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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

$2,999,000

Live authentically. Relish the majestic tree lined drive. Stone and glass architecture punctuates the landscape in a meaningful and enduring way. Nestled in Greenspring Valley on 12.3 acres, this light-filled estate is designed for gathering, celebrating, and connecting. Modern floor plan. Expanses of glass that make every space a joy to be in. Live connected to nature. Experience chromatherapy. Vivid, saturated color washes throughout the home make you feel vibrant. Glowing glass gallery. Inviting screened porch, expansive terrace, enchanting gardens. Two-story guest house, studio for creative pursuits with full bath, and dog run. Sparkling pool, private tennis and pickleball court (lined for both), and barn/stables ready to embrace your aesthetic. A 150-year-old American beech tree, ancient and sculptural, anchors the view from the living and dining rooms and has cradled generations of young climbers in its branches. A lively estate that celebrates intimate and grand gatherings with ease. Epic mudroom. Verizon Fios Internet. Cultivate your existence. The art of uniting human and home. LOCAL FLAVOR AND PROVISIONS Stone Mill Bakery, John Brown Store, Graul's Market, Moms, Whole Foods, and Wegmans. Favorite local dining at The Valley Inn, Linwoods, Tarks, Petit Louis, The Milton Inn, The Oregon Grill, Peerce's. Head north to The Butler Cabin, and The Filling Station. Tap into local breweries, such as Inverness Brewing, Farmacy Brewing and Big Truck Farm Brewery. OUTINGS AND LEISURES If you love the outdoors, Lake Roland is perfect for hiking and picnics. Oregon Ridge Park provides a beautiful fishing lake. The park also hosts events and concerts during the summer. Take a stroll through Meadowood Regional Park. Loch Raven Reservoir offers scenic beauty and water activities. Explore the NCR Trail. A 21-mile flat, crushed-stone trail open to hikers, bikers, and horses, it runs along the scenic Gunpowder Falls river. Go tubing on the Gunpowder River. Enjoy Ladew Topiary Gardens... these gardens are 22 acres of spectacular, award-winning gardens, more than 100 remarkable topiaries, a mile-long Nature Walk, and native Butterfly House. Explore The Manor Mill, a pre-revolutionary grist mill that now houses a wide variety of art and entertainment events. Tee off at Woodholme Country Club, Fox Hollow Golf Course, Pine Ridge Golf Course, Hunt Valley Country Club or Hayfields Country Club. Visit The National Lacrosse Hall of Fame and Museum which honors the history and legends in the sport. PROXIMITY About 21 minutes to Hunt Valley, and about 17 minutes to Towson. Approximately 20 minutes to Downtown Baltimore, 30 minutes to BWI and 21 minutes to Penn Station. 3 hours, 29 minutes to New York, 1 hour 25 minutes to Washington D.C. REGION Stevenson is known for its scenic horse country, rolling hills, and historic estates, it blends a quiet, rural feel with close proximity to Baltimore.

6 Beds ⋅ 8 Baths

Live authentically. Relish the majestic tree lined drive. Stone and glass architecture punctuates the landscape in a meaningful and enduring way. Nestled in Greenspring Valley on 12.3 acres, this light-filled estate is designed for gathering, celebrating, and connecting. Modern floor plan. Expanses of glass that make every space a joy to be in. Live connected to nature. Experience chromatherapy. Vivid, saturated color washes throughout the home make you feel vibrant. Glowing glass gallery. Inviting screened porch, expansive terrace, enchanting gardens. Two-story guest house, studio for creative pursuits with full bath, and dog run. Sparkling pool, private tennis and pickleball court (lined for both), and barn/stables ready to embrace your aesthetic. A 150-year-old American beech tree, ancient and sculptural, anchors the view from the living and dining rooms and has cradled generations of young climbers in its branches. A lively estate that celebrates intimate and grand gatherings with ease. Epic mudroom. Verizon Fios Internet. Cultivate your existence. The art of uniting human and home. LOCAL FLAVOR AND PROVISIONS Stone Mill Bakery, John Brown Store, Graul's Market, Moms, Whole Foods, and Wegmans. Favorite local dining at The Valley Inn, Linwoods, Tarks, Petit Louis, The Milton Inn, The Oregon Grill, Peerce's. Head north to The Butler Cabin, and The Filling Station. Tap into local breweries, such as Inverness Brewing, Farmacy Brewing and Big Truck Farm Brewery. OUTINGS AND LEISURES If you love the outdoors, Lake Roland is perfect for hiking and picnics. Oregon Ridge Park provides a beautiful fishing lake. The park also hosts events and concerts during the summer. Take a stroll through Meadowood Regional Park. Loch Raven Reservoir offers scenic beauty and water activities. Explore the NCR Trail. A 21-mile flat, crushed-stone trail open to hikers, bikers, and horses, it runs along the scenic Gunpowder Falls river. Go tubing on the Gunpowder River. Enjoy Ladew Topiary Gardens... these gardens are 22 acres of spectacular, award-winning gardens, more than 100 remarkable topiaries, a mile-long Nature Walk, and native Butterfly House. Explore The Manor Mill, a pre-revolutionary grist mill that now houses a wide variety of art and entertainment events. Tee off at Woodholme Country Club, Fox Hollow Golf Course, Pine Ridge Golf Course, Hunt Valley Country Club or Hayfields Country Club. Visit The National Lacrosse Hall of Fame and Museum which honors the history and legends in the sport. PROXIMITY About 21 minutes to Hunt Valley, and about 17 minutes to Towson. Approximately 20 minutes to Downtown Baltimore, 30 minutes to BWI and 21 minutes to Penn Station. 3 hours, 29 minutes to New York, 1 hour 25 minutes to Washington D.C. REGION Stevenson is known for its scenic horse country, rolling hills, and historic estates, it blends a quiet, rural feel with close proximity to Baltimore.

2026 Greenspring Valley Rd, Stevenson

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921

$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