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Annapolis, MD 2-Story Homes for Sale

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  • /41

    $745,000

    • 4 Beds
    • 3 Baths
    • 2,348 Sq Ft

    7 Silopanna Rd, Annapolis, MD 21403

    Welcome to this beautifully restored and thoughtfully updated 1942 gem. Step inside to find gleaming hardwood floors, sunlit living spaces, and original archtectural details blended seamlessly w contemporary updates. Outdoors, enjoy a peaceful side and rear garden, ideal for morning coffee or quiet evenings under the stars. Just a short walk is a scenic footbridge over Spa Creek to Truxton

    Don Adams Long & Foster Real Estate, Inc.

    7 Silopanna Rd, Annapolis, MD 21403
  • /35

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,812 Sq Ft

    1262 Green Holly Dr, Annapolis, MD 21409

    Discover the home of your dreams with this stunning, completely renovated from top to bottom; 3 bedroom, 2 full bath gem in Green Holly. This remarkable property showcases the epitome of lovely living located on the Broadneck Peninsula. Step inside and be captivated by the grandeur that awaits you. Every corner of this meticulous home boasts exquisite craftsmanship and attention to detail. From

    Jessica Gosman-Bowen Curtis Real Estate Company

    1262 Green Holly Dr, Annapolis, MD 21409
  • /70

    $399,888

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

    1029 Commanders Way N, Annapolis, MD 21409

    Welcome home to this updated three bedroom, two and a half bath townhouse on the sought after Broadneck Peninsula. Walk into a tiled foyer adjacent to the living room with wood flooring. The kitchen is on the back side of the house with fine cabinets and stainless appliances. Ceramic tile flooring and the dining room, which has a slider to the backyard. Upstairs find a primary bedroom with an

    Christopher Fuller Long & Foster Real Estate, Inc.

    1029 Commanders Way N, Annapolis, MD 21409
  • /48

    $589,000

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    406 Edgemere Dr, Annapolis, MD 21403

    Stunning Hillsmere Shores Home – Water-Privileged & Move-In Ready! Brand New HVAC.Welcome to this beautifully renovated 4-bedroom, 2.5-bathroom home in the highly sought-after Hillsmere Shores community. Nestled on a spacious, level lot, this home has undergone extensive upgrades, blending modern elegance with timeless charm. Recent Upgrades & Features:2021: Major

    Jason Donovan RE/MAX Leading Edge

    406 Edgemere Dr, Annapolis, MD 21403
  • /43

    $419,900

    • 2 Beds
    • 2.5 Baths
    • 1,392 Sq Ft

    911 Breakwater Dr, Annapolis, MD 21403

    REDUCED! WELCOME to this Updated Townhome presenting 2 Primary Bedrooms with Ensuites in the highly desired community of Mariners Landing where charm meets convenience. Open the door to this spacious home boasting approximately $40,000 in recent upgrades. Some of the numerous upgrades include new Kitchen Cabinets, Countertops, Microwave, all new Windows and Blinds, new HVAC, Carpeting, Vinyl

    Joan Eisenhardt RE/MAX Executive

    911 Breakwater Dr, Annapolis, MD 21403
  • /62

    $489,900

    • 5 Beds
    • 3 Baths
    • 1,724 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
  • /50

    $4,950,000

    • 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
  • /37

    $875,000

    • 3 Beds
    • 3.5 Baths
    • 4,060 Sq Ft

    1901 Eamons Way, Annapolis, MD 21401

    Welcome to this stunning 3 bedroom, 3.5 bath stone-front home situated on a large 9,289 sq .ft. corner lot in the sought-after Monticello community—just a short walk to shops and dining. The main level features an open living/dining area, gourmet kitchen with stainless appliances and granite counters, a spacious family room with gas fireplace that opens to a large screened-in porch, perfect for

    Peggy Love Long & Foster Real Estate, Inc.

    1901 Eamons Way, Annapolis, MD 21401
  • /73

    $1,399,000

    • 4 Beds
    • 3 Baths
    • 3,398 Sq Ft

    1227 Cross Rd, Annapolis, MD 21403

    Discover elegance at 1227 Cross Road in Annapolis, Maryland, a stunning 2023-built home in the water-privileged Oyster Harbor community, elevated by upgrades made by the current owner since purchase. Enter through grand double doors into an open foyer with hickory hardwood floors, soaring ceilings, and crown molding. The great room impresses with a coffered ceiling, ceiling fan, fireplace, and

    Patrick DeLeonibus TTR Sotheby's International Realty

    1227 Cross Rd, Annapolis, MD 21403
  • /46

    $555,000

    • 1 Bed
    • 1 Bath
    • 660 Sq Ft

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

    Location! Location! Location! Perched on the top floor of The Tecumseh—Maryland’s first condominium building—this rarely available two-level loft offers water views, thoughtful updates, and an unbeatable Eastport lifestyle and access to all the charm and excitement of coastal living in Annapolis. W401 overlooks Spa Creek with views of Ego Alley, the community marina, and Severn Avenue. This

    Ashley Stanwick Coldwell Banker Realty

    312 Severn Ave Unit W-401, Annapolis, MD 21403
  • /50

    $2,775,000

    • 3 Beds
    • 3.5 Baths
    • 3,320 Sq Ft

    22 E Lake Dr, Annapolis, MD 21403

    Previous Buyer's financing fell thru so back on the market with a huge 200k price reduction . Take advantage of this opportunity to vacation at home this summer and enjoy it now!Welcome to 22 East Lake, located in the sought-after waterfront community of Bay Ridge. This 3 bedroom 3.1 bath exceptional home blends refined sophistication with relaxed coastal living, offering the perfect space

    Betsy Dunigan TTR Sotheby's International Realty

    22 E Lake Dr, Annapolis, MD 21403
  • /60

    $797,000

    • 5 Beds
    • 3 Baths
    • 2,288 Sq Ft

    3117 Port Way, Annapolis, MD 21403

    Dramatic Price Reduction - Priced to Sell: Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community: Welcome to 3117 Port Way, a beautifully updated home nestled in the highly desirable Anchorage Waterfront community of Annapolis. This spacious 5-bedroom, 3-bathroom residence offers approximately 2,400 square feet of open-concept living space on a 0.34-acre lot, complete with a

    Ani Gonzalez-Brunet Coldwell Banker Realty

    3117 Port Way, Annapolis, MD 21403
  • /29

    $1,175,000

    • 2 Beds
    • 1.5 Baths
    • 1,656 Sq Ft

    179 Green St, Annapolis, MD 21401

    Experience the Essence of Annapolis Charm at 179 Green StreetNestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, this location offers the very best of city living in one of the city's most coveted

    David Yee Long & Foster Real Estate, Inc.

    179 Green St, Annapolis, MD 21401
  • /90

    $1,980,000

    • 5 Beds
    • 3 Baths
    • 2,353 Sq Ft

    201 Nottingham Hill, Annapolis, MD 21405

    PRICE REDUCTION - Exciting Opportunity in Sherwood Forest – Enjoy breathtaking panoramic water vistas of Brewers Pond and Round Bay on the Severn River. Observe Bald Eagles, Herons, and Osprey soaring amidst the stunning backdrop from your water view deck or spacious living room adorned with floor-to-ceiling windows. This elegantly designed home, nestled in the hillside, seamlessly blends modern

    Brian Wood Long & Foster Real Estate, Inc.

    201 Nottingham Hill, Annapolis, MD 21405
  • /50

    $6,995,000

    • 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
  • /71

    $650,000

    • 5 Beds
    • 2.5 Baths
    • 2,014 Sq Ft

    130 Great Lake Dr, Annapolis, MD 21403

    PRIVATE WATER COMMUNITY! 5 BEDROOM 2.5 FULL BATH BRICK HOME SITS ON .42 ACRE LOT IN SOUGHT AFTER HILLSMERE ESTATES! FRESHLY PAINTED THROUGHOUT! UPPER LEVEL HARDWOOD FLOORS HAVE BEEN REFINISHED! UPDATED KITCHEN W/ SS APPLIANCES, QUARTZ COUNTER TOPS, TILED BACKSPLASH, TABLE SPACE W/ BREAKFAST BAR & RECESSED LIGHTING. LIVING ROOM HAS BRICK FIREPLACE AND MANTEL, HARDWOOD FLOORS, BAY WINDOW W/

    Jennifer Drennan Taylor Properties

    130 Great Lake Dr, Annapolis, MD 21403
  • /48

    $1,875,000

    • 4 Beds
    • 2.5 Baths
    • 2,606 Sq Ft

    1924 Hidden Point Rd, Annapolis, MD 21409

    Nestled at the end of a quiet cul-de-sac and set on over half an acre, this rare waterfront opportunity on Mill Creek offers stunning panoramic views, tranquil privacy, and a lifestyle centered around the water. With a deep-water pier, a dock with a single slip, and a mean low water depth of 8 feet, the property can comfortably accommodate 80 foot vessels making it a dream for serious boaters and

    Kristi Neidhardt Northrop Realty

    1924 Hidden Point Rd, Annapolis, MD 21409
  • /95

    $1,499,000

    • 4 Beds
    • 3 Baths
    • 2,341 Sq Ft

    541 Second St, Annapolis, MD 21403

    A Rare Find in the Heart of Eastport! Built in 2006 with timeless Eastport charm, this beautifully maintained home offers the perfect blend of traditional style and modern convenience. Enjoy off-street parking for 2 cars and a host of high-end features throughout. Step inside to discover hardwood flooring on all 3 levels, radiant floor heat, and zoned heating and cooling – including a private

    Betty Jans Berkshire Hathaway HomeServices PenFed Realty

    541 Second St, Annapolis, MD 21403
  • /17

    $1,350,000

    • 3 Beds
    • 1 Bath
    • 964 Sq Ft

    1407 Chesapeake Ave, Annapolis, MD 21403

    Embrace the opportunity to create your dream waterfront retreat on this expansive 10,072 sq ft (0.24-acre) property, strategically located on the tranquil shores of Chesapeake Ave in the coveted Venice Beach area. This combined offering includes Lots 3 & 4 Block C (Tax #020288602739800), providing a unique canvas for your architectural vision.Whether you choose to renovate the existing

    Shalamar Muhammad TTR Sotheby's International Realty

    1407 Chesapeake Ave, Annapolis, MD 21403
  • /7

    $850,000

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

    316 Chester Ave, Annapolis, MD 21403

    If you're looking for a charming home in the sought out neighborhood of Eastport. This home has beautiful hardwood floors and spacious back yard - perfect for entertaining. Ready for the next home owner to make it their own! Great water views of Seashell Marina and Butlers Marina. For the love of nature and water views you will be right at home! The home will need some TLC. Seller is sharing

    Vita Makle Clark Realty Group, LLC

    316 Chester Ave, Annapolis, MD 21403
  • /43

    $3,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,250 Sq Ft

    54 River Dr, Annapolis, MD 21403

    Gorgeous coastal style home in the coveted Bay Ridge community with stunning and thoughtful renovations that highlight the expansive Chesapeake and Bay Bridge views! The extensive renovation by M Homes elevated the appeal and functionality of the home by adding 2 additional ensuite bedrooms and laundry room on the 2nd level and much more. No expense was spared to make this a home of distinction,

    Brad Kappel TTR Sotheby's International Realty

    54 River Dr, Annapolis, MD 21403
  • /53

    $849,000

    • 2 Beds
    • 2.5 Baths
    • 1,708 Sq Ft

    336 Severn Rd, Annapolis, MD 21401

    Waterfront Living in Epping Forest with Stunning Views!Nestled in the exclusive, gated community of Epping Forest, this beautifully maintained 2-bedroom, 2.5-bath home offers serene water views and a relaxed yet sophisticated lifestyle. Designed for effortless living, the open floor plan features 10-foot ceilings, gleaming hardwood floors, and a cozy fireplace in the Great Room. The

    Candice Bothun CENTURY 21 New Millennium

    336 Severn Rd, Annapolis, MD 21401
  • /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
  • /44

    $2,245,000

    • 3 Beds
    • 2.5 Baths
    • 3,243 Sq Ft

    2908 Southwater Point Dr, Annapolis, MD 21401

    Fabulous waterfront "Deck Home" with heated saltwater pool and unprecedented views across Broad Creek out to the South River. This special residence located in the Southwater Point enclave of waterfront homes offers the perfect elevation to oversee the stunning sunset and water views. The layout of the home is perfectly designed to enjoy the ever changing scenery from almost every room in the

    Brad Kappel TTR Sotheby's International Realty

    2908 Southwater Point Dr, 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 renowned local architect as the culmination of an award winning career. The unsurpassed attention to architectural details, exquisitely curated finishes and breathtaking views of Spa Creek places this trophy home in a league of its own. Tucked away at the end of a quiet street in a premier

    Brad Kappel TTR Sotheby's International Realty

    1 Shipwright Harbor, Annapolis, MD 21401
  • /29

    $519,500

    • 4 Beds
    • 3 Baths
    • 2,160 Sq Ft

    1971 Dominoe Rd, Annapolis, MD 21401

    Welcome to this Wonderful home very close to Annapolis & the properties to be in a private area but close proximity to be in the City of Annapolis! Located in close proximity to restaurants , shopping, and entertainmemt . You will enjoy summer evenings dining - out in the over large deck out back! The Home offers an open floor plan that leads you to entertaining with a spacious living

    Alda Lourenco RE/MAX Realty Group

    1971 Dominoe Rd, Annapolis, MD 21401
  • /80

    $985,000

    • 3 Beds
    • 3 Baths
    • 2,041 Sq Ft

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403

    Welcome to this DESIGNER SHOWCASE including a custom painted entry that draws you in the moment you open the door. Owner worked with a reputable interior designer to select all finishes to include designer light fixtures, gorgeous real hardwood floors, custom designed bathrooms, and so many interesting trim details. Transitional timeless design with a coast twist. ONE OF A KIND and RARE

    Ann Chumney Coldwell Banker Realty

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
  • /2

    $1,700,000 New Construction

    • 4 Beds
    • 3 Baths
    • 3,640 Sq Ft

    400 Jefferson St, Annapolis, MD 21403

    Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Maryland. This home will feature a perfect blend of classic Eastport and luxury coastal craftsman design. Permitting is complete. This expansive 3600 +/- (approx. 850 unfinished) sq. foot home will offer 4 bedrooms and 3 baths with an open floor plan concept. Truly an entertainer’s dream with hardwood floors,

    Brian Jacobs Coldwell Banker Realty

    400 Jefferson St, Annapolis, MD 21403
  • /40

    $649,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 3 Baths
    • 2,328 Sq Ft

    2664 Ogleton Rd, Annapolis, MD 21403

    This lovely rancher in the coveted, amenity rich neighborhood of Annapolis Roads boasts 5 bedrooms and 3 full bathrooms. Sale price includes a rare additional .38 lot (2664 A) , for a total of 3/4 acres! Privately and peacefully situated in a canopy of beautiful mature trees and walking distance to the neighborhood beach, vacation will feel permanent! The main level is wonderful for

    Kelly Parks Coldwell Banker Realty

    2664 Ogleton Rd, Annapolis, MD 21403
  • /57

    $800,000 Open House 9/06

    • 5 Beds
    • 4.5 Baths
    • 4,084 Sq Ft

    1583 Keswick Place, Annapolis, MD 21401

    Property is being offered at Public Auction by Witman Auctioneers, Inc. to settle an Estate. List Price of $800,000 is opening bid-Estate of Geoffrey J. Dive - ONLINE PUBLIC REAL ESTATE AUCTIONLOCATION: 1583 Keswick Place “The Downs”, Annapolis, MD 21401Severn Downs Community- Anne Arundel County(The Downs – Lot 187 Sc 12) Thursday, September 18, 2025 Real Estate 6:00 PM To View

    Zachary Shelley Streett Hopkins Real Estate, LLC

    1583 Keswick Place, Annapolis, MD 21401

Showing Results 41 - 71, Page 2 of 2

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