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1258 Reliance Rd, Middletown
$9,000,000
4 Beds ⋅ 2 Baths
Discover an exceptional investment opportunity with this expansive 361.24-acre farm (consisting of 9 parcels of land). This property is a canvas for your vision, offering a multitude of possibilities. The lot features a unique blend of partly wooded areas and open spaces, providing a perfect backdrop for various agricultural ventures or recreational developments. With its agricultural use along with the presence of historical resources, the land is a great candidate for conservation tax credits. The potential is limitless, and the natural beauty of the land enhances its appeal. With road frontage along I-66 and Reliance Road (State Route 627), and its close proximity to the Virginia Inland Port, accessibility is a key advantage, ensuring that your investment is not only visible but also easily reachable. This feature is crucial for any future development or agricultural operations, allowing for seamless transportation of goods. There are two farmhouses located on the property, but both will require substantial renovations for livability. Seven out of the nine parcels included in the sale receive a reduced tax assessment due to being located within an agricultural land use designation. Two of the parcels were too small to receive the designation. Property is being sold "As-Is, Where-Is."

1258 Reliance Rd, Middletown

Listing courtesy of Farms & Acreage, Inc.. Contact:

1343 Bohemia Mill Rd, Middletown
$5,100,000
15 Beds ⋅ 13 Baths
Candyland – A Once-in-a-Generation Equestrian Estate in Middletown, Delaware Welcome to Candyland, a landmark estate unlike anything the Middletown, Delaware market has seen in over 30 years. This extraordinary 120 plus acre equestrian property is more than a farm—it is a private world of luxury, privacy, and possibility. Encompassing three separate parcels, Candyland features five residences and two in-ground pools, offering a rare blend of multigenerational living, income potential, or private retreat opportunities all within one breathtaking estate. From the moment you enter, Candyland feels like a place suspended between imagination and reality. Rolling pastures stretch across the landscape, morning mist rises over open fields, and the quiet rhythm of horses sets the tone for each day. This is a property where life slows down, space expands, and every view feels intentional. At the heart of the estate stands the main residence, a thoughtfully designed showcase of modern luxury and timeless elegance. The home features an open-concept layout designed for both grand entertaining and everyday comfort. A dramatic foyer welcomes you in, setting the tone with refined finishes and curated design elements, while the gourmet kitchen serves as the centerpiece of the home with high-end appliances, generous workspace, and seamless flow into the main living areas. Beyond the primary residence, Candyland unfolds across its additional homes, each offering its own character and charm. Whether used for guests, extended family, caretakers, or rental opportunities, the flexibility of five total residences across three parcels creates a level of versatility rarely found in luxury equestrian estates. For the equestrian enthusiast, Candyland is fully equipped and thoughtfully designed for horse care and training at the highest level. Multiple barns provide premium shelter and functionality, complemented by run-in sheds throughout the property. Automatic water systems support ease of care, while expansive open land and dedicated spaces allow for riding, training, and enjoying the sport in its purest form. This is a property built for both performance and peace, where horses thrive as much as their owners. Life at Candyland extends far beyond its structures. Ride for miles across scenic acreage, host unforgettable gatherings under open skies, or simply enjoy the serenity of a private estate that feels worlds away while still being conveniently located in Middletown. Every corner of the property has been designed—intentionally or naturally,to inspire connection, relaxation, and a sense of escape. Rarely does a property of this scale, versatility, and beauty become available in such a desirable location. Candyland is not just a home or a farm, it is a legacy estate designed for those who value space, freedom, and extraordinary living. Candyland consists of three parcels totaling over 120 acres, five homes, and two in-ground pools. Public water hook-up is available. The square footage referenced reflects the main residence only. For safety and privacy, the property is shown by appointment only. Please do not enter Candyland Lane without a scheduled showing. ( the amount of bedrooms and bathrooms, consist of all of the homes on the property) There are not interior photos online, due to privacy reasons. They can be sent per request. Thank you

1343 Bohemia Mill Rd, Middletown

Listing courtesy of Thyme Real Estate Co LLC. Contact:

1343 Bohemia Mill Rd, Middletown
$5,100,000
11 Beds ⋅ 10 Baths
Candyland – A Once-in-a-Generation Equestrian Estate in Middletown, Delaware Welcome to Candyland, a landmark estate unlike anything the Middletown, Delaware market has seen in over 30 years. This extraordinary 120 plus acre equestrian property is more than a farm,it is a private world of luxury, privacy, and possibility. Encompassing three separate parcels, Candyland features five residences and two in-ground pools, offering a rare blend of multigenerational living, income potential, or private retreat opportunities all within one breathtaking estate. From the moment you enter, Candyland feels like a place suspended between imagination and reality. Rolling pastures stretch across the landscape, morning mist rises over open fields, and the quiet rhythm of horses sets the tone for each day. This is a property where life slows down, space expands, and every view feels intentional. At the heart of the estate stands the main residence, a thoughtfully designed showcase of modern luxury and timeless elegance. The home is immaculate, and features an open-concept layout designed for both grand entertaining and everyday comfort. A dramatic foyer welcomes you in, setting the tone with refined finishes and curated design elements, while the gourmet kitchen serves as the centerpiece of the home with high-end appliances, generous workspace, and seamless flow into the main living areas. Beyond the primary residence, Candyland unfolds across its additional homes, each offering its own character and charm. Whether used for guests, extended family, caretakers, or rental opportunities, the flexibility of five total residences across three parcels, each with their own septic and well, creates a level of versatility rarely found in luxury equestrian estates. For the equestrian enthusiast, Candyland is fully equipped and thoughtfully designed for horse care and training at the highest level. Multiple barns provide premium shelter and functionality, complemented by run-in sheds throughout the property. Automatic water systems support ease of care, while expansive open land and dedicated spaces allow for riding, training, and enjoying the sport in its purest form. This is a property built for both performance and peace—where horses thrive as much as their owners. Life at Candyland extends far beyond its structures. Ride for miles across scenic acreage, host unforgettable gatherings under open skies, or simply enjoy the serenity of a private estate that feels worlds away while still being conveniently located in Middletown. Every corner of the property has been designed,intentionally or naturally—to inspire connection, relaxation, and a sense of escape. Rarely does a property of this scale, versatility, and beauty become available in such a desirable location. Candyland is not just a home or a farm, it is a legacy estate designed for those who value space, freedom, and extraordinary living. Candyland consists of three parcels totaling over 120 acres, five homes, and two in-ground pools. Public water hook-up is available. The square footage referenced reflects the main residence only. For safety and privacy, the property is shown by appointment only. Please do not enter Candyland Lane without a scheduled showing. No interior photos due to privacy reasons, I do have photos I can send if interested. ( The bedrooms include all of the properties)

1343 Bohemia Mill Rd, Middletown

Listing courtesy of Thyme Real Estate Co LLC. Contact:

1080 Dutch Neck Rd, Middletown
$3,125,000
4 Beds ⋅ 4 Baths
Hidden behind roughly 1,200 feet of mature arborvitae, this gated estate of approximately 27 acres combines a 4 bedroom 3.5 bth main residence w/ a 2 car attached garage and 4 car detached garage. A guest house built in 2023 which is 2 bed, 2bth and a stone-front professional office also built in 2023 can be converted to another dwelling, as well as a complete equestrian and livestock facility, all inside one perimeter fence with two separate gated entrances. The main residence offers hardwood floors, a two-story foyer, a formal dining room and a two-story recreation room with a floor-to-ceiling wood-burning fireplace. The chef’s kitchen features a Wolf double oven and six-burner range with griddle, full-size commercial refrigeration, an island ice maker and heated tile floors. The first-floor primary suite includes a custom walk-in closet and a spa bath with heated floors and a dual-head shower. Outside: a gunite pool with automatic cover, hot tub, outdoor fireplace and a one-acre fenced pond with lighted fountains, an island and a bridge. The guest house is leased month to month. The office has a reception area, conference room, two private offices, kitchen and full bath. Equestrian and ag improvements include a five-stall barn with tack room, covered heavy-use pad with handling equipment, seven pastures with heated automatic waterers, a large clear-span storage building and a two-story barn. Two wells, two 22 kW generators, two owned propane tanks, two electric services and two fiber internet lines provide full redundancy. New HVAC and electrical panels in 2025. Preserved land on one side and thousand acre marsh behind. Enjoy ATV trail, access to hunting stands and also access to C&D Canal for duck hunting. All the garages and buildings are operated by MyQ and the entire estate is paved from one gate to another. Almost maintenance free with a cattle operator who grazes the pastures in exchange for grounds maintenance and he may stay for new owner. (Cattle do not convey with sale) Appointment only. Two parcels being sold together.

1080 Dutch Neck Rd, Middletown

Listing courtesy of RE/MAX Associates-Hockessin. Contact:

1115 Chapel Rd, Middletown
$3,100,000
3 Beds ⋅ 3 Baths
Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern living. A few of the Key Features Include: Panoramic Mountain Views in every direction, Automatic Waterers in each pasture—low maintenance, year-round convenience, Horse-Ready Barn with two stalls, Signature Magnolia Tree adding timeless Southern elegance, Home with Dual-Level Balconies—ideal for sunrise coffee or sunset unwinding, Cross-Fenced and ready for livestock or rotational grazing, Just Minutes from the Interstate—secluded but accessible, Possible Subdivide Opportunity—invest or expand! Whether you're looking to build your legacy homestead or develop for future value, this property offers rare versatility and classic Southern beauty. A place where refined elegance meets rustic beauty. Nestled amid rolling pastures and panoramic mountain views, this property boasts a classic English boxwood garden—a tranquil, evergreen sanctuary that adds both prestige and peace to the landscape. Whether you're strolling through boxwood-lined paths, sipping sweet tea on the balcony, or watching your horses graze at sunset, this property captures the romance of the South with timeless sophistication.

1115 Chapel Rd, Middletown

Listing courtesy of Mountains Edge Realty LLC. Contact:

1115 Chapel Rd, Middletown
$3,100,000
3 Beds ⋅ 3 Baths
Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern living. A few of the Key Features Include: Panoramic Mountain Views in every direction, Automatic Waterers in each pasture—low maintenance, year-round convenience, Horse-Ready Barn with two stalls, Signature Magnolia Tree adding timeless Southern elegance, Home with Dual-Level Balconies—ideal for sunrise coffee or sunset unwinding, Cross-Fenced and ready for livestock or rotational grazing, Just Minutes from the Interstate—secluded but accessible, Possible Subdivide Opportunity—invest or expand! Whether you're looking to build your legacy homestead or develop for future value, this property offers rare versatility and classic Southern beauty. A place where refined elegance meets rustic beauty. Nestled amid rolling pastures and panoramic mountain views, this property boasts a classic English boxwood garden—a tranquil, evergreen sanctuary that adds both prestige and peace to the landscape. Whether you're strolling through boxwood-lined paths, sipping sweet tea on the balcony, or watching your horses graze at sunset, this property captures the romance of the South with timeless sophistication.

1115 Chapel Rd, Middletown

Listing courtesy of Mountains Edge Realty LLC. Contact:

2857 E Harrisburg Pike, Middletown
$2,100,500
Prime Investment Opportunity on a 12+ Acre Corner Lot! This conveniently located commercial/residential property sits at the corner of E. Harrisburg Pike and Toll House Road, offering excellent visibility and easy access to Route 283. The property includes multiple outbuildings and is currently being utilized as an auto body shop, providing immediate income or business potential. At the front of the property is a 3-bedroom, 1.5-bath home that is currently tenant-occupied and generating rental income. The rear portion of the property is flat and open, presenting a strong opportunity for future development or expansion. Property is being sold as-is. All showings must be scheduled during daylight hours with a minimum of 24-hour notice. Don’t miss this unique opportunity—schedule your private showing today! Londonderry Township is the best point of contact to discuss the permitted uses.

2857 E Harrisburg Pike, Middletown

Listing courtesy of Samson Properties. Contact:

9237 Frostown Rd, Middletown
$1,999,999
Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown Valley and South Mountain to 1960s design roots, to modern comfort, the home embodies seclusion without sacrificing accessibility. At the heart of the living spaces, a grand fireplace anchors the flow, guiding the eye and gathering rooms into a seamless continuum. The layout invites conversations to drift from indoor to outdoor and back again, with spaces merging around this warm, sculptural anchor. From Kentucky pink sandstone and cedar exteriors to warm interior touches—wood floors, custom concrete sinks, maple doors and trim, and a well-organized mudroom and laundry area—every surface speaks to craft and longevity. On the main level the Center Room is designed for living and entertaining. It is enriched by commissioned art, beautiful Kentucky sandstone fireplace and huge windows that look out over the Middletown Valley. A wrap around deck allows transition from the indoors to out, with just a few footsteps. A dedicated library with custom maple shelving creates a quiet, sunlit mezzanine of ideas—is a perfect retreat for reading, group study, or inspiration. The stunning kitchen was designed in collaboration with local architect, Clyde Burger. The two 12’ long walnut islands and all the kitchen cabinetry is hand-built Mennonite woodwork. The work surfaces are polished concrete, and the built-in appliances are professional grade. A kitchen lounge houses built-in cabinetry and encourages family and social time as meals are prepared and enjoyed. An 18-foot NanaWall opens to dissolve the boundary between inside and outdoor. The main level laundry has clean lines, beautiful carpentry, wonderful hand built floating shelves, custom concrete surfaces and sink as well as a wet floor and direct access to the decks and yard. The mudroom and powder room also feature custom cabinetry and specially designed features, such as the concrete sink and the floating concrete benches. The primary suite is un-filled, architectural artistry with an imported floor, two walk-in closets (one cedar-lined), and a bath featuring terrazzo floors and a standout view. Two en-suite bedrooms, renovated December 2025, have wood floors with custom Navajo-inspired wood inlays. Commissioned furnishings fill of the rooms and both enjoy nature views. The lower-level spaces are also remarkable. The second grand room has a vibrant MCM fireplace and is ideal for family activities, mediation or intimate gatherings. The windows showcase the valley view, and the doors open directly to the saltwater pool. Two private rooms are ready to use as bedrooms or office spaces. The full bathroom also has a custom concrete vanity and floor and warm cork tiling. This wing of the lower-level embraces angles and has built floating shelves in the lower library. Additionally, this level offers a bright, versatile studio providing space for creativity of all types—art, writing, design, or restorative projects— to inspire and nurture imagination. The exterior grounds are a living landscape. The 5-acre parcel unfolds as a natural paradise with park-like landscaping and hundreds of flowering trees seen from every window. The long drive lined with light poles and the parking area edged by planters sets a welcoming tone as you approach the home. A multi-level Brazilian hardwood deck overlooks a heated saltwater pool; a detached barn houses a traditional Scandinavian sauna and a lounge for year-round wellness. The homes systems are wellness-oriented including geothermal HVAC, a brand-new roof with a 50-year warranty, a multi-stage water softening system.

9237 Frostown Rd, Middletown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

9237 Frostown Rd, Middletown
$1,999,999
4 Beds ⋅ 5 Baths
Five private acres above the Middletown Valley, with South Mountain on the horizon and protected conservation land on two sides. This is a home built around how you want to spend your days: coffee in a kitchen with two 12-foot walnut islands and an 18-foot NanaWall that opens straight to the deck, afternoons at the heated saltwater pool, evenings by the Kentucky sandstone fireplace with the whole valley in the windows. When the day is done, the detached barn holds a Scandinavian sauna and a lounge for year-round unwinding. The layout works for daily life and for hosting. Three bedrooms are on the main level, including a primary suite with two walk-in closets (one cedar-lined) and a terrazzo bath. Two en-suite bedrooms were renovated in December 2025. A sunlit library with custom maple shelving sits above the main living space. Downstairs, a second great room with its own fireplace opens to the pool. Two flex rooms suit guests or a home office, and a bright studio is ready for art, writing, or design work. The main-level laundry and mudroom open directly to the deck and yard. It's built to last: geothermal heating and cooling, a brand-new roof with a 50-year warranty 2026, multi-stage water softening, hand-built Mennonite cabinetry, polished concrete surfaces, and a two-car attached garage. A long, lighted drive leads to complete privacy, yet 3 minutes to Middletown, 10 to Frederick, and 5 to [I-70/major commuter route].

9237 Frostown Rd, Middletown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

3150 Bidle Rd, Middletown
$1,719,900
5 Beds ⋅ 8 Baths
To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is a premier 12 lot luxury estate home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 7 beautiful acres, 3150 Bidle Rd (Lot 3E) is a gorgeous build-ready homesite with a 5BR septic approval and high yield 10gpm well already installed. Advertised is the ACL5 plan which features over 6,000 finished sqft, 5 bedrooms (including dual owner's suites), 4 full baths and 3 half baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, parlor/enterainment room, formal dining room, morning room, upper level bonus room, primary suites on both main and upper levels, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3150 Bidle Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

992 Port Penn Rd, Middletown
$1,599,000
4 Beds ⋅ 4 Baths
With lots of charm and character this 61 acre farm is located near the village of Port Penn, visited by William Penn in 1682 and named after him. Mostly rolling cropland with some marsh and woods to the rear of the property, The Farm would be a great place for raising farm animals and kids. Featuring four bedrooms two full and two half baths with updated kitchen, new sunroom, many thoughtful updates throughout the home, porch, pool, pond, and numerous outbuildings for animals, dirt bikes, or hunting as The Farm is located within a large wildlife area with lots of deer and Canadian geese. An adjacent property is owned by Delaware Wildlands as sanctuary for extensive ducks and geese. Additionally, there is a three bedroom two bath one story rental home renting at two thousand dollars a month. Great for multi-generational living! Located very near the Delaware River to the east and Rte. 1 interchange several miles away. A must see for those seeking tranquil country living. Pre-qualification required for showing

992 Port Penn Rd, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

220 Nighthawk Dr, Middletown
$1,550,000
5 Beds ⋅ 4 Baths
A truly extraordinary opportunity to own a restored piece of Delaware history, 220 Nighthawk Drive—historically known as the Mrs. Templeman Farmhouse—is a remarkable circa-1830 residence where nearly two centuries of character have been preserved and paired with modern luxury. Set on 5.81 acres, this approximately 5,500 sq. ft., 5-bed, 3.5-bath home underwent an extensive renovation completed in 2026 with superior craftsmanship and high-end finishes, while preserving many original architectural elements. Original boxwood trees remain along the drive, offering a glimpse into the property’s past as you approach the historic farmhouse and its outbuildings. Brick paver walkways lead toward the home and grounds. Step through the original wooden front door to find rich red oak hardwood flooring, solid wood doors and the preserved original staircase. To the left of the foyer, the living room features oversized crown molding and a gas fireplace framed by its original brick surround. To the right, the formal dining room is filled with natural light and enhanced by a tray ceiling and oversized crown molding. Continue to the stunning kitchen, where handcrafted solid wood cabinetry is paired with quartz countertops, a striking hickory wood island and walk-in pantry. Shiplap walls add warmth, while original exposed wooden ceiling beams preserve the farmhouse character. A double-sided fireplace connects the kitchen and adjoining sunroom and features a mantel constructed from fieldstone found on the property. The sunroom features brick flooring, recessed lighting and a fireplace surrounded by original fieldstone. Double doors from the kitchen open onto a brick patio, creating a connection to the surrounding acreage. A beautifully appointed powder room completes the first floor. Upstairs are three bedrooms, two full bathrooms and a dedicated second-floor laundry room. The expansive primary suite offers a walk-in closet, ensuite bathroom and direct access to the third-floor loft. The primary bath features a classic claw-foot tub paired with a frameless glass shower. The third floor offers two additional bedrooms with Jack-and-Jill access to a full bathroom. The finished basement is not to be missed. Portions of the original stone foundation walls have been strengthened, preserved and left exposed as a dramatic architectural feature. Wood-paneled walls and ceilings create incredible ambiance, while Bilco doors provide convenient yard access. While the home's character has been carefully preserved, its infrastructure has been extensively modernized. The 2026 renovation includes all-new electrical and plumbing, roof, Andersen windows, appliances, four HVAC systems and a tankless water heater. Recessed lighting is found throughout, and both the detached garage and barn received new foundations. The property itself is equally remarkable. The oversized, heated 24' x 36' detached two-car garage provides generous parking, workspace and storage. Nearby, the original chicken house remains as another connection to the property’s agricultural past. The impressive 31' x 26' barn features a new foundation and floored upper level for additional storage. Even stormwater management has been thoughtfully considered, with the home's downspouts directed to a rain garden. Historically documented as the Mrs. Templeman Farmhouse and associated with the former Lovett Farm/Chestnut Grove Farm. 220 Nighthawk Drive is far more than a renovated farmhouse. It is the thoughtful restoration of a nearly 200-year-old property where modern systems, luxurious finishes and exceptional craftsmanship have been carefully integrated without erasing its irreplaceable character. From the 5.81-acre setting to the historic farmhouse, barn, original chicken house and preserved architectural details, this is a rare opportunity to become the next steward of an exceptional piece of DE history.

220 Nighthawk Dr, Middletown

Listing courtesy of Compass. Contact:

134 Ayshire Dr, Middletown
$1,499,900
4 Beds ⋅ 4 Baths
Nestled in the prestigious Highlands at Back Creek, this exquisite residence embodies the perfect blend of luxury and comfort. Built in 2022, this stunning detached home showcases a captivating Colonial and A-Frame architectural style, offering a timeless elegance that welcomes you from the moment you arrive. As you step inside, you are greeted by an expansive layout that seamlessly integrates modern design with warm, inviting spaces. The heart of the home features a spacious living area bathed in natural light, perfect for both intimate gatherings and grand entertaining. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and ample counter space, making meal preparation a delight. With four generously sized bedrooms and three and a half beautifully appointed bathrooms, this home provides an abundance of space for relaxation and rejuvenation. The master suite is a true sanctuary, complete with luxurious finishes and a spa-like en-suite bathroom that invites you to unwind after a long day. The full, unfinished basement offers endless possibilities for customization, whether you envision a home theater, gym, or additional living space. Step outside to discover your own personal oasis-a private pool surrounded by lush landscaping, perfect for summer days spent lounging in the sun or hosting unforgettable poolside gatherings. The property sits on a sprawling 0.81-acre lot, providing ample outdoor space for recreation and relaxation. The side-entry attached garage accommodates three vehicles, ensuring convenience and ease for you and your guests. This home is not just a residence; it's a lifestyle. Enjoy the tranquility of suburban living while being just moments away from vibrant local amenities. The Highlands at Back Creek community offers a serene environment, perfect for those seeking a peaceful retreat without sacrificing accessibility to shopping, dining, and entertainment. Experience the epitome of luxury living in this remarkable home, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. Don't miss the opportunity to make this dream home your reality. Schedule your private tour today and step into a world of elegance and comfort.

134 Ayshire Dr, Middletown

Listing courtesy of EveryHome Realtors. Contact:

7453 Heritage Oak Ter, Middletown
$1,349,900
4 Beds ⋅ 4 Baths
To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 3.78 beautiful acres, 7452 Heritage Oak Terr (Lot 4W) is a gorgeous build-ready homesite with perc approval and well installed. Advertised is the ACL4 plan which features over 4,400 finished sqft, 4 bedrooms and 3.5 baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, formal dining room, morning room, private office, a stately Owner's suite w/260 sqft walk-in closet, Hardie Plank siding and full stone water table are just a few standard options in this model. Advertised is the base price for the ACL4 model on this lot. Photos are of a previously built ACL4 model a modern farmhouse elevation. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

7453 Heritage Oak Ter, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

864 Old School House Rd, Middletown
$1,300,000
3 Beds ⋅ 3 Baths
Tucked away on 11 pristine, private acres in Middletown, this home offers a rare blend of sweeping natural beauty, effortless single-level luxury, and incredible versatility. From the moment you pull up the drive, the gorgeous, park-like setting establishes a profound sense of peace and privacy that is hard to find, yet keeps you incredibly close to local conveniences. Step inside the main residence and you are immediately greeted by the warmth of rich hardwood floors and the airy, expansive feel of soaring vaulted ceilings. Designed for seamless everyday living and effortless entertaining, the heart of this home is a true gourmet kitchen. Outfitted with gleaming quartz countertops and top-of-the-line stainless steel appliances, it flows beautifully into both the inviting family room and the grand great room. Whether you are hosting holiday dinners or enjoying quiet mornings watching the sunrise over your acreage, this layout adapts perfectly to your lifestyle. The main home features three spacious bedrooms and two and a half baths, including a serene primary retreat. A dedicated first-floor office provides the ideal, quiet sanctuary for remote work or creative pursuits, tucked away from the main living areas. Just steps away sits a remarkable asset: a fully detached, separate second dwelling. This self-contained space is perfect for multi-generational living, long-term guests, or an inspiring studio. It features a bright loft, a large, comfortable great room, a convenient kitchenette, one bedroom, and two full bathrooms—offering complete independence and comfort without sacrificing privacy. Completing this exceptional estate is an oversized, three-car detached garage, offering abundant space for vehicles, a workshop, or recreational storage. This isn't just a home; it’s a private retreat where modern luxury meets eleven acres of quiet, gorgeous Delaware countryside. You have the opportunity to purchase an additional 14 acres, MLS NUMBER MLS# DENC2098214 & tax ID 13-012.00-151 to make this a wonderful 26 acre estate!

864 Old School House Rd, Middletown

Listing courtesy of Thyme Real Estate Co LLC. Contact:

7783 Main St, Middletown
$1,300,000
Unlock the potential of a timeless landmark with the Wayside Inn, a historic gem nestled in the heart of Middletown, Virginia. This unique property not only boasts a rich history dating back to the 18th century but also offers 22 suites all with bathrooms, 3 bars (tavern, bourbon & Speakeasy, The RED HAT), huge entertaining space for events. This is a prime commercial opportunity with an expansive land for expansion. Just under 4 acres zoned B1. With 4 acres of commercially-zoned land at your disposal, envision the expansion possibilities that could elevate this historic landmark into a thriving hub of activity. Take advantage of the ample space to create a vibrant commercial district that complements the historic character of the Wayside Inn, making it a destination for locals and tourists alike. Situated in the picturesque Shenandoah Valley, the Wayside Inn offers a scenic backdrop that enhances the allure of any commercial venture. The expansive grounds provide ample room for outdoor amenities, gardens, or additional structures to further enhance the property's appeal. Benefit from the strategic location of Middletown, with easy access to major transportation routes. The Wayside Inn's proximity to popular attractions, historic sites, and a supportive local community makes it an ideal location for a successful and sustainable business venture. Don't miss the chance to own a piece of history with a promising future. The Wayside Inn presents a rare investment opportunity where historic charm meets commercial potential. Whether you're an entrepreneur seeking a unique venture or a developer with a vision, this property is your canvas to create something extraordinary. Seize the moment and transform the future of the Wayside Inn. Embrace the legacy, write the next chapter, and make this historic landmark a cornerstone of Middletown's thriving community. Fully running and doing great, we have changed management and its now positive cash flow. its prime for an owner occupant. call for details and appointments. Open to lease option and owner financing available. Kitchen and tavern are leased. Have grants applied for in the millions to renovate it. Have insurance claim coming for a new roof as well.

7783 Main St, Middletown

Listing courtesy of RE/MAX Allegiance. Contact:

217 N Broad St, Middletown
$1,250,000
6 Beds ⋅ 4 Baths
The Dr. Dorsey Lewis House — A Middletown Landmark! One of Middletown's most distinguished historic manor residences, this magnificent Colonial Revival home occupies nearly an acre in the heart of town. An expansive, columned front porch welcomes you into a grand center hall, generously proportioned rooms, beautiful hardwood floors, rich architectural details, and multiple fireplaces. Offering six bedrooms and three full and one half baths, the residence was featured as a 2011 Decorator Show House. Outside, a private backyard oasis features an in-ground swimming pool, spa, inviting patios, and mature landscaping. An extraordinary collection of outbuildings includes a detached two-car garage, a 14-bay carriage building, and a 2,700-square-foot detached pole-building currently serving as a decorator/retail storefront with its own six-car parking lot. Lovingly maintained by its current owners, this remarkable estate offers a rare opportunity to become the next steward of a treasured piece of Middletown history. Truly one of a kind and nearly impossible to replicate today!

217 N Broad St, Middletown

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

3130 Bidle Rd, Middletown
$1,249,900
4 Beds ⋅ 4 Baths
To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 4.65 beautiful acres, 3130 Bidle Rd (Lot 1E) is a gorgeous build-ready homesite that offers a perfect combination of protected woodlands and rolling pastoral landscape. Advertised is the ACL3 plan which features over 3,000 finished sqft, 4 bedrooms, 3.5 baths including a main level owner's suite. Additional standard features include a spacious open concept kitchen with large center island and high end cabinetry, beautiful 2 story foyer, morning room, private office, luxurious Owner's suite, Hardie Plank siding and full stone water table. Photos are of a home that builder recently finished in Frederick County. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3130 Bidle Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

5901 Cloudberry Ct, Middletown
$1,148,990
4 Beds ⋅ 4 Baths
HOME TO BE BUILT! - Don't miss the final opportunity to build your new custom home! Experience the breathtaking mountain views and modern luxury in your new construction home to be built by Grossnickle Construction, nestled in the heart of Middletown Valley. This thoughtfully designed 4-bedroom, 3.5 bath home offers the perfect blend of elegance, comfort and functionality. Step inside to discover an open concept floor plan featuring spacious living areas, abundant natural light and high-end finishes throughout. The gourmet kitchen will impress with premium cabinetry, quartz countertops, oversized island and seamless flow into the dining and family rooms - perfect for entertaining or everyday living. Conveniently located near charming downtown Middletown, parks and commuter route, this exceptional to be built home offers the rare opportunity to personalize your dream home.

5901 Cloudberry Ct, Middletown

Listing courtesy of Charis Realty Group. Contact:

1 Wagon Shed Ln, Middletown
$1,100,000
5 Beds ⋅ 6 Baths
Welcome to 1 Wagon Shed Lane, a stunning five-bedroom, five-full- and one-half-bath Colonial offering nearly 7,000 square feet of luxurious living space in the sought-after Glenbrook community of Middletown. Polished elegance, sophisticated details, and design-inspired finishes distinguish every level, including classic moldings, wainscoting, stately columns, gleaming hardwood floors, soaring ceilings, and expansive windows. The open-concept main level is filled with natural light and offers an inviting, versatile layout ideal for everyday living and entertaining. At the heart of the home, the gourmet eat-in kitchen is beautifully appointed with granite countertops, stainless steel appliances, a center island, breakfast bar, decorative backsplash, display cabinetry, and a convenient planning station. A sun-filled breakfast room and adjoining sitting area provide direct access to the custom deck and patio. Just beyond, the impressive two-story great room takes center stage with coffered ceilings, dramatic Palladian windows, and a stacked-ledgestone fireplace and hearth. Formal living and dining rooms offer elegant settings for special occasions, while a private office with French doors, powder room, and thoughtfully designed arrival center with a laundry room and Kohler cast-iron sink complete the main level. Upstairs, the luxurious primary suite provides a private retreat featuring a spacious sitting room, expansive walk-in closet, and spa-inspired en-suite bath with separate vanities, a soaking tub, private water closet, and glass-enclosed shower. Three additional bedrooms, each with a private en-suite full bath, and rich Lifescapes Hevea distressed solid hardwood flooring throughout the second level complete the upper-level accommodations. Superior craftsmanship continues into the expansive finished lower level, offering an impressive game room, exercise room, hobby room with built-in shelving, versatile bonus room, fifth bedroom, full bath, and abundant storage. Additional storage is available through numerous closets and custom garage cabinetry. Outside, professionally landscaped grounds are enhanced by mature plantings, fencing, a deck, custom hardscaping, and spectacular Middletown Valley sunsets. A heated three-car garage and generous driveway parking complete this exceptional property. The home has been thoughtfully enhanced with significant updates, including two new high-efficiency variable-capacity HVAC systems and a new 75-gallon natural gas water heater in 2026. The HVAC improvements include Ecobee smart thermostats, indoor and outdoor surge protection, germicidal UV-light protection for both systems, and a large-capacity Aprilaire humidifier. Exterior improvements completed in 2025 include a CertainTeed Landmark Pro roof, six-inch gutters and downspouts, and replacement window screens. Additional enhancements include a whole-house water-softening system, updated lighting and ceiling fans, luxury carpeting and padding, added trim and crown moldings, replaced and recently resealed driveway, along with a Nutone Central Vac System that serves all three levels of the home. Enjoy a tranquil community setting with the convenience of public water and sewer and access to the amenities of Middletown. Nearby destinations include Richland Golf Club, the Middletown Branch Library, Remsberg Park, the renovated Middletown Community Park, grocery stores, restaurants, pharmacies, and everyday services. The home is served by Middletown schools, with a new co-located elementary and middle school campus currently under construction and anticipated for completion in 2027. Convenient access to I-70, I-270, US-340, US-15, and US-40 provides connections to Frederick, Hagerstown, and surrounding areas.

1 Wagon Shed Ln, Middletown

Listing courtesy of Northrop Realty. Contact:

415 Marcus Rd, Middletown
$1,099,000
4 Beds ⋅ 4 Baths
Modern Luxury Meets Timeless Craftsmanship on a Private 1-Acre Estate. Welcome to this stunning custom-built luxury residence, meticulously designed to combine modern elegance, high-end finishes, and thoughtful functionality. Situated on a perfectly flat 1- acre lot, this exceptional home offers over 3,000 square feet of living space, every detail curated for comfort and sophistication. The exterior features bold black windows, James Hardie board & batten siding, premium vinyl siding, and metal roofing and architectural shingles. Car enthusiasts and hobbyists will appreciate the 800 square feet of garage space, including a 2-car turned garage and a separate 1- car front-facing garage, both featuring high ceilings and recessed lighting—perfect for storage, a workshop, or a car lift setup. The oversized, concrete front porch has beautiful rough-cut cedar posts, while a beautifully designed hardscape walkway guides you to the entrance featuring an 8-foot craftsman front door. Once inside you’ll notice the architecturally pleasing open floor plan, the 9-foot ceilings, the wide-board white oak hardwood flooring that flows throughout the main level, and the white oak railings with sleek black horizontal metal balusters that adds a modern architectural touch to the grand staircase. The main floor also boasts 8-foot craftsman-style interior doors, custom trim work, modern custom floor vents, and full recessed lighting throughout. Chef’s Dream Kitchen The heart of the home is a gourmet kitchen that redefines luxury and function. Features include 42-inch custom cabinetry with detailed crown molding and under-cabinet lighting, a hidden walk-in pantry seamlessly integrated into the cabinetry, Additional pantry cabinets with rollout drawers for effortless organization , a Custom vent hood flanked by built-in spice cabinets and a 36-inch gas range, Full quartz countertops and backsplash plus a massive quartz slab island with a farmhouse sink, Integrated microwave drawer for clean a modern convenience. Enjoy cozy evenings in the spacious living room featuring vaulted ceilings and a gas fireplace with a custom barn beam mantle. The main level features the primary bedroom as well as a second bedroom/in-law suite with access to another full bathroom and laundry room. The primary suite features a large walk-in closet and barn doors that leads into the spa-inspired bathroom. This beautiful custom bathroom features large format tiles floors, a freestanding soaking tub, a floating double vanity, and a custom tiled walk-in shower with a frameless glass door. Upstairs, discover two additional bedrooms, a full bathroom with custom tile and shower, a second laundry area, and a spacious lounge area with a half bath—perfect for a media room, playroom, or home office. Additionally, the basement is over 2000 square feet and features 9-foot ceilings, offering unlimited potential for customization. This home is the perfect blend of luxury, practicality, and custom craftsmanship—an ideal sanctuary for modern living. Whether you're entertaining, working from home, or simply relaxing, every inch of this home has been designed with lifestyle in mind.

415 Marcus Rd, Middletown

Listing courtesy of Coldwell Banker Realty. Contact:

105 Ridgemont Rd, Middletown
$995,000
Rare opportunity to own 63.48± acres in northern Warren County featuring a scenic mix of open fields, mature woodlands, and West Run Creek winding through the property. Whether you're seeking a private estate, recreational retreat, hunting property, or long-term land investment, this property offers exceptional privacy and natural beauty with potential for future low-density residential development and subdivision opportunities subject to county approvals. Existing well, septic, electric service, and a 1,430 SF manufactured home convey as-is. Enjoy a secluded rural setting while remaining conveniently located near Front Royal, Middletown, Strasburg, and Winchester, with excellent access to Route 522, I-66, I-81, shopping, restaurants, and regional employment centers.

105 Ridgemont Rd, Middletown

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

251 Dillon Cir, Middletown
$985,000
4 Beds ⋅ 4 Baths
Presenting a distinguished 4-bedroom, 4 full-bathroom, Colorado II model in Summit Pointe, a newly built boutique community, crafted by K. Hovnanian Homes. This property, only 3½ years old, offers 4,725 square feet of living space with an expanded floor plan (please refer to the attached floor plans, noting the upgraded, extended areas marked in blue), with a primarily brick front elevation. Situated on a premium lot, the yard adjoins open space and farmland, providing a serene and private environment. The community streets are very wide, with elegant streetlights and sidewalks on both sides. The residence has been meticulously maintained and is conveniently located near the University of Delaware, Delaware beaches, I-95, major East Coast cities, as well as airports and train stations. Upon touring the home, observe the elegant hardwood floors on the first level, oversized windows, a blend of cathedral and 9’ ceilings, an extended floor plan across all three levels including a walk-out from the finished basement, and enhanced millwork and wainscoting. Entering from the front porch, you are greeted by a wide two-story foyer featuring a grand, impressive staircase. Natural light generously illuminates the rooms. The open and bright formal living room is situated to the right, while the elegant and spacious dining room is on the left. The first floor includes a full bathroom, study or home office, and a laundry room adjacent to the kitchen. The open concept family room and kitchen is highlighted by a two-story stone wall surrounding a gas fireplace. The kitchen is equipped with GE Profile appliances, including a wall oven, wall microwave, dishwasher, gas cooktop, side-by-side refrigerator, and hood vent. The upgraded and wide quartz countertops and Subway tile backsplash complement the 42” white cabinets, creating an inviting space for gatherings. The island is the centerpiece of the kitchen measuring 11’x5’ and has seating for 5-6 people comfortably. For entertaining guests or family, consider the finished basement with a full bath. The lower level, with walk-out access to the yard, facilitates easy indoor/outdoor activities. The expansive backyard is ideal for barbeques and games. Two large storage rooms provide additional space for seasonal or outdoor items. The home is equipped with two HVAC systems, two 200-amp electric panels, and two 50-gallon water heaters to adequately serve all occupants. The upper level houses three spacious bedrooms, two with walk-in closets and one with a double closet, along with a full hall bath. The primary suite is exceptional, offering extended upgraded space that can function as a sitting area, office, exercise area, or nursery. The primary bathroom features a walk-in shower, soaking tub, dual sinks and vanities, and two walk-in closets. This residence boasts an outstanding floor plan, offering numerous amenities, offering a full experience of the convenience and happiness of living, working, and studying at home. Schedule your appointment today to view this remarkable home.

251 Dillon Cir, Middletown

Listing courtesy of Compass. Contact:

218 Mistmeadow Dr, Middletown
$979,900
5 Beds ⋅ 5 Baths
PROFESSIONAL PHOTOS COMING SOON. Space, style, and thoughtful upgrades come together at 218 Mistmeadow Drive in Silver Wind Estates. Built in 2020 and situated on approximately three-quarters of an acre, this impressive home offers approximately 5,650 square feet, five bedrooms, four full bathrooms, and a half bath. A welcoming covered front porch, stone accents, and established landscaping create an inviting introduction, while the three-car garage and the expanded asphalt driveway, with fresh seal coating, extends toward the rear of the property and provides generous additional parking. Inside, hardwood flooring throughout the first floor, an oak staircase with metal balusters, and decorative details give the home a polished feel. The living room features an accent wall and additional side windows, while chair rail and wall molding lend character to the dining room. A gas fireplace with stone extending to the ceiling anchors the family room, creating a striking gathering space. The kitchen features a cooktop, wall ovens, an added backsplash, and a large pantry offering generous storage. A main-level bedroom suite with its own full bathroom offers flexibility for guests or those seeking bedroom accommodations on the first floor, while a separate half bath adds convenience. Upstairs, the primary suite and a separate Princess Suite offer comfortable retreats, complemented by additional bedrooms and a loft that provides flexible living space. Recessed lighting throughout multiple rooms enhances the home’s thoughtful appointments. The expansive, partially finished basement offers space for entertaining, recreation, or a home gym, with a wet bar and wine cooler adding to its appeal. Two substantial unfinished areas provide ample storage and opportunities to customize additional space to suit your needs. Outside, the widened driveway extends toward the rear of the property, while an irrigation system serves the front, both sides, and a portion of the backyard. Ideally located in Middletown within the Appoquinimink School District, the home is just minutes from shopping, dining, parks, and schools. HOA services include trash collection, snow removal, and maintenance of community open space. An added benefit: the sellers will pay off the remaining solar panel balance at settlement.

218 Mistmeadow Dr, Middletown

Listing courtesy of BHHS Fox & Roach-Greenville. Contact:

204 Stover Ct, Middletown
$949,990
5 Beds ⋅ 5 Baths
Welcome to 204 Stover Court, located in the Estates of Cedar Lane. This stunning brick home located on an exceptional lot with a serene wooded backdrop has a back yard oasis awaiting you. This beautiful home features a two-story family room with a coffered ceiling, gas fireplace and open to the large kitchen. The kitchen is a chef's delight, boasting a large island that comfortably seats five and an oversized morning room filled with windows, perfect for enjoying natural light. The home offers five spacious bedrooms and four and a half bathrooms, ensuring ample space for everyone. The finished basement is an entertainer's dream with a walk-out, a gorgeous bar, an exercise room, a full bathroom, and an additional bedroom, perfect for guests or extended family. The mudroom is thoughtfully designed with custom lockers, offering functional storage solutions. Experience the perfect blend of luxury, comfort, and functionality in this exceptional home. Here are some of the best upgrades....a 3 car garage, a large deck, a custom paver patio ...In 2022 solar panel added, the basement finished with all permits full bathroom, an unbelievable bar with a sink, quartz countertops custom stone work....a large bedroom with a murphy bed and large closets, new outdoor well pump, in 2024 new hot water heater, primary bedroom closet designed, ceiling rack storage added to garage and just to add more to the list a new dishwasher 2026...............so much to see. VA buyers if you qualify there is a 2.85% assumable mortgage

204 Stover Ct, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

8939 Hawbottom Rd, Middletown
$949,000
3 Beds ⋅ 3 Baths
Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want their permanent home to feel like a fortress of solitude without sacrificing modern comforts. The interior features a recently updated kitchen equipped with new appliances and granite countertops. While there is a propane furnace, there is also a classic woodstove that provides a high-efficiency heating source and a focal point for the entertainment area in the basement. The home’s footprint is anchored by an expansive rear deck designed for four-season use; whether you’re hosting or decompressing, the integrated hot tub offers total privacy, screened by a dense canopy of mature timber to create an outdoor living room that feels completely removed from the outside world. This isn't just a woodlot; it's a gateway. The property borders Gambrill State Park, providing exploration and recreational opportunities right out your back door. For the serious outdoorsman or the family seeking an active lifestyle, the land offers endless utility for hiking, scouting, and wildlife management. The long, wooded approach ensures a level of seclusion and security that is increasingly rare, making this an ideal primary residence for those seeking a quiet, secure environment. Practicality meets potential inside and out, with a walkout basement that provides the ideal entertainment area or can be converted into a home office, gym, or additional bedrooms to grow with your needs. An existing shed provides organized storage for ATVs and maintenance equipment, keeping your primary living spaces clutter-free. Shown by appointment only, this is more than a getaway—it is a rare opportunity to own a significant piece of acreage with your ideal mountain retreat on your own recreational land in the Catocin Mountains.

8939 Hawbottom Rd, Middletown

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

909 Ash Farm Way, Middletown
$935,000
4 Beds ⋅ 5 Baths
Welcome to 909 Ash Farm Way, an exceptional Middletown residence offering more than 4,650 square feet of beautifully finished living space, where sophisticated design meets outstanding craftsmanship. This Model-Quality home must be seen to be appreciated with custom millwork, refined architectural details, and thoughtfully selected upgrades creating an elevated atmosphere throughout. The heart of the home is the stunning gourmet kitchen, featuring premium finishes, GE Monogram appliances and an oversized center island ideal for entertaining, casual dining, and everyday gatherings. The kitchen flows seamlessly into the dramatic two-story family room, highlighted by custom millwork and a gas fireplace that creates a warm and inviting focal point. Professional Office, Formal Living Room and Dining Room complete this level. Upstairs, hardwood flooring carries through the Primary Owner's Suite, completed with a Sitting Room with vaulted ceiling and spa-like full bath. The first guest Bedroom is ensuite with it's own Full Bath. 2 additional generously-sized guest bedrooms and share a Jack-and-Jill Bath providing comfort and flexibility, while the finished lower level expands the living space with a second family room, full bath, and versatile areas perfectly suited for recreation, guests, or a private retreat. A 3-car garage offers exceptional storage and functionality. Outside, a custom composite deck overlooks professionally designed landscaping, custom accent landscape lighting and mature specimen plantings, providing a picturesque setting for relaxing or entertaining. Meticulously maintained and beautifully appointed, this remarkable property delivers luxurious, move-in-ready living in one of Middletown’s most desirable settings.

909 Ash Farm Way, Middletown

Listing courtesy of EXP Realty, LLC. Contact: