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Annapolis, MD 2-Story Homes for Sale

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  • 121 Conley Dr, Annapolis, MD 21403
    121 Conley Dr, Annapolis, MD 21403
    121 Conley Dr, Annapolis, MD 21403
    /38

    $330,000

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

    121 Conley Dr, Annapolis, MD 21403

    Welcome to this home nestled in the heart of Annapolis. Offering a blend of comfort, functionality, and convenience, this property features spacious living areas, abundant natural light, and a layout designed for everyday living and entertaining. Enjoy a generous backyard perfect for relaxing or hosting gatherings, along with easy access to local shopping, dining, marinas, parks, and major

    Ms. Kristina Boyd Keller Williams Preferred Properties

    121 Conley Dr, Annapolis, MD 21403
  • 111 Ellershaw Ct, Annapolis, MD 21401
    111 Ellershaw Ct, Annapolis, MD 21401
    /2

    $1,395,000

    Coming Soon
    • 4 Beds
    • 4.5 Baths
    • 3,600 Sq Ft

    111 Ellershaw Ct, Annapolis, MD 21401

    ***Coming Soon- Professional photos to be uploaded 5/22****** Rare Opportunity to own a newer home tucked away on a private cul-de-sac just a short stroll from everything Downtown Annapolis has to offer. Completed in 2022, this exceptional home showcases top of the line finishes throughout. Designer kitchen with Quartz countertops, custom cabinetry and high end GE Cafe appliances. Wide Plank

    Ryan Turner Coldwell Banker Realty

    111 Ellershaw Ct, Annapolis, MD 21401
  • 721 Fairway Dr, Annapolis, MD 21409
    721 Fairway Dr, Annapolis, MD 21409
    721 Fairway Dr, Annapolis, MD 21409
    /44

    $585,000

    • 4 Beds
    • 3 Baths
    • 2,080 Sq Ft

    721 Fairway Dr, Annapolis, MD 21409

    Elegant brick and siding split-foyer residence offering 4 bedrooms and 3 renovated full bathrooms on a beautifully sized 0.21-acre lot. The thoughtfully designed upper level features a sun-filled living room, formal dining area, well-appointed brand new kitchen with new appliances, and seamless access to the rear deck—perfect for refined indoor-outdoor living. Three bedrooms and two full baths

    Michael Ozigi KW Metro Center

    721 Fairway Dr, Annapolis, MD 21409
  • 906 Perry Landing Ct, Annapolis, MD 21401
    906 Perry Landing Ct, Annapolis, MD 21401
    906 Perry Landing Ct, Annapolis, MD 21401
    /59

    $574,900

    $35K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,569 Sq Ft

    906 Perry Landing Ct, Annapolis, MD 21401

    Improved price! Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and an unmatched lifestyle. Now priced better, 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

    Jack Papaleonti Academy Realty Inc.

    906 Perry Landing Ct, Annapolis, MD 21401
  • 1132 Bay Ridge Rd, Annapolis, MD 21403
    1132 Bay Ridge Rd, Annapolis, MD 21403
    /2

    $720,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft

    1132 Bay Ridge Rd, Annapolis, MD 21403

    PHOTOS coming soon. SCHEDULE NOW FOR SHOWINGS starting on Active date May 27. Live the Annapolis dream in this beautiful, well maintained, quality home surrounded with professional landscaping. This home delivers the ultimate move in ready experience. Fantastic location on private lane with lots of “New”. New roof, skylight and gutters in 2026, New heat pump in 2026 (with 10-year parts and labor

    Wendy Trebbe Blackwell Real Estate, LLC

    1132 Bay Ridge Rd, Annapolis, MD 21403
  • 422 First St, Annapolis, MD 21403
    422 First St, Annapolis, MD 21403
    422 First St, Annapolis, MD 21403
    /19

    $870,000

    • 2 Beds
    • 1.5 Baths
    • 1,094 Sq Ft

    422 First St, Annapolis, MD 21403

    Welcome to Eastport—just steps from downtown Annapolis. This adorable duplex offers the perfect blend of charm, convenience, and a coastal lifestyle. This inviting two-bedroom, 1.5-bath home is freshly painted and features numerous updates, including new hardwood floors throughout, new windows in the living room and kitchen, a new wood-burning stove, and a new A/C heat pump—making it move-in

    Cindy Nairn Coldwell Banker Realty

    422 First St, Annapolis, MD 21403
  • 10 Sandstone Ct, Annapolis, MD 21403
    10 Sandstone Ct, Annapolis, MD 21403
    10 Sandstone Ct, Annapolis, MD 21403
    /17

    $305,000

    • 3 Beds
    • 2 Baths
    • 1,333 Sq Ft

    10 Sandstone Ct, Annapolis, MD 21403

    Spring has arrived, and this beautifully updated 3-bedroom, 2-bath condo offers the perfect opportunity to enjoy the best of the Annapolis lifestyle. Located on the 3rd floor, this light-filled home combines modern upgrades, comfort, and unbeatable access to outdoor recreation and waterfront attractions. Inside, the open-concept living, dining, and kitchen area creates a warm and inviting flow,

    Sharee Covington Smart Realty, LLC

    10 Sandstone Ct, Annapolis, MD 21403
  • 20 Washington Dr, Annapolis, MD 21401
    20 Washington Dr, Annapolis, MD 21401
    20 Washington Dr, Annapolis, MD 21401
    /40

    $480,000

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

    20 Washington Dr, Annapolis, MD 21401

    Welcome to this beautifully updated home in the heart of Annapolis offering incredible flexibility, space, and opportunity! Situated on almost half an acre, this property features 5 bedrooms, 2 full bathrooms, two full kitchens, and a fully finished walk-out basement — perfect for multi-generational living, extended guests, rental potential, or anyone needing extra space. Seller financing may

    Yvette Flores Samson Properties

    20 Washington Dr, Annapolis, MD 21401
  • 7 Mizzen Ct, Annapolis, MD 21403
    7 Mizzen Ct, Annapolis, MD 21403
    7 Mizzen Ct, Annapolis, MD 21403
    /21

    $390,000

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

    7 Mizzen Ct, Annapolis, MD 21403

    Coming soon! Beautiful home in Mariner's Landing. Well maintained 2 primary suite home! New kitchen!

    Lauren Emrick Innovative Properties, Inc.

    7 Mizzen Ct, Annapolis, MD 21403
  • 179 Green St, Annapolis, MD 21401
    179 Green St, Annapolis, MD 21401
    179 Green St, Annapolis, MD 21401
    /40

    $979,000

    Open Wed 2PM - 4PM $21K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,656 Sq Ft

    179 Green St, Annapolis, MD 21401

    Welcome to the heart of downtown Annapolis at 179 Green Street. This charming home blends timeless character with modern comfort, this is just a block from Main Street and City Dock, few block from the Naval Academy, State Capitol building, boutique shopping, and Annapolis Elementary School. Located in one of the city’s most desirable neighborhoods, it offers exceptional walkability and vibrant

    Sergey Taksis Long & Foster Real Estate, Inc.

    179 Green St, 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
  • 2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    /53

    $739,000

    • 2 Beds
    • 2 Baths
    • 1,618 Sq Ft

    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403

    Life at Chesapeake Harbour feels like being on vacation every single day. Mornings begin with coffee on the balcony as the sun rises over the marina and the Chesapeake Bay. Even simple moments feel special here, whether it’s curling up with a book by the fireplace on a rainy afternoon, taking an evening stroll along the shoreline, or enjoying dinner on the deck as the sky changes colors over the

    Jennifer Schaub EXP Realty, LLC

    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
  • 34 Pinkney St, Annapolis, MD 21401
    34 Pinkney St, Annapolis, MD 21401
    34 Pinkney St, Annapolis, MD 21401
    /20

    $695,000

    Coming Soon
    • 2 Beds
    • 1.5 Baths
    • 1,040 Sq Ft

    34 Pinkney St, Annapolis, MD 21401

    How many times have you strolled Annapolis' streets and thought, "I wish I lived here!"? 34 Pinkney is your opportunity to be in the center of the good life Annapolis has to offer! This renovated home is the perfect pied-à-terre. Cozy living room flows to the dining with fun shiplap walls and built-in seating. The well-planned renovated kitchen has access to the private brick courtyard, just the

    Alex Tower Sears TTR Sotheby's International Realty

    34 Pinkney St, Annapolis, MD 21401
  • 1252 Creek Dr, Annapolis, MD 21403
    1252 Creek Dr, Annapolis, MD 21403
    1252 Creek Dr, Annapolis, MD 21403
    /39

    $565,000

    • 3 Beds
    • 2 Baths
    • 1,555 Sq Ft

    1252 Creek Dr, Annapolis, MD 21403

    Stunning Oyster Harbor – Coastal Charm Meets Comfort This gorgeous property blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat ramp, and

    Jessica Ricciardi Welder Keller Williams Flagship

    1252 Creek 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
  • 1531 Hickory Wood Dr, Annapolis, MD 21409
    1531 Hickory Wood Dr, Annapolis, MD 21409
    1531 Hickory Wood Dr, Annapolis, MD 21409
    /15

    $439,900

    $100K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 916 Sq Ft

    1531 Hickory Wood Dr, Annapolis, MD 21409

    FRESHLY PAINTED AND NEW CARPET THROUGHTOUT. WALKOUT BASEMENT.THANK YOU FOR SHOWING

    Curtis LeMay Real Estate Depot

    1531 Hickory Wood Dr, Annapolis, MD 21409
  • 2646 Quiet Water Cove, Annapolis, MD 21401
    2646 Quiet Water Cove, Annapolis, MD 21401
    2646 Quiet Water Cove, Annapolis, MD 21401
    /60

    $450,000

    $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,354 Sq Ft

    2646 Quiet Water Cove, Annapolis, MD 21401

    MASSIVE PRICE DROP! PRICE NOW RELECTS NEED FOR UPDATES. THIS IS THEE LOWEST PRICED SEMI-DETACHED HOME WITH A GARAGE IN HERITAGE HARBOUR INTHE PAST YEAR! 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

    Martin Lanzino Douglas Realty, LLC

    2646 Quiet Water Cove, Annapolis, MD 21401
  • 300 Hilltop Ln Unit 300I, Annapolis, MD 21403
    300 Hilltop Ln Unit 300I, Annapolis, MD 21403
    300 Hilltop Ln Unit 300I, Annapolis, MD 21403
    /61

    $280,000

    $119K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,321 Sq Ft

    300 Hilltop Ln Unit 300I, Annapolis, MD 21403

    BIG LOFT AREA**NEW PRICE-GREAT VALUE***Welcome home to this spacious two bedroom two full bath condo with a loft. Stainless appliances in the kitchen, the stove is brand new, fine cabinets and granite countertops. Hardwood flooring in the living room and dining room, and a nice balcony though the living room slider. The primary bedroom has a large walk-in closet and attached full bath. And, the

    Christopher Fuller Long & Foster Real Estate, Inc.

    300 Hilltop Ln Unit 300I, Annapolis, MD 21403
  • 201 Bonny Way Unit 36036625, Annapolis, MD 21403
    201 Bonny Way Unit 36036625, Annapolis, MD 21403
    201 Bonny Way Unit 36036625, Annapolis, MD 21403
    /45

    $1,079,990

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,483 Sq Ft

    Admiral Plan at Parkeside Preserve - Manor, Annapolis, MD 21403

    The largest floorplan in this collection, this expansive two-story home combines comfort with modern elegance. Standing at the heart of the first floor is an open-plan Great Room with a center fireplace, which melds into a well-equipped kitchen and both casual and formal dining areas to prioritize ease of living. All four bedrooms and a loft occupy the top level, including the lavish owner’s

    Lennar Builder
    201 Bonny Way Unit 36036625, Annapolis, MD 21403
  • 108 Conley Dr, Annapolis, MD 21403
    108 Conley Dr, Annapolis, MD 21403
    108 Conley Dr, Annapolis, MD 21403
    /18

    $395,000

    $90K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,880 Sq Ft

    108 Conley Dr, Annapolis, MD 21403

    Owner is offering $ 5,000.00 for helping buyer with closings costs!!Great location! Sweet, cozy, and lovely semi-detached home. 3 bedroom, 1 1/2 baths and semi finished basement. The house is ready for your personal touch! NEW ROOF 2023. Close to Truxtun Park and easy access to downtown Annapolis and US 50 /97 HWY. GREAT OPPORTUNITY! Bring your best offer.

    Edilene Barros Keller Williams Select Realtors of Annapolis

    108 Conley Dr, Annapolis, MD 21403
  • 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
  • 1005 Hyde Park Dr, Annapolis, MD 21403
    1005 Hyde Park Dr, Annapolis, MD 21403
    1005 Hyde Park Dr, Annapolis, MD 21403
    /44

    $489,000

    • 2 Beds
    • 1 Bath
    • 1,190 Sq Ft

    1005 Hyde Park Dr, Annapolis, MD 21403

    Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering classic charm and modern updates throughout. Featuring beautiful hardwood floors and a traditional layout, this home provides comfort and functionality in every room. The updated kitchen boasts a center island, granite and a spacious pantry all perfect for meal prep or casual dining. The bathroom has been

    Michael Simi Douglas Realty LLC

    1005 Hyde Park Dr, 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
  • 996 Headwater Rd, Annapolis, MD 21403
    996 Headwater Rd, Annapolis, MD 21403
    996 Headwater Rd, Annapolis, MD 21403
    /59

    $1,150,000

    • 4 Beds
    • 3.5 Baths
    • 2,288 Sq Ft

    996 Headwater Rd, Annapolis, MD 21403

    Waterfront home nestled in the serene enclave of Kitty Creek; located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy

    Amanda Greenfield Engel & Völkers Annapolis

    996 Headwater Rd, Annapolis, MD 21403
  • 1509 Duvall Rd, Annapolis, MD 21409
    1509 Duvall Rd, Annapolis, MD 21409
    1509 Duvall Rd, Annapolis, MD 21409
    /39

    $575,000

    • 3 Beds
    • 1 Bath
    • 1,512 Sq Ft

    1509 Duvall Rd, Annapolis, MD 21409

    Opportunity awaits in sought-after St. Margarets! This 3-bedroom, 1-bath home with hardwood floors, situated on a gorgeous 1-acre lot offering plenty of space and potential. Solid built home they don't make houses like this any longer, needs updating, making it the perfect chance to bring your ideas and renovate to your personal taste. Most major systems updated within last 10 years. Whether you

    Kathleen Armiger Coldwell Banker Realty

    1509 Duvall Rd, Annapolis, MD 21409
  • 1189 Highview Dr, Annapolis, MD 21409
    1189 Highview Dr, Annapolis, MD 21409
    1189 Highview Dr, Annapolis, MD 21409
    /34

    $565,000

    • 4 Beds
    • 2 Baths
    • 2,500 Sq Ft

    1189 Highview Dr, Annapolis, MD 21409

    Charming cedar sided chalet style set in the wooded and beach access community of Cape St Claire.Enter into a dramatic cathedral ceiling living and dining space with skylights, looking through to a three season clerestory windowed addition where you will welcome family and friends. Sliders from the tall window surrounded sun room open onto a deck with room for feasts and relaxing. Memories

    Sherry Young RE/MAX Executive

    1189 Highview Dr, Annapolis, MD 21409
  • 113 Legion Ave, Annapolis, MD 21401
    113 Legion Ave, Annapolis, MD 21401
    113 Legion Ave, Annapolis, MD 21401
    /40

    $515,000

    $40K PRICE INCREASE
    • 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
  • 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
  • 3328 Shore Dr, Annapolis, MD 21403
    3328 Shore Dr, Annapolis, MD 21403
    3328 Shore Dr, Annapolis, MD 21403
    /19

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    3328 Shore Dr, Annapolis, MD 21403

    Amazing opportunity! Situated in one of Annapolis’ most desirable waterfront communities, Oyster Harbor, 3328 Shore Drive offers a premier corner-lot location with beautiful second-floor water views. Enjoy the coastal lifestyle with easy access to marinas, parks, the community beach, local dining, and the charm of nearby historic Annapolis. This property presents an incredible opportunity for

    Joanna Dalton Coldwell Banker Realty

    3328 Shore Dr, Annapolis, MD 21403
  • 4 Boxwood Rd, Annapolis, MD 21403
    4 Boxwood Rd, Annapolis, MD 21403
    4 Boxwood Rd, Annapolis, MD 21403
    /24

    $389,900

    • 3 Beds
    • 2 Baths
    • 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

Showing Results 41 - 70, Page 2 of 2

Maryland Anne Arundel County Annapolis

2-Story Homes for Sale in Annapolis, MD

Popular Home Searches in Annapolis, MD

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

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In Annapolis, there are currently 70 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.

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