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$1,950,000
2 Beds ⋅ 2 Baths
Exceptional opportunity to own a private equestrian estate situated on approximately 91+ acres just minutes from the Chesapeake Bay, marinas, and waterfront amenities. Surrounded by mature woods, open pasture, and riding areas, this unique property offers tremendous potential for horse enthusiasts, boarding operations, training facilities, multi-generational living, or a private country retreat. The main residence features 4 bedrooms, 2 full baths, multiple living areas, two kitchens, and approximately 2,300 square feet of living space, creating excellent flexibility for extended family, guest accommodations, or separate living quarters. A large wraparound deck overlooks the peaceful setting and provides the perfect place to relax and enjoy the surrounding wildlife and natural beauty. Equestrian improvements include an impressive center aisle bank barn with multiple stalls, tack room, hay storage, wash areas, and large covered work spaces. Additional horse facilities include another stable building with multiple stalls and turnout areas, fenced paddocks, run-in sheds, and riding areas. Several additional outbuildings greatly enhance the property's versatility, including a large equipment building storage and garage space, a separate storage building with six finished rooms that could serve numerous purposes, and additional workshop and storage areas throughout the property. The acreage offers a combination of fenced pasture, wooded trails, open riding areas, and privacy rarely found in today's market. Conveniently located near Chesapeake City & Elkton, marinas, boating, and major commuting routes while still providing a secluded country setting. Whether you're seeking a working horse farm, private family compound, recreational retreat, or investment opportunity, this one-of-a-kind property delivers endless possibilities.

99 E Lewis Shore Rd, Elkton

Listing courtesy of Integrity Real Estate. Contact:

$739,900
4 Beds ⋅ 3 Baths
A little piece of Paradise on your own 10.20+- Acres surrounded by woods & stream for the outdoor enthusiast that enjoys taking walks or want to hunt on THEIR own land....includes 2 hunting blinds that stays! If you just want to relax, then you will LOVE the beautiful landscaped yard that has gorgeous flowers, fruit trees & raised garden beds to grow your own veggies and comes with it's own compost containers! A 24x32x10 POLE BARN with a wood burning stove, cabinets, work bench, 100 amp electric & Dust to Dawn lights & motion detectors all set up for the person which loves to TINKER or just want to have their own space to do their own thing! Large shed in back yard 10 x 12 for outside storage! 1000 LP tank...owned by owners...use whomever you wish without being tied to one vendor. There is just so much, much more to say about this property ...... I haven't even started on the inside.....It's IN BEAUTIFUL CONDITION!! Another GREAT FEATURE about it.....(what so many people looking for. these days).. is a IN-LAW-SUITE, with a SRE-3000 Stairlift , designed for someone that may have difficulty doing stairs but want to have their own space and privacy! All appliances stays up and down! 2-sets washers/dryers; 2 microwaves, 2 refrigerators; 2 stoves, Sprinkler System throughout home with its own water storage tank. FEEL FREE TO GIVE ME A CALL IF ANY QUESTIONS!! IT'S A BEAUTY AND YOU WILL WANT TO CALL THIS ONE HOME!!

2316 Theodore Rd, North East

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: (800) 383-3535
$1,469,000
5 Beds ⋅ 3 Baths
Welcome to your private waterfront paradise on the Elk River! In a stunning setting on 30+ acres, the home beckons those seeking serenity and an abundance of land to call their own. A former Christmas tree farm, the property ranges from mature forest with towering trees, to sprawling, tillable meadows, to marshland, a beach area with huge potential, and the Elk River a short distance from the expanse of the Chesapeake. Not in an HOA, and has the potential to be an amazing vacation rental. You'll love the house, designed with an abundance of glass to maximize the views of the sprawling landscape and the bay beyond. It's an Acorn Deck House (learn more at deckhouse.com), which has it's own well-deserved fan base. Entering the front doors, you'll be greeted by a wide open living space with vaulted ceilings and the wall of windows. In this space is the large fireplace, and next to it the spacious, custom kitchen, designed thoughtfully with entertaining in mind. The spacious deck wraps around the rear of the home overlooking the pool, a wonderful place to unwind and take in the views. Also on the main floor is a large space overlooking the water that's been cleared out to make way for what is begging to be a gorgeous primary suite, with large windows overlooking the water. Downstairs, you'll find four spacious, daylight bedrooms, with 3 of them having bay views and patio doors opening at ground level, with the pool just beyond. One features a private bath of its own, along with a second full bath that serves the remaining guest rooms. This level also features a spacious laundry area and the utility room. Note that a major upgrade completed by the owners is the installation of a geothermal system for efficiency of heating and cooling. Back outside, you'll find the pool an incredibly beautiful space; custom designed by the owners, it's practically brand new, a concrete pool build with only the best in mind. Roaming the outdoors, you'll find wildlife to be a part of life here with bald eagles having a nest on the property (imagine being able to say that!), a thriving deer herd, along with lots of other creatures. Fish in the creek and the Elk River, and the bay beyond, or hunt, or just soak it all in. A floating dock is in place for smaller boats, and a new dock can be build for larger boats, and to access to the beautiful beach area beyond the marshland. With your finishing touches, this home can become the haven of your dreams, or a stunning vacation rental. Homes in a setting like this don’t come along often, schedule your private tour today and experience the glory of waterfront living!

85 Green Haven Dr, Elkton

Listing courtesy of Astoria Realty Advisors LLC. Contact: 7174256264
$595,000
Very nice 21.6‑acre wooded property featuring an old home, barn, and additional outbuildings in need of demolition or major renovation. Onsite electric, well, and an old septic system. A beautiful stream runs through the property, though the bridge has been washed out this is a perfect location to build your dream home. Property borders PA state line. Extremely secluded with excellent hunting property.

95 Frog Hollow Ln, Rising Sun

Listing courtesy of Fisher Realty. Contact: 7172198000
$10,000,000
This offering marks an extraordinary opportunity to acquire one of North America’s most prestigious properties. While the 437.5 acre farm is globally celebrated for its history of breeding, training, and raising excellence and many world-class sport horse champions, the focus now turns to the sale of the physical estate, a masterpiece of equestrian infrastructure and natural beauty now available for its next chapter. The property is defined by its remarkable landscape, featuring 200 wooded acres of mature trees, 220 acres of pastureland, and 15 acres of impervious structures across the gently rolling terrain of Cecil County. Bordered by 1.3 miles of tranquil waters of the Octoraro Creek, the land offers a rare combination of high-performance utility and serene privacy. The sale includes comprehensive, established equestrian infrastructure, highlighted by a 36-stall main barn, 2 outdoor arenas, 12 fields, 31 paddocks, 14 dwellings, 2 additional barns, and numerous equine facilities that have served as the benchmark for elite sport horse development for decades. The true value of Hilltop Farm’s footprint lies in its versatility; it is a canvas limited only by the scale of one’s imagination. While its equestrian pedigree is unrivaled, the estate invites a bold repurposing as a world-class Agri-Tourism Destination or a Private Legacy Compound. The riverfront and woodlands are perfectly suited for a Luxury Wellness Retreat, with riparian trails just a stone's throw from the urban corridors of Philadelphia, Baltimore, and DC. As this historic operational chapter concludes, the property is now positioned for a new curator to inherit a landscape of immense function and beauty. This is a rare chance to own a sanctuary that has been both a stage for international sport and a community standard-bearer. This property includes multiple parcels and should be referenced in conjunction with MLS# MDCC2020402 (Tax ID: 0806025811) and MLS# MDCC2020404 (Tax ID: 0806012450).

1089 Nesbitt Rd, Colora

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$10,000,000
This offering marks an extraordinary opportunity to acquire one of North America’s most prestigious properties. While the 437.5 acre farm is globally celebrated for its history of breeding, training, and raising excellence and many world-class sport horse champions, the focus now turns to the sale of the physical estate, a masterpiece of equestrian infrastructure and natural beauty now available for its next chapter. The property is defined by its remarkable landscape, featuring 200 wooded acres of mature trees, 220 acres of pastureland, and 15 acres of impervious structures across the gently rolling terrain of Cecil County. Bordered by 1.3 miles of tranquil waters of the Octoraro Creek, the land offers a rare combination of high-performance utility and serene privacy. The sale includes comprehensive, established equestrian infrastructure, highlighted by a 36-stall main barn, 2 outdoor arenas, 12 fields, 31 paddocks, 14 dwellings, 2 additional barns, and numerous equine facilities that have served as the benchmark for elite sport horse development for decades. The true value of Hilltop Farm’s footprint lies in its versatility; it is a canvas limited only by the scale of one’s imagination. While its equestrian pedigree is unrivaled, the estate invites a bold repurposing as a world-class Agri-Tourism Destination or a Private Legacy Compound. The riverfront and woodlands are perfectly suited for a Luxury Wellness Retreat, with riparian trails just a stone's throw from the urban corridors of Philadelphia, Baltimore, and DC. As this historic operational chapter concludes, the property is now positioned for a new curator to inherit a landscape of immense function and beauty. This is a rare chance to own a sanctuary that has been both a stage for international sport and a community standard-bearer. his property includes multiple parcels and should be referenced in conjunction with MLS# MDCC2020402 (Tax ID: 0806025811) and MLS# MDCC2020400 (Tax ID: 0806025811)

1089 Nesbitt Rd, Colora

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$8,995,000
6 Beds ⋅ 5 Baths
Set on 93 private acres with 6,100 feet of shoreline along the picturesque Sassafras River and Cox Creek. The estate includes a main house, guest house, pool house and riverside pavilion, offering ample delightful space for large groups to gather, unwind and experience the activities and natural beauty of the upper Chesapeake. Showcasing exceptional design, materials, craftsmanship, the living spaces are framed by expansive views of the Sassafras River. The main residence includes six spacious bedrooms and four and a half baths. The heart of the home is a gourmet kitchen and adjacent generous breakfast room wrapped in 180-degree river views, a setting that enhances every meal. The home flows naturally into multiple large gathering spaces built for entertaining, and into quieter, more intimate rooms designed for reflection and rest. The guest house ensures that you can accommodate family and friends. With three generously sized bedrooms and one and a half baths, full kitchen, fireplace and brick patio, it offers a self-contained retreat that gives guests their own space while keeping everyone together on the estate. The pool complex redefines what a backyard amenity can be. At its center is a 52,000-gallon swimming pool with a retractable electric cover, positioned to frame sweeping panoramic river views. An adjoining heated spa and a oversized pool deck complete a setting that invites long, unhurried afternoons in the sun. Elevating the experience further, it offers a full bath, generous living and dining areas, and amenities more commonly found at a high-end resort - a large, well-equipped gym and an eight-person steam room -providing the perfect end to an active day. Perched at the water's edge, the recently constructed two-story pavilion is the social and recreational heart of the estate's waterfront. It's a front-row seat to everything that makes the Sassafras River so beloved: working crab boats in the early morning, sailboats gliding past at midday, and the sky turning gold over the water at dusk. Spend a lazy afternoon on the pavilion's upper level as the river life unfolds below, then head down to launch your own boat from the private boat lift or boat ramp. The Sassafras and Cox Creek offer boundless activities including boating, water skiing, tubing, wakeboarding, sailing, paddleboarding, and kayaking, all awaiting just steps away. After fun on the water, return to the pavilion for lunch, dinner, or simply a seat with one of the best views on the upper Bay. Adjacent to the grassy wharf, the nearly 1,000-foot private sandy beach is a rare and remarkable amenity ideal for an afternoon stroll with friends or a quiet moment watching the sunset or moon rise over the river. Other improvements along the waterfront include a 1000+ stone revetment protecting the shoreline, a 13,000lb boat lift, and a boat ramp. The grounds reflect a thoughtful balance of beauty, privacy, and long-term stewardship, with carefully planned enhancements designed to complement the natural setting while supporting comfortable estate living. Mature trees and established landscaping create a sense of arrival and continuity across the property, while curated sightlines and open lawn areas transition naturally into wooded edges and surrounding countryside. A network of trails invites exploration through the woods, offering quiet vantage points and seasonal changes that reinforce the property’s connection to the Eastern Shore landscape. The property's blend of fields, woods and waterfront habitats, complemented by offshore hunting rights offers productive hunting. The land supports healthy populations of deer, wild turkey, ducks & geese, creating a sportsman's haven throughout the seasons. Enjoy fishing and crabbing from the dock ideally located on the edge of the deep water channel. Major mid-Atlantic cities, international airports & train stations are within easy reach, making the estate accessible for full-time residents and weekend escapes.

750 Cassidy Wharf Rd, Earleville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$19,900,000
4 Beds ⋅ 5 Baths
Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class dressage. At the heart of the property is a spectacular 31-stall, 45,000-square-foot indoor dressage show barn. Built with unmatched craftsmanship and old-world charm second to none. Visitors are welcomed through a charming, covered porch and elegant, glass-paneled double doors into a grand reception area featuring a central stone fireplace and a private meeting room, all adorned with custom millwork throughout. Overlooking the 100’ x 200’ indoor dressage arena are stunning glass-enclosed observation areas on both the first and second floors, that are brilliantly filled with natural light and character. This impressive space includes twin service bars, a conveniently located commercial-grade kitchen, and a spacious area ideal for entertaining. An ornate wide-plank staircase leads to a lofted second level with private office suites, an exercise room, and a lounge area. The barn itself is thoughtfully designed, featuring barreled ceilings, six grooming/wash stalls, two well-appointed tack rooms, a central eat-in kitchen/break area, a laundry room, and a three-season sitting room offering panoramic views through grand window walls on two sides. The barn’s layout seamlessly flows through a bank of 31 spacious (mostly 14’ x 14’) stalls, curving into an additional wing with even more accommodations. Complementing the equestrian facilities is a beautifully appointed 9,000-square-foot brick manor home of Georgian architectural style, offering four bedrooms and 3 full & 2 half bathrooms. This wonderful home features an updated kitchen, brick and antique wood flooring, beamed ceilings, a sunken living room, multiple fireplaces, a spacious game room, and a detached three-car garage. The extensive grounds are thoughtfully and professionally landscaped. It artfully blends traditional character with modern conveniences—perfectly suited for today’s lifestyle. Also included within this breathtaking property is a luxurious guest home featuring a chef’s kitchen and an enclosed timber-framed pavilion over a heated indoor pool. Additionally, there is a 15-stall center-aisle block barn with a six-horse Kraft Eurocizer, as well as numerous ancillary operational buildings, including a fully functional brick office building—and numerous double-fenced fields and paddocks with approximately 10 miles of four-rail post-and-board fencing offering unparalleled views throughout the farm. RiverEdge is set within one of Maryland’s largest agricultural preservation areas and is protected by a conservation easement, ensuring its beauty and legacy for generations to come. The property includes 4 parcels: 0802016206 - 109.4 acres, 0802019078 - 186.7 acres, 0802029049 - 106 acres, and 0802029537 - 109.4 acres.

1455 Cayots Corner Rd, Chesapeake City

Listing courtesy of Monument Sotheby's International Realty. Contact: 3026546500
$19,900,000
4 Beds ⋅ 5 Baths
Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class dressage. At the heart of the property is a spectacular 31-stall, 45,000-square-foot indoor dressage show barn. Built with unmatched craftsmanship and old-world charm second to none. Visitors are welcomed through a charming, covered porch and elegant, glass-paneled double doors into a grand reception area featuring a central stone fireplace and a private meeting room, all adorned with custom millwork throughout. Overlooking the 100’ x 200’ indoor dressage arena are stunning glass-enclosed observation areas on both the first and second floors, that are brilliantly filled with natural light and character. This impressive space includes twin service bars, a conveniently located commercial-grade kitchen, and a spacious area ideal for entertaining. An ornate wide-plank staircase leads to a lofted second level with private office suites, an exercise room, and a lounge area. The barn itself is thoughtfully designed, featuring barreled ceilings, six grooming/wash stalls, two well-appointed tack rooms, a central eat-in kitchen/break area, a laundry room, and a three-season sitting room offering panoramic views through grand window walls on two sides. The barn’s layout seamlessly flows through a bank of 31 spacious (mostly 14’ x 14’) stalls, curving into an additional wing with even more accommodations. Complementing the equestrian facilities is a beautifully appointed 9,000-square-foot brick manor home of Georgian architectural style, offering four bedrooms and 3 full & 2 half bathrooms. This wonderful home features an updated kitchen, brick and antique wood flooring, beamed ceilings, a sunken living room, multiple fireplaces, a spacious game room, and a detached three-car garage. The extensive grounds are thoughtfully and professionally landscaped. It artfully blends traditional character with modern conveniences—perfectly suited for today’s lifestyle. Also included within this breathtaking property is a luxurious guest home featuring a chef’s kitchen and an enclosed timber-framed pavilion over a heated indoor pool. Additionally, there is a 15-stall center-aisle block barn with a six-horse Kraft Eurocizer, as well as numerous ancillary operational buildings, including a fully functional brick office building—and numerous double-fenced fields and paddocks with approximately 10 miles of four-rail post-and-board fencing offering unparalleled views throughout the farm. RiverEdge is set within one of Maryland’s largest agricultural preservation areas and is protected by a conservation easement, ensuring its beauty and legacy for generations to come. The property includes 4 parcels: 0802016206 - 109.4 acres, 0802019078 - 186.7 acres, 0802029049 - 106 acres, and 0802029537 - 109.4 acres.

1455 Cayots Corner Rd, Chesapeake City

Listing courtesy of Monument Sotheby's International Realty. Contact: 3026546500
$2,200,000
5 Beds ⋅ 6 Baths
Welcome to where dreams come true in an exclusive Waterfront neighborhood located in Sunset Pointe, Earleville MD....This stunning 2 story Sprawling Ranch is on 19.32 acres of breathtaking views of fields, wildlife and the open waters of Pond Creek. This meticulously renovated property featuring a beautifully redesigned family room with a wood-burning fireplace that has been tiled from floor to ceiling with custom tile, also featuring electric blinds just added to the specular windows that take all the views in.... The kitchen boasts new Bosch appliances, granite counter tops, wine refrigerator, counters galore, sub zero refrigerator, new above lighting cabinets, instant hot water at the sink, new sink and so much space... The Large dining area leads to an expanded deck with composite flooring and stone pillars. The office/sunroom which is located off the kitchen area has beautiful full glass etched french doors fireplace that compliments the family rooms...The solid door off this room that has a designer staircase down to the lower level patio ....As you walk through the kitchen there is a half bath that is located next to the large mudroom with another door that exists to another new deck expanded also with composite floors and an overhang.....This mudroom has space for everyone .... separate locker area and a dogs haven with a doggie water bowl filler....Now lets head back to the other side of the family room ....Welcome to the primary suite that has it's own gazebo deck private to you with sliding glass doors that also exit from this suite....This newly renovated primary bathroom has heated floors, custom cabinets, large Jacuzzi tub including an oil diffuser and automatic dryer ....marble shelve with a TV .... the shower will WOW you with a shaving station with it's own faucet and mirror....and custom tiling like no other.... The laundry room is outside of the the primary bedroom with all custom closets and is conveniently within access of the other first floor bedrooms .....Bedroom 2 and 3 on the first floor have custom closets and share a jack and jill bathroom with stunning updates....also another Jacuzzi and walk-in shower. Now lets head back to the foyer and down to the lower level .....First you are greeted with a large game room that has beautiful sliding doors out to the new salt water pool ....This lower level has 2 full bathrooms one that is handicap-accessible and connects to a beautiful 4th bedroom with it's own set of sliding glass doors leading out to a lovely patio....Wait!!! there is more.... a theater room features great a 100 inch screen, movie lights, platform seating with counter top seating to eat your popcorn... decorated with great design and to top it off a kitchenette completes this impressive space..... Are you ready to step outside and see this impressive yard.....again the New salt water pool, the dyed concrete decking around the pool, the hardscaping, landscaping, and a wood trellis with planting features..... Additional highlights include a full house generator, invisible dog fence, and outdoor lighting. This property is a truly a one-of-a-kind gem! Just in case that was not enough to impress here are 2 more features....The large 3 car garage has new door openers, and above it is an efficiency apartment has been fully renovated with high ceilings and small kitchenette, new small deck, new large full bathroom ...did I mention this studio has wood walls that are from ........This is also a hunters enclosed 2 person deer blind, great fishing and crabbing a great outdoors persons dream.....10 acres are currently being farmed agriculturally..

248 Pond Creek Ln, Earleville

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100