Winchester, MD homes for sale & real estate

16 homes

Sort:

Recommended

ABOUT THIS HOME
Winchester, MD Homes for Sale
Welcome to 1221 Ashburton St — a beautifully renovated 3-bedroom, 1.5-bath home blending modern style with everyday comfort. The main level features new LVP flooring and an open floor plan living area highlighted by a custom accent wall that adds a designer touch. The brand-new kitchen impresses with quartz countertops, a stylish backsplash, and stainless steel appliances. Upstairs, you’ll find three comfortable bedrooms and a stylish full bath with large, dramatic wall tile and sleek black fixtures. The finished basement offers additional living space and a convenient half bath. A fenced-in yard provides private outdoor enjoyment. Located on a quiet street in a growing area wit

$189,990

3 beds1.5 baths1,710 sq ft

1221 Ashburton St, Baltimore, MD 21216

Open floor plan • Quartz countertops • Renovated home

(410) 814-2400

ABOUT THIS HOME
Winchester, MD Homes for Sale
Discover exceptional value and untapped potential with this beautifully updated 3-bedroom, 1-bath home brimming with character. Thoughtfully renovated, it features modern stainless steel appliances, luxury vinyl tile, and plush wall-to-wall carpeting. Enjoy the charm of a covered front porch, host memorable gatherings in the finished basement with a built-in bar, and relax by the decorative fireplace or on the rear balcony — perfect for morning coffee or quiet evenings. With existing ductwork already in place for easy central air installation and an FHA appraisal on hand at $135,000, this property offers outstanding affordability. Surrounded by community homes selling in the low to mi

$130,000

3 beds1 bath1,730 sq ft

2732 Riggs Ave, Baltimore, MD 21216

Covered front porch • Decorative fireplace • Existing ductwork

(443) 660-9229

3D WALKTHROUGH

ABOUT THIS HOME
Winchester, MD Homes for Sale
Discover a fantastic investment opportunity with 1044 Ellicott Driveway, Baltimore, MD 21216—a fully renovated 2-bedroom, 1-bath home in the Winchester neighborhood. This property delivers strong rental potential and modern appeal. Renovated between 2020–2021, the home features a bright and stylish kitchen complete with stainless steel appliances, quartz countertops, and updated flooring. Generous storage throughout the home ensures comfortable living, while the enclosed rear yard offers privacy and the potential to add a parking pad for added convenience.

$155,000

2 beds1 bath900 sq ft

1044 Ellicott Driveway, Baltimore, MD 21216

Built 1950 • Listed 19 days

(703) 378-8810

COMING SOON

ABOUT THIS HOME
Winchester, MD Homes for Sale
Welcome to 2741 Winchester Street, a traditional-style interior row/ townhome offering a well-maintained, income-producing opportunity. This property features three bedrooms, one full bathroom, and one half bath, with luxury vinyl flooring throughout. Fully renovated in 2020, the home includes an updated kitchen with upgraded countertops and stainless steel appliances. Whether you’re expanding your portfolio or seeking a turnkey rental, this is an opportunity you won’t want to miss.

$175,000

3 beds1.5 baths1,356 sq ft

2741 Winchester St, Baltimore, MD 21216

Built 1920 • Listed 9 days

(703) 378-8810

ABOUT THIS HOME
Winchester, MD Homes for Sale
Price Reduction. Bank Owned Property. Due to condition, anyone wanting to enter the property has to sign the Hold Harmless Agreement which is included in the documents section. Serious buyers only Home is strictly sold AS-IS, offer with inspection or other contingencies will not be accepted. Buyer to verify if Ground Rent exists.

$29,900

3 beds1 bath1,575 sq ft

2714 Riggs Ave, Baltimore, MD 21216

Built 1912 • Listed 120 days

(410) 465-1770

Property at 1204 N Longwood St, Baltimore, MD 21216, 5 beds, 2 baths

$144,500

5 beds2 baths1,276 sq ft

1204 N Longwood St, Baltimore, MD 21216

(888) 860-7369

Property at 1215 Poplar Grove St, Baltimore, MD 21216, 4 beds, 2 baths

$59,900

4 beds2 baths1,512 sq ft

1215 Poplar Grove St, Baltimore, MD 21216

(866) 807-9087

Property at 1209 Dukeland St, Baltimore, MD 21216, 3 beds, 1 bath

$130,000

3 beds1 bath1,240 sq ft

1209 Dukeland St, Baltimore, MD 21216

(443) 318-8800

Property at 2807 Winchester St, Baltimore, MD 21216, 3 beds, 1 bath

$25,000

3 beds1 bath1,384 sq ft

2807 Winchester St, Baltimore, MD 21216

(410) 488-3124

Property at 1221 Poplar Grove St, Baltimore, MD 21216, 3 beds, 2 baths

$160,000

3 beds2 baths1,512 sq ft

1221 Poplar Grove St, Baltimore, MD 21216

(301) 850-0255

Property at 2754 Riggs Ave, Baltimore, MD 21216

$60,000

— beds— baths1,452 sq ft

2754 Riggs Ave, Baltimore, MD 21216

(301) 388-2600

Property at 2810 Ellicott Dr, Baltimore, MD 21216, 3 beds, 1.5 baths

$81,900

3 beds1.5 baths1,200 sq ft

2810 Ellicott Dr, Baltimore, MD 21216

(410) 220-4648

Property at 1209 Oakhurst Pl, Baltimore, MD 21216, 3 beds, 1 bath

$82,500

3 beds1 bath1,408 sq ft

1209 Oakhurst Pl, Baltimore, MD 21216

(410) 828-4700

Property at 2826 Winchester St, Baltimore, MD 21216, 3 beds, 1 bath

$85,000

3 beds1 bath1,382 sq ft

2826 Winchester St, Baltimore, MD 21216

(443) 405-2535

Property at 2706 Winchester St, Baltimore, MD 21216, 3 beds, 1 bath

$104,500

3 beds1 bath1,260 sq ft

2706 Winchester St, Baltimore, MD 21216

(202) 740-6708

Property at 1136 N Longwood St, Baltimore, MD 21216, 4 beds, 1 bath

$79,500

4 beds1 bath1,480 sq ft

1136 N Longwood St, Baltimore, MD 21216

(877) 840-0144

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

ABOUT THIS HOME
Winchester, MD Homes for Sale
Investor’s ALERT. Great opportunity for Investor to buy renovated and hold or fix and flip as they choose. This 3 bedroom, 1 bath is offer as-is CASH , Hard money or private lenders. ! Buyer pays all closing and recordation fees . Sold strictly as is. Buyer to verify all listing information. please text showing contact for more information. Due to condition, anyone wanting to enter the property has to sign the Hold Harmless agreement and email to the listing agent.

$54,000

3 beds1 bath1,540 sq ft

1420 Poplar Grove St, Baltimore, MD 21216

Built 1915 • Listed 4 days

(443) 320-1344

ABOUT THIS HOME
Winchester, MD Homes for Sale
Welcome to 2712 Mosher St. , Baltimore, MD 21216 — a fully renovated 3-bedroom, 2-bath home offering modern comfort and timeless charm. Enjoy an open floor plan with a spacious living and dining area, a beautifully updated kitchen with granite countertops and white cabinets, and durable LVP flooring throughout. This home features a brand-new HVAC system and updated electrical for peace of mind. The bedrooms are generously sized, and both bathrooms have been tastefully updated. Conveniently located near schools, parks, amenities, and transportation, this move-in-ready home is the perfect blend of style and convenience.

$200,000

3 beds2 baths1,288 sq ft

2712 W Mosher St, Baltimore, MD 21216

Fully renovated • Open floor plan • White cabinets

(410) 740-7100

ABOUT THIS HOME
Winchester, MD Homes for Sale
Charming home located in Baltimore City. 3 bedrooms 1 bath. Unfinished basement for storage or added living space. Fenced in rear yard. Close to shops schools and transportation. Don't miss out on this one!

$70,000

3 beds1 bath1,680 sq ft

1508 Poplar Grove St, Baltimore, MD 21216

Close to schools • Unfinished basement • Fenced in rear yard

(844) 845-9576

ABOUT THIS HOME
Winchester, MD Homes for Sale
ONLINE AUCTION: Bidding begins 1/2/2026 @ 10:00 AM. Bidding ends 1/6/2026 @ 12:50 PM. List Price is Suggested Opening Bid. Deposit: $5,000. 2 Story Townhouse located in the Mosher area. JUST MINUTES to Gwynns Falls Park and Coppin State University. Easy access to major traffic artery W Franklin Rd. Property is vacant.

$20,000

2 beds1 bath960 sq ft

910 N Dukeland St, Baltimore, MD 21216

Gwynns falls park • 2 story townhouse • Built 1920

(410) 488-3124

ABOUT THIS HOME
Winchester, MD Homes for Sale
This updated townhome offers fresh paint, new flooring, and a clean layout that works well for both homeowners and investors. The main level provides a bright living area with good flow into the kitchen. Upstairs you will find comfortable bedrooms and a full bath. The lower level gives you additional storage and flexible space. The rear yard offers room for outdoor use. Convenient access to major commuter routes, local parks, and city amenities makes this property a practical choice for anyone looking for value and potential in the West Baltimore area.

$160,000

3 beds1 bath1,288 sq ft

2711 Riggs Ave, Baltimore, MD 21216

Flexible space • Bright living area • Rear yard

(410) 729-7700

ABOUT THIS HOME
Winchester, MD Homes for Sale
* * * 𝗠𝗼𝗿𝗲 𝗱𝗲𝘁𝗮𝗶𝗹𝘀 𝗰𝗼𝗻𝘁𝗮𝗰𝘁 𝗖𝗼-𝗟𝗶𝘀𝘁𝗲𝗿. * * * Motivated Seller. * * * Seller prefers to use KTL Title for settlement/title services as they've already performed title work on the subject property. * * Stunning End-of-Row Townhouse with Modern Updates – Move-In Ready! * * Welcome to your dream home! This beautifully decorated end-of-row townhouse offers a perfect blend of modern features and spacious living. Don't miss the chance to make it yours! - * * New roof (2021). - * * * * Hardwood Floors Throughout: Gleaming hardwood floors (2023) create a warm, seamless feel across the entire home. - * * Fresh paint throughout, A/C, Heating system, and Wat

$275,000

3 beds2.5 baths1,824 sq ft

1036 Poplar Grove St, Baltimore, MD 21216

Built 1935 • Listed 33 days

(703) 378-8810

Property at 1405 N Longwood St, Baltimore, MD 21216, 3 beds, 2.5 baths

$215,000

3 beds2.5 baths1,932 sq ft

1405 N Longwood St, Baltimore, MD 21216

(410) 367-6500

Property at 1031 N Ashburton St, Baltimore, MD 21216, 3 beds, 1 bath

$15,000

3 beds1 bath1,470 sq ft

1031 N Ashburton St, Baltimore, MD 21216

(410) 488-3124

Property at 2902 W Mosher St, Baltimore, MD 21216, 3 beds, 1.5 baths

$129,000

3 beds1.5 baths1,128 sq ft

2902 W Mosher St, Baltimore, MD 21216

(410) 498-5408

Property at 3119 Brighton St, Baltimore, MD 21216, 3 beds, 1 bath

$80,000

3 beds1 bath1,160 sq ft

3119 Brighton St, Baltimore, MD 21216

(410) 488-3124

Property at 3206 Westmont Ave, Baltimore, MD 21216, 3 beds, 1 bath

$130,000

3 beds1 bath1,280 sq ft

3206 Westmont Ave, Baltimore, MD 21216

(240) 737-5000

Property at 3118 Normount Ave, Baltimore, MD 21216, 3 beds, 2 baths

$174,900

3 beds2 baths1,725 sq ft

3118 Normount Ave, Baltimore, MD 21216

(571) 292-5377

Property at 2737 Riggs Ave, Baltimore, MD 21216, 3 beds, 1.5 baths

$235,000

3 beds1.5 baths1,412 sq ft

2737 Riggs Ave, Baltimore, MD 21216

(410) 312-0000

Property at 945 Ellicott Drwy, Baltimore, MD 21216, 3 beds, 1 bath

$64,900

3 beds1 bath1,260 sq ft

945 Ellicott Drwy, Baltimore, MD 21216

(410) 224-2200

Property at 2721 W Mosher St, Baltimore, MD 21216, 2 beds, 1.5 baths

$215,900

2 beds1.5 baths1,288 sq ft

2721 W Mosher St, Baltimore, MD 21216

(443) 318-8800

Property at 2915 W Mosher St, Baltimore, MD 21216, 3 beds, 1 bath

$30,000

3 beds1 bath1,408 sq ft

2915 W Mosher St, Baltimore, MD 21216

(410) 488-3124

Property at 1013 Poplar Grove St, Baltimore, MD 21216, 4 beds, 2.5 baths

$130,000

4 beds2.5 baths1,968 sq ft

1013 Poplar Grove St, Baltimore, MD 21216

(443) 542-2251

Property at 3057 Brighton St, Baltimore, MD 21216, 3 beds, 2 baths

$90,000

3 beds2 baths1,336 sq ft

3057 Brighton St, Baltimore, MD 21216

(410) 531-0321

Property at 2917 Belmont Ave, Baltimore, MD 21216, 4 beds, 2.5 baths

$124,999

4 beds2.5 baths1,820 sq ft

2917 Belmont Ave, Baltimore, MD 21216

(301) 970-2447

$160,000

4 beds3.5 baths2,102 sq ft

1025 Poplar Grove St, Baltimore, MD 21216

(240) 535-7711

Average home prices near Winchester, MD

Cities

Neighborhoods

Hampden homes for sale
$350,000
Reservoir Hill homes for sale
$392,490
Upton homes for sale
$259,450
Greenspring homes for sale
$225,000
Bolton Hill homes for sale
$437,495
Washington Village-Pigtown homes for sale
$162,500
Morrell Park homes for sale
$135,000
Ashburton homes for sale
$375,000
Remington homes for sale
$349,999
Downtown Baltimore homes for sale
$199,000

Winchester, MD real estate trends

All Home Types trends in Winchester, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$97,000

+100.0% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Winchester, MD

$97,000

+100.0%

See more Winchester, MD market insights

More to explore in Winchester, MD

How to buy a house in Winchester, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.