38

Homes for Sale in Annapolis, MD with 5-Bedrooms

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  • 17151717 Porters Hill Rd, Annapolis, MD 21401
    17151717 Porters Hill Rd, Annapolis, MD 21401
    17151717 Porters Hill Rd, Annapolis, MD 21401
    /37

    $4,950,000

    • 7 Beds
    • 7 Baths
    • 7,500 Sq Ft

    17151717 Porters Hill Rd, Annapolis, MD 21401

    Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715-1717 Porters Hill Road is a unique heritage property with over a century of history. Set on a 2.96 acre lot with 429 ft of waterfrontage, the property is comprised of two separate parcels and includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures.

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (443) 960-7039

    17151717 Porters Hill Rd, Annapolis, MD 21401
  • 1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
    /84

    $3,199,950

    • 5 Beds
    • 2 Baths
    • 5,522 Sq Ft

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409

    Welcome to 1979 Baltimore Annapolis Blvd — where original charm meets opportunity. Set along one of the Severn River’s most desirable stretches with unobstructed views of the U.S. Naval Academy, this distinctive residence offers 5,522 finished square feet across three levels—seamlessly blending timeless character with a 2015 expansion and thoughtful modern updates. Enjoy a front-row seat to the

    Agent Photo

    Angelica Dennis

    Keller Williams Capital Properties

    (443) 781-6808

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
  • 1349 Yorktown Rd, Annapolis, MD 21409
    1349 Yorktown Rd, Annapolis, MD 21409
    1349 Yorktown Rd, Annapolis, MD 21409
    /35

    $2,799,000

    • 16 Beds
    • 6 Baths
    • 5,719 Sq Ft

    1349 Yorktown Rd, Annapolis, MD 21409

    This brand new, fully renovated 16-bedroom, 6-bathroom residence in Annapolis offers an exceptional opportunity for assisted living or specialized care operations. Thoughtfully redesigned and fully permitted with the county for use as an assisted living facility, the property combines modern upgrades with full regulatory compliance. The spacious layout features three separate living areas,

    Agent Photo

    Karen Rollings

    EXP Realty, LLC

    (443) 296-5581

    1349 Yorktown Rd, Annapolis, MD 21409
  • 1292 Spa Rd, Annapolis, MD 21403
    1292 Spa Rd, Annapolis, MD 21403
    1292 Spa Rd, Annapolis, MD 21403
    /62

    $1,595,000

    • 5 Beds
    • 4.5 Baths
    • 4,672 Sq Ft

    1292 Spa Rd, Annapolis, MD 21403

    CASUAL ELEGANCE BEST DESCRIBES THIS COASTAL HOME INSPIRED BY ARCHITECT A. HAYS TOWN. THIS HOME IS AN ENTERTAINER'S DREAM. THIS 5-BEDROM, 4.FULL & 2 HALF-BATH(2ND HALF BATH IN THE POOL HOUSE) HAS IT ALL! EXQUISITE DETAILS THROUGHOUT, RESORT STYLE HEATED SALT WATER POOL W/SUN DECK & WATER FEATURES. THERE IS AN AMAZING POOL HOUSE W/BATH, OUTDOOR TV, GORGEOUS WOOD BEAM PAVILION THAT LEADS TO AN

    Pamela Tierney Coldwell Banker Realty

    1292 Spa Rd, Annapolis, MD 21403
  • 605 Lighthouse Landing Ln, Annapolis, MD 21409
    605 Lighthouse Landing Ln, Annapolis, MD 21409
    605 Lighthouse Landing Ln, Annapolis, MD 21409
    /51

    $1,018,000

    • 6 Beds
    • 4.5 Baths
    • 4,041 Sq Ft

    605 Lighthouse Landing Ln, Annapolis, MD 21409

    Welcome to 605 Lighthouse Landing Ln, located on a quiet corner lot. This home has 6 bedrooms, 4 1⁄2 baths, designed with an open floor plan. The great room on the first level has a den with fireplace, breakfast nook, and kitchen. Also on the first floor is the living room, foyer, dining room, and a primary bedroom with shower and soak in tub also there are two large, his and hers walk in

    Nathalie Mullinix Nathalie Mullinix Realty Universal, Inc.

    605 Lighthouse Landing Ln, Annapolis, MD 21409
  • 1519 Winchester Rd, Annapolis, MD 21409
    1519 Winchester Rd, Annapolis, MD 21409
    1519 Winchester Rd, Annapolis, MD 21409
    /34

    $849,000 Open Sat 11AM - 3PM

    • 5 Beds
    • 3 Baths
    • 2,375 Sq Ft

    1519 Winchester Rd, Annapolis, MD 21409

    Set on a beautifully landscaped 0.34-acre corner lot in sought-after Winchester-on-the-Severn, this thoughtfully renovated residence offers a seamless blend of style, comfort, and everyday livability. A fully fenced backyard creates a private outdoor retreat, complete with a deck, patio, garden, playground, and storage shed, perfectly designed for both entertaining and relaxed daily living.

    Brad Kappel TTR Sotheby's International Realty

    1519 Winchester Rd, Annapolis, MD 21409
  • 767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    /50

    $1,175,000

    • 5 Beds
    • 4 Baths
    • 3,255 Sq Ft

    767 Bon Haven Dr, Annapolis, MD 21401

    Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive water access community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including

    Sean O'Connor Coldwell Banker Realty

    767 Bon Haven Dr, Annapolis, MD 21401
  • 141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    /56

    $1,125,000 Open Fri 5PM - 7PM

    • 5 Beds
    • 4.5 Baths
    • 5,140 Sq Ft

    141 Stilly Way, Annapolis, MD 21403

    She’s one and a half years young. She’s flawless. She’s Annapolis. Welcome to 141 Stilly Way — a barely lived-in, fully upgraded showpiece in the sought-after Parkside Preserve, offered in true mint condition. This is not a builder sale. This is the finished product — every bump-out, every upgrade, every design decision already made at the highest level. No waiting. No construction. No

    Wendy Oliver Coldwell Banker Realty

    141 Stilly Way, Annapolis, MD 21403
  • 1716 Severn Forest Dr, Annapolis, MD 21401
    1716 Severn Forest Dr, Annapolis, MD 21401
    1716 Severn Forest Dr, Annapolis, MD 21401
    /81

    $5,775,000

    • 5 Beds
    • 6 Baths
    • 6,573 Sq Ft

    1716 Severn Forest Dr, Annapolis, MD 21401

    Set on 4.5 scenic acres along the Severn River, this exceptional Tudor/French Country estate blends timeless architecture with high-end craftsmanship just 10 minutes from downtown Annapolis. Panoramic views of the Severn, set the tone for this exceptional property, complemented by a conditiioned detached two-car garage with private guest quarters complete with a kitchenette and full bath. Outdoor

    Georgie Berkinshaw Coldwell Banker Realty

    1716 Severn Forest Dr, Annapolis, MD 21401
  • 1106 Mainsail Dr, Annapolis, MD 21403
    1106 Mainsail Dr, Annapolis, MD 21403
    1106 Mainsail Dr, Annapolis, MD 21403
    /57

    $895,000

    • 5 Beds
    • 2.5 Baths
    • 2,059 Sq Ft

    1106 Mainsail Dr, Annapolis, MD 21403

    At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more.This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated

    Jill Windsor Long & Foster Real Estate, Inc.

    1106 Mainsail Dr, Annapolis, MD 21403
  • 2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    /50

    $3,850,000

    • 6 Beds
    • 4.5 Baths
    • 3,818 Sq Ft

    2 River Dr, Annapolis, MD 21403

    2 River with its stunning water views of the Severn River and of the Chesapeake Bay epitomizes the Annapolis Lifestyle! Located in this beloved multi-generational community of Bay Ridge, this exquisitely renovated classic home seamlessly blends the timeless updates and fabulous original detail such as leaded glass windows and brass chandeliers. The main level has the most incredible, breezy

    Alex Tower Sears TTR Sotheby's International Realty

    2 River Dr, Annapolis, MD 21403
  • 3280 Arundel on The Bay Rd, Annapolis, MD 21403
    3280 Arundel on The Bay Rd, Annapolis, MD 21403
    3280 Arundel on The Bay Rd, Annapolis, MD 21403
    /52

    $850,000

    • 5 Beds
    • 4.5 Baths
    • 3,144 Sq Ft

    3280 Arundel on The Bay Rd, Annapolis, MD 21403

    Significant Price Improvement!! A rare opportunity! Priced to sell, won't last long. Welcome to this beautifully maintained 5 bed, 4.5 bath, colonial home situated on almost a half of acre and only 2 blocks to the Chesapeake Bay where you can hear the sounds of the ships passing by in your backyard! Located in the very desirable and relaxed Oyster Harbor Community. This move-in ready home

    Deanna Marshall The KW Collective

    3280 Arundel on The Bay Rd, Annapolis, MD 21403
  • 52 Primrose Hill Ln, Annapolis, MD 21403
    52 Primrose Hill Ln, Annapolis, MD 21403
    52 Primrose Hill Ln, Annapolis, MD 21403
    /73

    $949,900

    • 5 Beds
    • 4.5 Baths
    • 3,978 Sq Ft

    52 Primrose Hill Ln, Annapolis, MD 21403

    Modern accents meet classic Georgian design in a downtown Annapolis private enclave of customized homes. Monthly neighborhood get togethers, progressive dinners, holiday celebrations and lovingly curated green spaces for outdoor living. Self managed HOA includes yard care and snow removal for lock and leave convenience. If you’re looking for rolling acres with grass to cut weeds to pull beds to

    Richard Curtis Curtis Real Estate Company

    52 Primrose Hill Ln, Annapolis, MD 21403
  • 13 German St, Annapolis, MD 21401
    13 German St, Annapolis, MD 21401
    13 German St, Annapolis, MD 21401
    /44

    $1,170,000

    • 5 Beds
    • 3 Baths
    • 2,590 Sq Ft

    13 German St, Annapolis, MD 21401

    Welcome to 13 German Street, a hidden gem perfectly positioned in sought-after Murray Hill where you can walk to everything in town while still feeling distinctly residential and refined. From front-row access to the St. Patty's Day Parade to summer evenings at Dinner Under the Stars on West Street, this fully renovated three-level bungalow places you at the center of it all. City Dock, the Arts

    Michele Deckman TTR Sotheby's International Realty

    13 German St, Annapolis, MD 21401
  • 1707 Ritchie Hwy, Annapolis, MD 21409
    1707 Ritchie Hwy, Annapolis, MD 21409
    1707 Ritchie Hwy, Annapolis, MD 21409
    /27

    $1,325,000

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

    1707 Ritchie Hwy, Annapolis, MD 21409

    Escape to your own private Estate. 6100+ sqf of finished space with 2.2 acres of land in the most desirable location of Annapolis. 5 Bedrooms, 2 Offices, 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. Direct

    Mary Saba Hayden Realty & Development, LLC

    1707 Ritchie Hwy, Annapolis, MD 21409
  • 856 St Edmonds Place, Annapolis, MD 21401
    856 St Edmonds Place, Annapolis, MD 21401
    856 St Edmonds Place, Annapolis, MD 21401
    /129

    $2,795,000

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

    856 St Edmonds Place, Annapolis, MD 21401

    **Open House - Sunday, March 29th, 11-1 pm** Welcome to 856 St Edmonds Place! Newly positioned $700k below recent appraisal! Have it all with stunning views from nearly every room, deep water, privacy, and a spacious 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

    James Schaecher Keller Williams Flagship

    856 St Edmonds Place, Annapolis, MD 21401
  • 90 E Lake Dr, Annapolis, MD 21403
    90 E Lake Dr, Annapolis, MD 21403
    90 E Lake Dr, Annapolis, MD 21403
    /67

    $3,495,000 Open Sat 2PM - 4PM

    • 5 Beds
    • 5.5 Baths
    • 4,204 Sq Ft

    90 E Lake Dr, Annapolis, MD 21403

    Come explore the shores of Bay Ridge. As Annapolis's premiere waterfront community, Bay Ridge boasts an Olympic-sized swimming pool, a marina with 120 slips, and a private clubhouse. Serving as home to the Chesapeake Bay Foundation, this community stewards and embodies all of the finer aspects of living on the Chesapeake. With miles of shoreline, private beaches, and breathtaking views, Bay Ridge

    Colleen Smith EXP Realty, LLC

    90 E Lake Dr, Annapolis, MD 21403
  • 39 Southgate Ave, Annapolis, MD 21401
    39 Southgate Ave, Annapolis, MD 21401
    39 Southgate Ave, Annapolis, MD 21401
    /67

    $3,495,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 6,789 Sq Ft

    39 Southgate Ave, Annapolis, MD 21401

    This Murray Hill masterpiece is a 5-bedroom, 4 bathroom home that was originally built in 1913 and underwent a complete custom renovation a few years ago. Situated on a double lot on one of the most desirable streets in Annapolis. It blends formal sophistication with modern luxuries including an elevator! Tucked behind the home is a surprising expansive lot that feels much larger than you would

    Glenn Sutton TTR Sotheby's International Realty

    39 Southgate Ave, Annapolis, MD 21401
  • 1002 Tyler Ave, Annapolis, MD 21403
    1002 Tyler Ave, Annapolis, MD 21403
    1002 Tyler Ave, Annapolis, MD 21403
    /33

    $565,000

    • 5 Beds
    • 2 Baths
    • 1,920 Sq Ft

    1002 Tyler Ave, Annapolis, MD 21403

    Location Location location!!Modern rancher style home located near everything Annapolis has to offer! It's just minutes to Downtown Annapolis. The House is much bigger than it looks. A beautiful fenced in backyard with a composite decking awaits for outdoor entertaining. This house also features 5 bedrooms and two full bath. This home is almost 2,000 sf. finished. Entire home was fully

    Cecilia Beltran Smart Realty, LLC

    1002 Tyler Ave, Annapolis, MD 21403
  • 812 Coachway, Annapolis, MD 21401
    812 Coachway, Annapolis, MD 21401
    812 Coachway, Annapolis, MD 21401
    /75

    $3,449,999

    • 6 Beds
    • 7 Baths
    • 7,766 Sq Ft

    812 Coachway, Annapolis, MD 21401

    Repriced to Sell as of 1.26.26 !! Wake up to Severn River views, not dock maintenance! 812 Coachway is an all-brick waterfront estate in The Downs on the Severn, offering 6 bedrooms, 7 baths, and over 7,500 square feet of refined indoor-outdoor living. Thoughtfully updated to merge timeless architecture with modern luxury, nearly every room frames stunning Severn River views. A two-story foyer

    Keisha McClain Hubble Bisbee Christie's International Real Estate

    812 Coachway, Annapolis, MD 21401
  • 778 Bon Haven Dr, Annapolis, MD 21401
    778 Bon Haven Dr, Annapolis, MD 21401
    778 Bon Haven Dr, Annapolis, MD 21401
    /95

    $2,800,000

    • 6 Beds
    • 4 Baths
    • 5,094 Sq Ft

    778 Bon Haven Dr, Annapolis, MD 21401

    Exquisite South River Waterfront Estate Experience waterfront living at its finest in this rare South River estate situated at the end of a quiet cul-de-sac. Elevated above the water on a private 1.07-acre lot with 132 feet of premier frontage, this stunningly remodeled 4,900+ sq. ft. rancher offers timeless elegance, modern sophistication, and panoramic river views from nearly every room. The

    Steven Knopf Engel & Völkers Annapolis

    778 Bon Haven Dr, Annapolis, MD 21401
  • 1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    /106

    $3,250,000

    • 5 Beds
    • 4.5 Baths
    • 5,260 Sq Ft

    1486 Downham Market, Annapolis, MD 21401

    1486 Downham Market is the ultimate Annapolis deep-water estate—designed for those who demand luxury, security, and boating excellence. Perfectly positioned at the mouth of Clements Creek—one of the safest hurricane holes on the Severn River—this home pairs architectural brilliance with one of the region’s most coveted waterfront settings. A commanding 180’ pier with three boat slips, 50-amp

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • 553 Choptank Cove Ct, Annapolis, MD 21401
    553 Choptank Cove Ct, Annapolis, MD 21401
    553 Choptank Cove Ct, Annapolis, MD 21401
    /47

    $1,050,000

    • 5 Beds
    • 4 Baths
    • 3,759 Sq Ft

    553 Choptank Cove Ct, Annapolis, MD 21401

    Days on market reflects seller ability to show because of illness.English Tudor featuring a stone front patio, covered front porch for nature lovers and bird watchers. Driveway paved and widened in 2021, extensive gardens and plantings. House surrounded by mature trees for tons of shade and privacy. Rear deck is 45 ft by 16 ft and built to hold a large hot tub. Constructed in 2016 for

    Linda Patterson Long & Foster Real Estate, Inc.

    553 Choptank Cove Ct, Annapolis, MD 21401
  • 2644 Claibourne Rd, Annapolis, MD 21403
    2644 Claibourne Rd, Annapolis, MD 21403
    2644 Claibourne Rd, Annapolis, MD 21403
    /56

    $1,384,000 New Construction

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

    2644 Claibourne Rd, Annapolis, MD 21403

    Waterfront Views - Annapolis Roads Community! AMAZING BRAND NEW WATER VIEW HOME in a desirable Annapolis, MD location! This stunning 5 bedroom, 3 full bathroom residence offers all the amenitiew of Annapolis Roads and lock and leave lifestyle. 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. Special

    George Bailey Keller Williams Flagship

    2644 Claibourne Rd, Annapolis, MD 21403
  • 4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    /12

    $3,285,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 5,312 Sq Ft

    4 Shiley St, Annapolis, MD 21401

    This exceptional TO-BE-BUILT opportunity awaits in the coveted West Annapolis community —a rare 0.61-acre offering with endless potential. The custom new build was designed to seamlessly incorporate onto the expansive lot, providing your dream residence in one of the area’s most sought-after neighborhoods. The approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural

    Brad Kappel TTR Sotheby's International Realty

    4 Shiley St, Annapolis, MD 21401
  • 148 Jefferson St, Annapolis, MD 21403
    148 Jefferson St, Annapolis, MD 21403
    148 Jefferson St, Annapolis, MD 21403
    /29

    $925,000 New Construction

    • 5 Beds
    • 3 Baths
    • 2,330 Sq Ft

    148 Jefferson St, Annapolis, MD 21403

    Perfectly positioned in Eastport, Annapolis, just moments from downtown, this brand-new home places you in the heart of it all: boat shows, waterfront dinners, parades, morning coffee walks, and sunset strolls along the harbor. Leave the car behind and lean into the Annapolis lifestyle. Inside, the home blends modern design with thoughtful flexibility. With 5 bedrooms and 3 full baths, including

    Kevin Brown Long & Foster Real Estate, Inc.

    148 Jefferson St, Annapolis, MD 21403
  • 703 Glendon Ave, Annapolis, MD 21403
    703 Glendon Ave, Annapolis, MD 21403
    703 Glendon Ave, Annapolis, MD 21403
    /35

    $2,750,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 4,116 Sq Ft

    703 Glendon Ave, Annapolis, MD 21403

    A brand-new home for the brand-new you. You’ve worked hard to get here—now you deserve a home that reflects it. With Whitehall Building & Company, your dream home becomes reality through a flexible design/build process, a guaranteed delivery date, and a fixed-price contract. This exceptional to-be-built waterfront residence in coveted Parkwood offers the perfect blend of Eastport living with the

    Colleen Smith EXP Realty, LLC

    703 Glendon Ave, Annapolis, MD 21403
  • 1907 Mackiebeth Ct, Annapolis, MD 21401
    1907 Mackiebeth Ct, Annapolis, MD 21401
    1907 Mackiebeth Ct, Annapolis, MD 21401
    /6

    $1,575,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 5,437 Sq Ft

    1907 Mackiebeth Ct, Annapolis, MD 21401

    PHOTOS TO BE UPDATED BY THE END OF MARCH! This is a rare opportunity to own a newly built, beautifully designed home on a large lot in an established neighborhood-with nature at your doorstep and everything Annapolis has to offer just minutes away. This home is estimated to be completed by the end of April, 2026. With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms

    Marilyn Hendley EXP Realty, LLC

    1907 Mackiebeth Ct, Annapolis, MD 21401
  • 1207 Thomas Point Ct, Annapolis, MD 21403
    1207 Thomas Point Ct, Annapolis, MD 21403
    1207 Thomas Point Ct, Annapolis, MD 21403
    /15

    $1,750,000 Coming Soon

    • 5 Beds
    • 4 Baths
    • 4,589 Sq Ft

    1207 Thomas Point Ct, Annapolis, MD 21403

    WELCOME TO THIS BEAUTIFULLY DESIGNED 5/6 BEDROOM, 4 FULL BATH BRICK BEAUTY IN THE HIGHLY SOUGHT AFTER WATER-PRIVILEGED COMMUNITY OF FISHING CREEK FARM! FROM THE MOMENT YOU ENTER, THE HOME FEELS BOTH ELEVATED AND INVITING WITH WELL-APPOINTED SPACES, NATURAL FLOW, AND QUALITY FINISHES THROUGHOUT. THE MAIN LEVEL OFFERS A TWO STORY FOYER AND A HOME OFFICE (OR MAIN LEVEL BEDROOM) WITH PLANTATION

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    1207 Thomas Point Ct, Annapolis, MD 21403
  • 1787 Beachfield Rd, Annapolis, MD 21409
    1787 Beachfield Rd, Annapolis, MD 21409
    1787 Beachfield Rd, Annapolis, MD 21409
    /46

    $3,499,000 Open Sat 11AM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 6,360 Sq Ft

    1787 Beachfield Rd, Annapolis, MD 21409

    Welcome to a thoughtfully designed waterfront home on Whitehall Creek, where elevated positioning, wide open views, and a private deep-water pier with approximately 12 feet of mean low water, define the experience from the start. Step inside and the water immediately becomes the focal point. Natural light fills the home, and open sightlines carry those views throughout the main living spaces,

    Brad Kappel TTR Sotheby's International Realty

    1787 Beachfield Rd, Annapolis, MD 21409
  • 301 Kingsberry Dr, Annapolis, MD 21409
    301 Kingsberry Dr, Annapolis, MD 21409
    301 Kingsberry Dr, Annapolis, MD 21409
    /47

    $1,675,000 Coming Soon

    • 5 Beds
    • 4.5 Baths
    • 3,372 Sq Ft

    301 Kingsberry Dr, Annapolis, MD 21409

    Tucked at the end of a quiet cul-de-sac on the coveted shores of Mill Creek, this exceptional waterfront retreat captures sweeping views that stretch outward to Whitehall Bay and ultimately the Chesapeake Bay, an ever-changing backdrop of light, sky, and water. The home is thoughtfully designed to embrace its setting, with newly refinished wood floors guiding you through the main level where an

    Brad Kappel TTR Sotheby's International Realty

    301 Kingsberry Dr, Annapolis, MD 21409
  • 712 Coybay Dr, Annapolis, MD 21401
    712 Coybay Dr, Annapolis, MD 21401
    712 Coybay Dr, Annapolis, MD 21401
    /6

    $840,000 Coming Soon

    • 5 Beds
    • 4.5 Baths
    • 3,395 Sq Ft

    712 Coybay Dr, Annapolis, MD 21401

    Welcome to The Somerfield in “English Style,” where timeless architecture meets modern comfort on one of the most desirable streets in Kingsport. From the moment you arrive, you’ll notice the striking brick façade with arched transom windows and formal pediments, all set along a tree-lined street with sidewalks and exceptional curb appeal, with the community pool located directly across the wide

    Tina Marie Biggs EXP Realty, LLC

    712 Coybay Dr, Annapolis, MD 21401
  • 1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    /50

    $6,995,000 Coming Soon

    • 7 Beds
    • 5.5 Baths
    • 9,024 Sq Ft

    1524 Cedar Lane Farm Rd, Annapolis, MD 21409

    Escape to another world with this striking French modern waterfront estate. Exquisitely sited on a premium and private 4.15 acre lot with 600 feet of impressively rip-rapped water frontage, coveted waterfront pool, tennis court and picturesque views of the serene waters of Whitehall Creek. This ultra-luxe 9,000+ square-foot, 7 bedroom, 5.5 bathroom custom built home has been completely renovated.

    Brad Kappel TTR Sotheby's International Realty

    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
  • 219 Wardour Dr, Annapolis, MD 21401
    219 Wardour Dr, Annapolis, MD 21401
    219 Wardour Dr, Annapolis, MD 21401
    /44

    $3,595,000 Coming Soon

    • 5 Beds
    • 6.5 Baths
    • 8,296 Sq Ft

    219 Wardour Dr, Annapolis, MD 21401

    Located in the coveted Wardour community, this stately home combines timeless architecture with an enviable walkable location near West Annapolis’ shops and restaurants and just minutes from downtown. With stunning curb appeal, spacious 0.55 acre lot, expansive front yard and water views from nearly every room in the home, this property offers a rare combination of privacy and community, where

    Brad Kappel TTR Sotheby's International Realty

    219 Wardour Dr, Annapolis, MD 21401
  • 125 S Winchester Rd, Annapolis, MD 21409
    125 S Winchester Rd, Annapolis, MD 21409
    125 S Winchester Rd, Annapolis, MD 21409
    /47

    $8,750,000 Coming Soon

    • 5 Beds
    • 7 Baths
    • 11,269 Sq Ft

    125 S Winchester Rd, Annapolis, MD 21409

    This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection

    Brad Kappel TTR Sotheby's International Realty

    125 S Winchester Rd, Annapolis, MD 21409
  • 326 Cedar Ln, Annapolis, MD 21403
    326 Cedar Ln, Annapolis, MD 21403
    326 Cedar Ln, Annapolis, MD 21403
    /30

    $715,000 Coming Soon

    • 5 Beds
    • 3 Baths
    • 3,110 Sq Ft

    326 Cedar Ln, Annapolis, MD 21403

    Professional Photography as well as remarks, coming soon. This property will go active on Thursday April, 9th 2026.

    Ryan Briggs Anne Arundel Properties, Inc.

    326 Cedar Ln, Annapolis, MD 21403
  • 20 Washington Dr, Annapolis, MD 21401
    20 Washington Dr, Annapolis, MD 21401
    /2

    $480,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 1,828 Sq Ft

    20 Washington Dr, Annapolis, MD 21401

    Coming Soon in Annapolis! Charming single-family home located in a well-established neighborhood. This home offers great potential with a spacious lot and inviting curb appeal. Conveniently located near shopping, dining, and major commuter routes. Stay tuned for more details and professional photos—this one won’t last!

    Yvette Flores Samson Properties

    20 Washington Dr, Annapolis, MD 21401
  • 113 Legion Ave, Annapolis, MD 21401
    113 Legion Ave, Annapolis, MD 21401
    /2

    $475,000 Coming Soon

    • 6 Beds
    • 3 Baths
    • 1,949 Sq Ft

    113 Legion Ave, Annapolis, MD 21401

    Tucked just off West Street in Annapolis, this well-maintained split foyer blends space and flexibility. Freshly painted with new flooring throughout, the home offers a bright, refreshed feel from the moment you step inside. With 6 bedrooms and 3 full baths—3 bedrooms on each level—the layout is ideal for multi-generational living, guests, or work-from-home needs. The main level bath was

    Juli Blanton Keller Williams Flagship

    113 Legion Ave, Annapolis, MD 21401
Maryland Anne Arundel County Annapolis

5-Bedroom Homes for Sale in Annapolis, MD

Home Trends in Annapolis, MD

On average, homes in Annapolis, MD sell after 37 days on the market compared to the national average of 55 days. The median sale price for homes in Annapolis, MD over the last 12 months is $625,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$625,000
Median Single Family Sale Price
$825,000
Median Townhouse Sale Price
$450,000
Median 2 Bedroom Sale Price
$419,160
Median 1 Bedroom Sale Price
$453,700
Average Price Per Sq Ft
$355
Number of Homes for Sale
238
Last 12 months Home Sales
1,315
Months of Supply
2.20
Median List Price
$635,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%

Popular Home Searches in Annapolis, MD

In Annapolis, waterfront living and historic charm are top priorities, especially near Eastport and the historic district.

How to Buy a Home How to Finance a Home How to Sell a Home

In Annapolis, there are currently 38 5-bedroom homes for sale, offering expansive and versatile living spaces suitable for larger families or those desiring ample room for guests, home offices, or recreational areas. These properties provide flexibility and comfort, with generous bedroom counts accommodating various living arrangements and lifestyle needs. Whether you're in search of a spacious single-family home, a luxurious estate, or a custom-built residence with five or more bedrooms, there are options to cater to different lifestyles. Explore the selection of 5-bedroom homes for sale in Annapolis and find the perfect place to meet your needs.

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