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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
296
# of Listings
3
Avg # of Bedrooms
$470
Avg. $ / Sq.Ft.
$1,067,632
Med. List Price

Browse Annapolis Real Estate Listings

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106 Properties Found. Page 3 of 8.

Tucked away on a peaceful cul-de-sac in the desirable Georgetown Grove community, this beautifully maintained three-level waterfront home offers the perfect blend of privacy, comfort and convenience. Set on the largest lot in the neighborhood, the property abuts onto the headwaters of Back Creek. A picturesque, wooded lot surrounds the home and provides a blanket of greenery during the summer season. Stunning views of Back Creek and its boats are enjoyed the rest of the year. A protected wetland bird sanctuary is situated just behind the home, attracting blue herons, hawks, and an abundance of wildlife. The community also provides kayak and paddleboard access to the creek, affording you incredible views of boats and marinas, and the Chesapeake Bay. The home features an open concept living and dining area, a dramatic two-story vaulted ceiling, and a wall of feature windows that frame lush landscaping and provide abundant natural light. The kitchen features white cabinetry, granite countertops, pantry storage, and a sunlit table area overlooking the deck, trees and creek. Just beyond, the family room offers a cozy retreat with a fireplace and a triple-panel sliding glass door that leads to the multi-tiered entertainment deck, ideal for outdoor gatherings and peaceful relaxation. Upstairs, the primary suite includes two closets, a separate vanity area, and a spacious en suite bath with double vanity, soaking tub, and separate shower. Two additional bedrooms, one with a cathedral ceiling, share an updated full bath. The spacious, finished lower-level walkout provides a functional space that includes a large cedar closet, full bath with steam shower, and walk-out access to a stone patio surrounded by trees and a water view. If needed, this large space could serve as an in-law suite or rental unit. The property also offers a rare opportunity to experience the waterfront while living in the heart of Annapolis. Downtown historic Annapolis, the Naval Academy, Eastport, marinas, restaurants, grocery shopping and commuter routes to Washington DC are all just minutes away. Quiet Waters Park is a short walking/biking distance, providing family recreation, summer concert series, educational events, and watercraft rentals. A local marina, grocery store and restaurants are all within walking distance. Enjoy gracious living in this private Georgetown Grove home, along with a vibrant lifestyle that comes with living in the heart of Annapolis.
#MDAA2114986

ANNAPOLIS

39 WINDWHISPER LANE

3 Beds

3 Baths

3,193 Sq.Ft.

$750,000

MLS#: MDAA2114986

*💜💜💜💜💜💜💜💜💜💜💜💜💜💜💜* OPEN HOUSE Sunday, 8/31st from 1pm to 3pm!! **Luxury Living with all the Bells & Whistles! This Gorgeous Move-in-Ready 4-Finished level, End of Group Townhome Features 3-4 Bedrooms, 3-Full Bathrooms, 1-Half Bath; Two (2) Car rear load Garage with High Grade Epoxy Flooring and Custom bi-level Stone Accent Walls; Ample Storage, PLUS a Tesla charger! **Main Level is the Front Door and Garage Entry into a Cozy Family Room which features a Full Bathroom, as well as Additional Storage area. **2nd Level features a Spacious Open Floor Plan - Great for Entertaining! This Gourmet Kitchen provides Unparalleled Convenience Combined with Casual Comfort and Elegance. Plenty of Counter space with a Kitchen Island and Breakfast Bar; Sep Coffee/Bar Nook, PLUS a Walk-in Pantry and half bath! *Stainless Steel Appliances; Refrigerator with Water Filtration system; Soft Close Cabinetry. **Ascend to Your Owner's Suite for Ultimate Convenience of your daily routine. Deluxe Bathroom, Sep Water Closet, and a Huge Walk-in Closet; **Two (2) additional well-appointed Bedrooms offering Comfort and Privacy. Both rooms feature 9' Ceilings. **Shared Hall Bathroom. **Sep Laundry area; Sep Hall Linen Closet. **Venture to the 4th level (use as a 4th Bedroom or make this area a Personal Gym, Home Office, Serene Retreat) and Enjoy Evenings Under the Stars! Watch the Blue Angels Fly Over as well as July 4th Fireworks! **For a little down time, enjoy Sitting outside under your Covered Front Porch and soak in all the Peaceful surroundings! **Added Perks: Added a 'Flo by Moen' device which monitors water pressure, temperature, flow rate in real-time, plus offers features like leak detection and alerts. **Energy Star Certified Appliances; and Custom Window Blinds; and a Ring System ***Call Me for Details about GRANT Funds up to $10,000 towards Buyer's Closing Costs as well as the CHiP loan program (ZERO down payment with NO Mortgage Insurance). **FHLB money is back for a LIMITED TIME with higher amounts to HELP Buyers! This Program Offers $17,500 in funds to Buyer's -OR- $20,000 for buyers that are Community Partners (defined as buyers employed in or retired from any of the following professions: enforcement officers, educators, health care workers, firefighters, other first responders; veterans and active duty-military or their surviving spouse). Check out the FHLB Workforce Housing Plus+ Program which Offers $15,000 to any Buyer! **Click on the Movie icon next to the photos to Navigate through each Level of this Gorgeous Home!
#MDAA2118974

ANNAPOLIS

113 TREBLIS WAY

4 Beds

3 Baths

2,348 Sq.Ft.

$750,000

MLS#: MDAA2118974

Chic Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5-bath condo in the sought-after Acton's Landing community. Perfectly situated on the street level for effortless access, this unit combines convenience with luxury. The open-concept layout features a generous living space, a large kitchen with a center island, breakfast bar, and plenty of storage—ideal for a weekend getaway or everyday living. The separate den offers a perfect work-from-home setup or cozy retreat. The primary suite is a true haven, complete with a spa-inspired bath featuring a soaking tub, walk-in shower, and ample closet space. Enjoy easy access to the building’s parking garage just steps from your door. Community amenities include a fitness center, gym, party room, library, and more. Located just a short stroll from the water taxi and the vibrant shops, dining, and charm of historic downtown Annapolis—this is city living at its best. Don’t miss your chance to own in one of Annapolis’ most desirable communities!
#MDAA2120238

ANNAPOLIS

66 FRANKLIN STREET 20

1 Beds

1 Baths

1,342 Sq.Ft.

$750,000

MLS#: MDAA2120238

Amazing opportunity to own a beautiful parcel of land on desirable Shot Town Road area where large estates abound. Build a sprawling estate or subdivision potential giving three smaller estates.
#MDAA2113200

ANNAPOLIS

SHOT TOWN ROAD

None Beds

None Baths

7.83 acres

$750,000

MLS#: MDAA2113200

Don't miss this incredible opportunity to own a charming 5 bedroom (3 in main house, 2 in apartment) ranch-style home in the highly sought-after Parkwood community in Annapolis. Tucked away at the end of a private road and backing to the serene woods and Back Creek, this property offers a unique sense of privacy and tranquility with rental opportunity. The Parkwood community is a water-privileged haven, featuring a marina with a pier, multiple docks, and a convenient waitlist system for boat slips. You'll have front-row seats to exciting events like the Blue Angels and fireworks shows, all while being just steps away from the vibrant Eastport neighborhood and a short distance to the historic Downtown Annapolis, offering shopping, dining, entertainment, and the renowned Naval Academy. This sprawling home provides main-level living at its finest, with two well-designed additions that add extra space and versatility. The attached garage is a dream, accommodating up to four vehicles and boasting a recently updated apartment on the upper level. This apartment includes a great room, 2 bedrooms, a kitchen, and a full bath, making it an ideal in-law/guest suite, a haven for midshipmen, or a rental. Inside the main home, you'll find a cozy living room with crown molding and a brick-accented fireplace, creating the perfect gathering spot. The kitchen offers upgraded stone counters, a tile backsplash, slate flooring, and a convenient breakfast table space. The adjacent dining room features a built-in cabinet and buffet, adding convenience to your dining experiences. A wonderful family room addition is flooded with natural light through its beautiful windows, creating an inviting area for entertaining and hosting holiday gatherings. The primary bedroom boasts an en-suite bath, while two additional bedrooms and a full bath round out the living quarters. The breezeway between the house and garage is a versatile space that can serve as a recreation room or provide extra storage. This house is also equipped with a storage shed and Generac generator. With the perfect blend of comfort, convenience, and opportunity in one of Annapolis's most desirable communities, don’t miss this opportunity to make this house your home. Property Updates: Carpet, paint, HVAC, baths upgraded, electric panel box, family room windows, kitchen backsplash, apartment updates, and more!
#MDAA2096836

ANNAPOLIS

3 PARK LANE

5 Beds

3 Baths

3,235 Sq.Ft.

$750,000

MLS#: MDAA2096836

Commercially zoned C-1 pad site available adjacent to McDonald's and Wendy's. Just shy of 1 acre. Public Utilities. Great visibility from Rt. 50. Build your office building, a restaurant, retail center, mixed use building, residential apts or condos over ground floor commercial, etc. See documents section for more information.
#MDAA2018250

ANNAPOLIS

1440 WHITEHALL ROAD

None Beds

None Baths

0.92 acres

$749,900

MLS#: MDAA2018250

1.485 acre RLD zoned parcel/ lot available adjacent to McDonald's, Wendy's. Potential uses include daycare, veterinarian, assisted living, club, group home, kennel, plant nursery, produce stand, etc. All utilities are available. Easy access on and off of Rt. 50. Refer to documents section.
#MDAA2018258

ANNAPOLIS

1444 WHITEHALL ROAD

None Beds

None Baths

1.49 acres

$749,900

MLS#: MDAA2018258

Welcome to 303 Riding Ridge, Located in the Very Desirable Hunt Meadows neighborhood. This Well Cared for ONE OWNER home is Move In Ready, and Includes Many Desirable Upgrades Main Level Entrance features Easy Care Upgraded Luxury Vinyl flooring leading to Living Room with Large Easy Clean Tilt Sash Thermal Windows, Separate Dining Area featuring Oak Hardwood Floors, Overhead Lighting, and Tilt Sash Thermal Windows Eat In Kitchen features Easy Care Upgraded Luxury Vinyl flooring, Stainless steel appliances, Beautiful Granite Countertop, Pantry storage, and under counter lighting Convenient Powder room Includes Easy Care Luxury Vinyl Flooring, and newer toilet A few steps away is the expansive sunken family room with beautiful custom oak hardwood floors, Large Tilt Sash Thermal windows with view of private wooded lot, Ceiling fan, AND Raised Hearth Brick wood burning fireplace. ALSO Home Includes Natural Gas, for future conversion to a gas fireplace, Or Gas Cooktop stove in the kitchen Moving to the Third Level you will find ( 2 ) nice size bedrooms with good size closets, easy care tilt sash Thermal Windows and Ceiling fan in First bedroom. The ensuite primary bedroom features a ceiling fan, large closet with hidden lighting, Easy Care tilt sash Thermal Windows overlooking rear wooded private yard, and newer bath with marble counterop and shower walls. The Finished Lower Level includes a cedar closest, Bonus Room which can be a 4th Bedroom as has a closet and escape window, OR private office for those times when working from home is necessary.. The Highlight of the lower level is a Movie room to keep the family entertained with their favorite movie. Bose Surround Sound system and Sony stereo equipment included. Finally the Lower Level also has a wonderful Insulated floored crawlspace for storage, and a utility room with Included washer and Dryer The quiet cul-de-sac lot features trees for privacy ( No Homes can be built behind lot ) with beautiful autumn views, from expansive dual level decks ( great for entertaining, grilling out, or enjoying a propane firepit ) AND if you need additional back yard space, the rear yard can be cleared, as property line is APPROXIMATELY 48’ from rear of den ( See plot survey ) The included amenities of Hunt Meadows include an oversize pool, toddler pool, tennis courts, a reserve-able pavilion, perfect for hosting family and friend gatherings. Stroll along walking path and sidewalks, or take advantage of the nearby pathway, connecting directly to the beautiful Quiet Waters park along the scenic South river. The Convenient location of this beautiful home is close to downtown Annapolis, and an easy commute to DC or Baltimore.
#MDAA2121348

ANNAPOLIS

303 RIDING RIDGE ROAD

4 Beds

2 Baths

2,238 Sq.Ft.

$749,500

MLS#: MDAA2121348

Major Price Improvement! Welcome to luxury living in the highly sought-after Residence at Park Place, located in the heart of historic Annapolis! This beautifully maintained 2-bedroom, 2-full bath condo offers comfort, convenience, and top-tier amenities — all in a secure, resort-style building. Step inside to find generously sized bedrooms, gorgeous hardwood floors, and an open-concept layout filled with natural light. The chef’s kitchen has granite countertops, stainless steel appliances, and plenty of cabinet space — perfect for entertaining. Relax by the cozy fireplace or enjoy your morning coffee in the peaceful setting. The open-concept living area features gleaming hardwood floors, a gas fireplace with a nice white mantle and large windows that fill the space with natural light. This home has been freshly painted, professionally cleaned, and the floors have been buffed and waxed, making it move-in ready. The primary suite includes a spacious walk-in closet, a spa-like bathroom with a separate tub and walk-in shower, and a double vanity with ample counter space. The second bedroom also has its own private full bath with a stand-up shower, offering ideal comfort and privacy for guests. The second bedroom could also be used as a remote-home office. There are 2 deeded and assigned parking spaces in the gated, secure garage with access to secure interior elevators. This upscale building has many unique benefits including a 24-hour front desk concierge in the lobby. The first-class amenities include an outdoor pool, hot tub, fitness center, pool table, meeting rooms, full-kitchen in the common area and several places to gather with your family, friends and neighbors, inside and outside in the courtyard and patio and also has garden plots for the residents. The free Circular Trolley can pick you up right out front and take you to the Annapolis waterfront. This is a pet friendly building and even has its own dog park called Bark Place Dog Park! This exceptional condo combines modern luxury with timeless charm in one of Annapolis’s most sought-after communities. Whether you're looking for a full-time residence, weekend getaway, or investment property, this condo offers the ideal blend of comfort, security, and location. Just steps from the Annapolis waterfront, award-winning restaurants, boutique shopping, and historical landmarks – everything you love about Annapolis is right outside your door! Reasonable commute to Baltimore and Washington DC. Just a few blocks to the Navy-Marine Corps Stadium and not far from the U. S. Naval Academy, Maryland State Capital and is just a few blocks to Maryland Hall, which the center of the culture in this region. Live the Annapolis life in a way few others can. Call today to schedule an appointment!
#MDAA2121090

ANNAPOLIS

5 PARK PLACE 217

2 Beds

2 Baths

1,343 Sq.Ft.

$749,500

MLS#: MDAA2121090

Welcome to this beautifully restored and thoughtfully updated 1942 gem. Step inside to find gleaming hardwood floors, sunlit living spaces, and original archtectural details blended seamlessly w contemporary updates. Outdoors, enjoy a peaceful side and rear garden, ideal for morning coffee or quiet evenings under the stars. Just a short walk is a scenic footbridge over Spa Creek to Truxton Park's pool, tennis courts and nature trails. Whether you're drawn by the charm of a historic home, the proximity to the water, or the vibrant culture of nearby downtown Annapolis, this property is the perfect place to call home
#MDAA2120212

ANNAPOLIS

7 SILOPANNA ROAD

4 Beds

3 Baths

2,348 Sq.Ft.

$729,900

MLS#: MDAA2120212

This five-bedroom, three full-bath colonial is situated on a corner lot in the desirable Cape St. Claire neighborhood of Annapolis. This home boasts a charming front porch and relaxing side patio, along with ample off-street parking including a two-car garage and four-car driveway. Step inside to find a home that is truly move-in ready, featuring fresh paint throughout, gleaming hardwood floors, new carpet, crown molding and recessed lighting. The updated kitchen showcases new cabinets and new stainless-steel appliances. The living room features a cozy wood-burning fireplace, adding warmth and character to the heart of the home. A bright and spacious great room, with sunroom area, provides a versatile space perfect for entertaining or relaxing. The main level offers flexible living options with two bedrooms featuring new carpet and an updated full hall bath. Upstairs, the primary suite is a true retreat, featuring cathedral ceilings and an upgraded en-suite bathroom with soaking tub and separate shower. Two additional bedrooms and another updated full hall bath complete the upper level. The lower level includes convenient garage access, rec room with new carpet, laundry closet with a new washer and dryer and a tiled storage room. Nestled in a charming, well-established community known for its welcoming atmosphere and excellent amenities, this move-in ready colonial offers the perfect setting for enjoying the Annapolis lifestyle.
#MDAA2120586

ANNAPOLIS

1014 ST CHARLES DRIVE

5 Beds

3 Baths

3,680 Sq.Ft.

$729,900

MLS#: MDAA2120586

Welcome to this beautifully maintained split-level home in the sought-after waterfront community of Annapolis Roads—ideally situated just minutes from shopping, dining, and vibrant downtown Annapolis. Lovingly cared for, this home features a versatile, circular floor plan that effortlessly accommodates both everyday living and entertaining. The main level offers an inviting eat-in kitchen, a formal dining room with a cozy fireplace, and a spacious sunroom that feels like a private treehouse—complete with serene water views. Upstairs, the primary suite includes a private en suite bath, while two additional generously sized bedrooms share a full hall bathroom. The lower level expands your living space with a large recreation room featuring a second fireplace, a fourth bedroom/bonus room, a dedicated office or hobby room, and a convenient half bath. There's also a basement level offering laundry and ample storage space. Recent updates include beautifully refinished hardwood floors and fresh paint throughout, making this move-in ready home an exceptional opportunity in a prime location. Annapolis Roads offers many amenities without having a proper HOA! It is part of a special tax district, so the annual fee is part of the property taxes! Amenities include dock, kayak storage, beach area, fire pit, playground/tot lot, pavilion and more! The community is conveniently located only a couple miles to downtown Annapolis and near shopping and restaurants! Don't miss this one!
#MDAA2124210

ANNAPOLIS

1003 DULANEY LANE

4 Beds

2 Baths

3,122 Sq.Ft.

$724,900

MLS#: MDAA2124210

Welcome to 3505 Cohasset Ave, a beautifully updated single-family home in the sought-after Arundel on the Bay community—surrounded by water with water access on three sides! This spacious 4-bedroom, 3-bath home offers an inviting open layout with vaulted ceilings, skylights, and an abundance of natural light. Enjoy multiple outdoor living spaces, including a screened three-season room, an upper deck off the primary suite, a front porch/deck with carport underneath, and a backyard patio—perfect for entertaining or relaxing. A versatile storage space beneath the three-season room offers endless possibilities, whether for a workshop, man cave, or she shed. The home has been thoughtfully and continually updated with modern features: new countertops (2025), new front door (2024), kitchen herb window and split rail fencing (2023), rebuilt dining/three-season room with flat roof and new upper deck (2022), primary bath renovation (2021), pellet stove and basement bath (2020), plus siding, rebuilt front deck/carport, new washer & dryer (2019), and a new roof, upgraded lighting, landscaping, and patio (2018). With community water access and a prime Annapolis location, this home combines coastal charm, modern updates, and flexible living spaces—ready to enjoy!
#MDAA2124012

ANNAPOLIS

3505 COHASSET AVENUE

4 Beds

3 Baths

2,650 Sq.Ft.

$715,000

MLS#: MDAA2124012

we've had a price improvement! Stop by and see this beautiful home! OPEN HOUSE 8/24/25 Priced below market value!! Beautiful home in Heritage! Absolute turn-key! This home has a Wonderful, Open floor plan with 2 En Suites on the Main Level. Spacious, updated Kitchen with coffee bar, Living and Dining Area with Tons of Light. Sliding Glass Doors from the Kitchen Area to the Back Deck and on the Lower Level their are sliders to the Patio and Backyard. Renovated Lower Level with Fireplace and with space with doors for an office and workout room. Attached 2-Car Garage fresh paint and updates Galore! The location of the property is ideal with access to Eastport, Downtown and RT 50 within moments. The community pool is just around the corner from the house. There is not an HOA but a community pool included in the property taxes.
#MDAA2121446

ANNAPOLIS

407 MERRYMAN ROAD

4 Beds

3 Baths

1,850 Sq.Ft.

$699,999

MLS#: MDAA2121446

You’ve Got to See This One! Absolutely meticulous from top to bottom, this stunning 4-bedroom, 3-bath home in the charming community of Homewood is bigger than it looks and packed with upgrades. Step inside to find a spacious owner’s suite with a large walk-in closet and a well-designed bathroom, a gorgeous updated kitchen with quartz countertops, stylishly renovated bathrooms, luxury vinyl plank flooring, new carpet, fresh paint, and custom closet systems throughout. Enjoy over 2,400 sq ft of turn-key perfection—just move in and start living! Most windows have been replaced, and extras include a new washer and dryer, wood blinds, and more. Step out back to your screened porch, the perfect spot to relax and unwind. The fully fenced yard features a fire pit, shed, and plenty of space to entertain or play. All this just 1.5 miles from Downtown Annapolis and the Naval Academy—conveniently located near the Navy-Marine Corps Stadium, Poplar Park trails, West Annapolis, and everything downtown has to offer. A completely renovated home inside and out—come experience this incredible property today!
#MDAA2115252

ANNAPOLIS

10 N HOMELAND AVENUE N

4 Beds

3 Baths

2,444 Sq.Ft.

$699,900

MLS#: MDAA2115252

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