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$2,900,000

Discover Glenoak — a nearly 9-acre estate overlooking the Greenspring Valley Hunt Club Golf Course with truly unparalleled panoramic views. Steeped in the rich history of Greenspring Valley, Glenoak is a property of a caliber nearly impossible to replicate today. As you wind along the private drive toward the stone manor house, you feel like you are worlds away — yet so convenient to everything. Offering 7 bedrooms and 5.5 bathrooms, the home includes a versatile East Wing with its own exterior entrance — ideal for an in-law suite, au pair, or guests. Step outside to the patio and take in sweeping views of the golf course, private pool, mature trees, and beautifully landscaped grounds. An entertainer’s dream, the expansive setting provides the perfect backdrop for pool days, gatherings with family and friends, and effortless outdoor entertaining. With the Greenspring Valley Hunt Club just beyond your backyard, enjoy the fun and convenience of a true golf course lifestyle. Extensively updated from the inside out, the property has undergone a comprehensive transformation while thoughtfully preserving its historic character. Beyond the beautiful cosmetic enhancements, the infrastructure has been thoroughly modernized, including updated plumbing and electrical, refinished hardwood floors throughout, and extensive improvements to the major mechanical components. Meticulously maintained and impeccably cared for, the property offers the rare opportunity to enjoy the character and beauty of a historic estate with the comfort and confidence of a thoroughly modernized home. Glenoak is a truly special Greenspring Valley estate — the house so many have admired from afar, now ready to be called home.

7 Beds ⋅ 6 Baths

Discover Glenoak — a nearly 9-acre estate overlooking the Greenspring Valley Hunt Club Golf Course with truly unparalleled panoramic views. Steeped in the rich history of Greenspring Valley, Glenoak is a property of a caliber nearly impossible to replicate today. As you wind along the private drive toward the stone manor house, you feel like you are worlds away — yet so convenient to everything. Offering 7 bedrooms and 5.5 bathrooms, the home includes a versatile East Wing with its own exterior entrance — ideal for an in-law suite, au pair, or guests. Step outside to the patio and take in sweeping views of the golf course, private pool, mature trees, and beautifully landscaped grounds. An entertainer’s dream, the expansive setting provides the perfect backdrop for pool days, gatherings with family and friends, and effortless outdoor entertaining. With the Greenspring Valley Hunt Club just beyond your backyard, enjoy the fun and convenience of a true golf course lifestyle. Extensively updated from the inside out, the property has undergone a comprehensive transformation while thoughtfully preserving its historic character. Beyond the beautiful cosmetic enhancements, the infrastructure has been thoroughly modernized, including updated plumbing and electrical, refinished hardwood floors throughout, and extensive improvements to the major mechanical components. Meticulously maintained and impeccably cared for, the property offers the rare opportunity to enjoy the character and beauty of a historic estate with the comfort and confidence of a thoroughly modernized home. Glenoak is a truly special Greenspring Valley estate — the house so many have admired from afar, now ready to be called home.

211 Golf Course Rd, Owings Mills

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$2,450,000

Set on nearly five acres of exquisitely landscaped grounds, this extraordinary estate seamlessly blends historic character with sophisticated modern luxury. Anchored by an original log structure and thoughtfully expanded over time, the residence offers a rare combination of architectural significance, grand scale, and refined comfort. A gracious foyer introduces elegant formal spaces, including a beautifully proportioned living room, an inviting library/den with custom built-ins, and a distinguished dining room adorned with classic millwork. Designed for both intimate living and large-scale entertaining, the home unfolds into a stunning sunroom with limestone flooring, skylights, and multiple French doors opening to expansive bluestone terraces. At the heart of the home, the gourmet kitchen features marble surfaces, premium appliances, and custom cabinetry, flowing effortlessly into a warm and inviting breakfast room with fireplace. The dramatic family room—housed within the original historic log cabin—showcases vaulted beamed ceilings, wide-plank floors, and an impressive stone fireplace, creating a truly one-of-a-kind gathering space. The main-level primary suite offers a private retreat of exceptional scale, complete with its own fireplace, spa-inspired marble bath, dressing room, and direct access to outdoor terraces and a private shower balcony. Multiple additional en-suite bedrooms, including a secondary suite with sitting room, provide comfort and flexibility for family and guests. Additional amenities include a third-level recreation space, custom wine room, fitness studio, and a separate guest house with full living accommodations. Outdoors, the estate transforms into a resort-caliber setting with a heated pool, beautifully rebuilt pool house, outdoor kitchen, and extensive stone terraces surrounded by mature trees and curated landscaping. A rare offering that combines timeless elegance, rich history, and modern livability in a truly exceptional setting.

6 Beds ⋅ 7 Baths

Set on nearly five acres of exquisitely landscaped grounds, this extraordinary estate seamlessly blends historic character with sophisticated modern luxury. Anchored by an original log structure and thoughtfully expanded over time, the residence offers a rare combination of architectural significance, grand scale, and refined comfort. A gracious foyer introduces elegant formal spaces, including a beautifully proportioned living room, an inviting library/den with custom built-ins, and a distinguished dining room adorned with classic millwork. Designed for both intimate living and large-scale entertaining, the home unfolds into a stunning sunroom with limestone flooring, skylights, and multiple French doors opening to expansive bluestone terraces. At the heart of the home, the gourmet kitchen features marble surfaces, premium appliances, and custom cabinetry, flowing effortlessly into a warm and inviting breakfast room with fireplace. The dramatic family room—housed within the original historic log cabin—showcases vaulted beamed ceilings, wide-plank floors, and an impressive stone fireplace, creating a truly one-of-a-kind gathering space. The main-level primary suite offers a private retreat of exceptional scale, complete with its own fireplace, spa-inspired marble bath, dressing room, and direct access to outdoor terraces and a private shower balcony. Multiple additional en-suite bedrooms, including a secondary suite with sitting room, provide comfort and flexibility for family and guests. Additional amenities include a third-level recreation space, custom wine room, fitness studio, and a separate guest house with full living accommodations. Outdoors, the estate transforms into a resort-caliber setting with a heated pool, beautifully rebuilt pool house, outdoor kitchen, and extensive stone terraces surrounded by mature trees and curated landscaping. A rare offering that combines timeless elegance, rich history, and modern livability in a truly exceptional setting.

227 Greenspring Valley Rd, Owings Mills

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$1,049,000

There are homes in Greenspring Valley, and then there is this one. Originally established in 1921 and substantially rebuilt as a custom home in the early 2000s, 2628 Greenspring Valley Road offers the character and setting of a historic property with the bones, systems, and layout of modern construction. Set well back from the road on a private drive behind a canopy of mature trees, it offers something increasingly rare at this price point: genuine seclusion with a prestigious address, adjacent to Greenspring Valley Country Club and minutes from everything Baltimore has to offer. The home's signature feature is a wraparound porch measuring an impressive 40 by 38 feet, meticulously rebuilt in 2019 with new flooring. At this scale, it is not an amenity. It is a room. Morning coffee, evening entertaining, quiet afternoons with a book. This porch becomes the heart of the home from the first warm day of spring through the last of fall. Step inside to a main level with exceptional flow and versatility, where sun-drenched rooms transition naturally between everyday living and gracious entertaining. Two fireplaces anchor the main level, generous windows flood every room with natural light, and updated kitchen appliances (2024) and a water softening system (2022) deliver the modern comfort the bones of this home deserve. Upstairs, four generously proportioned bedrooms include a primary suite with a spa-like bath. For the buyer who wants to build equity from day one, the nearly 1,500-square-foot unfinished walkout lower level is where it happens. Finished, this space brings total square footage to approximately 5,000 feet. The vision is yours. The value is already here.

4 Beds ⋅ 4 Baths

There are homes in Greenspring Valley, and then there is this one. Originally established in 1921 and substantially rebuilt as a custom home in the early 2000s, 2628 Greenspring Valley Road offers the character and setting of a historic property with the bones, systems, and layout of modern construction. Set well back from the road on a private drive behind a canopy of mature trees, it offers something increasingly rare at this price point: genuine seclusion with a prestigious address, adjacent to Greenspring Valley Country Club and minutes from everything Baltimore has to offer. The home's signature feature is a wraparound porch measuring an impressive 40 by 38 feet, meticulously rebuilt in 2019 with new flooring. At this scale, it is not an amenity. It is a room. Morning coffee, evening entertaining, quiet afternoons with a book. This porch becomes the heart of the home from the first warm day of spring through the last of fall. Step inside to a main level with exceptional flow and versatility, where sun-drenched rooms transition naturally between everyday living and gracious entertaining. Two fireplaces anchor the main level, generous windows flood every room with natural light, and updated kitchen appliances (2024) and a water softening system (2022) deliver the modern comfort the bones of this home deserve. Upstairs, four generously proportioned bedrooms include a primary suite with a spa-like bath. For the buyer who wants to build equity from day one, the nearly 1,500-square-foot unfinished walkout lower level is where it happens. Finished, this space brings total square footage to approximately 5,000 feet. The vision is yours. The value is already here.

2628 Greenspring Valley Rd, Owings Mills

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3840

$654,900

BACK ON THE MARKET – SECOND OPPORTUNITY! Don't miss another chance to make 9 Rainbow Court your home. Now offered at an improved price of $654,900. Schedule your showing today. A rare opportunity to own a renovated single-family home in one of Greenspring Valley’s most distinguished settings. Nestled at the end of a quiet cul-de-sac on 1.12 wooded acres, this beautifully renovated five-bedroom home is located in the sought-after Rainbow Park community—an enclave within Greenspring Valley whose identity is closely tied to the nearby historic Rainbow Hill estate, once the residence associated with General Douglas MacArthur and his family. This setting reflects the enduring prestige and legacy that have long defined this celebrated corner of Baltimore County. Surrounded by mature trees and natural landscape, the property offers a rare sense of privacy and seclusion while remaining conveniently close to everyday amenities. The setting evokes the feel of a private country retreat, enhanced by extensive modern renovations that allow for effortless contemporary living. Designed for both comfort and entertaining, the home features a highly desirable first-floor owner’s suite, spacious secondary bedrooms, and flexible living spaces that adapt easily to a range of lifestyles. At the center of the home is a fully renovated gourmet kitchen featuring an impressive granite island, double wall oven, beautiful appliances, and generous space for gathering and connection. The open space family room provides a warm and inviting atmosphere with a wood-burning fireplace, a dramatic bay window, and built-in seating overlooking the peaceful, wooded backdrop. Upstairs, three generously sized bedrooms—including two large enough for king-sized furnishings—are complemented by a versatile bonus room ideal for a media space, home office, fitness studio, playroom, or creative retreat. Outdoor living is equally exceptional. A beautiful in-ground pool anchors the backyard, surrounded by expansive entertaining areas, fenced grounds, and a growing natural buffer of more than 25 evergreens, creating a tranquil outdoor space. Significant improvements completed since 2020 provide peace of mind and long-term value, including a new roof, all new windows, updated electrical and plumbing systems, high-efficiency furnace, whole-house water filtration system, electric tankless water heater, upgraded pool systems, fresh interior paint, new carpeting, a new retaining wall, and a newly completed driveway. Homes in Rainbow Park are seldom available. This is a unique opportunity to own a fully updated residence in a setting defined by character, warmth and charm. Welcome Home...

5 Beds ⋅ 4 Baths

BACK ON THE MARKET – SECOND OPPORTUNITY! Don't miss another chance to make 9 Rainbow Court your home. Now offered at an improved price of $654,900. Schedule your showing today. A rare opportunity to own a renovated single-family home in one of Greenspring Valley’s most distinguished settings. Nestled at the end of a quiet cul-de-sac on 1.12 wooded acres, this beautifully renovated five-bedroom home is located in the sought-after Rainbow Park community—an enclave within Greenspring Valley whose identity is closely tied to the nearby historic Rainbow Hill estate, once the residence associated with General Douglas MacArthur and his family. This setting reflects the enduring prestige and legacy that have long defined this celebrated corner of Baltimore County. Surrounded by mature trees and natural landscape, the property offers a rare sense of privacy and seclusion while remaining conveniently close to everyday amenities. The setting evokes the feel of a private country retreat, enhanced by extensive modern renovations that allow for effortless contemporary living. Designed for both comfort and entertaining, the home features a highly desirable first-floor owner’s suite, spacious secondary bedrooms, and flexible living spaces that adapt easily to a range of lifestyles. At the center of the home is a fully renovated gourmet kitchen featuring an impressive granite island, double wall oven, beautiful appliances, and generous space for gathering and connection. The open space family room provides a warm and inviting atmosphere with a wood-burning fireplace, a dramatic bay window, and built-in seating overlooking the peaceful, wooded backdrop. Upstairs, three generously sized bedrooms—including two large enough for king-sized furnishings—are complemented by a versatile bonus room ideal for a media space, home office, fitness studio, playroom, or creative retreat. Outdoor living is equally exceptional. A beautiful in-ground pool anchors the backyard, surrounded by expansive entertaining areas, fenced grounds, and a growing natural buffer of more than 25 evergreens, creating a tranquil outdoor space. Significant improvements completed since 2020 provide peace of mind and long-term value, including a new roof, all new windows, updated electrical and plumbing systems, high-efficiency furnace, whole-house water filtration system, electric tankless water heater, upgraded pool systems, fresh interior paint, new carpeting, a new retaining wall, and a newly completed driveway. Homes in Rainbow Park are seldom available. This is a unique opportunity to own a fully updated residence in a setting defined by character, warmth and charm. Welcome Home...

9 Rainbow Ct, Owings Mills

Listing courtesy of Douglas Realty, LLC. Contact: 8669873937