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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
301
# of Listings
3
Avg # of Bedrooms
$475
Avg. $ / Sq.Ft.
$1,085,449
Med. List Price

Browse Annapolis Real Estate Listings

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301 Properties Found. Page 13 of 21.

Model Home Now For Sale! Bright, spacious unit at second floor elevation showcasing stylish design upgrades throughout! Start an exciting new chapter in this amenity-rich 55+ community conveniently located mere minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. Reserved parking included. Turnkey luxury includes window treatments, full-size washer and dryer and more! Building One nearly sold out - tour this gorgeous staged model home today!!
#MDAA2110762

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 107

2 Beds

2 Baths

1,318 Sq.Ft.

$499,900

MLS#: MDAA2110762

Welcome to easy living in the highly sought-after 55+ community of Heritage Harbour where the amenities rival the finest resorts! This charming one-level home offers a perfect blend of comfort, style, and convenience, plus a private and serene back setting surrounded by trees for an added peaceful feeling. Featuring 2 spacious bedrooms, 2 full bathrooms, a den, and an updated kitchen, this residence is designed for modern living. You'll love the new flooring, fresh paint, and the private back patio—ideal for leisurely mornings or relaxing evenings. Enjoy the ease of a one-car garage and low-maintenance living while taking advantage of everything Heritage Harbour has to offer. Residents enjoy access to indoor and outdoor pools, a fully equipped fitness center, tennis and sport courts, a community library, performance hall, scenic walking trails, and water access for kayaking or boating. All this, plus convenient proximity to shopping, dining, and major commuter routes. Don't miss your chance to live in one of the area's premier active adult communities—where lifestyle meets location!
#MDAA2118638

ANNAPOLIS

2601 COMPASS DRIVE

2 Beds

2 Baths

1,514 Sq.Ft.

$496,500

MLS#: MDAA2118638

Charming Condo for sale in Heritage Harbour's 55+ Community. Step into a lifestyle of ease and sophistication in this beautiful condo, nestled within the vibrant 55+ community of Heritage Harbour in Annapolis. Perfect for active adults, this sought after neighborhood offers a host of amenities tailored to enhance your daily living. Enjoy access to a state-of-the-art clubhouse, indoor and outdoor swimming pools, tennis courts, a fitness center, scenic walking trails, and even a golf course and dock for your boat and kayaks. Socialize with friends through the community, grab a meal at the private community restaurant Wilder Fresh Kitchen, or simply unwind in the serene surroundings.
#MDAA2119226

ANNAPOLIS

940 ASTERN WAY 112

2 Beds

2 Baths

1,588 Sq.Ft.

$495,000

MLS#: MDAA2119226

OPEN HOUSE SATURDAY 9/6 11-1pm. Welcome to 1624 Katheryne Village Sq- This beautifully updated 4 bed/3 full bath townhome, in the lovely Courts at Belle Pointe, is move in ready! Main level greets you with newer LVP flooring (2021), gas fireplace with custom mantel, recessed lighting, updated kitchen with stainless steel appliances and more! Upper-level features 3 bedrooms with vaulted ceilings and new ceiling fans, large primary with walk-in closet and fully renovated primary and hallway baths (2024)! 4th bedroom, full bath and kitchenette are on the lower level with walk-out to fully fenced backyard, perfect for a separate living space or entertaining! Washer/Dryer 2022, HWH 2021, Roof and HVAC 2019. Great location with easy commuting access to Route 50, close to Cape St. Claire shopping center, new walk/bike trail, Broadneck and Sandy Point State Parks just around the corner!
#MDAA2124818

ANNAPOLIS

1624 KATHERYNE VILLAGE SQUARE

4 Beds

3 Baths

2,086 Sq.Ft.

$489,900

MLS#: MDAA2124818

Exceptionally beautiful 1 BR/1 Bath with stunning sunset views in like-new condition. The only unit available in this Luxurious Condo Building still priced below $500K. Many upgrades: New Bosch HVAC Heat Pump costing $10K, New designer walk-in shower costing $12 K , New carpeting in Bedroom., Hardwood floors, granite counters. Many amenities : 24/7 live person at the Lobby Front Desk, very secure building, One owned/ assigned underground garage parking space with remote opener, Fitness Center, Outdoor Pool and Hot Tub, Two Outdoor Gourmet BBQ kitchens, Gardening Area, Library, Party Room , TV Lounge , Free Shuttle Service to downtown, just blocks to City Dock attractions: restaurants, entertainment venues, shopping. The most luxurious condo residence in this county.
#MDAA2121784

ANNAPOLIS

5 PARK PLACE 431

1 Beds

1 Baths

839 Sq.Ft.

$489,900

MLS#: MDAA2121784

Price Reduction! Fantastic price for this gorgeous garage unit !! Enjoy a luxurious lifestyle in this beautiful and pristine 2BR/2BA condo in the very desirable and vibrant 55+ community of Four Seasons at St Margarets! Enter the very well-kept secure building and access your second floor home by stairs or elevator ...OR use your garage door remote and enter the building through your private, over-sized garage. The dramatic open floor plan is ideal with kitchen island overlooking the huge living room with gorgeous hardwood floors and plantation shutters. The living room leads to a large, private balcony. The primary bedroom is massive with a large bay window and an over-sized walk-in closet. The attached bathroom has a walk-in shower and separate soaking tub. The second bedroom has a bay window, two double closets and is served by a hall bath. A large laundry room and multiple closets complete this side of the condo. Nothing to do but move in and enjoy the incredible amenities - stunning community center has several beautifully furnished party areas to entertain your guests and meet with neighbors. There is a kitchen, bar, billiards room, library, fitness center and inviting outdoor pool with many tables and chairs to enjoy the beautiful weather and wooded surroundings. The location is ideal - tucked away, but very close to shopping, public library, hiking and bike trail, and easy access to downtown Annapolis! Smoking Restricted Community
#MDAA2114444

ANNAPOLIS

1509 FERAL DAE LANE 204

2 Beds

2 Baths

1,442 Sq.Ft.

$489,000

MLS#: MDAA2114444

Step into timeless character and charm in this lovely updated three-level townhome condo, where thoughtful details and upgrades create a truly special living experience. Outside, a blooming front cottage garden sets a warm and welcoming tone, bursting with color and texture in every season. Inside, the main level features hardwood floors throughout, arched doorways, replacement windows, and an abundance of natural light. The spacious living room opens to a lovely private patio with a privacy wall, wood gate, raised garden beds, and a shed for added storage. Relax in your own green haven, combining the feel of a countryside escape with the convenience of townhouse living—charming, low-maintenance, and full of personality. The tastefully newly remodeled kitchen blends style and function with all-wood custom cabinetry, granite countertops, stainless steel appliances, and a terracotta-style tile floor, adding warmth and Mediterranean flair. A deep-sill window fills the space with natural light. A convenient half bath completes this level. Upstairs, hardwood floors continue throughout the bedroom level. The primary bedroom features two closets and a private full bath with a custom decorative vanity and shower. The hall full bath, serving the two additional bedrooms, also features a custom vanity, matching mirrors, and lights. The lower level expands the home's livable space with a large, versatile room ideal for a media room, playroom, home office, or workout area. A generously sized utility/storage room houses the washer and dryer, plus ample space for hobbies, tools, and seasonal storage. Brand new CAC has just been installed! Parking & Community Perks - enjoy two dedicated parking spaces behind the home, plus additional unassigned spaces. A free shuttle from nearby Navy Stadium takes you to Historic downtown Annapolis, with its charming shops, restaurants, and waterfront attractions Beyond the home, enjoy the vibrant life of Admiral Heights Community including two waterfront areas—one with a dock for fishing and swimming, the other for launching kayaks/canoes, community pool membership, a full calendar of seasonal neighborhood events, and optional membership in a private boat club. Just minutes away, Historic Downtown Annapolis offers colonial charm and maritime tradition. Stroll along brick-lined streets with boutique shops, cozy cafes, award-winning restaurants, and the iconic Annapolis harbor where sailboats glide through sparkling waters. From waterfront dining to lively festivals and scenic views, Downtown Annapolis delivers an unmatched blend of nautical beauty, cultural richness, and small-town charm.
#MDAA2124870

ANNAPOLIS

1312 CEDAR PARK ROAD

3 Beds

2 Baths

2,160 Sq.Ft.

$488,000

MLS#: MDAA2124870

Welcome to a home that checks all the right boxes: space, convenience, and location. With four generously sized bedrooms and two full bathrooms, this townhouse offers room to grow, work from home, or host weekend guests who end up staying just a bit longer than planned. The living space features a bright, open layout with plenty of natural light—perfect for morning coffee, afternoon naps, or an impromptu dance party (no judgment). The kitchen and dining flow smoothly into the main living area, making entertaining easy and cleanup even easier. Step outside and enjoy a private outdoor space, great for grilling in the summer or sipping something warm in the fall. There's even an attached garage—a rare find in townhouse living—for convenient parking and additional storage. If you're into fresh air and weekend strolls, you're in luck. A scenic walking trail is just around the corner, while nearby parks offer playgrounds and green spaces. Thinking about school options? One of the area’s top-rated high schools is only a short distance away. When it's time to stock the fridge or grab takeout, local grocery stores and a variety of dining spots are close at hand. And if your weekdays involve commuting, you'll enjoy easy access to major routes connecting you to Annapolis, Baltimore, and Washington. Whether you're a first-time buyer or simply looking to simplify life without giving up comfort, this home offers the lifestyle you've been looking for—no compromising required.
#MDAA2120130

ANNAPOLIS

633 BAYSTONE COURT

4 Beds

2 Baths

1,868 Sq.Ft.

$484,995

MLS#: MDAA2120130

Step into an unparalleled opportunity to own a piece of Cape St. John — all for under $500,000! This rare gem offers the perfect blend of coastal charm, modern upgrades, and an enviable location in one of the area’s most beloved waterfront communities. Welcome to your dream retreat! Just a short stroll from your door, you’ll find one of the community’s best private beaches, complete with a sandy shoreline, kayak storage, boat ramp, designated swimming area, and dock along the majestic South River. This home packs a big punch for its price, featuring numerous upgrades on a beautifully maintained and usable .34-acre lot with seasonal water views. Imagine sipping your favorite beverage on the inviting front porch, surrounded by mature trees that provide privacy and a serene landscape setting. Location couldn’t be better — just minutes from Mike’s Crab House, Routes 50 and 97, and only 15 minutes from historic Annapolis, while shopping and everyday conveniences are just a short drive away. Why settle for a townhouse when you can have a private lot and single-family home, with multi-million-dollar waterfront estates just a few houses down? Don’t let this rare opportunity slip away — Cape St. John living awaits!
#MDAA2124512

ANNAPOLIS

251 CAPE SAINT JOHN ROAD

2 Beds

1 Baths

1,002 Sq.Ft.

$484,900

MLS#: MDAA2124512

Set on nearly an acre in the rolling hills of Saint Margaret’s, this one-level home combines move-in comfort with exciting potential. The backdrop of a neighboring red barn adds timeless countryside charm, while hardwood floors, a renovated kitchen, and updated baths create a warm and inviting interior. The home already offers many updates and is in move-in condition, yet there are a few projects still waiting to be finished — giving a handy buyer the opportunity to make it their own. Imagine how incredible the landscaping could be, picture a fully finished basement, or even plan for a future addition. With this property being offered as-is, the possibilities are limited only by your imagination. Best of all, there’s no homeowners association and plenty of space to spread out. Minutes from the restaurants, parks, and museums of Annapolis — and just a stone’s throw from the Naval Academy — this is a rare chance to enjoy countryside living with city convenience.
#MDAA2122338

ANNAPOLIS

1834 SAINT MARGARETS ROAD

3 Beds

1 Baths

2,688 Sq.Ft.

$475,000

MLS#: MDAA2122338

Price Adjustment! Welcome to 8 Ashford Ct — Modern Living in the Heart of Annapolis! Now offered at a new, more attractive price, this beautifully updated 2-bedroom, 1.5-bath contemporary townhouse is move-in ready and full of upgrades. Enjoy a spacious open floor plan featuring gleaming hardwood floors and a modern kitchen with stainless steel appliances. Located in the highly desirable Hunt Meadow community, residents have access to amenities including a pool, tennis courts, and scenic walking paths. All just minutes from downtown Annapolis, shopping, dining, and commuter routes — don’t miss this fantastic opportunity!
#MDAA2115574

ANNAPOLIS

8 ASHFORD COURT

2 Beds

1 Baths

1,248 Sq.Ft.

$465,000

MLS#: MDAA2115574

Popular Hunt Meadow townhome model ONE-LEVEL living-2 BDRM/2 BA - with basement! Wood floors throughout- tile in kitchen, vaulted ceilings, gas fireplace. Remodeled main Bathroom. Recent new roof and deck. Reasonable HOA fees of $250/mo. covers pool/tennis/jog-bike trails, prof off-site mgmt.; lawn maintenance; trash; snow shoveling to your front door!
#MDAA2119470

ANNAPOLIS

7 ASHFORD COURT

2 Beds

2 Baths

1,740 Sq.Ft.

$465,000

MLS#: MDAA2119470

Beautiful Condo on Spa Creek! PRICE IMPROVEMENT TO $460K. Great investment property, second home or live in downtown Annapolis! Located in the heart of desirable Eastport, this inviting condo offers the best of Annapolis nautically inspired living. 316 Burnside Street has big water views of the serene waters of Spa Creek! This home offers an ideal retreat for those seeking both tranquility in the city of Annapolis! Updated kitchen offers rich cherry cabinetry, gleaming granite countertops, and stainless steel appliances. The kitchen is both functional and stylish. Modern, nautical ash and cherry wood floors flow seamlessly throughout, adding warmth and style to this comfortable space. Recent upgrades includes all new HVAC 2022 of 2 units, freshly painted, and recessed lighting. The Burnside Condominium offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. These amenities provide residents with a serene retreat to enjoy sunsets, watch events like the Blue Angels' flyovers, NAVY commissioning week, and parade of lights. Partake in kayaking, and paddle boarding with private dock space. and water taxis. Deep water boat slips available for a rental fee. Entertain your friends and watch the Annapolis fireworks from your deck without fighting the crowds. The Burnside Condominiums in Annapolis offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. Take an easy stroll to some of the best waterside restaurants, yacht clubs, shopping, grocery store, and all the charm Annapolis has to offer! This is a secured building, with keyed entry, intercom system, and elevator access. There is laundry use on all condo levels and main floor storage unit for your condo space. Off street parking for residents on lot, and guest parking available. This a beautiful home and you will not want to miss a viewing! Move right in and enjoy Annapolis living at its very best!
#MDAA2114264

ANNAPOLIS

316 BURNSIDE STREET 304

1 Beds

1 Baths

526 Sq.Ft.

$460,000

MLS#: MDAA2114264

Tucked within The Landings community, this three-level townhome blends thoughtful updates with a convenient location and access to a wealth of amenities, including two community pools, tennis courts, and pickleball courts. An open concept floor plan welcomes you inside, where modern touches and character details create a warm and inviting atmosphere. To the right, the kitchen offers Silestone counters, stainless steel appliances, ample workspace, and a breakfast bar that makes both cooking and entertaining easy. Beyond the kitchen, the dining space flows naturally into the living room, anchored by a wood-burning fireplace with a reclaimed art deco-style mantel and a travertine hearth. A sliding glass door extends the living area to a composite deck, surrounded by mature trees that provide natural shade and privacy. Upstairs, the primary bedroom impresses with its generous size and a wall of closet space. A private vanity area complements the ensuite design, leading into a water room with a toilet and a tiled shower that has been enhanced with a row of aqua accent tiles and extended tilework that now reaches the ceiling. Two additional bedrooms and a full hall bath complete the upper level. The lower level expands the home’s flexibility with a partially finished space that can serve as a recreation room, exercise area, hobby space, or storage. A sliding glass door opens directly to the backyard, while a large laundry area and under-the-stair storage with custom doors add everyday convenience. Recent improvements include a roof in 2019, refinished lower-level stairs, updated light fixtures, a reclaimed mantel, and travertine landings, ensuring style and peace of mind. The Landings community maintains lawns, common areas, and snow removal, making low-maintenance living possible. Parking is unassigned, yet there are ample spaces available for both you and your guests. This location offers the best of Annapolis at your doorstep. Downtown Annapolis is only a few minutes away, providing waterfront dining, historic landmarks, and cultural attractions. The Pip Moyer Recreation Center and Truxton Park are within walking distance, while Quiet Waters Park offers 340 acres of trails, water access, and a dog-friendly beach. Blending modern updates, a flexible layout, and exceptional amenities, this townhome provides both comfort and convenience in a sought-after Annapolis setting.
#MDAA2124386

ANNAPOLIS

5 ROCKWELL COURT

3 Beds

2 Baths

2,165 Sq.Ft.

$450,000

MLS#: MDAA2124386

It’s rare to find a home that checks all the boxes—peaceful neighborhood, functional space, and a location that keeps you connected. This one does just that. Nestled on a quiet cul-de-sac in Whispering Woods, the setting feels tucked away while still offering easy access to everything Annapolis has to offer. Step outside and you’re just minutes from Broadneck parks, local shops, and waterfront dining—yet the neighborhood itself feels like a retreat, with wooded walking paths, a community playground, and neighbors who take pride in their surroundings. The fully fenced backyard backs to trees, offering privacy and room to enjoy the outdoors. Inside, the home’s layout is made for everyday living. Defined spaces flow naturally from one level to the next, with a cozy fireplace downstairs and extra room for whatever life throws your way—whether that’s working from home, hosting guests, or simply needing a bit more space. For anyone looking to put down roots in a neighborhood that feels established, welcoming, and close to it all—this is the kind of place where the next chapter can begin.
#MDAA2116680

ANNAPOLIS

414 BLOSSOM TREE COURT

3 Beds

1 Baths

1,560 Sq.Ft.

$444,900

MLS#: MDAA2116680

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