11

Winchester Homes for Sale

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  • 1156 N Longwood St, Baltimore, MD 21216
    1156 N Longwood St, Baltimore, MD 21216
    1156 N Longwood St, Baltimore, MD 21216
    /10

    $125,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,480 Sq Ft

    1156 N Longwood St, Baltimore, MD 21216

    Opportunity awaits! This 3-level interior townhome is ideal for a buyer, investor, or renovation enthusiast looking to complete an unfinished project and add significant value. The property was being renovated to feature 3 bedrooms and 3 full bathrooms The full basement spans the footprint of the home and includes a walkout to the rear. The renovation is incomplete, and the property is being sold

    Agent Photo

    Angel Tyler

    EXP Realty, LLC

    1156 N Longwood St, Baltimore, MD 21216
  • 1221 Ashburton St, Baltimore, MD 21216
    1221 Ashburton St, Baltimore, MD 21216
    1221 Ashburton St, Baltimore, MD 21216
    /30

    $174,900

    $4K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,140 Sq Ft

    1221 Ashburton St, Baltimore, MD 21216

    This beautifully renovated 3-bedroom, 2-bathroom rowhome is the perfect opportunity for a first-time homebuyer looking for style, comfort, and value. Step inside and enjoy a bright, modern interior featuring updated finishes, spacious living areas, and a thoughtfully designed layout that's ready for you to move right in. The updated kitchen offers contemporary cabinetry, sleek countertops, and

    Agent Photo

    William Savage

    Keller Williams Legacy

    1221 Ashburton St, Baltimore, MD 21216
  • 1130 N Longwood St, Baltimore, MD 21216
    1130 N Longwood St, Baltimore, MD 21216
    1130 N Longwood St, Baltimore, MD 21216
    /11

    $199,999

    • 4 Beds
    • 2 Baths
    • 1,642 Sq Ft

    1130 N Longwood St, Baltimore, MD 21216

    ** AVAILABLE SOON ** 4 BEDROOM 2 BATHROOM

    Agent Photo

    Pete France

    EXP Realty, LLC

    1130 N Longwood St, Baltimore, MD 21216
  • 1209 Oakhurst Place, Baltimore, MD 21216
    1209 Oakhurst Place, Baltimore, MD 21216
    1209 Oakhurst Place, Baltimore, MD 21216
    /14

    $75,000

    $8K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    1209 Oakhurst Place, Baltimore, MD 21216

    Price Improvement----Investors OR handy homeowners don’t miss out on this porch-front home! This property presents a golden opportunity to build equity and create your dream home. Put your makeover skills to work and unlock the hidden potential of this property. With its prime location and solid bones, the possibilities are limitless. Whether you’re an experienced investor or a first-time

    Andrea Means Berkshire Hathaway HomeServices PenFed Realty

    1209 Oakhurst Place, Baltimore, MD 21216
  • 2730 Winchester St, Baltimore, MD 21216
    2730 Winchester St, Baltimore, MD 21216
    2730 Winchester St, Baltimore, MD 21216
    /32

    $82,500

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft

    2730 Winchester St, Baltimore, MD 21216

    NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Buyer to pay all transfer and recording fees Minimum $2,000 EMD. Excellent Opportunity ...use your imagination! Property can be rehabbed for a nice rental investment or homeowner. Property sold "as is". Home Inspections for informational purposes only. Seller will make no repairs. . In

    Bob Simon Long & Foster Real Estate, Inc.

    2730 Winchester St, Baltimore, MD 21216
  • 1209 Dukeland St, Baltimore, MD 21216
    1209 Dukeland St, Baltimore, MD 21216
    1209 Dukeland St, Baltimore, MD 21216
    /21

    $119,900

    • 3 Beds
    • 1 Bath
    • 1,240 Sq Ft

    1209 Dukeland St, Baltimore, MD 21216

    Well-maintained and full of potential, this 3-bedroom, 1-bath home at 1209 Dukeland St offers bright living spaces, a functional layout, and great value for both homeowners and investors. Featuring a comfortable main level, spacious bedrooms, and a convenient Baltimore location close to parks, schools, shopping, and major commuter routes, this property is ready for its next chapter. Don't miss

    Sandra Echenique Samson Properties

    1209 Dukeland St, Baltimore, MD 21216
  • 2706 Winchester St, Baltimore, MD 21216
    2706 Winchester St, Baltimore, MD 21216
    2706 Winchester St, Baltimore, MD 21216
    /16

    $89,900

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft

    2706 Winchester St, Baltimore, MD 21216

    Welcome to 2706 Winchester Street, a well-kept three-bedroom, one-bath brick townhome offering classic Baltimore style and functional living space. The main level features a bright living room, a separate dining area, and a spacious kitchen with plenty of cabinet storage. Upstairs, you’ll find three comfortable bedrooms and a full bath with updated fixtures. The lower level provides clean, open

    Jason Ekus Pavilion Real Estates L.L.C.

    2706 Winchester St, Baltimore, MD 21216
  • 1020 Poplar Grove St, Baltimore, MD 21216
    1020 Poplar Grove St, Baltimore, MD 21216
    1020 Poplar Grove St, Baltimore, MD 21216
    /16

    $10,000

    $10K PRICE DROP
    • 1,384 Sq Ft

    1020 Poplar Grove St, Baltimore, MD 21216

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 7/27/2026, 10:00 AM. Bidding ends 7/29/2026, 12:10 PM. The list price is the suggested opening bid. Deposit: $5,000. This two-story townhouse is located in the Franklintown Road neighborhood of Baltimore City. Residents can enjoy the nearby attractions and facilities such as the Leon Day

    Adam Shpritz Ashland Auction Group LLC

    1020 Poplar Grove St, Baltimore, MD 21216
  • 2926 Riggs Ave, Baltimore, MD 21216
    2926 Riggs Ave, Baltimore, MD 21216
    2926 Riggs Ave, Baltimore, MD 21216
    /12

    $62,000

    • 3 Beds
    • 1.5 Baths
    • 1,676 Sq Ft

    2926 Riggs Ave, Baltimore, MD 21216

    NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Minimum $2,000 EMD. Excellent Opportunity ...use your imagination! Property can be rehabbed for a nice rental investment or homeowner. Property sold "as is". Home Inspections for informational purposes only. Seller will make no repairs. Ask LA about 5.75% financing program.

    Bob Simon Long & Foster Real Estate, Inc.

    2926 Riggs Ave, Baltimore, MD 21216
  • 2727 Ellicott Dr, Baltimore, MD 21216
    2727 Ellicott Dr, Baltimore, MD 21216
    2727 Ellicott Dr, Baltimore, MD 21216
    /30

    $179,900

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,710 Sq Ft

    2727 Ellicott Dr, Baltimore, MD 21216

    Newly Renovated Rowhome with 3 Finished Levels & Off-Street Parking! Exceptional value meets modern style in this beautifully renovated home offering spacious living across three finished levels. The open-concept main level features wood flooring throughout, a bright and inviting living room, dedicated dining area, and a stylish galley kitchen complete with Quartz countertops and stainless steel

    Chris Cooke Berkshire Hathaway HomeServices Homesale Realty

    2727 Ellicott Dr, Baltimore, MD 21216
  • 2826 Winchester St, Baltimore, MD 21216
    2826 Winchester St, Baltimore, MD 21216
    2826 Winchester St, Baltimore, MD 21216
    /22

    $65,000

    $3K PRICE INCREASE
    • 3 Beds
    • 1 Bath
    • 1,382 Sq Ft

    2826 Winchester St, Baltimore, MD 21216

    This is a 1,350 sq ft brick-front end-unit townhouse featuring three bedrooms, a full bath and an unfinished basement ready for customization. Situated in the heart of Baltimore’s Winchester neighborhood, this property offers easy access to Upton Park, Mondawmin Mall, and multiple bus routes, making it attractive to long-term tenants. The upside is endless with this prime investment opportunity

    Moti Khan Honest Realty INC

    2826 Winchester St, Baltimore, MD 21216
Maryland Baltimore City County Baltimore

Real Estate & Homes for Sale in Winchester, Baltimore

Why Live in Winchester
Winchester, a neighborhood in Baltimore, is located less than 4 miles from downtown and features brick row houses built between 1900 and 1940, with sizes ranging from 1,000 to 1,800 square feet. Architectural designs vary, with some homes showcasing bay windows and stone porches. Many are being remodeled or renovated Local amenities include Leon Day Park, which borders Gwynns Falls/Leakin Park and offers access to the Gwynns Falls Trail with over 20 miles of walkable paths. Indoor activities are available at Easterwood and Bentalou Recreation Centers, both about a mile away, offering fitness classes, youth basketball leagues and educational programs. Community engagement is fostered through organizations like Jonah House and the Alliance of Rosemont Community Organization, which focus on sustainability and neighborhood improvement. Dining options include Lucky’s Pizza, Subs & Wings for takeout and TGI Fridays at Mondawmin Mall, which houses retail stores on three levels. Public transportation is convenient with bus stops on Poplar Grove Street, and major highways like Interstate 83 and Interstate 695 provide easy access to surrounding areas.
Learn more about living in Winchester

Winchester Home Prices vs. Nearby Baltimore, MD Neighborhoods

Winchester Mosher Biddle Street Mondawmin
Median Home Price
$82,500
$70,000
$90,000
$99,450
Median Sale Price
$70,500
$56,000
+1% YoY
$73,450
-11% YoY
$80,000
Median Single Family Price
--
$69,325
$74,900
$79,900
Median Townhouse Price
$78,750
$74,900
$134,250
$100,000
Total Active Listings
11
16
9
30
Market Conditions
7 Months of Supply
Buyer's Market
6 Months of Supply
Buyer's Market
5 Months of Supply
Balanced Market
9 Months of Supply
Buyer's Market

Frequently Asked Questions

Is Winchester a good place to live?
Winchester is a good place to live. Winchester is considered fairly walkable and bikeable with good transit options. Winchester has 6 parks for recreational activities. It is very dense in population with 26.0 people per acre and a median age of 39. The average household income is $52,612 which is below the national average. College graduates make up 10.5% of residents. A majority of residents in Winchester are renters, with 56% of residents renting and 44% of residents owning their home. A local real estate agent serving Winchester can help you decide if this neighborhood is the right one for you. Learn more on our Winchester neighborhood guide.
Is Winchester, MD a safe neighborhood?
Winchester, MD is less safe than the average neighborhood in the United States. It received a crime score of 9 out of 10.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $82,500. If you put a 20% down payment of $16,500 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $410 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $18K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $53K.
What are the best public schools in Winchester?
The best public schools that serve Winchester are:
What are the most popular zip codes in Winchester, Baltimore, MD?
The most popular zip codes in Winchester, Baltimore, MD include 21216, 21229, 21223, 21217 and 21215.
What are the most popular neighborhoods near Winchester, Baltimore, MD?
The most popular neighborhoods near Winchester, Baltimore, MD are Coppin Heights, Winchester, Franklintown Road, Mosher and Walbrook.
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