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5-Bedroom Homes for Sale in 21409

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  • /35

    $3,800,000

    • 5 Beds
    • 3 Baths
    • 2,775 Sq Ft

    1741 Holly Beach Farm Rd, Annapolis, MD 21409

    Rare Waterfront Opportunity! Escape to your waterfront farmhouse retreat. Nestled on 3.5 picturesque acres overlooking the tranquil waters of protected Moss Pond, this charming historic property offers big views of and direct access to the Chesapeake Bay. Originally part of a working thoroughbred racehorse farm, this home is surrounded by parkland and privacy while still close to the city.

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    1741 Holly Beach Farm Rd, Annapolis, MD 21409
  • /61

    $1,125,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 4 Baths
    • 4,276 Sq Ft

    1509 Bromfield Way, Annapolis, MD 21409

    Open House Sat April 26th 11-1PM! Absolutely beautiful colonial style home on the Broadneck peninsula! Located in quiet neighborhood Colonial Manor, this home is located in a small, private cul da sac backing up to woods to provide the perfect privacy especially in spring/summer with full bloom. Offering over 4,000 finished square feet inside, come fall in love with this floor plan. This home

    Jessica DuLaney Next Step Realty

    1509 Bromfield Way, Annapolis, MD 21409
  • /68

    $3,500,000 Open Sat 12PM - 2PM

    • 6 Beds
    • 5.5 Baths
    • 6,732 Sq Ft

    1576 Bay Head Rd, Annapolis, MD 21409

    Boating season is here! Welcome to 1576 Bay Head Road, an exceptional waterfront estate where luxury living meets the ultimate Chesapeake Bay lifestyle. Perfectly situated on a private one-acre lot along the calm, protected waters of the Little Magothy River, this 6,700+ sq. ft. custom home offers the rare opportunity to be out on the Bay in under five minutes—just in time for boating season.

    Wendy Oliver Coldwell Banker Realty

    1576 Bay Head Rd, Annapolis, MD 21409
  • /41

    $6,498,000

    • 5 Beds
    • 5.5 Baths
    • 6,911 Sq Ft

    205 Winchester Beach Dr, Annapolis, MD 21409

    Winchester-on-the-Severn Waterfront! This modern home is only surpassed by the all encompassing, elevated views of the Severn River. Exquisite finishes are the hallmark of this elegant 5 bedroom 5.5 bath brick home where no details were compromised in presenting a home of distinction. Floor to ceiling sliding LaCantina glass doors blur the line of indoor and outdoor living and showcase the

    Brad Kappel TTR Sotheby's International Realty

    205 Winchester Beach Dr, Annapolis, MD 21409
  • /49

    $19,995,000

    • 7 Beds
    • 13 Baths
    • 35,435 Sq Ft

    1604 Winchester Rd, Annapolis, MD 21409

    THE FRIARY a Trophy property in a league of its own! Set on 23 private acres overlooking a gracious bend of the Severn River with 1,500ft of prime waterfrontage, just minutes from downtown Annapolis and less than an hour from the nation's capital, lies one of the most distinctive estates offered for sale on the East Coast. A true architectural masterpiece, this exquisite 35,000+ sqft

    Brad Kappel TTR Sotheby's International Realty

    1604 Winchester Rd, Annapolis, MD 21409
  • /34

    $1,325,000

    • 6 Beds
    • 4.5 Baths
    • 6,196 Sq Ft

    1707 Ritchie Hwy, Annapolis, MD 21409

    Back on the Market!Escape to your own private Estate. 6100+ sqf of finished space with 2.2 acres of land in the most desirable location of Annapolis. 6 Bedrooms, 4.5 Bathrooms, with > 1000sqf for Master Suite. Two Fireplaces. Move-in condition. Potential for subdivision (check with engineer/county). A stone's throw to downtown without the city taxes. Across from B&A bike

    Mary Saba Keller Williams Select Realtors of Annapolis

    1707 Ritchie Hwy, Annapolis, MD 21409
  • /30

    $4,950,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    1632 Winchester Rd, Annapolis, MD 21409

    Don't miss this incredible opportunity to build your dream luxury estate home on this amazing private 3.3 acre homesite with amazing waterviews and privacy. Tucked away back off of your 1/4 mile private driveway which sets the tone as you approach your very own oasis. Come witness our vision and be a part of creating a generational estate that Annapolis rarely sees. The main level boasts

    Colleen Smith EXP Realty, LLC

    1632 Winchester Rd, Annapolis, MD 21409
  • /71

    $749,900

    • 5 Beds
    • 3.5 Baths
    • 3,213 Sq Ft

    1043 Skyview Dr, Annapolis, MD 21409

    Welcome to your dream home, a meticulously maintained three-level residence featuring a stunning two-story foyer that sets the tone for elegance and comfort. This versatile layout offers both formal and informal spaces, perfect for any lifestyle. The gourmet kitchen is a chef's delight, equipped with stainless steel appliances, granite countertops, and stylish tile backsplashes, complemented by

    Stacy Early Long & Foster Real Estate, Inc.

    1043 Skyview Dr, Annapolis, MD 21409
  • /48

    $975,000

    • 5 Beds
    • 3 Baths
    • 3,230 Sq Ft

    1534 Circle Dr, Annapolis, MD 21409

    Incredible PRIVATE oasis, in sought after community of Winchester on the Severn. One of a kind home, surrounded by protected lands. One of the highest and largest lots in the community, overlooking the wooded glen. Custom hardscaping with multi level decks, and numerous stone patios. Enjoy the tiered golf putting green and the outdoor spa hot tub! There are 2 beautiful sunroom additions on

    Dawn Dougan Long & Foster Real Estate, Inc.

    1534 Circle Dr, Annapolis, MD 21409
  • /34

    $6,500

    • 6 Beds
    • 4.5 Baths
    • 4,796 Sq Ft

    1707 Governor Ritchie Hwy, Annapolis, MD 21409

    Escape to your own private Estate. 6000+ sqf of finished space with 2.2 acres of land in the most desirable location of Annapolis. 6 Bedrooms, 4.5 Bathrooms, with > 1000sqf for Master Suite. Two Fireplaces. Move-in condition. Potential for subdivision (check with engineer/county). A stone's throw to downtown without the city taxes. Across from B&A bike Trail & WWII Memorial.

    Mary Saba Keller Williams Select Realtors of Annapolis

    1707 Governor Ritchie Hwy, Annapolis, MD 21409
  • /33

    $600,000

    • 5 Beds
    • 2 Baths
    • 2,054 Sq Ft

    1410 Stepney Rd, Annapolis, MD 21409

    ***OPEN HOUSE SUNDAY 3/23 2:00-4:00*** Enjoy the "Land of Pleasant Living" in this ranch style home on a beautiful 1 acre lot in the Broadneck area. Imagine the possibilities in making this house your home with space to spare. The home contains a separate and well thought out in-law suite with 2 entrances and potential for rental income. The main portion of the house includes a front porch,

    Jill Windsor Long & Foster Real Estate, Inc.

    1410 Stepney Rd, Annapolis, MD 21409
  • /44

    $995,000

    • 5 Beds
    • 3.5 Baths
    • 3,028 Sq Ft

    1825 Johnson Rd, Annapolis, MD 21409

    ***Be at the forefront of the Neighborhood Property Expansions and Enjoy the Future Appreciation ofthis 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

    John Burgess Samson Properties

    1825 Johnson Rd, Annapolis, MD 21409
  • /2

    $399,000

    • 5 Beds
    • 3 Baths
    • 3,190 Sq Ft

    1328 Yorktown Rd, Annapolis, MD 21409

    4 Bedroom Rancher. Rare Find ! Fixer Upper. Huge yard.

    Shawna Booze Smart Realty, LLC

    1328 Yorktown Rd, Annapolis, MD 21409
  • /2

    $530,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 1,064 Sq Ft

    187 Browns Woods Rd, Annapolis, MD 21409

    Welcome to 187 Browns Woods Road – The Perfect Blend of Style, Space, and Versatility!Nestled in a peaceful Annapolis neighborhood, this beautifully updated rancher is the definition of move-in ready and packed with features that make it ideal for multi-generational living or anyone seeking flexible space. With 5 bedrooms, 2 full bathrooms, and two fully equipped kitchens, this home offers the

    Dee Akindoyo Coldwell Banker Realty

    187 Browns Woods Rd, Annapolis, MD 21409
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