Winchester, MD homes for sale & real estate

19 homes

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$30,000

3 beds1 bath1,140 sq ft

1202 Ashburton St, Baltimore, MD 21216

Built 1940 • Listed 7 days

(410) 488-3124

ABOUT THIS HOME
Winchester, MD Homes for Sale
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, this property provides a solid foundation with room to make it your own. The main level features an inviting entryway, spacious living room, and separate dining room, all showcasing wood flooring. The kitchen offers laminated wood flooring and provides a functional space for everyday living and entertain

$20,000

3 beds1.5 baths1,428 sq ft

1208 N Longwood St, Baltimore, MD 21216

Covered front porch • Wood flooring • Versatile bonus room

(410) 828-4838

3D WALKTHROUGH

ABOUT THIS HOME
Winchester, MD Homes for Sale
MOVE IN READY TOWNHOME IN BALTIMORE!! END ROW TOWNHOME FRESHLY PAINTED THROUGH OUT, UPDATED LVP FLOORING. .. PREVIOUS RENTAL PROPERTY - WAS RENTED FOR $1660 PER MONTH!! Welcome to 1044 Ellicott Driveway in Baltimore, MD, a charming and inviting home offering a wonderful combination of comfort, character, and convenience. This well-maintained residence features spacious living areas filled with natural light, creating a warm and welcoming atmosphere throughout. The thoughtfully designed layout provides comfortable everyday living along with flexible spaces perfect for entertaining, working from home, or relaxing with family and friends. The kitchen offers ample cabinetry, quartz counters, ga

$99,950

2 beds1 bath900 sq ft

1044 Ellicott Driveway, Baltimore, MD 21216

Quartz counters • End row townhome • Ample cabinetry

(410) 461-2800

ABOUT THIS HOME
Winchester, MD Homes for Sale
ONLINE AUCTION: Bidding begins 9/14/2026, 10:00 AM. Bidding ends 9/16/2026, 12:30 PM. List Price is Suggested Opening Bid. Deposit: $10,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. 2 Story Townhouse located in the Winchester area of Baltimore City. Residents can enjoy the nearby attractions such as Coppin State University, Leon Day Park, West Baltimore MARC Station, Mondawmin Mall, Walbrook Junction Shopping Center. Property is Vacant. Easy Access to Major Traffic Artery North Ave.

$50,000

3 beds2 baths1,140 sq ft

1231 Ashburton St, Baltimore, MD 21216

Leon day park • 2 story townhouse • Mondawmin mall

(410) 488-3124

ABOUT THIS HOME
Winchester, MD Homes for Sale
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 opportunity.

$64,900

3 beds1.5 baths1,200 sq ft

2810 Ellicott Dr, Baltimore, MD 21216

Heart of baltimore • Unfinished basement • Multiple bus routes

(877) 366-2213

Property at 1214 Dukeland St, Baltimore, MD 21216, 3 beds, 2 baths

$154,999

3 beds2 baths1,204 sq ft

1214 Dukeland St, Baltimore, MD 21216

(443) 318-8800

Property at 1137 Poplar Grove St, Baltimore, MD 21216, 3 beds, 2 baths

$110,000

3 beds2 baths1,440 sq ft

1137 Poplar Grove St, Baltimore, MD 21216

(410) 453-0500

Property at 1100 Ashburton St, Baltimore, MD 21216, 3 beds, 2 baths

$155,000

3 beds2 baths1,500 sq ft

1100 Ashburton St, Baltimore, MD 21216

(410) 814-2400

Property at 1221 Ashburton St, Baltimore, MD 21216, 3 beds, 1.5 baths

$174,900

3 beds1.5 baths1,140 sq ft

1221 Ashburton St, Baltimore, MD 21216

(443) 660-9229

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

$80,000

3 beds1 bath1,260 sq ft

2706 Winchester St, Baltimore, MD 21216

(202) 740-6708

Property at 2730 Riggs Ave, Baltimore, MD 21216, 3 beds, 1 bath

$70,000

3 beds1 bath1,384 sq ft

2730 Riggs Ave, Baltimore, MD 21216

(410) 793-7195

Property at 2727 Ellicott Dr, Baltimore, MD 21216, 4 beds, 2 baths

$179,900

4 beds2 baths1,710 sq ft

2727 Ellicott Dr, Baltimore, MD 21216

(410) 814-2400

Property at 1156 N Longwood St, Baltimore, MD 21216, 3 beds, 2 baths

$125,000

3 beds2 baths1,480 sq ft

1156 N Longwood St, Baltimore, MD 21216

(301) 434-4065

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

$70,000

3 beds1 bath1,408 sq ft

1209 Oakhurst Pl, Baltimore, MD 21216

(410) 828-4700

Property at 2730 Winchester St, Baltimore, MD 21216, 3 beds, 1 bath

$82,500

3 beds1 bath1,260 sq ft

2730 Winchester St, Baltimore, MD 21216

(410) 453-0500

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

$65,000

3 beds1 bath1,382 sq ft

2826 Winchester St, Baltimore, MD 21216

(443) 405-2535

Property at 1130 N Longwood St, Baltimore, MD 21216, 4 beds, 2 baths

$199,999

4 beds2 baths1,642 sq ft

1130 N Longwood St, Baltimore, MD 21216

(888) 860-7369

Property at 1136 N Longwood St, Baltimore, MD 21216, 4 beds, 1.5 baths

$69,900

4 beds1.5 baths1,480 sq ft

1136 N Longwood St, Baltimore, MD 21216

(877) 840-0144

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

$119,900

3 beds1 bath1,240 sq ft

1209 Dukeland St, Baltimore, MD 21216

(443) 317-8125

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End of results

Nearby homes that match your criteria

$50,000

3 beds1 bath1,142 sq ft

2865 W Lafayette Ave, Baltimore, MD 21216

Built 1920

(410) 488-3124

ABOUT THIS HOME
Winchester, MD Homes for Sale
Experience the epitome of modern luxury in this beautifully renovated townhouse, set to impress with its extensive upgrades completed in 2026. Nestled in the charming Mosher neighborhood, this residence seamlessly blends classic elegance with contemporary sophistication, offering a lifestyle that is both exclusive and inviting. Step inside to discover a thoughtfully designed interior that boasts four spacious bedrooms and two and a half luxurious bathrooms. The open-concept layout is perfect for both entertaining and everyday living, allowing natural light to flood the space and create a warm, welcoming atmosphere. The full daylight basement offers endless possibilities, whether you envisio

$249,000

4 beds2 baths1,932 sq ft

2719 Riggs Ave, Baltimore, MD 21216

Renovated townhouse • Low maintenance yard • Gourmet kitchen

(443) 336-5623

ABOUT THIS HOME
Winchester, MD Homes for Sale
ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform Bidding begins 9/22/2026 @ 10:00 AM. Bidding ends 9/24/2026 @ 11:30 AM. List Price is Suggested Opening Bid. Deposit: $5,000. This two-story, porch-front townhouse is located in the Franklintown Road neighborhood of Baltimore City. The property is vacant. It is situated near Leon Day Park, Gwynns Falls/Leakin Park, and Coppin State University. The property also offers access to major transportation routes, including the Franklin-Mulberry Expressway (U. S. Route 40), providing connections to surrounding areas of Baltimore.

$25,000

3 beds2 baths1,408 sq ft

2913 W Mosher St, Baltimore, MD 21216

Two story townhouse • Built 1920 • Listed 7 days

(410) 488-3124

FLOOR PLAN

$59,990

2 beds1 bath952 sq ft

1412 N Dukeland St, Baltimore, MD 21216

Built 1920 • Listed 12 days

(888) 860-7369

ABOUT THIS HOME
Winchester, MD Homes for Sale
ONLINE REAL ESTATE AUCTION!! Bidding Opens - Tuesday, September 29, 2026. Bidding Closes - Wednesday, September 30, 2026 at 11:15 AM. List price is opening bid only. 2818 Presstman Street is located in the “Northwest Community Action” neighborhood of west Baltimore, east of Poplar Grove Street, west of Dukeland Street, south of Baker Street and north of Ellicott Driveway. The surrounding area is mainly comprised of two story townhomes, built in the 1930s through 1950s. Homes are owner and tenant occupied. The location is convenient to public transportation, Coppin State University and Downtown Baltimore.

$10,000

3 beds1.5 baths1,400 sq ft

2818 Presstman St, Baltimore, MD 21216

Built 1940 • Listed 15 days

(410) 296-8440

ABOUT THIS HOME
Winchester, MD Homes for Sale
AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Welcome to 2737 Riggs Avenue in Baltimore, Maryland a beautifully renovated home where classic charm meets modern comfort. As you approach the property, you’ll be greeted by a brand-new front porch with durable Trex flooring, the perfect spot to enjoy your morning coffee or greet neighbors passing by. Step through the new front door, and you’ll immediately notice the attention to detail and high-quality craftsmanship throughout. The main level welcomes you with fresh paint, elegant crown molding, recessed lighting, and beautiful luxury vinyl plank flooring that flows seamlessly from the living room through the dining area and int

$145,000

3 beds1.5 baths1,412 sq ft

2737 Riggs Ave, Baltimore, MD 21216

Move-in ready • New front porch • Fenced backyard

(410) 312-0000

Property at 2825 Presstman St, Baltimore, MD 21216, 4 beds, 2 baths

$230,000

4 beds2 baths1,548 sq ft

2825 Presstman St, Baltimore, MD 21216

(888) 860-7369

Property at 2917 W Mosher St, Baltimore, MD 21216, 2 beds, 1 bath

$20,000

2 beds1 bath1,408 sq ft

2917 W Mosher St, Baltimore, MD 21216

(410) 488-3124

Property at 972 N Franklintown Rd, Baltimore, MD 21216, 5 beds, 3.5 baths

$269,900

5 beds3.5 baths1,360 sq ft

972 N Franklintown Rd, Baltimore, MD 21216

(443) 318-8800

Property at 2903 Winchester St, Baltimore, MD 21216, 4 beds, 3 baths

$189,000

4 beds3 baths1,456 sq ft

2903 Winchester St, Baltimore, MD 21216

(410) 258-3792

Property at 988 N Franklintown Rd, Baltimore, MD 21216, 3 beds, 1 bath

$34,900

3 beds1 bath1,380 sq ft

988 N Franklintown Rd, Baltimore, MD 21216

(888) 219-3009

Property at 3023 Brighton St, Baltimore, MD 21216, 3 beds, 2 baths

$84,900

3 beds2 baths1,320 sq ft

3023 Brighton St, Baltimore, MD 21216

(410) 531-0321

Property at 1308 N Longwood St N, Baltimore, MD 21216, 3 beds, 2 baths

$215,000

3 beds2 baths1,860 sq ft

1308 N Longwood St N, Baltimore, MD 21216

(443) 343-7660

Property at 1517 N Ellamont St, Baltimore, MD 21216, 4 beds, 2.5 baths

$239,900

4 beds2.5 baths2,186 sq ft

1517 N Ellamont St, Baltimore, MD 21216

(717) 755-5599

Property at 2802 W Lafayette Ave, Baltimore, MD 21216, 1 bath

$15,000

— beds1 bath1,176 sq ft

2802 W Lafayette Ave, Baltimore, MD 21216

(410) 488-3124

Property at 910 N Dukeland St, Baltimore, MD 21216, 2 beds, 1 bath

$20,000

2 beds1 bath960 sq ft

910 N Dukeland St, Baltimore, MD 21216

(410) 488-3124

Property at 2946 Presstman St, Baltimore, MD 21216, 3 beds, 2 baths

$145,000

3 beds2 baths1,446 sq ft

2946 Presstman St, Baltimore, MD 21216

(410) 465-8300

Property at 1411 N Rosedale St, Baltimore, MD 21216, 3 beds, 1.5 baths

$89,900

3 beds1.5 baths1,180 sq ft

1411 N Rosedale St, Baltimore, MD 21216

(410) 814-2400

Property at 2919 Belmont Ave, Baltimore, MD 21216, 4 beds, 1 bath

$59,900

4 beds1 bath1,400 sq ft

2919 Belmont Ave, Baltimore, MD 21216

(410) 814-2400

Property at 970 N Franklintown Rd, Baltimore, MD 21216, 3 beds, 2 baths

$149,900

3 beds2 baths1,180 sq ft

970 N Franklintown Rd, Baltimore, MD 21216

(410) 721-0103

Average home prices near Winchester, MD

Cities

Neighborhoods

Hampden homes for sale
$349,950
Reservoir Hill homes for sale
$384,995
Violetville homes for sale
$179,950
Bolton Hill homes for sale
$487,495
Morrell Park homes for sale
$144,950
Washington Village-Pigtown homes for sale
$139,999
Ashburton homes for sale
$355,000
Remington homes for sale
$259,900
Downtown Baltimore homes for sale
$150,000
Woodberry homes for sale
$319,950

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)

$124,940

+87.2% YoY | Aug 2026

1 year
3 year
5 year

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

Location

Data

Aug 2026

Growth

% YoY

Winchester, MD

$124,940

+87.2%

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15 Redfin agents serving Winchester

370

Deals*

4.8

Satisfaction

1880

Homes closed*

* Data from the last year

Popular Markets in Maryland

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