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Gwynn Oak, MD Homes for Sale under $500,000

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  • /18

    $499,900

    • 5 Beds
    • 2.5 Baths
    • 2,750 Sq Ft

    4021 Barrington Rd, Gwynn Oak, MD 21207

    Discover this charming single-family gem currently utilized as an assisted living facility. Boasting 5 spacious bedrooms, 2 full bathrooms, and 1 half bathroom, this home is perfect for a growing family or a business venture.Step into a gourmet kitchen equipped with a central island, perfect for culinary creations. Enjoy the elegance of hardwood floors throughout, enhancing the home's

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    William Savage

    Keller Williams Legacy

    (443) 398-3399

    4021 Barrington Rd, Gwynn Oak, MD 21207
  • /50

    $449,900

    • 6 Beds
    • 4 Baths
    • 3,169 Sq Ft

    2108 Sunbriar Ln, Gwynn Oak, MD 21207

    Welcome to 2108 Sunbriar Lane, a beautifully updated and expansive home offering over 3,000 square feet of versatile living space. With 6 spacious bedrooms and 4 full bathrooms, this property is perfect for multi-generational living, main floor living, or even a potential rental unit setup—the possibilities are endless!Freshly updated in 2025, the home features new carpet, fresh paint,

    Melany Diaz EXP Realty, LLC

    2108 Sunbriar Ln, Gwynn Oak, MD 21207
  • /55

    $450,000

    • 5 Beds
    • 2.5 Baths
    • 3,580 Sq Ft

    2500 Pickwick Rd, Gwynn Oak, MD 21207

    Step into history with this charming and iconic home, originally built in 1790. With tasteful updates and thoughtful additions over the years, this single-family detached property blends old-world character with modern comfort.One of its standout features is a separate, fully-equipped 1-bedroom, 1-bathroom guest house located at the rear of the property. Currently rented, this additional

    Brandon Hoffman Redfin Corp

    2500 Pickwick Rd, Gwynn Oak, MD 21207
  • /25

    $425,000

    • Studio
    • 2,280 Sq Ft

    4511 Prospect Cir, Baltimore, MD 21216

    Excellent investment opportunity in this well-maintained 2-unit multifamily home offering strong rental potential. The lower-level unit is tenant-occupied and features 2 bedrooms and 1 full bath, while the upper-level unit is vacant and ready for immediate occupancy with 3 bedrooms and 1 full bath. Each unit is equipped with its own washer and dryer, central heat and air, ceiling fans, and modern

    Hezeldee Del Callar Redfin Corp

    4511 Prospect Cir, Baltimore, MD 21216
  • /49

    $464,900

    • 5 Beds
    • 4 Baths
    • 2,025 Sq Ft

    3304 Oakfield Ave, Gwynn Oak, MD 21207

    Welcome to this beautifully renovated single-family home, offering the perfect blend of modern luxury and everyday comfort. Featuring 5 spacious bedrooms and 4 full bathrooms—including a full bath on every level—this home provides exceptional flexibility for guests, multigenerational living, or a growing family.Enjoy peaceful mornings or relaxing evenings on the charming front porch, an

    Robert Breeden Berkshire Hathaway HomeServices Homesale Realty

    3304 Oakfield Ave, Gwynn Oak, MD 21207
  • /24

    $499,900

    • 3 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    1902 Alto Vista Ave, Gwynn Oak, MD 21207

    PRICE REDUCTION....Welcome to 1902 Alto Vista Ave, a beautifully updated single-family home that perfectly blends timeless character with modern updates. Built in 1948, this property has been thoughtfully renovated and converted into an open-concept design, creating a bright, flowing space ideal for entertaining and everyday living. Offering an impressive 3,000 square feet of living space and

    Crystal Hunt Shoiyia Hunt Realty

    1902 Alto Vista Ave, Gwynn Oak, MD 21207
  • /70

    $474,999

    • 4 Beds
    • 3.5 Baths
    • 2,233 Sq Ft

    2441 N Forest Park Ave, Gwynn Oak, MD 21207

    Tucked along the wooded banks of the Gwynns Falls, the historic village of Dickeyville offers something incredibly rare in Baltimore: a true sense of place. Here, the year moves not by the pages of a calendar, but by traditions passed from one neighbor to the next. In spring, residents gather with gloves and garden tools for the village clean-up, tending to cobblestone walkways and 19th-century

    Miranda Sipes Keller Williams Flagship

    2441 N Forest Park Ave, Gwynn Oak, MD 21207
  • /49

    $489,900

    • 5 Beds
    • 4 Baths
    • 2,025 Sq Ft

    3304 Oakfield Ave, Gwynn Oak, MD 21207

    ** MOTIVATED SELLER **Welcome to this beautifully renovated single-family home featuring 5 spacious bedrooms and 4 full bathrooms, including a full bath on every floor—ideal for flexibility and convenience. The charming front porch is perfect for enjoying your morning coffee or relaxing with evening cocktails.Step inside to an open, light-filled interior with tons of natural light

    Robert Breeden Berkshire Hathaway HomeServices Homesale Realty

    3304 Oakfield Ave, Gwynn Oak, MD 21207
  • /53

    $499,000

    • 4 Beds
    • 3.5 Baths
    • 2,220 Sq Ft

    1109 Marksworth Rd, Gwynn Oak, MD 21207

    NEW PRICE!!! Located on a quiet cul-de-sac in the Brigadoon community, this brick home has been reimagined and completely renovated in 2025. With exceptional attention to detail and high end finishes throughout, there is nothing to do but move right in! Features include an open concept kitchen with adjoining family room with a woodburning fireplace. The new outside deck off of the dining room and

    Peter Charchalis Cummings & Co. Realtors

    1109 Marksworth Rd, Gwynn Oak, MD 21207
  • /34

    $475,000

    • 5 Beds
    • 4 Baths
    • 4,900 Sq Ft

    2423 Pickwick Rd, Gwynn Oak, MD 21207

    THE LIST PRICE REPRESENTS THE OPENING OFFER AMOUNT (NET TO SELLER). AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS.RARELY AVAILABLE! BEAUTIFUL, HISTORIC 5BR/3FB Stone House with over 5,000 sq ft of living space with 25+ ft ceilings! Absolutely Unique House with stunning artwork and sculptures throughout! An art Studio and home for a local Sculptor in the Dickeyville Historic District.

    Tom Atwood Keller Williams Legacy

    2423 Pickwick Rd, Gwynn Oak, MD 21207
  • /36

    $499,000

    • Studio
    • 2,492 Sq Ft

    4710 Liberty Heights Ave, Baltimore, MD 21207

    Savvy investors will not want to miss this phenomenal turnkey property. Construction was executed from the rendering of none other than the acclaimed B.C. Architectural Designs. This 1930's property was built to be zoned commercially, but this mixed-use building is not to be missed. Located within close proximity to the Baltimore County line, the Baltimore Beltway, 1_83, and Baltimore City

    Aviva Karpe Cummings & Co. Realtors

    4710 Liberty Heights Ave, Baltimore, MD 21207
  • /9

    $425,000

    • 3 Beds
    • 1 Bath
    • 1,164 Sq Ft

    2025 Wells Manor Ave, Gwynn Oak, MD 21207

    Three Bedroom, 1 bath home with lots of potential with old charm and a huge completely fenced yard. Also includes an additional lot located directly behind the fence is included in the sale. Seller is motivated.To show property: Call Reyana @ 443-355-3677

    Syed Zeeshan Prime Real Estate

    2025 Wells Manor Ave, Gwynn Oak, MD 21207
  • /49

    $410,000

    • 2 Beds
    • 2 Baths
    • 1,921 Sq Ft

    2301 Pickwick Rd, Gwynn Oak, MD 21207

    Welcome to 2301 Pickwick Rd – a beautifully refreshed 2-bedroom, 2-bath home in the heart of historic Dickeyville. This home has undergone a complete facelift, featuring a brand-new finished basement, fresh paint throughout, refinished hardwood floors, and all-new recessed lighting that brightens every room. The open-concept layout blends charm with modern convenience, offering spacious

    Adam Chubbuck Douglas Realty, LLC

    2301 Pickwick Rd, Gwynn Oak, MD 21207
  • /25

    $415,000

    • 3 Beds
    • 2.5 Baths
    • 1,986 Sq Ft

    7408 Shirley Rd, Gwynn Oak, MD 21207

    Drastically Reduced - Luxurious 3 BD, 2 1⁄2 BA Brick and Aluminum Siding Split Level with Attached Garage and 2 Car Parking Pad. The Huge Yard with patio is built for entertaining. This Shirley Hills Community is close proximity to 695, Liberty Road corridor, bus routes and subway station.Newly remodeled Kitchen with New Quarts Counter Tops, New soft closing Cabinets and all new appliances -

    Dellarees Morton-Smith Berkshire Hathaway HomeServices Homesale Realty

    7408 Shirley Rd, Gwynn Oak, MD 21207
  • /39

    $415,000

    • Studio
    • 2,422 Sq Ft

    4405 Liberty Heights Ave, Gwynn Oak, MD 21207

    "Revised Price to Reflect Market Opportunity!" Motivated Seller. Don’t miss this INCOME PRODUCING triplex located just steps from local shops, parks, and transportation. Whether you’re a first-time investor or looking to live in one unit and rent out the others, this property offers the ideal setup. UNIT 1: --2 bedrooms, 1 bath, fireplace, and new stove. Rent potential at $1,500/month.---UNIT

    Heather Williams Compass

    4405 Liberty Heights Ave, Gwynn Oak, MD 21207
  • /42

    $475,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    3812 Milford Ave, Baltimore, MD 21207

    Welcome to this stunning BRAND NEW CONSTRUCTION home in Howard Park built in 2025, thoughtfully designed with modern finishes and a spacious layout. Offering 4 bedrooms and 3.5 baths across three levels, this property combines style, comfort, and functionality for today’s lifestyle.The main level features coffered and tray ceilings, a separate living room, formal dining room, and a bright

    Will Featherstone Featherstone & Co.,LLC.

    3812 Milford Ave, Baltimore, MD 21207
  • /9

    $435,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,890 Sq Ft

    3655 Forest Garden Ave, Gwynn Oak, MD 21207

    COMING SOON...Professional Pix to be added this week! Beautiful Colonial single family home with fully finished basement (recently rented to tenant for $1000/mth). Many new upgrades including roof..more to come

    Eze Amadi Fathom Realty MD, LLC

    3655 Forest Garden Ave, Gwynn Oak, MD 21207
  • /48

    $449,900

    • 7 Beds
    • 4.5 Baths
    • 4,278 Sq Ft

    3200 Chelsea Terrace, Baltimore, MD 21216

    Stunning 7-Bedroom Colonial in West Forest Park – Move-In Ready! 3200 Chelsea Terrace, Baltimore, MDMust see! This gorgeous 7-bedroom, 4.5-bath colonial in the desirable West Forest Park neighborhood sits on a spacious corner lot and offers a perfect blend of classic charm and modern upgrades.As you arrive, a custom wrought iron gate, wide walkway, and a covered wraparound

    Hassan Symes Engel & Völkers Washington, DC

    3200 Chelsea Terrace, Baltimore, MD 21216
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