-bath home combines modern elegance with coastal charm. Step into the welcoming foyer, where an open-concept design unfolds with a soothing color palette freshly painted in 2022. Custom shades, including select electric-controlled options, add both privacy and convenience. The living and dining area boasts striking wood-look porcelain tile flooring, seamlessly blending gray and blue hues that echo the shimmering waters just beyond. Crown molding adds a refined touch, while the living room’s fireplace creates a cozy retreat. A three-panel sliding glass door leads to the expansive patio—larger than others in the community—where you can unwind in a private setting while soaking in the serene water views. The well-appointed kitchen is both stylish and functional, featuring stainless steel appliances, including a recently replaced dishwasher, range, and microwave. An antiqued glass tile backsplash reflects natural light, creating a luminous atmosphere, while a pantry provides ample storage. Another triple-panel sliding glass door opens to a front patio, making this space feel bright and airy. The primary bedroom is a tranquil haven, offering direct patio access through yet another sliding glass door, providing serene water views. The en-suite bath is a luxurious retreat with a double vanity topped with granite, a water closet, and a floor-to-ceiling tiled shower. A spacious walk-in closet with a built-in organizational system completes this private sanctuary. Down the hall, the second bedroom is generously sized, accompanied by an updated full bath with a modern vanity. A sleek, stacked washer and dryer are tucked away in the laundry room, rounding out the home’s well-designed layout. Storage is plentiful, with custom-built closet systems enhancing organization throughout. For peace of mind, the brand-new HVAC system was upgraded in 2025, including an added air purifier. Ample space is available for residents and guests in the unassigned parking lot. The community offers resort-style living with premier water access and exceptional amenities. Enjoy dining at the on-site Beacon Waterfront Galley & Bar, take a dip in one of two pools with bay views, or relax on the private sandy beach. Outdoor enthusiasts will love the fishing piers, kayak launch, and scenic walking and biking trails. Tennis courts and a picnic area provide additional recreation options. Electric car charging stations offer convenience. Boaters will appreciate the Chesapeake Harbour Marina, featuring 81 wet slips with fresh water, electricity, and WiFi, as well as a full-service yacht facility. Ideally situated near Historic Downtown Annapolis, Chesapeake Harbour provides a peaceful retreat while remaining within commuting distance of Baltimore and Washington, D.C. Experience coastal living at its finest—where the water meets effortless luxury. Property Updates: Porcelain tile flooring, dishwasher, range and microwave, washer & dryer, blinds, kitchen faucet and disposal, kitchen backsplash, interior paint, full bath vanity, closet built-ins, HVAC updates, and more!
#MDAA2108536

ANNAPOLIS

7024 CHANNEL VILLAGE COURT T2

2 Beds

2 Baths

1,177 Sq.Ft.

$535,000

MLS#: MDAA2108536

Enjoy resort-like living at Chesapeake Harbour, a gated community filled with amenities and beautiful water views of the Chesapeake Bay! This desirable 2 bedroom, 2 bathroom ground-floor unit offers access to dual covered terraces, a wood-burning fireplace, and updates throughout. The kitchen features new countertops and a new refrigerator as well as recently updated sink, stove, dishwasher, and cabinets. The owner's suite provides its own terrace entrance plus a walk-in closet and en-suite bath with double-sink vanity. This community offers a marina with a waterfront restaurant, summertime Tiki bar, two pools - including one that is bayfront- plus tennis courts, a private beach, pier, storage for your canoe or kayak, and onsite security. Ideal location just three miles from Historic Annapolis, near commuter corridors to DC and Baltimore, and just 30 minutes from BWI airport. Come and enjoy the abundant amenities and the convenience of living in the waterfront community of Chesapeake Harbour!
#MDAA2101380

ANNAPOLIS

7022 CHANNEL VILLAGE COURT T2

2 Beds

2 Baths

1,277 Sq.Ft.

$535,000

MLS#: MDAA2101380

Welcome to 1019 Timber Creek Drive—an updated 4-bedroom, 2-bath home nestled in a quiet, tree-lined Annapolis neighborhood just minutes from downtown and Eastport. Inside, you’ll find fresh paint, new carpet, and a bright layout featuring hardwood floors, a cozy wood-burning fireplace, and newly renovated bathrooms. The kitchen offers modern appliances and plenty of storage, while the spacious bedrooms provide flexibility for family, guests, or a home office. Enjoy peace of mind with a new high-efficiency HVAC system and newer Samsung washer/dryer. The private backyard backs to trees and offers space to relax or entertain, plus there are two off-street parking spots. Timber Creek is a close-knit community with a tot-lot playground and low HOA fees. Just moments from Quiet Waters Park, local shops, and all the charm of Annapolis—this is a move-in-ready gem you don’t want to miss.
#MDAA2109642

ANNAPOLIS

1019 TIMBER CREEK DRIVE

4 Beds

2 Baths

1,826 Sq.Ft.

$535,000

MLS#: MDAA2109642

Welcome to 316 Burnside Street, Unit #208 — a charming one-bedroom, one-bath condominium nestled in the heart of Annapolis. This inviting residence features beautiful luxury vinyl plank flooring, a recently installed water heater (2024), and central A/C for year-round comfort. This flexible layout offers additional sleeping accommodations with a Murphy bed in the dining area and a sleeper sofa. Residents will enjoy access to a rooftop pool with stunning water views, perfect for relaxing or entertaining. Ideally located near vibrant shops, restaurants, and waterfront attractions, this home offers the best of Annapolis living. Don't miss the opportunity to make it yours!
#MDAA2112714

ANNAPOLIS

316 BURNSIDE STREET 208

1 Beds

1 Baths

768 Sq.Ft.

$535,000

MLS#: MDAA2112714

NEW PRICE & OPEN Saturday, 5/31, 11-1! Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in one of Annapolis’s most amenity-rich waterfront communities. Nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay, Oyster Harbor offers the best of coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. This move-in ready home features a long list of updates, including a brand-new roof, new granite countertops, new dishwasher and recent mechanical improvements: a new heat pump and A/C compressor (2024), and new refrigerator, stove, washer, and dryer (2019). The fully fenced backyard boasts water peeks, a hot tub, and a spacious deck surrounded by beautiful landscaping—ideal for entertaining or quiet evening relaxation. Inside, the layout includes a welcoming living area, functional kitchen with plenty of cabinet space, and a light-filled dining area. Upstairs, the primary suite includes a private full bath, with two additional bedrooms and a full bath. But what truly sets this home apart are the amazing resort-style amenities: private community beach with swimming area and sea nettle nets, three marinas , fishing pier, boat ramp, kayak racks, beach volleyball, and playgrounds! Whether you’re looking for a full-time residence or a weekend retreat, this home and its community offer something truly special: a waterfront neighborhood that embraces recreation, relaxation, and the Chesapeake lifestyle.
#MDAA2114714

ANNAPOLIS

3331 ARUNDEL ON THE BAY ROAD

3 Beds

2 Baths

1,364 Sq.Ft.

$535,000

MLS#: MDAA2114714

WOW! Nestled along the Chesapeake Bay, this waterfront residence offers views of the community marina and the open water beyond. Situated in the sought-after gated community of The Village of Chesapeake Harbour, this beautifully updated two-bedroom, two-bath home combines modern elegance with coastal charm. Step into the welcoming foyer, where an open-concept design unfolds with a soothing color palette freshly painted in 2022. Custom shades, including select electric-controlled options, add both privacy and convenience. The living and dining area boasts striking wood-look porcelain tile flooring, seamlessly blending gray and blue hues that echo the shimmering waters just beyond. Crown molding adds a refined touch, while the living room’s fireplace creates a cozy retreat. A three-panel sliding glass door leads to the expansive patio—larger than others in the community—where you can unwind in a private setting while soaking in the serene water views. The well-appointed kitchen is both stylish and functional, featuring stainless steel appliances, including a recently replaced dishwasher, range, and microwave. An antiqued glass tile backsplash reflects natural light, creating a luminous atmosphere, while a pantry provides ample storage. Another triple-panel sliding glass door opens to a front patio, making this space feel bright and airy. The primary bedroom is a tranquil haven, offering direct patio access through yet another sliding glass door, providing serene water views. The en-suite bath is a luxurious retreat with a double vanity topped with granite, a water closet, and a floor-to-ceiling tiled shower. A spacious walk-in closet with a built-in organizational system completes this private sanctuary. Down the hall, the second bedroom is generously sized, accompanied by an updated full bath with a modern vanity. A sleek, stacked washer and dryer are tucked away in the laundry room, rounding out the home’s well-designed layout. Storage is plentiful, with custom-built closet systems enhancing organization throughout. For peace of mind, the brand-new HVAC system was upgraded in 2025, including an added air purifier. Ample space is available for residents and guests in the unassigned parking lot. The community offers resort-style living with premier water access and exceptional amenities. Enjoy dining at the on-site Beacon Waterfront Galley & Bar, take a dip in one of two pools with bay views, or relax on the private sandy beach. Outdoor enthusiasts will love the fishing piers, kayak launch, and scenic walking and biking trails. Tennis courts and a picnic area provide additional recreation options. Electric car charging stations offer convenience. Boaters will appreciate the Chesapeake Harbour Marina, featuring 81 wet slips with fresh water, electricity, and WiFi, as well as a full-service yacht facility. Ideally situated near Historic Downtown Annapolis, Chesapeake Harbour provides a peaceful retreat while remaining within commuting distance of Baltimore and Washington, D.C. Experience coastal living at its finest—where the water meets effortless luxury. Property Updates: Porcelain tile flooring, dishwasher, range and microwave, washer & dryer, blinds, kitchen faucet and disposal, kitchen backsplash, interior paint, full bath vanity, closet built-ins, HVAC updates, and more!
#MDAA2116088

ANNAPOLIS

7024 CHANNEL VILLAGE COURT T2

2 Beds

2 Baths

1,177 Sq.Ft.

$525,000

MLS#: MDAA2116088

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