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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

392

# of Listings

3

Avg # of Bedrooms

$454

Avg. $ / Sq.Ft.

$1,129,892

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

392 Properties Found. Page 8 of 27.

#MDAA2108738

ANNAPOLIS

827 JANICE DRIVE

4 Beds

4 Baths

4,000 Sq.Ft.

$1,195,000

MLS#: MDAA2108738

Welcome to Unit 508 at Severn 100—a rarely offered, elegant 1,173-square-foot, 2-bedroom, 2-bath residence offering front-row seats to the most vibrant views of The Annapolis Harbor, Spa Creek and The US Naval Academy. Located in the heart of Eastport, this luxurious condo blends upscale finishes with unmatched water views. Step inside to rich mahogany floors, a beautiful spacious kitchen with upscale KitchenAid stainless steel appliances and granite counter tops. Two renovated Spa-inspired marble baths, one with an air jet soaking tub and one with a large walk- in shower are designed with comfort and style in mind. Both have heated floors. Thoughtfully redesigned walls adding pocket doors creating more closet space. Walls of glass, frame ever-changing scenes of the bustling harbor—sailboats gliding by, sunsets painting the sky, and moonsets reflecting off the water. At night, the twinkling lights of downtown Annapolis create a magical, starlit backdrop. It truly is a real life movie playing out in front of you 24/7. Enjoy the ease of secure building access, a dedicated garage parking spot on the main level, and elevator service right to your door. Just outside, Eastport’s vibrant maritime district, restaurants, and marinas are all within walking distance—bringing the best of Annapolis to your doorstep.
Whether you’re watching the bustling harbor or soaking in the golden glow of a waterfront sunset, Unit 508 offers a lifestyle that’s as dynamic as it is peaceful. There’s never a dull moment on the harbor—come experience it for yourself.

ANNAPOLIS

100 SEVERN AVENUE 508

2 Beds

2 Baths

1,173 Sq.Ft.

$1,195,000

MLS#: MDAA2111360

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

#MDAA2113454

ANNAPOLIS

3536 SARATOGA AVENUE

4 Beds

3 Baths

2,368 Sq.Ft.

$1,100,000

MLS#: MDAA2113454

English Tudor featuring a stone front patio for nature lovers and bird watchers.
Surrounded by large trees for tons of shade and a 45 foot rear deck for large gatherings and rear lawn for play areas. Almost 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. The great room has cathedral ceilings, wood beams and wide plank redwood siding, wood burning fireplace. and sliders to rear deck. The community has water privileges with fishing pier and canoe storage and sidewalks for dog walking or strolling the neighborhood.
Convenient location for commuting to Baltimore or D.C. and 20 minutes to BWI Airport.
Six miles to Downtown Annapolis for great shopping and restaurants.

ANNAPOLIS

553 CHOPTANK COVE COURT

5 Beds

4 Baths

3,569 Sq.Ft.

$1,100,000

MLS#: MDAA2117832

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

Welcome to this captivating “Country Cape” reproduction, inspired by an original 1754 home in New Milford, Connecticut. Nestled in the prestigious waterfront community of Broadview Estates in Annapolis, this exceptional property offers both historical charm and modern-day elegance.
Crafted with intention and care, the home features hand-built cabinetry in the kitchen and wet bar—designed and constructed by the owner—as well as artisan-crafted interior doors and rich wood-beamed ceilings that lend warmth and character throughout. The main living areas flow seamlessly from kitchen to dining to living room, opening effortlessly onto a private brick patio and professionally designed gardens—a serene extension of the home that invites year-round enjoyment.
Outdoors, the grounds are a true masterpiece. Curated by a Master Gardener, the landscape has earned its place in the Maryland Garden Tours and Home of the Week features. From morning coffee among the blooms to evening chats on the inviting front porch, this property is designed for peaceful, refined living.
The cozy living room, anchored by a classic wood-burning fireplace, is perfect for intimate gatherings or quiet nights in. A spacious eat-in kitchen offers the ideal setting for entertaining, while a dedicated office on the main level provides flexibility as a work-from-home space or additional bedroom.
Upstairs, the primary suite is a restful retreat with an en-suite bath. Two additional bedrooms—one with a charming skylight overlooking the gardens—offer comfort for guests or family.
A deeded 12’ x 25’ boat slip in Broadview’s private marina conveys with the property, providing easy access to the Chesapeake Bay lifestyle. Additional features include a two-car garage, workshop, garden shed, and ample storage.
This is more than a home—it’s a lifestyle. Classic architecture, artisan details, and breathtaking gardens make this a rare offering in one of Annapolis’ most desirable neighborhoods.

ANNAPOLIS

356 BROADVIEW LANE

4 Beds

3 Baths

1,906 Sq.Ft.

$1,099,000

MLS#: MDAA2119266

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

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