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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 su...
One of the most popular communities provided by Maryland Sandbox
384
# of Listings
3
Avg # of Bedrooms
$490
Avg. $ / Sq.Ft.
$1,159,423
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

384 Properties Found. Page 8 of 26.

Experience the Essence of Annapolis Charm at 179 Green Street Nestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, this location offers the very best of city living in one of the city's most coveted neighborhoods. Inside on the main level, you'll find wide-board pine floors, a thoughtfully updated kitchen with new cabinetry and appliances, and inviting front and side porches perfect for morning coffee or evening relaxation. Rarely found in downtown Annapolis, two oversized off parking spaces add incredible convenience. Upstairs, the home features two spacious bedrooms and a versatile third room—ideal for a home office, den, or oversized walk-in closet. The newly fenced backyard offers a private oasis for entertaining, dining al fresco, or simply enjoying the outdoors. Living at 179 Green Street means immersing yourself in a lifestyle rich with history and culture. Stroll cobblestone streets to award-winning restaurants, art galleries, and the iconic City Dock. Enjoy sailing, community events, and the vibrant energy of downtown—right outside your door. Don’t miss your chance to own a piece of Annapolis charm. Schedule your private tour today.

ANNAPOLIS

179 GREEN STREET

2 Beds

1 Baths

1,656 Sq.Ft.

$1,175,000

MLS#: MDAA2111662

Sellers are offering $25,000 to go towards siding replacement. This beautiful property offers three levels of spacious, comfortable living in the neighborhood of Epping Forest. Walking through the front door, vaulted ceilings and natural light greet you in the dining/living room area off the kitchen. A main level bedroom suite offers convenience and a second suite upstairs boasts extra privacy. The Severn River can be seen through the trees off the double level deck which is accessed through the dining room, primary suite, or basement common room. On the bottom level, two bedrooms share a full bath and a common living space. Sliding doors add more natural light and additional exits to the lower deck. The private neighborhood beach and clubhouse offer peak enjoyment in the summer months! The club house offers family and golf cart friendly community for all ages! Ample storage, parking, and living space make this home unique in the gated community! HVAC replaced in October of 2020 Both decks replaced in December of 2020 Water treatment system replaced in February of 2022 Roof replaced in November of 2023 Buyer must review and acknowledge Epping Forest Constitution and Bylaws. See Documents.

ANNAPOLIS

319 EPPING WAY

4 Beds

3 Baths

2,372 Sq.Ft.

$1,150,000

MLS#: MDAA2095698

Live the Eastport Dream – Luxury, Water Access & Walkability at 827 Janice Drive. Step into a rare opportunity to own a custom-built showpiece in Eastport’s best-kept secret—Green Acres. Welcome to 827 Janice Drive, where elevated design meets the unbeatable Annapolis lifestyle. This 4,000+ square foot home, meticulously constructed by Cedar Square Homes, is more than just beautiful—it's move-in ready, thoughtfully curated, and built to impress at every turn. From the moment you arrive, the home makes a statement—grand entry, sunlit spaces, and a floor plan that flows effortlessly. At the heart is a chef’s kitchen that doesn’t hold back: massive quartz island, premium stainless appliances, 42-inch custom cabinetry, and designer lighting. Whether you're hosting a crowd or enjoying a quiet morning coffee, this kitchen delivers. The main level also includes a gas fireplace in the family room, private office, and expansive entertaining spaces. Upstairs, escape to a luxurious primary suite with spa-like bath, featuring a freestanding soaking tub, oversized glass shower, and serene finishes. Three additional bedrooms and two more designer baths complete the upper level, offering room for everyone. Downstairs? It’s the ultimate flex space: a fully finished basement with rec room, den, and full bath—perfect for guests, workouts, media nights, or whatever your lifestyle demands. But what truly sets this home apart is location and community. Green Acres is an enclave of tranquility in the heart of Eastport, with tree-lined streets, friendly neighbors, and private water access to Back Creek including a residents-only pier with kayak and paddleboard storage. Launch into adventure from your own neighborhood. Walk or bike to Downtown Annapolis, the marina, restaurants, and the iconic Eastport charm. It’s all just minutes away. This isn’t just another luxury home—it’s a once-in-a-generation lifestyle opportunity. And it’s ready for you, right now. New, never lived in, and ready for immediate occupancy. Showings are easy—schedule yours today and experience why 827 Janice Drive stands in a league of its own.

ANNAPOLIS

827 JANICE DRIVE

4 Beds

4 Baths

4,000 Sq.Ft.

$1,150,000

MLS#: MDAA2114928

Your dream home in the coveted, water-privileged community of Arundel on the Bay is waiting! Enjoy stunning, year-round water views of Fishing Creek just off the Chesapeake Bay from this beautifully designed four-bedroom, three-bathroom custom contemporary home. Perfectly positioned on an expansive 0.34-acre corner lot, the property is embraced by mature trees and lush landscaping, offering privacy, tranquility, and the feeling of a personal oasis. Expansive multi-level decks invite you to bask in breathtaking sunrises and sunsets, making everyday living feel like a getaway. Inside, the bright and immaculate interior features elegant hardwood floors, a brand-new window package (2023) flooding the home with natural light, and a warm, inviting ambiance throughout. The formal living room, centered around a cozy fireplace and framed by wide water views, offers the perfect place to gather, while the formal dining room boasts stylish built-ins for storage and charm. The open-concept kitchen is a chef’s delight, updated with crisp white cabinetry, neutral granite countertops, stainless steel appliances, and water views from the kitchen window. A cozy family room with a second fireplace extends from the kitchen, creating an inviting flow ideal for entertaining or everyday living. A main-level bedroom and updated full bath offer tremendous flexibility — ideal for guests, a home office, or multi-generational living. Upstairs, the primary suite is a true retreat, complete with water views, a fireplace, a luxurious spa-inspired bathroom featuring heated floors, a dual granite vanity, a freestanding soaking tub, and a large glass-enclosed shower. A custom-designed walk-in closet elevates the suite with style and function. Two additional oversized bedrooms share an updated Jack-and-Jill bathroom, and one of the bedrooms leads out to a private upper deck — a perfect spot to enjoy your morning coffee while soaking in the serene views. A convenient second-floor laundry room adds thoughtful practicality. The home's outdoor spaces are equally impressive: professionally landscaped front and back yards, two outdoor sheds for kayaks, water toys, and garden equipment, and a newly paved circular driveway (2022) offering ample parking. Additional features include an automated doggie door, an electric pet fence, central A/C (2020), a new water system (2022), a washer and dryer (2022), and a new shed (2023) — ensuring peace of mind for years to come. Living in Arundel on the Bay means more than just a beautiful home — it’s a lifestyle. Residents enjoy exclusive access to a private, recently updated sandy beach, a boat ramp, a long pier with available boat slips, kayak and canoe racks, a basketball court, a playground, and picnic and grilling areas right along the Chesapeake Bay. Whether you're launching a paddleboard, taking a sunset sail, or simply enjoying the vibrant, coastal community spirit, you’ll experience the very best of waterfront living — all just minutes from downtown Annapolis, the Naval Academy, shopping, restaurants, and an easy commute to Washington D.C. and Baltimore. This is waterfront living without the hassle or cost — no flood insurance required. Your coastal dream home awaits at 3536 Saratoga Avenue!

ANNAPOLIS

3536 SARATOGA AVENUE

4 Beds

3 Baths

2,368 Sq.Ft.

$1,100,000

MLS#: MDAA2113454

Immerse yourself in the epitome of sophisticated living at GrandView, where luxury meets meticulous craftsmanship in this impeccably renovated condo at the heart of the Annapolis Town Center. This residence has been transformed with an unwavering commitment to detail, creating a haven of transitional design elegance. As you enter, the home welcomes you with a seamless open-concept design, illuminated by an abundance of natural light pouring through expansive wall-to-wall windows. The gourmet kitchen, adorned with stainless steel Thermador appliances and marble countertops with full height marble backsplash, offers a perfect blend of functionality and style. A cozy breakfast nook and bright white cabinetry add a touch of warmth to the culinary space. Step outside onto the spacious covered corner balcony, where you can bask in the ambiance of Town Center activities, creating the perfect backdrop for outdoor relaxation and entertaining. Discover tranquility in the two generously-sized bedrooms, each thoughtfully outfitted with custom designed closet storage solutions. The primary owner's suite is a sanctuary of luxury, featuring a dressing room, a spa-like bathroom and curved elevation of tinted windows for added privacy and style. This residence boasts a myriad of updates, including custom electronic window treatments, exquisite marble flooring/countertops and shower walls, built-in closet organizers, premium trim throughout, and all new and custom cabinetry throughout, all new plumbing fixtures and kitchen appliances. With 10’ 6” high ceilings enhancing the sense of space, every detail has been carefully curated to elevate your living experience. GrandView offers a true sense of community, providing residents with access to a rooftop sky lounge, rooftop pool, outdoor kitchen, state-of-the-art fitness center, and a club/party room. The professionally managed concierge staff ensures convenience and security. Conveniently located, GrandView is just a stroll away from Annapolis' finest restaurants, Whole Foods, Target, Life Time Fitness Club, banking, and local shops. Minutes from Historic downtown Annapolis, the US Naval Academy, Anne Arundel Medical Center, and Annapolis Mall, this residence is a commuter's dream with easy access to Route 50 and 97. Don't miss the opportunity to experience refined urban living at its finest. Schedule a showing today and embark on a new chapter of sophisticated living in this captivating residence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 504

2 Beds

2 Baths

1,945 Sq.Ft.

$1,099,500

MLS#: MDAA2101336

This expansive two-story home showcases a gracious design with abundant room to grow and entertain. Off the foyer is a formal dining room that complements the casual nook and breakfast room, plus a gourmet kitchen and a Great Room with a charming fireplace. On the second floor is a loft surrounded by three secondary bedrooms and a luxurious owner’s suite with a spa-style bathroom. A lower-level recreation room presents endless possibilities. Home is on smart rent lock for your viewing pleasure.

ANNAPOLIS

120 STILLY WAY

6 Beds

5 Baths

4,934 Sq.Ft.

$1,097,990

MLS#: MDAA2118098

Welcome to 1002 Covington Way, a stately home nestled on a private street and surrounded by trees, but just minutes from downtown Annapolis. This gorgeous French-style home offers gracious living inside and out! From the stunning entranceway to the light filled great room, classic elegance is the hallmark of this expansive property sited on a 2+ acre lot. With almost 7,000 square feet of living space in addition to a finished basement, everyone will find their perfect space in this five bedroom property . A light and open foyer leads to defined dining and entertaing areas. The warm and welcoming kitchen includes bar seating, granite counters, and stainless steel appliances, and connects to the two-story great room with stone fireplace. An expansive deck off the main level provides a beautiful flow for entertaining and the perfect spot to relax and enjoy your private view of the woods. A main floor primary suite includes the walk-in closet space of your dreams and an elegant primary bath. Upstairs, three additional bedrooms include one suite with private bathroom and two bedrooms with a shared bath. The finished basement includes a large bedroom, full bath, and living space that would make a perfect au-pair or in-law suite. Entertain in style with a built-in bar, pool table room, and entertaining space with fireplace. The lower level walks out to an in-ground pool! Sold in its as-is condition, this home is priced to let you make your dreams of an elegant Annapolis estate become a reality! 1002 Covington Way is an easy commute to Annapolis and near Routes 50 and 97 for an easy commute to Washington, DC or Baltimore. Enjoy dining, shopping and boating in Annapolis, with additional access to marinas on the Severn River or South River. Welcome home!

ANNAPOLIS

1002 COVINGTON WAY

5 Beds

5 Baths

8,955 Sq.Ft.

$1,095,000

MLS#: MDAA2118012

Primrose Hill is a secluded enclave of 25 newer luxury homes conveniently located in the City of Annapolis. The homes here are tucked away on a private drive, nestled in a beautiful natural setting, and well situated atop the City’s highest ground. Downtown Annapolis and Eastport are 5-minute destinations, while affording easy access to routes 50 and 97. Truxtun Park, Annapolis’ main city park and a flagship recreational facility, is a short stroll. The community’s grand namesake manor house, one of the oldest homes in the region, is in historic preservation. Discover Primrose Hill – where history, charm and extraordinary privacy meet modern-day luxury in a one-of-a-kind location. Primrose Hill is the highest point in Annapolis and is estimated at 92 feet above sea level. This community boasts expansive outdoor communal areas, with all grounds meticulously maintained by the HOA.. Primrose Hill is architecturally significant on account of its mid-18th century Georgian design and construction, and the property is historically important with its direct association to the American portraitist, John Hesselius (1728-1778), who resided in the manor house between c. 1763 and his death. The two-story, four-room plan brick dwelling, dating around 1760, was built on an elaborate scale in line with other gentry houses in Anne Arundel County. A sleek, designer kitchen with upgraded appliances flows effortlessly into an open-concept main living area—ideal for entertaining or relaxed everyday living. The inviting family room is anchored by custom built-ins and a gas fireplace, adding warmth and architectural interest. This 5-bedroom, 4.5-bath home is designed for comfort and style. The upper level features four spacious bedrooms, including a luxurious owner’s suite with cathedral ceilings, an expansive walk-in closet, and a spa-inspired bathroom retreat. Bedroom two boasts its own private ensuite, offering flexibility for guests or multigenerational living. A conveniently located upstairs laundry enhances everyday functionality. The fully finished lower level includes a generous recreation room and a versatile bonus room—perfect for a home gym, office, or guest bedroom. A rare two-car garage with additional driveway parking adds convenience, especially valuable in this in-town location. Residents enjoy exclusive access to nearby amenities such as the Pip Moyer Recreation Center with tennis and pickleball courts, fitness classes and a swim club. The park like setting and intentional green spaces serve as the perfect backdrop for weekly neighborhood wine nights and social gatherings throughout the year fostering a welcoming and connected sense of community. This location provides a quick commute to DC and Baltimore. CHECK OUT THE VIRTUAL TOUR;

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

3,978 Sq.Ft.

$1,095,000

MLS#: MDAA2113794

Exuding grace at the moment of entry, this expansive two-story home features an open-plan layout ideal for modern living. A fireplace anchors the Great Room, which flows into the dining area and gourmet kitchen with a versatile island. Upstairs are three bedrooms, a loft suite sitting room, and a luxurious owner’s suite with spa-style bath. Extra space abounds with a main-level study, upstairs loft, bright morning room, and finished basement with a recreation room—offering room for work, play, and everything in between.

ANNAPOLIS

118 STILLY WAY

5 Beds

5 Baths

4,934 Sq.Ft.

$1,065,990

MLS#: MDAA2118102

This stunning log home on 2.48 scenic acres offers the perfect blend of rustic elegance and thoughtful upgrades. Surrounded by lush landscaping, the property provides treetop views and a glimpse of the water during the winter months. The impressive two-story living room showcases a dramatic wood-burning fireplace and flows effortlessly into the dining area and the gourmet kitchen, which features granite countertops, a breakfast bar, ample cabinet space, and all major appliances. Three generously sized bedrooms are located on the main level, each with gleaming hardwood floors. The primary suite includes a ceiling fan, walk-in closet, a spa-like bathroom with a soaking tub and separate shower, and private access to the deck. Upstairs, a sunlit loft with oversized skylights offers flexible space for a home office, family room, or den and includes a full bathroom. The finished basement adds even more living space, with a spacious recreation room featuring wall-to-wall carpeting and recessed lighting, a fourth bedroom, a laundry area, and plenty of storage. Outdoor living is just as inviting, with a large rear deck that backs to wooded privacy and a welcoming front paver walkway and deck. The driveway provides ample parking, and the home is just a short walk from community beach access. Ideally located near major highways and downtown Annapolis, this home offers tranquil surroundings with convenient access to shopping, dining, and everyday necessities.

ANNAPOLIS

2977 SOUTHAVEN DRIVE

4 Beds

4 Baths

3,200 Sq.Ft.

$1,050,000

MLS#: MDAA2113476

This stunning home, available for delivery in April, boasts high-end upgrades throughout. It features a first-floor owner's suite, plus three additional bedrooms on the second level, along with two full bathrooms and a spacious loft. The gourmet kitchen is a chef’s dream, complete with custom cabinetry and an open-concept design. The impressive two-story family room with soaring ceilings creates a dramatic focal point, while the finished basement rec room, featuring a wet bar with a refrigerator and sink, is perfect for entertaining. Experience luxury living at its finest—schedule your tour today! Photos for illustration purposes only. Agent must attend first visit.

ANNAPOLIS

106 STILLY WAY

4 Beds

4 Baths

4,594 Sq.Ft.

$1,047,590

MLS#: MDAA2103810

New Construction - Move In Ready March 2025! Please go to Model home to tour! Welcome to the Lynnfield model at Parkside Preserve, where luxury meets tranquility in this stunning new construction adjacent to the serene Quiet Waters Park. With over 5,017 finished square footage this meticulously designed living space across four levels, featuring 5-bedrooms, 5.5-bathrooms, 4th level loft, and finished lower level with a a true walk-out basement is a perfect fit for modern living. Step inside and be captivated by the elegance of the owner’s suite, featuring a tray ceiling and a spacious walk-in closet. Enjoy the comfort of 9' ceilings throughout, including in the finished basement, and cozy up by the gas fireplace in the expansive living area. The exterior impresses with a blend of brick and HardiePlank, complemented by a welcoming front porch and a front-entry garage. The heart of the home—the kitchen—is a chef’s dream. It boasts two 36' wall ovens (one with an air fryer), a 30' gas cooktop, a stainless steel hood, and a built-in microwave. The staggered white maple cabinetry, complete with under-cabinet lighting and display glass door cabinets, pairs beautifully with the iced white quartz countertops and tiled backsplash. All full bathrooms feature maple cabinetry, quartz countertops, and oversized ceramic tile for a touch of luxury. The finished basement is an entertainer’s paradise with an enormous rec. room, a wet bar, and the fourth full bath. This is more than just a home—it’s a lifestyle. Don’t miss the opportunity to be the first to live in this spectacular residence at Parkside Preserve. Photos are for illustration purposes only.

ANNAPOLIS

110 STILLY WAY

5 Beds

5 Baths

5,017 Sq.Ft.

$1,039,990

MLS#: MDAA2098972

Welcome to 711 Genessee Street – where modern luxury meets the heart of Annapolis charm. Located in the coveted West Annapolis School District, this newer construction stunner (built in 2021) offers the perfect blend of upscale finishes, smart design, and unbeatable location—all within walking distance to shops, dining, and everything you love about Annapolis living. Step inside to find a main level designed for both everyday comfort and effortless entertaining. The open-concept layout is grounded by wide plank wood flooring, enhanced by custom moldings, and anchored by a cozy gas fireplace. The chef’s kitchen is a standout feature, boasting 42” custom cabinetry, quartz countertops, a top-of-the-line appliance package, and a gas cooktop—perfect for everything from weekday meals to weekend gatherings. Custom oak stairs and railings tie the space together with warmth and character. Upstairs, retreat to your primary suite complete with cathedral ceilings and a spa-like ambiance. The upper level continues the upscale feel with 9-foot ceilings and custom tray ceilings, creating a spacious, airy vibe throughout the bedrooms and baths. The fully finished lower level adds even more versatility, featuring a large recreation room, an additional bedroom, a full bath, and plenty of storage space—ideal for guests, hobbies, or a second living area. Outside, enjoy a welcoming front porch that invites morning coffee and neighborhood chats, while the rear paver patio offers the perfect spot for outdoor dining or summer soirées. The fully fenced-in backyard is a private escape, ready for pets, play, or peaceful lounging. Don't miss your chance to own this thoughtfully upgraded, move-in ready gem in one of Annapolis' most desirable neighborhoods. 711 Genessee Street is more than a home—it’s a lifestyle upgrade.

ANNAPOLIS

711 GENESSEE STREET

4 Beds

3 Baths

3,148 Sq.Ft.

$999,900

MLS#: MDAA2108296

Recently updated colonial with all new custom kitchen cabinets, stainless appliances, dual oven w/gas cooktop. Family room with built in surround sound speakers-bring your own equipment. Primary suite with custom bath large shower with dual heads, nice soakiing tub, border-lighted mirror and a towel warming bar. Laundry closet on 2nd floor. Parrtial unfinished basement with utilities plus space for a possible movie/man cave. Attached oversized 2 car garage with extra storage area. 3 car-plus garage 10' doors 13' ceilings, car lift-great for those do-it-yourself folks, tons of space above to finish for rooms-in-law/teenage apartment! House sits on a double lot space for a pool? Plenty of room for boats, RV's or other toys? Access to back of lot by a gravel driveway

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$999,900

MLS#: MDAA2111664

***Be at the forefront of the Neighborhood Property Expansions and Enjoy the Future Appreciation of this stunning five-bedroom, three full and one-half bath colonial is located in the Mulberry Hill community. Situated on a large corner lot, this home boasts a covered front porch, rear deck and attached three-car garage. Inside, you will find beautiful hardwood floors, recessed lighting, crown molding and fresh paint throughout. The main level features a formal living room, separate dining room and step-down family room with a gas fireplace and mantel. The spacious, table-space kitchen boasts granite countertops, center island, stainless steel appliances and a bay-window breakfast nook. Upstairs, the primary suite offers a luxurious retreat with hardwood floors, a private bath and a bonus room. Three additional bedrooms with new carpet and an updated full hall bath complete the upper level. The finished, walk-up lower level offers a versatile recreation room, a flexible fifth bedroom, perfect for use as a home office, den or guest room and a full bathroom. Located in a quiet setting, just minutes from the Naval Academy and the Naval Academy Golf Course, yet close to everything that Annapolis has to offer, this home is truly a dream come true!

ANNAPOLIS

1825 JOHNSON ROAD

5 Beds

3 Baths

3,028 Sq.Ft.

$985,000

MLS#: MDAA2098830

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