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Newest Homes for Sale in Winchester

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  • /19

    $30,000

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft

    1202 Ashburton St, Baltimore, MD 21216

    Adam Shpritz Ashland Auction Group LLC

    1202 Ashburton St, Baltimore, MD 21216
  • /42

    $20,000

    • 3 Beds
    • 1.5 Baths
    • 1,428 Sq Ft

    1208 N Longwood St, Baltimore, MD 21216

    List price is Opening Bid at the Online auction to be conducted on Auctioneers website.- Auction ends Thursday, September 24, 2026 at 11:00 AM. Welcome to 1208 N Longwood St., a classic Baltimore City townhouse offering a functional layout, multiple living spaces, and a covered front porch in the Winchester area. Whether you're looking for a primary residence or an investment opportunity,

    Carley Cooper Alex Cooper Auctioneers, Inc.

    1208 N Longwood St, Baltimore, MD 21216
  • /28

    $144,999

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1214 Dukeland St, Baltimore, MD 21216

    Welcome to 1214 Dukeland Street, a move-in-ready 3 bedroom, 2 full-bath brick home offering comfortable living space on three levels. Step inside to find new updated flooring, recessed lighting and a bright, inviting living area. The kitchen features granite countertops, stainless-steel appliances, gas cooking and a convenient breakfast bar, creating a functional space for both everyday meals and

    Glenda Rodalunas Keller Williams Gateway LLC

    1214 Dukeland St, Baltimore, MD 21216
  • /39

    $64,900

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    2810 Ellicott Dr, Baltimore, MD 21216

    2810 Ellicott Drive is a 1,200 sq ft brick-front townhouse featuring three bedrooms, a full bath and an unfinished basement ripe 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

    Stephen Pipich LPT Realty, LLC

    2810 Ellicott Dr, Baltimore, MD 21216
  • /26

    $189,000

    $50K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,456 Sq Ft

    2903 Winchester St, Baltimore, MD 21216

    Welcome to 2903 Winchester Street, a fully renovated 4-bedroom, 3-bathroom home on Baltimore’s west side that delivers modern finishes without losing its city character.Great Investment property. Currently occupied but can be delivered vacant. More equity in propertyThis property is eligible for up to $10,000 through Baltimore City’s Vacants to Value Booster program (buyer must

    Corey Brown CORE Principles Real Estate Group

    2903 Winchester 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
  • /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

    Agent Photo

    Angel Tyler

    HomeSmart

    1156 N Longwood 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
  • /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
  • /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
  • /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
  • /11

    $199,999

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

    1130 N Longwood St, Baltimore, MD 21216

    ** AVAILABLE SOON ** 4 BEDROOM 2 BATHROOM

    Pete France EXP Realty, LLC

    1130 N Longwood 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

    Agent Photo

    Sandra Echenique

    Samson Properties

    1209 Dukeland St, Baltimore, MD 21216
  • /16

    $80,000

    $25K 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. "One or more photos have been virtually staged or digitally altered for illustrative purposes"Upstairs, you���ll find

    Jason Ekus Pavilion Real Estates L.L.C.

    2706 Winchester St, Baltimore, MD 21216
  • /14

    $70,000

    $13K 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
  • /2

    $69,900

    $35K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,480 Sq Ft

    1136 N Longwood St, Baltimore, MD 21216

    BACK ON THE MARKET WITH A NEW PRICE! Investor opportunity at 1136 N Longwood St, now offered at $69,900.Calling all investors, rehabbers, and buyers ready to bring a vision to life! 1136 N Longwood St offers an opportunity to renovate and reimagine a Baltimore City rowhome at an attractive price point. This property is in need of a full renovation and is being sold strictly **AS-IS**,

    Shannel Porter T&G Real Estate Advisors, Inc.

    1136 N Longwood St, Baltimore, MD 21216

Winchester, Baltimore, MD Home Prices vs. Nearby Neighborhoods

Winchester Four By Four Mosher Biddle Street
Median Home Price
$99,250
$115,000
$71,250
$90,000
Median Sale Price
$84,500
+30% YoY
$125,000
-2% YoY
$68,750
+39% YoY
$73,450
-2% YoY
Avg. Price per Square Foot
$59
$77
$55
$239
Median Townhouse Price
$80,000
$119,000
$75,000
$134,250
Total Active Listings
16 listings
15 listings
15 listings
6 listings
Market Conditions
11 Months of Supply
Buyer's Market
6 Months of Supply
Balanced Market
6 Months of Supply
Balanced Market
3 Months of Supply
Seller'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.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $99,250. If you put a 20% down payment of $19,800 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $530 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $23K 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, 21223, 21229, 21217 and 21215.
What are the most popular neighborhoods near Winchester, Baltimore, MD?
The most popular neighborhoods near Winchester, Baltimore, MD are Mosher, Coppin Heights, Rosemont, Franklintown Road and Bridgeview-Greenlawn.
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