33

5-Bedroom Houses for Sale in Annapolis, MD

Section Image
  • /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
  • /67

    $2,695,000

    • 5 Beds
    • 4 Baths
    • 3,415 Sq Ft

    2680 Claibourne Ct, Annapolis, MD 21403

    Nestled on Chase Pond along the serene shores of the Chesapeake Bay, 2680 Claibourne Court offers an unparalleled waterfront living experience. This meticulously renovated coastal contemporary-style residence boasts 5 bedrooms, 4 full bathrooms, and seamlessly blends luxury with comfort. Set on a generous 2.62-acre waterfront lot, the property features a private pier with boat lifts and a beach,

    Doc Keane Washington Fine Properties, LLC

    2680 Claibourne Ct, Annapolis, MD 21403
  • /14

    $3,675,000

    • 5 Beds
    • 4 Baths
    • 3,305 Sq Ft

    3 Eastern Ave, Annapolis, MD 21403

    Eastern Avenue Waterfront! A rare offering, this premium waterfront property on prestigious Eastern Avenue in Eastport provides awe-inspiring panoramic views of Chesapeake Bay, Severn River and Back Creek. This property suits a variety of needs and its expansive footprint provides endless possibilities for renovations or a full re-build. Civil Engineer plans by CPJ Associates, Inc. as well as

    Brad Kappel TTR Sotheby's International Realty

    3 Eastern Ave, Annapolis, MD 21403
  • /56

    $4,850,000

    • 6 Beds
    • 8 Baths
    • 13,495 Sq Ft

    3054 Rundelac Rd, Annapolis, MD 21403

    Welcome to 3054 Rundelac Road, a quintessential Annapolis waterfront estate located on Aberdeen Creek. Nestled on nearly 4 acres in a quiet neighborhood, this extraordinary home offers thoughtful luxury and amenities ensuring the ultimate experience in waterfront living. The landscaped gardens include a welcoming front yard and a private backyard. Off the extensive swimming pool patio, the lawn

    Gail Chisholm Compass

    3054 Rundelac Rd, Annapolis, MD 21403
  • /68

    $3,500,000

    • 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
  • /112

    $6,750,000

    • 6 Beds
    • 8.5 Baths
    • 11,045 Sq Ft

    803 Coachway, Annapolis, MD 21401

    This Severn River Waterfront Estate is a rare and breathtaking Annapolis retreat. Experience the ultimate in waterfront living in this exquisite residence, a true masterpiece offering unparalleled panoramic water views. Nestled on a pristine one-acre site in the prestigious Point of The Downs, this custom-built legacy home has been meticulously updated to perfection, creating the ideal setting

    Georgie Berkinshaw Coldwell Banker Realty

    803 Coachway, Annapolis, MD 21401
  • /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
  • /55

    $1,390,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 5,062 Sq Ft

    9 Rusty Red Dr, Annapolis, MD 21401

    NEW CONSTRUCTION - MOVE IN READY!!!!!!Luxury Living in the Heart of AnnapolisWelcome to 9 Rusty Red Drive—a brand-new, meticulously crafted residence nestled in the sought-after Homewood neighborhood. This 5,000+ square foot masterpiece seamlessly blends upscale finishes with thoughtful design, offering an unparalleled living experience just moments from downtown Annapolis. Key Features: •

    James Ellis Coldwell Banker Realty

    9 Rusty Red Dr, Annapolis, MD 21401
  • /62

    $1,484,000 New Construction

    • 6 Beds
    • 4 Baths
    • 3,702 Sq Ft

    2644 Claibourne Rd, Annapolis, MD 21403

    AMAZING BRAND NEW WATER VIEW HOME - This stunning 6 bedroom, 4 full bathroom residence offers 3,702 sq ft of finished space with breathtaking views of Lake Heron and the Chesapeake Bay. Situated in the sought-after Annapolis Roads community, the home occupies a premium 20,125 sq ft corner lot and features a 2-car side load garage. The main level showcases 9-foot ceilings and LVP hardwood floors

    Brian Wood Long & Foster Real Estate, Inc.

    2644 Claibourne Rd, Annapolis, MD 21403
  • /31

    $1,350,000 Pre-Foreclosure

    • 6 Beds
    • 8 Baths
    • 11,350 Sq Ft

    1254 Washington Dr, Annapolis, MD 21403

    Ready to build your dream home? Buyer Fell through. Priced to sell fast! This project is mostly demo'ed and ready for you to take over and make it your own. You can run with our plans as rended in the pictures or make your own. ****NO Walking on the property without an appointment. Showings by appointment with hold harmless signed as the property is

    Brendan Spear Caprika Realty

    1254 Washington Dr, Annapolis, MD 21403
  • /34

    $649,900

    • 5 Beds
    • 2 Baths
    • 2,592 Sq Ft

    1356 Moyer Ct, Annapolis, MD 21403

    Welcome to 1356 Moyer Ct, located on an expansive 1.2 acre lot & within walking distance to PAL Park! This charming home exudes mid-century modern vibes, featuring vaulted ceilings, an open floor plan, and tons of natural lighting, especially in the sun filled great room! The home also boasts a lovely screened porch, two beautifully updated full baths, and a sleek kitchen with granite counters,

    Yael Beckman Coldwell Banker Realty

    1356 Moyer Ct, Annapolis, MD 21403
  • /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
  • /61

    $1,125,000

    • 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
  • /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
  • /35

    $550,000

    • 6 Beds
    • 2 Baths
    • 2,039 Sq Ft

    201 Janwall St, Annapolis, MD 21403

    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

    Madeleine Melgar Alltrade Real Estate

    201 Janwall St, Annapolis, MD 21403
  • /46

    $3,250,000

    • 5 Beds
    • 4 Baths
    • 5,167 Sq Ft

    145 Spa Dr, Annapolis, MD 21403

    Exceptionally built custom waterfront home with spectacular panoramic views of Spa Creek. Attention to detail and high-end finishes are the hallmark of this wonderful home with 12 ft ceilings on the main level. Over 4,500 sqft of living space on 3 finished levels, 5 spacious bedrooms and 4 baths. The stunning Primary suite has a private balcony with panoramic views up and down Spa Creek and the

    Brad Kappel TTR Sotheby's International Realty

    145 Spa Dr, Annapolis, MD 21403
  • /67

    $3,500,000

    • 6 Beds
    • 4.5 Baths
    • 5,020 Sq Ft

    1486 Downham Market, Annapolis, MD 21401

    An extraordinary opportunity to own a premier property in The Downs has arrived. This expansive contemporary on almost 2 acres offers over 5,000sqft of open living with direct views of Clements Creek from seven rooms and a 180ft pier. This home has some serious wow factors including; a hexagonal dining room... double entry doors...an enclosed hot tub area with river views...an exquisitely

    Robert Sobczak Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • /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
  • /104

    $3,100,000

    • 5 Beds
    • 7 Baths
    • 5,930 Sq Ft

    1856 Severn Grove Rd, Annapolis, MD 21401

    Waterfront home available for sale on sought-after Saltworks Creek. Home features nearly 6,000 sq/ft luxury living, 5 bedrooms, 7 baths, situated on a stunning 3-acre private waterfront lot just off the Severn River yet close to everything Annapolis has to offer! The estate has a private 6’ deep-water dock with 2 boatlifts a short walk from the house. The rear of the home has a large

    Patrick DeLeonibus TTR Sotheby's International Realty

    1856 Severn Grove Rd, Annapolis, MD 21401
  • /128

    $3,249,000

    • 5 Beds
    • 4.5 Baths
    • 6,412 Sq Ft

    856 St Edmonds Place, Annapolis, MD 21401

    OPEN HOUSE SATURDAY 4/26 12-2!!!Have it all with stunning views from nearly every room, deep water, privacy, and large floorplan for multi generational living! Spectacular custom built waterfront home in the sought after Downs community of Annapolis! Breathtaking views await you from every corner of this updated and well conceived home. Dramatic details throughout highlight the open floorplan

    James Schaecher Keller Williams Flagship

    856 St Edmonds Place, Annapolis, MD 21401
  • /61

    $540,000

    • 5 Beds
    • 3 Baths
    • 2,457 Sq Ft

    901 Chesterfield Rd, Annapolis, MD 21401

    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

    Lois Alberti Alberti Realty, LLC

    901 Chesterfield Rd, Annapolis, MD 21401
  • /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
  • /29

    $574,900

    • 5 Beds
    • 2 Baths
    • 1,854 Sq Ft

    1022 Tyler Ave, Annapolis, MD 21403

    Location! Location! Resort living between two rivers in this lovely split level home! Twenty year homeowner never stopped improving the home, including recent architectural roof, HVAC with humidity control, home water filtration system, and a jumbo 75 gallon hot water heater. Oak patterned laminate floors throughout provide a warm & classy feel. The upper floor offers three bedrooms that are

    Doug Rice Fathom Realty MD, LLC

    1022 Tyler Ave, Annapolis, MD 21403
  • /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
  • /25

    $499,000

    • 5 Beds
    • 2 Baths
    • 1,755 Sq Ft

    86 Summerfield Dr, Annapolis, MD 21403

    Lovely 5 Bedroom and 2 Full Bath home plus Finished Basement in the desirable neighborhood of Stevens Park, part of Eastport. Main Floor has Two bedrooms, Full Bath, Livingroom and Kitchen with Breakfast Nook. Upper Level has Two Bedrooms and Full Bath. Basement has One Bedroom, Large Family Room with Stepped Rear Walkout, and Laundry-Utility-Storage Room. New Roof and Gutters with Leaf Covers

    Paul Leckinger EXP Realty, LLC

    86 Summerfield Dr, Annapolis, MD 21403
  • /52

    $850,000

    • 5 Beds
    • 3.5 Baths
    • 3,235 Sq Ft

    3 Park Ln, Annapolis, MD 21403

    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

    Keri Weis Northrop Realty

    3 Park Ln, Annapolis, MD 21403
  • /89

    $1,234,000

    • 5 Beds
    • 5.5 Baths
    • 7,616 Sq Ft

    301 Unity Ln, Annapolis, MD 21401

    Walk in and be amazed with a beautiful and luxurious remodeled open floor concept. Open the front door and look to the gorgeous living room with electric fire place that produces up to 5,000 BTU of heat for the comfort on cold and snowy days. Living room flows into your brand new gourmet style kitchen set up for fabulous days of entertaining friends and family. Main floor offers a spectacular

    Fanny Kranwinkel Sunshine Properties Inc.

    301 Unity Ln, Annapolis, MD 21401
  • /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
  • /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
  • /30

    $2,950,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 4,400 Sq Ft

    2762 Bon Haven Ln, Annapolis, MD 21401

    Welcome to an unparalleled opportunity to own a magnificent waterfront retreat in the prestigious community of Bon Haven. Perfectly positioned on over an acre of pristine land along the scenic South River, this to-be-built custom home offers a rare blend of sophisticated design, modern luxury, and breathtaking water views. Crafted with the finest finishes, this exceptional residence boasts

    Colleen Smith EXP Realty, LLC

    2762 Bon Haven Ln, Annapolis, MD 21401
  • /39

    $1,039,990 Open Sat 12PM - 3PM

    • 5 Beds
    • 5.5 Baths
    • 5,017 Sq Ft

    110 Stilly Way, Annapolis, MD 21403

    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

    Mary Anne Long Keller Williams Realty Centre

    110 Stilly Way, Annapolis, MD 21403
  • /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

Home Trends in Annapolis, MD

Home Trends

Median Price (12 Mo)
$601,750
Median Single Family Price
$783,500
Median Townhouse Price
$490,000
Median 2 Bedroom Price
$410,000
Median 1 Bedroom Price
$342,998
Average Price Per Sq Ft
$354
Number of Homes for Sale
216
Last 12 months Home Sales
1,066
Months of Supply
2.40
Median List Price
$615,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home