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Annapolis, MD 2-Story Homes for Sale

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  • 2058 Quaker Way Unit 12, Annapolis, MD 21401
    2058 Quaker Way Unit 12, Annapolis, MD 21401
    2058 Quaker Way Unit 12, Annapolis, MD 21401
    /27

    $372,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    2058 Quaker Way Unit 12, Annapolis, MD 21401

    Nestled within the serene Windgate Condominium community, this exquisite 2-bedroom, 2-bathroom, loft residence offers a harmonious blend of contemporary design and luxurious comfort. Spanning 1,440 square feet, this thoughtfully designed unit is perfect for those seeking an elevated lifestyle. As you step inside, you are greeted by an inviting open floor plan that seamlessly connects the living

    Agent Photo

    Bob Swarm

    Keller Williams Select Realtors of Annapolis

    (410) 896-6929

    2058 Quaker Way Unit 12, Annapolis, MD 21401
  • 933 Breakwater Dr, Annapolis, MD 21403
    933 Breakwater Dr, Annapolis, MD 21403
    933 Breakwater Dr, Annapolis, MD 21403
    /20

    $390,000

    • 2 Beds
    • 2.5 Baths
    • 1,319 Sq Ft

    933 Breakwater Dr, Annapolis, MD 21403

    This spacious and well-maintained townhouse offers comfortable living in a highly desirable Annapolis location. The main level features a welcoming living room centered around a classic wood-burning fireplace, creating a warm focal point and cozy atmosphere, while the French doors provide access to the backyard, allowing natural light to fill the space while offering an easy transition to outdoor

    Agent Photo

    Scott Smolen

    RE/MAX Leading Edge

    (443) 323-0308

    933 Breakwater Dr, Annapolis, MD 21403
  • 3029 Solstice Ln, Annapolis, MD 21401
    3029 Solstice Ln, Annapolis, MD 21401
    3029 Solstice Ln, Annapolis, MD 21401
    /23

    $729,000

    • 3 Beds
    • 2 Baths
    • 1,894 Sq Ft

    3029 Solstice Ln, Annapolis, MD 21401

    Welcome to 3029 Solstice Lane, located in the exclusive Riva Trace community of Annapolis, Maryland—an area prized for its waterfront lifestyle and close proximity to historic downtown Annapolis. This home offers exceptional one-level living with a spacious open floor plan, soaring vaulted ceilings, and abundant natural light throughout. Brand-new carpet enhances the bright, airy interior.The

    Agent Photo

    Shawna Moore

    Long & Foster Real Estate, Inc.

    (410) 849-6712

    3029 Solstice Ln, Annapolis, MD 21401
  • 860 Woodmont Rd, Annapolis, MD 21401
    860 Woodmont Rd, Annapolis, MD 21401
    860 Woodmont Rd, Annapolis, MD 21401
    /55

    $629,000 Open Sat 2PM - 3:30PM

    • 3 Beds
    • 2 Baths
    • 1,623 Sq Ft

    860 Woodmont Rd, Annapolis, MD 21401

    Welcome to this beautifully updated 3-bedroom, 2-bath single-family home in the highly sought-after, amenity-rich Heritage Harbour community in Annapolis. Thoughtfully designed for comfortable main-level living, this home features a spacious primary suite with a gorgeous updated bath and walk-in closet, along with a second bedroom, 2nd updated full bath, and convenient main-level laundry.The

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (410) 883-7342

    860 Woodmont Rd, Annapolis, MD 21401
  • 3307 Harness Creek Rd, Annapolis, MD 21403
    3307 Harness Creek Rd, Annapolis, MD 21403
    3307 Harness Creek Rd, Annapolis, MD 21403
    /44

    $3,145,000

    • 3 Beds
    • 2.5 Baths
    • 2,570 Sq Ft

    3307 Harness Creek Rd, Annapolis, MD 21403

    Welcome to 3307 Harness Creek Road: a Nantucket style, coastal home set on a private peninsula with spectacular water views, a serene backyard oasis and two deep-water piers on protected Harness Creek. This waterside gem, with 190 ft of waterfrontage, is situated directly across from Quiet Waters Park and offers quick access to the South River and the Chesapeake Bay.Inside, you’re greeted by

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (410) 762-4260

    3307 Harness Creek Rd, Annapolis, MD 21403
  • 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
  • 111 Janwall St, Annapolis, MD 21403
    111 Janwall St, Annapolis, MD 21403
    /2

    $540,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,754 Sq Ft

    111 Janwall St, Annapolis, MD 21403

    Charming 3-Bedroom Home on Quiet Cul-de-Sac Near Downtown Annapolis Welcome to this beautifully maintained 3-bedroom, 2.5-bath single-family home, perfectly situated on a peaceful cul-de-sac just minutes from downtown Annapolis. Offering a blend of comfort, convenience, and charm, this home is ideal for both relaxing and entertaining. Step inside to find a bright and inviting interior with a

    Agent Photo

    Amy Juras

    Long & Foster Real Estate, Inc.

    (443) 940-6438

    111 Janwall St, Annapolis, MD 21403
  • 91 Heritage Ct, Annapolis, MD 21401
    91 Heritage Ct, Annapolis, MD 21401
    91 Heritage Ct, Annapolis, MD 21401
    /28

    $285,000

    • 3 Beds
    • 1.5 Baths
    • 1,134 Sq Ft

    91 Heritage Ct, Annapolis, MD 21401

    Welcome to this rare 3 bedroom, 1.5 bath end of group townhome in the Hilltop neighborhood just outside of downtown Annapolis. This neighborhood is conveniently located near everything that Annapolis has to offer and has its own community swimming pool and playground. Entering into this end of group townhome brings you to the main floor with LVP flooring throughout. There is a living room area,

    Agent Photo

    Daniel McGhee

    Homeowners Real Estate

    (443) 586-9586

    91 Heritage Ct, Annapolis, MD 21401
  • 2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    /69

    $750,000

    • 3 Beds
    • 3 Baths
    • 1,645 Sq Ft

    2018 Quay Village Ct Unit 201, Annapolis, MD 21403

    Welcome to an exceptional living experience at Chesapeake Harbour, where this well maintained 3 bedroom, 3 full bath condo offers not just a home but a lifestyle. Perfectly situated in a premium location, this residence boasts breathtaking views of the Bay Bridge and the sparkling waters of the Bay, providing a serene backdrop to your daily life. Step into a well-designed space that seamlessly

    Agent Photo

    Lorna Kaim

    Compass

    (410) 305-9422

    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
  • 48 Rockwell Ct, Annapolis, MD 21403
    48 Rockwell Ct, Annapolis, MD 21403
    48 Rockwell Ct, Annapolis, MD 21403
    /21

    $350,000

    • 2 Beds
    • 1.5 Baths
    • 1,222 Sq Ft

    48 Rockwell Ct, Annapolis, MD 21403

    This is a great opportunity to get into Annapolis at an affordable price! Welcome to 48 Rockwell Ct, conveniently located in the Painters Hill community—just a short stroll to Downtown Annapolis and moments from Rt 665, Rt 50, West St, Annapolis Harbour Center, Annapolis Mall, and so much more. The layout is simple, spacious, and efficient—offering everything you need and nothing you don’t.

    Joshua Shapiro Douglas Realty, LLC

    48 Rockwell Ct, Annapolis, MD 21403
  • 102 Oak Dr, Annapolis, MD 21403
    102 Oak Dr, Annapolis, MD 21403
    102 Oak Dr, Annapolis, MD 21403
    /22

    $498,000

    • 2 Beds
    • 2 Baths
    • 1,433 Sq Ft

    102 Oak Dr, Annapolis, MD 21403

    Located in the highly desirable Hillsmere Shores community, 102 Oak Drive offers a comfortable lifestyle in one of Annapolis’ most well-established neighborhoods. Conveniently located just minutes from downtown Annapolis, the U.S. Naval Academy, and major commuter routes, this home provides easy access to shopping, dining, and everyday essentials. Residents of Hillsmere Shores also enjoy easy

    Amy Presley Samson Properties

    102 Oak Dr, Annapolis, MD 21403
  • 99 Summerfield Dr, Annapolis, MD 21403
    99 Summerfield Dr, Annapolis, MD 21403
    99 Summerfield Dr, Annapolis, MD 21403
    /55

    $524,900

    • 4 Beds
    • 3 Baths
    • 1,980 Sq Ft

    99 Summerfield Dr, Annapolis, MD 21403

    Charming rancher in the heart of Annapolis! Hardwood throughout, updates to the kitchens and bathrooms, fully finished basement with full bathroom, screened-in porch, large backyard. 2.5 miles to Historic Downtown Annapolis, just over a mile to Eastport restaurants. Ask about 2.375% assumable FHA loan!

    Jack Papaleonti Academy Realty Inc.

    99 Summerfield Dr, Annapolis, MD 21403
  • 1407 Brenwoode Rd, Annapolis, MD 21409
    1407 Brenwoode Rd, Annapolis, MD 21409
    1407 Brenwoode Rd, Annapolis, MD 21409
    /34

    $575,000

    • 3 Beds
    • 3 Baths
    • 2,390 Sq Ft

    1407 Brenwoode Rd, Annapolis, MD 21409

    Welcome to 1407 Brenwoode Rd. This spacious 3-bedroom home (with potential 4th bedroom /bonus room in basement), is ideally situated in one of Annapolis’ most sought-after communities on the Broadneck Peninsula. Experience the charm of neighboring Cape St. Claire, where community, convenience, and coastal living come together. Freshly painted and ready for your finishing touches, the home

    Andrea Scheidt Engel & Völkers Annapolis

    1407 Brenwoode Rd, Annapolis, MD 21409
  • 4 Boxwood Rd, Annapolis, MD 21403
    4 Boxwood Rd, Annapolis, MD 21403
    /2

    $389,900

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    4 Boxwood Rd, Annapolis, MD 21403

    Located at the corner of Spa Road and Boxwood Drive, this property offers an excellent Annapolis location with convenient access to downtown, shopping, dining, and major commuter routes. The home sits on a prominent corner lot and presents a great opportunity for investors, builders, or buyers looking to renovate and customize a home to their own vision. The property is in need of updating and is

    Rick Gloekler RE/MAX Executive

    4 Boxwood Rd, Annapolis, MD 21403
  • 566 Foxpaw Trail, Annapolis, MD 21409
    566 Foxpaw Trail, Annapolis, MD 21409
    566 Foxpaw Trail, Annapolis, MD 21409
    /67

    $549,900

    • 4 Beds
    • 3.5 Baths
    • 2,676 Sq Ft

    566 Foxpaw Trail, Annapolis, MD 21409

    Welcome to 566 Fox Paw Trail, an exceptional end-unit townhome in the highly sought-after Woods Landing community of Annapolis, offering over 2,300 square feet of beautifully maintained living space surrounded by nature. Perfectly positioned with mature trees along the side, this home enjoys a private, tranquil setting that feels like a retreat. From the side of the property, you can access a

    David Webber RE/MAX Leading Edge

    566 Foxpaw Trail, Annapolis, MD 21409
  • 2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    /93

    $675,000

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403

    Now is your chance to call this HOME! Welcome to this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. Whether you're looking for a worry-free vacation spot or a serene place to call home, this 3-bedroom, 3 full bath sanctuary with a gourmet kitchen and totally updated baths has you covered with over 1,700 square feet of style and comfort. This Bayfront community

    Lorna Kaim Compass

    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
  • 22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    /79

    $2,550,000 Open Sat 3PM - 5PM

    • 3 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    22 E Lake Dr, Annapolis, MD 21403

    Welcome to 22 E Lake Drive! This exceptional waterfront residence offers striking architectural elements with expansive, light-filled interiors and seamless indoor-outdoor living along the Chesapeake Bay.The main level open floor plan is designed for effortless flow and everyday living. The living room anchors the space, featuring a floor-to-ceiling stone fireplace and a wall of bi-fold glass

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    22 E Lake Dr, Annapolis, MD 21403
  • 220 West St, Annapolis, MD 21401
    220 West St, Annapolis, MD 21401
    220 West St, Annapolis, MD 21401
    /41

    $924,900

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    220 West St, Annapolis, MD 21401

    Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced,

    Vishal Doddanna Keller Williams Realty Centre

    220 West St, Annapolis, MD 21401
  • 1223 Madison St, Annapolis, MD 21403
    1223 Madison St, Annapolis, MD 21403
    1223 Madison St, Annapolis, MD 21403
    /36

    $609,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,488 Sq Ft

    1223 Madison St, Annapolis, MD 21403

    Fully updated 4-bedroom, 2-bath home in the heart of Eastport offering modern finishes, flexible living space, and a walkable location just minutes from downtown Annapolis, marinas, restaurants, and waterfront parks. The main level features a bright living room, dining area, and upgraded kitchen with stainless steel appliances. Three bedrooms and one full bath complete this level, along with

    Michelle Boretti Coldwell Banker Realty

    1223 Madison St, Annapolis, MD 21403
  • 906 Perry Landing Ct, Annapolis, MD 21401
    906 Perry Landing Ct, Annapolis, MD 21401
    906 Perry Landing Ct, Annapolis, MD 21401
    /59

    $609,900

    • 2 Beds
    • 2.5 Baths
    • 2,569 Sq Ft

    906 Perry Landing Ct, Annapolis, MD 21401

    Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and an unmatched lifestyle.This spacious end-unit villa boasts over 2,500 square feet of living space and is filled with natural light thanks to its desirable end-unit location. Freshly painted throughout with brand new flooring and carpet, this home is truly move-in ready and features soaring ceilings

    Jack Papaleonti Academy Realty Inc.

    906 Perry Landing Ct, Annapolis, MD 21401
  • 198 Clay St, Annapolis, MD 21401
    198 Clay St, Annapolis, MD 21401
    198 Clay St, Annapolis, MD 21401
    /30

    $389,000

    • 2 Beds
    • 1.5 Baths
    • 902 Sq Ft

    198 Clay St, Annapolis, MD 21401

    Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water views of College Creek and a short stroll to downtown and West Annapolis, where shops, dining, entertainment, and the U.S. Naval Academy are right at your doorstep. The location also provides easy commuter access to Routes 50 and 97 for Washington, D.C., Baltimore, and BWI Airport. Thoughtfully updated in

    Kerry O'Hara Engel & Völkers Annapolis

    198 Clay St, Annapolis, MD 21401
  • 2646 Quiet Water Cove, Annapolis, MD 21401
    2646 Quiet Water Cove, Annapolis, MD 21401
    2646 Quiet Water Cove, Annapolis, MD 21401
    /60

    $499,900

    • 3 Beds
    • 2 Baths
    • 2,354 Sq Ft

    2646 Quiet Water Cove, Annapolis, MD 21401

    Popular, one level floor plan in the 55+ community of Heritage Harbour offering just the right amount of space to enjoy the next phase of your life. You will feel right at home when you turn into this lovely, cul de sac with mature trees and attractive, brick or stone front homes. Pull into your one car garage with automatic door opener & immediate access to the kitchen for easy unloading of

    Martin Lanzino Douglas Realty, LLC

    2646 Quiet Water Cove, Annapolis, MD 21401
  • 730 Rosedale St, Annapolis, MD 21401
    730 Rosedale St, Annapolis, MD 21401
    730 Rosedale St, Annapolis, MD 21401
    /41

    $595,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    730 Rosedale St, Annapolis, MD 21401

    Welcome to 730 Rosedale St, Annapolis, MD 21401—a traditional detached home offering a comfortable and functional layout in a convenient location. This residence features three bedrooms, two full bathrooms, and one half bathroom, providing ample space for a variety of living arrangements. Inside, the home features hardwood flooring on the first floor and carpet flooring throughout the remaining

    Bob Chew Samson Properties

    730 Rosedale St, Annapolis, MD 21401
  • 101 Huse Dr, Annapolis, MD 21403
    101 Huse Dr, Annapolis, MD 21403
    101 Huse Dr, Annapolis, MD 21403
    /45

    $800,000 Open Sat 10:30AM - 12:30PM

    • 4 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    101 Huse Dr, Annapolis, MD 21403

    YES, YOU CAN HAVE IT ALL. Completely remodeled from top to bottom in one of the most sought-after neighborhoods around—this one checks ALL the boxes. The kitchen, the great room... this is the hub. The heart of the home. And the best part? You’re not dreaming about what it could be—the work is already done. Big island, open flow—everyone ends up here. Whether you’re cooking, hanging out, or just

    Kristi Krankowski RE/MAX One

    101 Huse Dr, Annapolis, MD 21403
  • 2150 Hideaway Ct Unit 28, Annapolis, MD 21401
    2150 Hideaway Ct Unit 28, Annapolis, MD 21401
    2150 Hideaway Ct Unit 28, Annapolis, MD 21401
    /40

    $459,990

    • 3 Beds
    • 2.5 Baths
    • 1,760 Sq Ft

    2150 Hideaway Ct Unit 28, Annapolis, MD 21401

    *Doctor Loans Available 100% Financing = Zero Downpayment* This Property Is Less Than 1 Mile to Luminis Medical Newer HVAC (2025) + Newer Flooring Throughout HOA Fees Cover Exterior Maintenance Including Roof Welcome to 2150 Hideaway Court! A Light-Filled & Tucked-Away Townhome in Coveted Creekside Cove. Three Bedrooms, Two Full & 1/2 Baths. This Home Is a Must-See for Those Who Want To be In The

    Linda Pelton Taylor Properties

    2150 Hideaway Ct Unit 28, Annapolis, MD 21401
  • 1014 Wells Ave, Annapolis, MD 21403
    1014 Wells Ave, Annapolis, MD 21403
    1014 Wells Ave, Annapolis, MD 21403
    /45

    $430,000

    • 4 Beds
    • 1.5 Baths
    • 880 Sq Ft

    1014 Wells Ave, Annapolis, MD 21403

    Welcome Home to Eastport. Walk to the Eastport Shopping center for breakfast or to downtown Annapolis for lunch or dinner. This cute 4-bedroom (egress in basement)1.5 bath rancher with eat-in kitchen and traditional floor plan living and dining room is perfect for you and your family. Relax and entertain on the size able deck off the kitchen. Enjoy central air conditioning, oil heating, electric

    VIKKI MASON EXIT Spivey Professional Realty Co.

    1014 Wells Ave, Annapolis, MD 21403
  • 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
  • 1036 Mountain Top Dr, Annapolis, MD 21409
    1036 Mountain Top Dr, Annapolis, MD 21409
    1036 Mountain Top Dr, Annapolis, MD 21409
    /78

    $725,000

    • 4 Beds
    • 3 Baths
    • 2,692 Sq Ft

    1036 Mountain Top Dr, Annapolis, MD 21409

    Welcome Home - this beautiful property is located in the sought after Cape St. Claire community. First floor living meets comfort and charm. This beautifully designed home features a spacious primary suite with a stunning ensuite bath and private access to the backyard, creating a seamless indoor-outdoor retreat. Situated on a rare double lot, the outdoor space is truly exceptional. Enjoy your

    Jessica Ricciardi Welder Keller Williams Flagship

    1036 Mountain Top Dr, Annapolis, MD 21409
  • 1 Shipwright Harbor, Annapolis, MD 21401
    1 Shipwright Harbor, Annapolis, MD 21401
    1 Shipwright Harbor, Annapolis, MD 21401
    /39

    $5,898,000

    • 3 Beds
    • 3.5 Baths
    • 3,108 Sq Ft

    1 Shipwright Harbor, Annapolis, MD 21401

    Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career. Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a

    Brad Kappel TTR Sotheby's International Realty

    1 Shipwright Harbor, Annapolis, MD 21401
  • 1041 Skyview Dr, Annapolis, MD 21409
    1041 Skyview Dr, Annapolis, MD 21409
    1041 Skyview Dr, Annapolis, MD 21409
    /63

    $584,900

    • 4 Beds
    • 3 Baths
    • 1,960 Sq Ft

    1041 Skyview Dr, Annapolis, MD 21409

    Welcome to this beautifully updated split foyer home in the highly desirable community of Cape St. Claire! Offering 4 spacious bedrooms and 3 full bathrooms, this turnkey property combines modern upgrades with comfortable living. The fully renovated kitchen features brand-new cabinetry, stylish countertops, and new stainless steel appliances — perfect for everyday living and entertaining alike.

    Paulo Machado Keller Williams Flagship

    1041 Skyview Dr, Annapolis, MD 21409
  • 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
  • 2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    /39

    $725,000

    • 3 Beds
    • 3 Baths
    • 1,748 Sq Ft

    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403

    WATCH THE SUNSETS & ENJOY THE BREATHTAKING MARINA VIEWS FROM THIS BEAUTIFUL 3 BEDROOM, 3 FULL BATH CONDO IN CHESAPEAKE HARBOUR! ENJOY LIFE BY THE WATER IN THIS TURN KEY RENOVATED CONDO. BOTH THE WATERSIDE PRIMARY AND LIVING ROOM HAVE SLIDERS TO THE WATERSIDE BALCONY. FEATURES INCLUDE GOURMET KITCHEN, DESIGNER LIGHTING, NEW ENTRY WAY, COUNTERTOPS, HVAC, SLIDERS, STAINLESS STEEL APPLIANCES,

    Pamela Tierney Coldwell Banker Realty

    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
  • 100 Carroll Dr, Annapolis, MD 21403
    100 Carroll Dr, Annapolis, MD 21403
    100 Carroll Dr, Annapolis, MD 21403
    /59

    $649,000

    • 4 Beds
    • 2 Baths
    • 1,935 Sq Ft

    100 Carroll Dr, Annapolis, MD 21403

    Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and

    Timothy Caropreso Keller Williams Flagship

    100 Carroll Dr, Annapolis, MD 21403
  • 1014 Cedar Ridge Ct, Annapolis, MD 21403
    1014 Cedar Ridge Ct, Annapolis, MD 21403
    1014 Cedar Ridge Ct, Annapolis, MD 21403
    /43

    $390,000

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    1014 Cedar Ridge Ct, Annapolis, MD 21403

    Welcome to 1014 Cedar Ridge Ct in beautiful Annapolis , a stylish 3-bedroom, 2 full bath, 1 half bath townhome designed for easy living in a prime location (21403). This is not your typical HOA. The association fee includes roof repair and replacement, all exterior maintenance (painting and staining), landscaping, gutter cleaning, and parking lot maintenance. Inside, the home is completely

    Bob Chew Samson Properties

    1014 Cedar Ridge Ct, Annapolis, MD 21403
  • 57 Town Pines Ct, Annapolis, MD 21401
    57 Town Pines Ct, Annapolis, MD 21401
    57 Town Pines Ct, Annapolis, MD 21401
    /35

    $275,000

    • 3 Beds
    • 1.5 Baths
    • 1,037 Sq Ft

    57 Town Pines Ct, Annapolis, MD 21401

    NEW PRICE !!! Welcome to Annapolis! This beautifully updated 3-bedroom, 1 full and 1 half-bath townhome offers a fantastic opportunity to own in one of Maryland’s most historic and charming locations.Fully renovated from top to bottom, this home features updated bathrooms, a renovated kitchen with brand-new stainless steel appliances, new LVP flooring on both levels, a new washer and dryer, a

    Yury Garamyan Jason Mitchell Group

    57 Town Pines Ct, Annapolis, MD 21401
  • 312 Severn Ave, Annapolis, MD 21403
    312 Severn Ave, Annapolis, MD 21403
    312 Severn Ave, Annapolis, MD 21403
    /51

    $515,000

    • 1 Bed
    • 1 Bath
    • 660 Sq Ft

    312 Severn Ave, Annapolis, MD 21403

    Welcome to 312 Severn Ave., Unit W405, where the charm of Eastport living meets modern comfort at Tecumseh on Spa Creek. This bright and inviting one-bedroom loft condo features an open-concept design with soaring vaulted ceilings, a striking brick fireplace, and a thoughtfully crafted loft layout that maximizes both space and style. Located on the fourth floor with convenient elevator access,

    Dayna Blumel Compass

    312 Severn Ave, Annapolis, MD 21403
  • 312 Severn Ave Unit W-401, Annapolis, MD 21403
    312 Severn Ave Unit W-401, Annapolis, MD 21403
    312 Severn Ave Unit W-401, Annapolis, MD 21403
    /49

    $485,000

    • 1 Bed
    • 1 Bath
    • 660 Sq Ft

    312 Severn Ave Unit W-401, Annapolis, MD 21403

    Perched on the top floor of The Tecumseh, Maryland’s first condominium building, this two-level loft offers beautiful water views and an exceptional Eastport lifestyle. W401 overlooks Spa Creek with views of Ego Alley, the community marina, and Severn Avenue. This 1-bedroom, 1-bath residence features an open-concept main level with living and dining areas, a well-equipped kitchen, mechanical

    Ashley Stanwick Coldwell Banker Realty

    312 Severn Ave Unit W-401, Annapolis, MD 21403
  • 12 Harbour Heights Dr, Annapolis, MD 21401
    12 Harbour Heights Dr, Annapolis, MD 21401
    12 Harbour Heights Dr, Annapolis, MD 21401
    /21

    $399,999

    • 3 Beds
    • 2.5 Baths
    • 1,566 Sq Ft

    12 Harbour Heights Dr, Annapolis, MD 21401

    AMAZING NEW PRICE! Welcome to this adorable home backing to woods in the heart of Annapolis! Ideally located near Anne Arundel Medical Center, Annapolis Mall, downtown Annapolis, shopping, dining and major commuter routes. This home offers comfort, space, and convenience. The kitchen features upgraded stainless steel appliances, granite countertops, a slate backsplash, and opens to a large

    Rachel Gontkovic EXP Realty, LLC

    12 Harbour Heights Dr, Annapolis, MD 21401
  • 7022 Channel Village Ct Unit 101, Annapolis, MD 21403
    7022 Channel Village Ct Unit 101, Annapolis, MD 21403
    7022 Channel Village Ct Unit 101, Annapolis, MD 21403
    /39

    $675,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    7022 Channel Village Ct Unit 101, Annapolis, MD 21403

    Look no further! Welcome to Chesapeake Harbour, one of Annapolis' most sought after waterfront communities. This beautifully renovated 2 BR | 2 BA | 1200 SF condo on the second level is truly turn key offering over $100K in high end improvements crafted with top of the line materials throughout. Enjoy stunning tranquil marina views from your deck and living space, creating a peaceful coastal

    Moe Farley Coldwell Banker Realty

    7022 Channel Village Ct Unit 101, Annapolis, MD 21403
  • 2568 Glen Cove, Annapolis, MD 21401
    2568 Glen Cove, Annapolis, MD 21401
    2568 Glen Cove, Annapolis, MD 21401
    /52

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft

    2568 Glen Cove, Annapolis, MD 21401

    OPEN HOUSE SUNDAY 3/8 11-1. Tucked away at the end of a quiet cul-de-sac, this two-level home offers privacy and tranquility, surrounded by mature trees and lush landscaping. Inside, the updated main level features durable and stylish LVP flooring, and it's truly move-in ready. The kitchen, remodeled in 2015, includes Corian countertops, a tile backsplash, updated cabinets, a stainless steel

    Laura Gayvert Compass

    2568 Glen Cove, Annapolis, MD 21401

Showing Results 1 - 40, Page 1 of 2

Maryland Anne Arundel County Annapolis

2-Story 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
$822,500
Median Townhouse Sale Price
$447,500
Median 2 Bedroom Sale Price
$419,160
Median 1 Bedroom Sale Price
$447,500
Average Price Per Sq Ft
$355
Number of Homes for Sale
240
Last 12 months Home Sales
1,313
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 71 two-story homes for sale, offering abundant choices for those who prioritize both convenience and functionality in their living space. Whether you're in the market for a traditional two-story house or considering the versatility of a two-story townhome, these properties provide a wealth of options to explore. Ranging from compact yet cozy condos to expansive family residences, the two-story homes for sale in Annapolis, MD come in various sizes and floorplans, ensuring there's something to accommodate every lifestyle and preference.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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