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View All Latest Caroline 7500+ Sq. Ft. Properties for Sale

$2,560,000
8 Beds ⋅ 16 Baths ⋅ MDCM2006492 MLS
A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind property. The main residence spans over 9,364 square feet and is thoughtfully designed for refined living and grand-scale entertaining. A dramatic two-story foyer with sweeping double staircases opens to richly appointed formal and informal living spaces accented by custom millwork, crown moldings, hardwood flooring, and four fireplaces. At the heart of the home, the chef’s kitchen impresses with coffered ceilings, expansive island, commercial-grade range, double wall ovens, and premier Viking, Sub-Zero, and Wolf appliances, along with an induction cooktop and icemaker. A well-appointed butler’s pantry ensures seamless entertaining, while the adjoining Grill Room—featuring an infrared grill, Viking beverage cooler, and Sub-Zero icemaker—offers a relaxed gathering space. The primary suite is a private retreat with fireplace, mood lighting, generous walk-in closets, and dual doors leading to a private balcony overlooking the grounds. The spa-inspired bath includes double vanities, a tiled shower, and soaking tub. All additional bedrooms in the main residence are ensuite, offering comfort and privacy for family and guests. Outdoor living rivals a private resort, highlighted by a 40’ x 20’ heated saltwater infinity pool with swim ledge, hot tub, outdoor kitchen, covered porch, expansive patios, and firepit—perfect for year-round enjoyment amid mature landscaping, a tranquil pond, and sweeping rural views. Automobile collectors will appreciate the estate’s unparalleled garage facilities. A detached brick automotive gallery features a nine-bay, climate-controlled showcase garage with CHI aluminum tinted glass doors, polished concrete floors, and premium climate control—ideal for preserving and displaying a museum-quality collection. Above, a fully appointed three-bedroom, two-bath guest residence offers a kitchen and multiple living spaces. Two additional fully insulated, climate-controlled 50’ x 75’ garages with 12-foot overhead doors and professional-grade lifts provide exceptional flexibility. An oversized storage building and run-in to the rear further enhances the property’s versatility. Hobbyists, from automobile collectors to equestrian enthusiasts, will be delighted to make use of the many large accessory structures on the property. Additional features include a comprehensive security and surveillance system, private gated entrance, 60-zone irrigation system, whole-property surround sound, & Comcast fiber internet. This is more than a home—it is a destination estate offering an elevated lifestyle for those who value privacy, craftsmanship, and automotive excellence in a refined Eastern Shore setting. IMPORTANT NOTES: Property consists of three parcels with separate addresses/taxes, portions of which are leased for agricultural use through December 2025. The irrigation system has a mainline break beneath a garage and will not be repaired by the seller. Quotes for repair or replacement are available for review.in documents. Front garage has suffered water damage and in the process of being remediated but seller will not be making repairs to the garage or apartment. Estimates for the remediation (which seller is doing) and the repair of damaged area is uploaded in MLS disclosure docs. All agents/buyers touring MUST sign a Hold Harmless Document prior to entering the garage/apartment. Property is being sold AS-IS/WHERE-IS with all faults. Contact listing agent(s) with any questions. ***Please do not enter lane to property without a confirmed appointment.

4218 Harmony Road, Preston
$2,400,000
8 Beds ⋅ 9 Baths ⋅ CVR-2525654 MLS
Step into a world of peace and tranquility at this exquisite Virginia estate, beautifully reimagined and redesigned to serve as the ultimate retreat center. Nestled in a picturesque country setting, this 184-acre property offers endless possibilities for relaxation, recreation, and rejuvenation. The newly remodeled main house epitomizes modern luxury with its 8 spacious bedrooms, 8.5 elegantly updated bathrooms, and a gourmet kitchen featuring all new appliances. Every corner of this home has been thoughtfully updated to blend contemporary comfort with timeless elegance. In addition to the main house, the estate includes a contemporary two-bedroom villa and a charming three-bedroom guest house, providing ample space for guests or extended family. For those seeking a unique experience, the property also features five glamping tents and an adobe hut, each ready to be transformed into personalized retreats. Outdoor amenities are designed for ultimate comfort and enjoyment. A custom-built swimming pool offers a private oasis for relaxation, while numerous walking trails invite exploration and connection with nature. The expansive rolling pastures are perfect for horses or cattle, adding to the estate's charm and versatility.

14186 Devils Three Jump Road, Milford
$690,000
5 Beds ⋅ 6 Baths ⋅ CVR-2401241 MLS
Welcome to 17520 Lakewood Rd.! This CUSTOM BUILT sprawling brick rancher features over 5300 finished square feet, a FULL BASEMENT, 2 KITCHENS, 5 bedrooms, 5.5 baths, ATTACHED AND DETACHED GARAGES , and all on a 15+ ACRE HARDWOOD LOT. Upon arriving at the home, you will notice the paved driveway that winds it's way through the mature woods and leads to the circular driveway and concrete parking area. The exterior of the home features all brick construction, a dimensional shingled roof(2015), a covered brick front porch, a side concrete porch, a rear brick patio, a detached brick 2 car garage(28x28) that is heated, an attached 2 car garage(28x28), and a detached pole shed. Once inside the home you will notice the custom features including the molding/trim, woodwork, built-ins, cabinetry, wood closet kits in every closet, tile in every bathroom, and so much more. Upon entering the home, you are greeted by the large foyer and the gorgeous HARDWOOD FLOORS. To the left is the large Great Room with HW floors, vaulted ceilings, and crown molding. This leads into the large dining room that features HW floors, and crown and chair molding. The large eat-in kitchen features Cherry cabinets, a large island with cooktop, a wall oven, and custom built-ins around the Fireplace. The sunroom is off of the kitchen and features a CF, tons of natural light, and overlooks the PARK LIKE YARD. There is a utility room between the kitchen and the garage as well as a half bath and a laundry room. The Study features HW floors and crown molding. Down the hallway you will find the primary bath that features carpet, CF, crown, and primary bath with dual closets and double vanity. Rounding out the first floor is 2 other large bedrooms(one with it's own bath), and a hall bath. Downstairs you will find the 2nd kitchen with nice cabinetry, wall over, cooktop, and large pantry. There is a 2nd laundry room as well. There are 2 other large bedrooms, 2 bathrooms, and a HUGE REC ROOM. So private and peaceful, but so close to all the amenities in town!

17520 Lakewood Road, Bowling Green
$3,100,000
8 Beds ⋅ 16 Baths ⋅ MDCM2002302 MLS
This first-time offering is a unique Eastern Shore estate that is the perfect marriage of serenity and style. No expense or detail was spared in building this custom family compound encompassing stunning indoor and outdoor spaces. The tree-lined circular driveway leads you to a gracious, brick manor home designed with large-scale entertaining in mind, starting with the two-story, double staircase foyer. The custom gourmet kitchen will satisfy any chef and provide a welcoming gathering spot for friends and family. Top-of-the-line appliances include Viking, Subzero, and Wolf, as well as an induction cooktop and icemaker. The butler's pantry is perfect for staging and storing everything you need to put on the perfect holiday gathering. For casual entertaining, The Grill Room offers a Viking beverage cooler, an infrared grill, and a Subzero icemaker. The spacious primary suite has a fireplace flanked by two doors accessing the outdoor balcony. The lavishly appointed primary bath features double vanities, a tiled shower, and a large soaking tub. The additional bedrooms within the main house are also en suite. Meticulous trim work, four fireplaces, and other special touches highlight the attention to detail throughout the home. Once you step outside, you'll notice the same emphasis on entertaining and luxurious spaces. The amenities abound, starting with a 40x20 heated saltwater infinity pool with a swim ledge providing relaxation and fun throughout the summer and an ideal gathering spot for friends and family. The outdoor kitchen includes all you need for informal poolside gatherings. You can enjoy most seasons outdoors by using the covered porch, sun-drenched patio, or outdoor firepit on cooler evenings. Hobbyists, from automobile collectors to equestrian enthusiasts, will be delighted to make use of the many large accessory structures on the property. The nine-bay climate-controlled primary garage is ideally suited to showcase and preserve your museum-caliber automotive collection with CHI aluminum tinted glass and polished concrete flooring. This custom-built structure also features three-bedroom, two-bath guest quarters with a kitchen, living, and family room. Two separate, fully insulated, and climate-controlled garages (50 x 75) provide additional storage space with 12-foot overhead doors. These spaces could have many alternate uses, including first-class horse stables. Additional features include a 60-zoned irrigation system, Comcast Fiber internet, surround sound, a state-of-the-art security and surveillance system, and an 80 KW Generac generator. A truly exceptional property.

4218 Harmony Road, Preston
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7500+ Sq. Ft. Caroline Real Estate