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Affordable Homes for Sale in Annapolis, MD under $497,000

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  • 633 Baystone Ct, Annapolis, MD 21409
    633 Baystone Ct, Annapolis, MD 21409
    633 Baystone Ct, Annapolis, MD 21409
    /32

    $484,995

    • 4 Beds
    • 2 Baths
    • 1,868 Sq Ft

    633 Baystone Ct, Annapolis, MD 21409

    Welcome to a home that checks all the right boxes: space, convenience, and location. With four generously sized bedrooms and two full bathrooms, this townhouse offers room to grow, work from home, or host weekend guests who end up staying just a bit longer than planned.The living space features a bright, open layout with plenty of natural light—perfect for morning coffee, afternoon naps, or

    Vikas Goel Fairfax Realty of Tysons

    633 Baystone Ct, Annapolis, MD 21409
  • 2601 Compass Dr, Annapolis, MD 21401
    2601 Compass Dr, Annapolis, MD 21401
    2601 Compass Dr, Annapolis, MD 21401
    /55

    $496,500 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,514 Sq Ft

    2601 Compass Dr, Annapolis, MD 21401

    Welcome to easy living in the highly sought-after 55+ community of Heritage Harbour where the amenities rival the finest resorts! This charming one-level home offers a perfect blend of comfort, style, and convenience, plus a private and serene back setting surrounded by trees for an added peaceful feeling. Featuring 2 spacious bedrooms, 2 full bathrooms, a den, and an updated kitchen, this

    Dee Dee Miller Long & Foster Real Estate, Inc.

    2601 Compass Dr, Annapolis, MD 21401
  • 1029 Commanders Way N, Annapolis, MD 21409
    1029 Commanders Way N, Annapolis, MD 21409
    1029 Commanders Way N, Annapolis, MD 21409
    /70

    $395,000

    • 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
  • 300 Hilltop Ln Unit 300K, Annapolis, MD 21403
    300 Hilltop Ln Unit 300K, Annapolis, MD 21403
    300 Hilltop Ln Unit 300K, Annapolis, MD 21403
    /21

    $279,000

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    300 Hilltop Ln Unit 300K, Annapolis, MD 21403

    Move in today! This beautiful garden-style 2-bedroom, 2-bathroom condo is located on the top floor of a charming 4-story building, offering privacy and serene treetop views. The open-concept layout is filled with natural light, featuring a spacious living area, modern kitchen, and private balcony perfect for morning coffee or evening relaxation. Both bedrooms are generously sized, with the

    Christian Dimenna Cummings & Co. Realtors

    300 Hilltop Ln Unit 300K, Annapolis, MD 21403
  • 940 Astern Way Unit 112, Annapolis, MD 21401
    940 Astern Way Unit 112, Annapolis, MD 21401
    940 Astern Way Unit 112, Annapolis, MD 21401
    /49

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,588 Sq Ft

    940 Astern Way Unit 112, Annapolis, MD 21401

    Charming Condo for sale in Heritage Harbour's 55+ Community. Step into a lifestyle of ease and sophistication in this beautiful condo, nestled within the vibrant 55+ community of Heritage Harbour in Annapolis. Perfect for active adults, this sought after neighborhood offers a host of amenities tailored to enhance your daily living.Enjoy access to a state-of-the-art clubhouse,

    Jack Papaleonti Academy Realty Inc.

    940 Astern Way Unit 112, Annapolis, MD 21401
  • 577 Francis Nicholson Way, Annapolis, MD 21401
    577 Francis Nicholson Way, Annapolis, MD 21401
    577 Francis Nicholson Way, Annapolis, MD 21401
    /35

    $489,000

    • 3 Beds
    • 3.5 Baths
    • 2,024 Sq Ft

    577 Francis Nicholson Way, Annapolis, MD 21401

    An incredible find; Welcome home to 577 Francis Nicholson Way, a rarely available end unit townhome residence in the highly desirable Tidewater Community! With fresh carpet on the main & upper floors along with new roof (1 year old), newer HVAC (under 2 years old), and newer hot water heater, move in complete peace of mind! Past the hardwood laden foyer, the kitchen flows with hardwoods, granite

    Alexander Lerner TTR Sotheby's International Realty

    577 Francis Nicholson Way, Annapolis, MD 21401
  • 216 Gross Ave, Annapolis, MD 21401
    216 Gross Ave, Annapolis, MD 21401
    /2

    $225,000

    • Land
    • 0.14 Acre
    • $1,607,143 per Acre

    216 Gross Ave, Annapolis, MD 21401

    ***Opportunity to build in Annapolis*** Grading permit was approved by the City of Annapolis, but expired December 2024 during the building permit review. The Seller has filed a request for renewal of the grading permit and awaits approval. Once the grading permit is approved the building permit will follow. House to be built is the Wexford (84 Lumber). Choose your builder,

    Pier Butler Curtis Real Estate Company

    216 Gross Ave, Annapolis, MD 21401
  • 2900 Shipmaster Way Unit 302, Annapolis, MD 21401
    2900 Shipmaster Way Unit 302, Annapolis, MD 21401
    2900 Shipmaster Way Unit 302, Annapolis, MD 21401
    /30

    $345,000

    • 1 Bed
    • 2 Baths
    • 1,089 Sq Ft

    2900 Shipmaster Way Unit 302, Annapolis, MD 21401

    By no fault at all of the seller, this beauty is back on the market! Their loss is your gain! Welcome home to 2900 Shipmaster Way #302- a rare opportunity to own a stunning corner penthouse condo in the sought-after Clipper Cay building, offering year-round water views of the South River and bathed in natural light from every angle. Fully rebuilt in 2023, this pristine residence blends timeless

    Kathleen Moore Engel & Völkers Annapolis

    2900 Shipmaster Way Unit 302, Annapolis, MD 21401
  • 414 Blossom Tree Ct, Annapolis, MD 21409
    414 Blossom Tree Ct, Annapolis, MD 21409
    414 Blossom Tree Ct, Annapolis, MD 21409
    /44

    $458,000

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    414 Blossom Tree Ct, Annapolis, MD 21409

    It’s rare to find a home that checks all the boxes—peaceful neighborhood, functional space, and a location that keeps you connected. This one does just that. Nestled on a quiet cul-de-sac in Whispering Woods, the setting feels tucked away while still offering easy access to everything Annapolis has to offer.Step outside and you’re just minutes from Broadneck parks, local shops, and

    James Bowerman Douglas Realty, LLC

    414 Blossom Tree Ct, Annapolis, MD 21409
  • 7101 Bay Front Dr Unit 204, Annapolis, MD 21403
    7101 Bay Front Dr Unit 204, Annapolis, MD 21403
    7101 Bay Front Dr Unit 204, Annapolis, MD 21403
    /43

    $320,000

    • 1 Bed
    • 1.5 Baths
    • 1,000 Sq Ft

    7101 Bay Front Dr Unit 204, Annapolis, MD 21403

    Gorgeous 1 bedroom, 1.5 bath condo on the second floor. Freshly painted and new carpet have been installed. This is one MOVE IN READY. Enjoy all the ammenities that Baywoods has to offer and enjoy being directly on the Chesapeake Bay. Luxury and convenience at it's finest.

    Crystal Smith RE/MAX Executive

    7101 Bay Front Dr Unit 204, Annapolis, MD 21403
  • 3268 Kitty Duvall Dr, Annapolis, MD 21403
    3268 Kitty Duvall Dr, Annapolis, MD 21403
    3268 Kitty Duvall Dr, Annapolis, MD 21403
    /31

    $324,000

    • Land
    • 0.62 Acre
    • $522,581 per Acre

    3268 Kitty Duvall Dr, Annapolis, MD 21403

    Rare Opportunity – Serene .62-Acre Homesite Near Downtown AnnapolisBuild the custom home of your dreams on this peaceful, wooded .62-acre lot tucked away on a private gravel lane. With a flat topography, access to public sewer, and significant preliminary engineering already completed, this property offers a rare blend of natural beauty and readiness for development. Enjoy the

    Jill Lapides Cummings & Co. Realtors

    3268 Kitty Duvall Dr, Annapolis, MD 21403
  • 1167 Green Holly Dr, Annapolis, MD 21409
    1167 Green Holly Dr, Annapolis, MD 21409
    1167 Green Holly Dr, Annapolis, MD 21409
    /10

    $165,000

    • Land
    • 0.21 Acre
    • $785,714 per Acre

    1167 Green Holly Dr, Annapolis, MD 21409

    Welcome to the sought-after community of Cape St. Claire! This lot is being offered as an addition to a home for sale. Please contact the county for possible development.

    Darlene Winegardner RE/MAX Executive

    1167 Green Holly Dr, Annapolis, MD 21409
  • 7101 Bay Front Dr Unit 400, Annapolis, MD 21403
    7101 Bay Front Dr Unit 400, Annapolis, MD 21403
    7101 Bay Front Dr Unit 400, Annapolis, MD 21403
    /58

    $265,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    7101 Bay Front Dr Unit 400, Annapolis, MD 21403

    MOTIVATED SELLER, JUST REDUCED ANOTHER $10,000!! Brand new hardwood flooring throughout the entire unit and complete professional interior painting. Lovely end unit with a row of extra windows that allows for wonderful natural light throughout. Are you ready to relax and let someone else do the cooking and cleaning? ONE MONTHLY PAYMENT TAKES CARE OF FOOD, ALL UTILITIES, TAXES, INSURANCE,

    Diane Gavin Long & Foster Real Estate, Inc.

    7101 Bay Front Dr Unit 400, Annapolis, MD 21403
  • 655 Burtons Cove Way Unit 11, Annapolis, MD 21401
    655 Burtons Cove Way Unit 11, Annapolis, MD 21401
    655 Burtons Cove Way Unit 11, Annapolis, MD 21401
    /21

    $349,000

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    655 Burtons Cove Way Unit 11, Annapolis, MD 21401

    Price Just Reduced. Extremely rare 3-bedroom 2-bathroom top floor condo in the Windgate community. The condo was purchased in 2022 and was completely renovated. Please look through the photos to be walked through everything this wonderful condo has to offer its next owner. The entire condo was painted in 2022 and new flooring, kitchen cabinets, kitchen counter tops and appliances were installed

    Frank Livingston Cook Real Estate Brokerage

    655 Burtons Cove Way Unit 11, Annapolis, MD 21401
  • 319 6th St Unit SLIP 39, Annapolis, MD 21403
    319 6th St Unit SLIP 39, Annapolis, MD 21403
    319 6th St Unit SLIP 39, Annapolis, MD 21403
    /15

    $65,000

    319 6th St Unit SLIP 39, Annapolis, MD 21403

    Boating season is just around the corner—embrace the maritime lifestyle with your very own waterfront slip at 319 6th Street, Annapolis, MD 21403. Boat size is limited to 34' length overall. Situated in the heart of Eastport, this sought-after marina places you in the Sailing Capital of the World, where boating isn’t just a pastime—it’s a way of life. Beyond the convenience of docking in a

    Wendy Oliver Coldwell Banker Realty

    319 6th St Unit SLIP 39, Annapolis, MD 21403
  • 8 Ashford Ct, Annapolis, MD 21403
    8 Ashford Ct, Annapolis, MD 21403
    8 Ashford Ct, Annapolis, MD 21403
    /34

    $465,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    8 Ashford Ct, Annapolis, MD 21403

    Price Adjustment! Welcome to 8 Ashford Ct — Modern Living in the Heart of Annapolis!Now offered at a new, more attractive price, this beautifully updated 2-bedroom, 1.5-bath contemporary townhouse is move-in ready and full of upgrades. Enjoy a spacious open floor plan featuring gleaming hardwood floors and a modern kitchen with stainless steel appliances. Located in the highly desirable Hunt

    Amanda Callahan Long & Foster Real Estate, Inc.

    8 Ashford Ct, Annapolis, MD 21403
  • 1012 Carrs Rd, Annapolis, MD 21403
    1012 Carrs Rd, Annapolis, MD 21403
    /2

    $98,000

    • Land
    • 0.16 Acre
    • $612,500 per Acre

    1012 Carrs Rd, Annapolis, MD 21403

    Level lot, 2017 perc evaluation indicated a possible home up to a 2,500 sq ft . Buyer to verify all information.

    John Freeman Coldwell Banker Realty

    1012 Carrs Rd, Annapolis, MD 21403
  • 0 Cypress Trail Unit MDAA2116604, Crownsville, MD 21032
    0 Cypress Trail Unit MDAA2116604, Crownsville, MD 21032
    /2

    $6,000

    • Land
    • 0.06 Acre
    • $100,000 per Acre

    0 Cypress Trail Unit MDAA2116604, Crownsville, MD 21032

    Herald Harbor was platted in the late 1920s/early 1930s. It is surrounded by water on three sides. The community is served by public water. The trustee will consider offers. Estimated 2500 sq ft lot is non-buildable. Would benefit an existing home/structure Lot 5, Bk 23 on Cypress Trail .See seller documents for Tobys Legacy 501c3 nonprofit.pdf Your donation is tax deductible, per trust

    Kelly Kindig Douglas Realty, LLC

    0 Cypress Trail Unit MDAA2116604, Crownsville, MD 21032
  • 29 Collison Rd, Annapolis, MD 21401
    29 Collison Rd, Annapolis, MD 21401
    /2

    $300,000

    • Land
    • 0.29 Acre
    • $1,034,483 per Acre

    29 Collison Rd, Annapolis, MD 21401

    MAJOR PRICE ADJUSTMENT on this lovely flat lot in a private, convenient neighborhood.This lot was subdivided many years ago and used by the present owners for picnics and famly gatherings. Please contact the listing agent with any questions. And drive by but do not walk the lot without prior authorization.Please contact the listing agent regarding the potential availability of the

    Stealey Ashley Coldwell Banker Realty

    29 Collison Rd, Annapolis, MD 21401
  • 1221 Creek Dr, Annapolis, MD 21403
    1221 Creek Dr, Annapolis, MD 21403
    /2

    $55,000

    • Land
    • 0.26 Acre
    • $211,538 per Acre

    1221 Creek Dr, Annapolis, MD 21403

    Excellent opportunity to fulfill your dream of constructing your own dream custom home. This lot is located in a beach community with lots of creeks. Enjoy the lazy days on or by the water with lots of activities. Make this a second home to just relax and enjoy being away from the hustle and bustle of city life.

    Melissa Smith Samson Properties

    1221 Creek Dr, Annapolis, MD 21403
  • 930 Astern Way Unit 412, Annapolis, MD 21401
    930 Astern Way Unit 412, Annapolis, MD 21401
    930 Astern Way Unit 412, Annapolis, MD 21401
    /33

    $495,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,477 Sq Ft

    930 Astern Way Unit 412, Annapolis, MD 21401

    Welcome to effortless living in the vibrant 55+ community of Heritage Harbour! This beautifully appointed 2-bedroom, 2-bath condominium offers a spacious open-concept design that combines comfort and elegance. At the heart of the home is a stunning gourmet kitchen featuring a center island with built ins and breakfast bar, granite countertops, stainless appliances and ample cabinetry—perfect for

    John Collins Long & Foster Real Estate, Inc.

    930 Astern Way Unit 412, Annapolis, MD 21401
  • 13 Silverwood Cir Unit 6, Annapolis, MD 21403
    13 Silverwood Cir Unit 6, Annapolis, MD 21403
    13 Silverwood Cir Unit 6, Annapolis, MD 21403
    /27

    $260,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,402 Sq Ft

    13 Silverwood Cir Unit 6, Annapolis, MD 21403

    Welcome to 13 Silverwood Circle, Unit #6 – fantastically located 2-bedroom, 2-bath condo is nestled in the sought-after Fairwinds community of Annapolis. This spacious home offers comfortable living with a thoughtful layout, large living area, dining space, two generously sized bedrooms, office space/flex space, balcony and ample storage.Enjoy all the amenities Fairwinds has to offer,

    Matthew Spence The KW Collective

    13 Silverwood Cir Unit 6, Annapolis, MD 21403
  • 40 Oak Ct, Annapolis, MD 21401
    40 Oak Ct, Annapolis, MD 21401
    40 Oak Ct, Annapolis, MD 21401
    /15

    $389,900

    • 2 Beds
    • 2 Baths
    • 1,061 Sq Ft

    40 Oak Ct, Annapolis, MD 21401

    Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring

    Gregory Golding ExecuHome Realty

    40 Oak Ct, Annapolis, MD 21401
  • 1945 Marconi Cir, Annapolis, MD 21401
    1945 Marconi Cir, Annapolis, MD 21401
    1945 Marconi Cir, Annapolis, MD 21401
    /12

    $397,000

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

    1945 Marconi Cir, Annapolis, MD 21401

    Heritage Harbour community offers it all for its residents. Move into the convenience of one level living here. Home is also partially fenced for some added privacy. Subject is sold in as is condition, seller nor buyer can make any repairs prior to closing. Property is owned by the US Dept. of HUD, HUD Case #241-916291. Insurability Code: ie. Seller makes no representations or warranties as to

    Dana Byrd Thurston Wyatt Real Estate, LLC

    1945 Marconi Cir, Annapolis, MD 21401

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Real Estate & Homes in Annapolis, MD under $497,000

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