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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

359

# of Listings

3

Avg # of Bedrooms

$479

Avg. $ / Sq.Ft.

$1,097,034

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

127 Properties Found. Page 7 of 9.

This stunning home is a true standout! Thoughtfully maintained by a meticulous owner, it boasts an inviting open floor plan with 2,698 sqft of finished space, soaring vaulted ceilings, elegant custom light fixtures, and beautiful vinyl flooring throughout.

On the main level, enjoy a spacious living room, along with a bright and airy den featuring skylights and a cozy wood-burning fireplace. Step out onto the deck, which offers serene views of acres of county-owned wooded parkland. There are 3 bedroom and 2 full recently update bathrooms on the main level as well.

The recently update well-appointed kitchen offers ample space for cooking and entertaining, with a sunny breakfast nook perfect for casual meals.

The basement features a bonus room with a full bath, ideal for a guest suite, plus a ground-level entrance from the adjacent family room. Custom-built bookcases add charm and function, while an expansive 26x19 unfinished area provides abundant storage space. The impressive Media Room is your go-to spot for game days and movie nights—the seller is even including the theater seating and a 75" HD media screen!

Located in the premier 55+ community of Heritage Harbour, this home comes with access to exceptional amenities, including golf (separate membership), a clubhouse, restaurant, tennis & pickleball courts, billiards, indoor & outdoor pools, a bocce ball court, and a state-of-the-art fitness center with an aerobics studio. Residents also enjoy a private pier on the South River with ten 30-ft. boat slips, as well as a vibrant selection of special interest groups. A one-time recreational fee of $2,055 is due at settlement.

ANNAPOLIS

505 COOVER ROAD

3 Beds

3 Baths

2,698 Sq.Ft.

$575,000

MLS#: MDAA2102314

This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaking panoramic views and an abundance of natural light from its sunny southern exposure. Featuring two generously sized bedrooms with expansive closets, this upscale residence combines comfort and style.
Inside, you’ll find beautiful hardwood floors, soaring 10-foot ceilings, and elegant granite countertops throughout. The freshly painted interiors are complemented by custom window treatments that add both privacy and sophistication. Step outside to your private balcony and enjoy sweeping views of the surrounding area.

Key Features:

2 spacious bedrooms with large closets
Gorgeous hardwood floors
Soaring 10-ft ceilings for an open, airy feel
Granite countertops in kitchen and baths
Freshly painted with custom window treatments
Private balcony with stunning views
Assigned parking space for convenience

Building Amenities:

Rooftop pool with panoramic vistas
State-of-the-art fitness center
Elegant club rooms for gatherings and relaxation
Concierge service for a luxurious living experience
Ideally located in the vibrant Annapolis Towne Centre, this condo puts you within walking distance of premier shopping, dining, and entertainment options. Whether you're enjoying a meal at one of the area's finest restaurants or exploring local boutiques, everything you need is just moments away.
This is a must-see home that blends modern living with the best of Annapolis! Don't miss out on the chance to call this spectacular property yours.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 502

2 Beds

2 Baths

1,485 Sq.Ft.

$575,000

MLS#: MDAA2100426

PRICE REDUCED. Picture this for your next home in historic Annapolis: a bright, open, two-bedroom, two-bath condo in the gorgeous Residences at Park Place. Conveniently located near Rt. 50 and Rt. 97, with easy access to Washington, D.C., Baltimore, and BWI Airport, this home is just a short walk from Annapolis’s finest restaurants, unique boutiques, live entertainment, and the iconic U.S. Naval Academy. Surrounded by the charm of cobblestone streets, waterfront views, and the lively energy of City Dock and Ego Alley, this condo offers luxury living with amenities like a private outdoor pool, an enclosed pet park, a well-equipped exercise room, a community room, secure garage parking for two vehicles, and on-site professional property management. The furnishings in the images have been virtually staged to help you picture the home’s full potential and layout possibilities. Contact your real estate professional to schedule a private tour.

ANNAPOLIS

5 PARK PLACE 314

2 Beds

2 Baths

1,056 Sq.Ft.

$574,000

MLS#: MDAA2108870

The epitome of luxury living resides in Annapolis at Grand View! Reduced for QUICK SALE and best value in the building with a 10th floor location. Experience the pinnacle of sophistication in this exquisite high-rise condominium. Step into a world of elegance as you enter through the secured entrance, providing you with peace of mind and a sense of exclusivity. With on site friendly staff, you can rest assured, your packages will be delivered and handled and you will be greeted with kindness. The moment you step foot into this stunning residence, you'll be captivated by the sleek and stylish wood floors that adorn the living spaces, adding a touch of warmth and refinement. The high ceilings create an atmosphere of grandeur, while the expansive windows allow an abundance of natural light to flood the rooms, creating an inviting and cheerful ambiance. Prepare to be mesmerized by the breathtaking views that surround you from every angle, providing a constant reminder of the beauty that Annapolis has to offer. Indulge in the luxurious amenities that this building has to offer. Take a dip in the rooftop pool, providing you with a tranquil oasis to unwind and soak up the sun. Elevate your social gatherings in the exclusive lounge area, perfect for entertaining guests or simply relaxing in style. Maintain your fitness routine in the state-of-the-art fitness center, ensuring that your well-being is always prioritized. For your convenience, secured storage is included on the basement level, allowing you to stow your belongings with ease and peace of mind. Never worry about finding parking again, as covered parking is provided, with 2 assigned spaces, one near the entry, ensuring your vehicle is protected. To top it all off, a private balcony awaits you, offering a serene outdoor space to enjoy your morning coffee as the sun comes up or a glass of spirits as the sun sets. Don't miss out on this incredible opportunity to elevate your lifestyle to new heights. Experience the luxury, comfort, and conveniences that await you in this high-rise condominium, steps to top restaurants, ease of shopping, and entertainment. Make this exceptional residence your new home and immerse yourself in a world of opulence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1013

2 Beds

2 Baths

1,485 Sq.Ft.

$569,900

MLS#: MDAA2078120

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 kitchen, new flooring, 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.

ANNAPOLIS

1019 TIMBER CREEK DRIVE

4 Beds

2 Baths

1,826 Sq.Ft.

$565,000

MLS#: MDAA2114232

Walk out of your living room and dining room onto your private deck overlooking Back Creek! This bright and airy end-unit allows light to come in on three sides. All rooms (except the baths) have windows! And there are ceiling fans in two bedrooms. There are water views from the large living room and dining room and even from the kitchen. The large primary bedroom has an ensuite bath. The living room, dining room and all three bedrooms are carpeted and have upgraded padding. In 2021 a new kitchen blind was installed. New windows and bedroom blinds were added in 2022 and the flooring in the kitchen was replaced in 2024. Severn House is a gem of a place, with a waterside pool, covered deck, and marina. The condo fee incudes basic cable, heat, water, trash pickup, snow removal and parking. The only utility you pay for is electricity. Severn House is convenient to shopping, restaurants, a fitness center and most of the year a local outdoor market. Not to mention, you are minutes from the Historic District. (Pets are not allowed.)

ANNAPOLIS

762 FAIRVIEW AVENUE 762 C

3 Beds

2 Baths

N/A

$560,000

MLS#: MDAA2111196

A great value and opportunity to own a beautiful spacious home in Heritage Harbour’s coveted “Skipjack Landing"! Step into sophisticated comfort with this spacious 2,640 sq. ft. end of group colonial townhouse, that feels like a single family home. Designed for easy living and entertaining, this sun-drenched two story home boasts generously sized rooms and a smart, flowing layout affording plenty of privacy and space to gather. An inviting entrance hall leads to a gracious formal living room, with a wood-burning fireplace and a stunning crystal chandelier. The chandelier even lowers electronically for effortless maintenance. The elegant dining room, eat-in kitchen, and charming, fully fenced, low-maintenance backyard with a deck offer the perfect blend of formal and casual dining—ideal for hosting guests or enjoying a quiet morning with coffee. This home has 3 spacious ensuite bedrooms, all Bedrooms have a walk-in closet (one on the main level), ensuring comfort and privacy for family and guests. The large main level bedroom, is currently used as an art studio (taking advantage of the home’s abundant natural light.) A bonus room offers flexible space, perfect as a study, den, or 4th bedroom. Ample storage, an attached garage, and abundant natural light make this beautifully maintained home both functional and inviting. Enjoy resort-style 55+ living with tennis, pickleball, kayaking, indoor and outdoor pools, a fitness center, library, workshops, and a lively social scene. A one-time $2,075 initiation buyer fee is required at settlement in addition to monthly HOA fees. From the community website: Heritage Harbour is an established community in Annapolis, offering beautiful wooded lots and featuring a wide variety of recreational, cultural, social, and educational activities for its residents. Residents can participate in over 90 activities, clubs and committees. The center of community activities is the Lodge, which features a welcoming atrium, an auditorium, indoor and outdoor pools, fitness center, library, boutique, activities room, woodwork shop, game rooms, coffee corner and meeting rooms. Behind the Lodge, residents enjoy a picnic area, horseshoes, bocce ball and kayaking on our waterfront on the South River. We also offer multiple tennis and pickleball courts, a nine-hole golf course, a pro shop, a clubhouse dining room, a pier with boat slips and RV and boat storage on a lot in the community. Residents enjoy the convenience of regular bus trips to shopping centers and special bus trips to cultural destinations, as well as volunteer drivers for medical appointments. Our pet-friendly community of active residents always welcomes newcomers!

ANNAPOLIS

915 BOOM WAY

3 Beds

3 Baths

2,640 Sq.Ft.

$555,000

MLS#: MDAA2105510

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”

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!

ANNAPOLIS

508 HARBOR DRIVE

4 Beds

1 Baths

1,620 Sq.Ft.

$550,000

MLS#: MDAA2110028

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.

ANNAPOLIS

1302 MYRTLE AVENUE

3 Beds

2 Baths

1,664 Sq.Ft.

$549,900

MLS#: MDAA2111546

#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!

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.

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.

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!!

ANNAPOLIS

901 CHESTERFIELD ROAD

5 Beds

3 Baths

2,457 Sq.Ft.

$540,000

MLS#: MDAA2103668

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