Vintage homes for sale & real estate in 21244, MD

12 homes

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ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
Fall in love with this expansive single family split-level home with a 2-car garage, approximately 2300 square feet, that features THREE (3) BEDROOMS and TWO (2) FULL BATHS, along with a spacious basement area and nice walkout patio that overlooks a large beautiful backyard in the picturesque and charming WINDSOR MILL COMMUNITY in Windsor Mill, MD. Boasting the distinction of being one of the largest homes in the development, this residence sits on a 23,958 sq ft lot (0.55 acre) and offers an opulent blend of space and style. With multiple bedrooms and bathrooms, this home unfolds with triple levels, offering an abundance of living space for your family's needs. Gleaming hardwood floors in

$499,900

4 beds2 baths2,298 sq ft

8711 Windsor Ml, Windsor Mill, MD 21244

Quartz countertops • Large backyard • Walkout patio

(301) 355-6104

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
We have multiple Offers On This Property, Seller is Asking for Highest and Best offer By December 29,2025 by 12 noon!! Owner has started the renovation, but could not complete them. Here's a great opportunity for you to take advantage immediate profit. Possible 4 Bedrooms and 2 Baths * Homes in the area has sold for around $350,000.00. Updated forced air heating and cooling system, Plus updated circuit breaker box. 10 minutes to Liberty Road and 696 Beltway.

$199,900

3 beds1 bath1,220 sq ft

3417 Gaither Rd, Windsor Mill, MD 21244

6,875 sq ft lot • Built 1953 • Listed 6 days

(410) 465-0083

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
Welcome to 3620 Rockdale Ter—an exceptional opportunity to transform a solid structure into your ideal home. Full of potential, this diamond in the rough is ready for your vision and personal touches. The home features 4 bedrooms and 2 baths and is conveniently located close to public transportation, shopping, and schools. Offering both accessibility and opportunity, this townhouse is ready for its next chapter. Don’t miss your chance to make it yours.

$239,900

4 beds2 baths2,092 sq ft

3620 Rockdale Ter, Windsor Mill, MD 21244

0.27 acre lot • Built 1950 • Listed 14 days

(703) 675-6100

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
Great investment opportunity in the sought-after Windsor Mill community! This three-bedroom, one full bath rancher sits on a large lot and offers endless potential for investors or savvy buyers ready to restore and reimagine. The property has fire damage from a previous small fire and is being sold as-is. Features include an expansive, fully fenced backyard with a shed and plenty of space for outdoor enjoyment or future improvements. Conveniently located near all major highways and zoned for Baltimore County Public Schools. A rare chance to add value in a desirable neighborhood—bring your vision!

$264,900

3 beds1 bath1,408 sq ft

8011 Remington Ave, Windsor Mill, MD 21244

Large lot • 0.5 acre lot • 2 parking spots

(888) 860-7369

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
This spacious 6-bed, 3-bath home in Windsor Mill delivers rare versatility, offering multiple finished levels that work perfectly for large households, multi-generational living, or rental/house-hack setups. With generous common areas, private bedroom wings, and flexible lower-level space, the layout adapts easily to guests, work-from-home needs, or long-term investment potential. The location adds major convenience: you're just minutes from I-695, I-70, Security Blvd, and Route 40, making commuting simple in any direction. Nearby amenities include local parks, shopping centers, grocery stores, restaurants, fitness options, and more. Schools and everyday essentials are all close by, roundin

$420,000

6 beds3 baths2,606 sq ft

3124 Cresson Ave, Windsor Mill, MD 21244

7,620 sq ft lot • 2 parking spots • Built 1955

(443) 573-9200

Property at 3126 Rices Ln, Windsor Mill, MD 21244, 5 beds, 3 baths

$514,990

5 beds3 baths2,026 sq ft

3126 Rices Ln, Windsor Mill, MD 21244

(410) 833-5400

Property at 3629 Marriotts Ln, Windsor Mill, MD 21244, 3 beds, 1 bath

$282,000

3 beds1 bath1,470 sq ft

3629 Marriotts Ln, Windsor Mill, MD 21244

(410) 531-0321

Property at 3508 Joann Dr, Windsor Mill, MD 21244, 5 beds, 2 baths

$439,000

5 beds2 baths2,500 sq ft

3508 Joann Dr, Windsor Mill, MD 21244

(443) 632-3000

Property at 8400 Liberty Rd, Windsor Mill, MD 21244, 3 beds, 3.5 baths

$449,900

3 beds3.5 baths1,786 sq ft

8400 Liberty Rd, Windsor Mill, MD 21244

(301) 346-5286

Property at 5713 Old Court Rd, Windsor Mill, MD 21244, 3 beds, 3 baths

$349,900

3 beds3 baths2,587 sq ft

5713 Old Court Rd, Windsor Mill, MD 21244

(410) 312-0000

Property at 3715 Washington Ave, Windsor Mill, MD 21244, 3 beds, 2 baths

$399,900

3 beds2 baths3,788 sq ft

3715 Washington Ave, Windsor Mill, MD 21244

(410) 486-4504

Property at 8305 Windsor Mill Rd, Windsor Mill, MD 21244, 3 beds, 1 bath

$389,900

3 beds1 bath2,886 sq ft

8305 Windsor Mill Rd, Windsor Mill, MD 21244

(443) 838-4044

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
Welcome to 801 Sturgis Place, a thoughtfully designed raised ranch nestled in the established Williamsburg neighborhood of Pikesville—a community well-loved for its quiet streets, walkability, and convenient access to everyday essentials. Built in 1959, this solid brick home offers nearly 1,800 square feet of comfortable living space, with a layout that lends itself beautifully to main-level, one-floor living. The primary living areas, bedrooms, and full bath are all conveniently located on the main level—ideal for those seeking fewer stairs and easy daily living. The home features three generously sized bedrooms and one and a half bathrooms, providing flexibility for guests, ho

$328,000

3 beds1.5 baths1,184 sq ft

801 Sturgis Pl, Pikesville, MD 21208

8,712 sq ft lot • Built 1959

(410) 312-0000

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
Coming soon!

$399,900

4 beds2 baths1,920 sq ft

6727-H Windsor Mill Rd, Gwynn Oak, MD 21207

8,100 sq ft lot • Built 1938 • Listed 6 days

(888) 455-6040

COMING SOON

$484,951

4 beds4 baths1,953 sq ft

4761 Bonnie Brae Rd, Pikesville, MD 21208

8,842 sq ft lot • Garage • Built 1959

(410) 453-0500

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
Welcome to 3213 Dorycon Drive, a well-maintained detached brick rancher in the established Milford Gardens community. Step inside to beautiful hardwood floors throughout the main level, 3 spacious bedrooms, and 1.5 updated baths. The updated kitchen offers modern finishes and great functionality for everyday living. The fully open lower level is a true blank canvas—create the rec room, family retreat, home office, gym, or man cave you’ve been dreaming about. The lower level features carpeting, gas heat, sump pumps, washer/dryer, and plenty of storage. Outside, enjoy off-street parking, a storage shed, and a peaceful backyard that backs to trees for added privacy. Solid brick con

$320,000

3 beds1.5 baths2,262 sq ft

3213 Doycron Ct, Gwynn Oak, MD 21207

Storage shed • Updated kitchen • Off-street parking

(443) 233-6156

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
Located in the charming and sought-after Historic Fieldstone community of Randallstown, this 3-bedroom, 1-bath Colonial offers a rare opportunity to restore a piece of local history. Set on a quiet street with classic Colonial architecture, the home features a traditional floor plan with spacious rooms, original details, and solid bones—ready for a full renovation. This property presents an ideal canvas for buyers or investors looking to customize a home in a well-established neighborhood known for its character and long-standing charm. Bring your vision and creativity—this is a chance to reimagine a home in one of Randallstown’s most unique and historic communities. Sched

$170,000

3 beds1 bath2,020 sq ft

3603 Fieldstone Rd, Randallstown, MD 21133

Original details • Full renovation • 0.25 acre lot

(410) 988-4929

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21244, MD:
COMING SOON !!!

$359,000

4 beds2 baths1,783 sq ft

3525 Essex Rd, Gwynn Oak, MD 21207

6,937 sq ft lot • Built 1951 • Listed 15 days

(301) 298-1001

Property at 7017 Lancaster Rd, Pikesville, MD 21207, 3 beds, 3 baths

$399,900

3 beds3 baths2,450 sq ft

7017 Lancaster Rd, Pikesville, MD 21207

(410) 729-7700

Property at 8504 Fieldway Dr, Randallstown, MD 21133, 3 beds, 2 baths

$400,000

3 beds2 baths1,594 sq ft

8504 Fieldway Dr, Randallstown, MD 21133

(410) 729-7700

Property at 1005 Parkvalley Ct, Pikesville, MD 21208, 4 beds, 2 baths

$364,900

4 beds2 baths1,507 sq ft

1005 Parkvalley Ct, Pikesville, MD 21208

(410) 453-0500

Property at 906 Scotts Hill Dr, Pikesville, MD 21208, 4 beds, 2 baths

$379,900

4 beds2 baths1,662 sq ft

906 Scotts Hill Dr, Pikesville, MD 21208

(410) 453-0500

Property at 9210 Liberty Rd, Randallstown, MD 21133, 3 beds, 2 baths

$309,000

3 beds2 baths1,445 sq ft

9210 Liberty Rd, Randallstown, MD 21133

(443) 317-8125

Property at 3 Bright Cir, Gwynn Oak, MD 21207, 3 beds, 1 bath

$285,000

3 beds1 bath1,088 sq ft

3 Bright Cir, Gwynn Oak, MD 21207

(301) 966-0035

Property at 704 Cloudyfold Dr, Pikesville, MD 21208, 3 beds, 2.5 baths

$359,990

3 beds2.5 baths1,838 sq ft

704 Cloudyfold Dr, Pikesville, MD 21208

(866) 987-3937

Property at 6907 Schissler Ave, Gwynn Oak, MD 21207, 5 beds, 2 baths

$329,990

5 beds2 baths960 sq ft

6907 Schissler Ave, Gwynn Oak, MD 21207

(301) 439-9500

Property at 3700 Crossleigh Ct, Randallstown, MD 21133, 4 beds, 1.5 baths

$350,000

4 beds1.5 baths1,628 sq ft

3700 Crossleigh Ct, Randallstown, MD 21133

(410) 729-7700

Property at 8205 Arrowhead Rd, Pikesville, MD 21208, 4 beds, 2 baths

$365,000

4 beds2 baths1,732 sq ft

8205 Arrowhead Rd, Pikesville, MD 21208

(410) 544-2931

Property at 3497 Hillsmere Rd, Gwynn Oak, MD 21207, 4 beds, 3 baths

$379,900

4 beds3 baths1,688 sq ft

3497 Hillsmere Rd, Gwynn Oak, MD 21207

(410) 255-3690

Property at 3821 Brownhill Rd, Randallstown, MD 21133, 3 beds, 3.5 baths

$425,000

3 beds3.5 baths2,706 sq ft

3821 Brownhill Rd, Randallstown, MD 21133

Property at 6500 Gilmore, Gwynn Oak, MD 21207, 4 beds, 2 baths

$370,000

4 beds2 baths1,480 sq ft

6500 Gilmore, Gwynn Oak, MD 21207

(301) 352-4065

$310,000

3 beds1.5 baths1,754 sq ft

3401 Yataruba Dr, Gwynn Oak, MD 21207

(240) 737-5000

Vintage Homes for Sale in 21244

There are currently 12 vintage homes for sale in 21244 at a median listing price of $325K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21244 stay on the market for 43 days and receive 1 offers. This map is refreshed with the newest listings in 21244 every 15 minutes.

In the past month, 23 homes have been sold in 21244. In addition to houses in 21244, there were also 7 condos, 31 townhouses, and 1 multi-family unit for sale in 21244 last month. Find your dream home in 21244 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21244 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21244. If you're looking to sell your home in the 21244 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21244 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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