Middleburg VA Real Estate, Homes with Pool for Sale

Welcome home to Woodland Farm: a legacy equestrian estate in the heart of Loudoun County. Experience the pinnacle of Loudoun County living on this extraordinary 16-acre sanctuary. Woodland Farm offers a rare convergence of country elegance, professional equestrian facilities, and multi-generational flexibility. Pass through stately stone pillars and follow a winding paved drive that crosses a clear, spring-fed stream. Resting atop a private knoll, the custom stone and hardiplank manor commands panoramic views of rolling hills and lush pastures. This is more than a home; it is a retreat designed for both peace and presence. Inside, the home reveals a careful balance of grandeur and warmth. Sunlight pours through expansive windows beneath soaring 14-foot ceilings, illuminating spaces designed for both gathering and quiet retreat. The great room anchors the home, where floor-to-ceiling french doors open onto a sweeping pool terrace, inviting the outdoors in. At its center, a striking double-sided stone wood-burning fireplace creates a natural flow into the formal dining room, making it easy to imagine evenings filled with conversation, laughter, and celebration. Nearby, the library offers a more intimate setting, where a gas fire flickers softly during quiet conversations, while the main-level theater room promises immersive cinematic nights. The kitchen serves as the heart of it all—a place where daily life and entertaining intertwine. With its expansive social island and seamless connection to dining spaces, it becomes a natural gathering point, whether for casual mornings or lively dinner parties. The home’s thoughtful design extends to its private wings, where the east wing offers a serene primary suite alongside two additional bedrooms, while the west wing provides two oversized bedrooms each with their own ensuite bathroom, creating a sense of separation and comfort for family and guests alike. Beyond the main residence, Woodland Farm fully embraces its identity as a working equestrian estate. A five-stall center aisle barn stands ready for daily routines, complemented by a fenced riding arena and four well-maintained paddocks that support rotation and turnout. The land itself invites exploration—gentle acreage for riding, wooded trails for wandering, and the ever-present stream offering a place to pause and reflect. There is room here not just to live, but to grow, with space for future barns, arenas, or expanded facilities. Enjoy warm summer days gathering around the pool, where wide stone patios and covered wood decks set the stage for long Virginia evenings under open skies. And tucked away with their own entrance and parking, two private guest apartments overlook the woods and stream, offering flexibility for extended family, rental opportunities, or a peaceful remote workspace. Though the property feels deeply secluded, it remains closely connected to the world beyond. Starlink high-speed internet supports modern living, while the nearby village of Middleburg provides access to fine dining, charming boutiques, and the surrounding wine country. Woodland Farm is a place where elegance meets function, where open land meets thoughtful design, and where each day carries a sense of both escape and belonging.

38386 Little River Tpke, Middleburg

Listing courtesy of MAXVALUE, REALTORS. Contact:

$4,850,000

7 Beds ⋅ 10 Baths

"Gamecreek", imposing, 10,000 sq.ft., grand country house very privately situated on 31 acres in a sought-after location, seven minutes to the town of Middleburg and ten minutes to Foxcroft School. This home offers 7 bedrooms, 8 full and 2 half baths, 5 fireplaces, 12 foot ceilings on the ground floor, and a dream first floor primary bedroom suite including a sitting room with stone patio, a yoga parlor, private laundry room, large bath with a soaking tub and shower with 5 shower heads and steam bath, his and hers walk-in closets, and a bed chamber with fireplace and French doors to a second stone patio. The Baronial-style living room has striking features with 20 plus foot ceilings and a massive stone fireplace, pub beams, three French doors to a terrace and a wrap-around library on the second level overlooking the living room. The dining room features a serving alcove served by a walk-through pantry from the kitchen and three French doors to the garden. The fully fitted kitchen has a center island and a see-thru fireplace to a bright and airy breakfast room. A well-planned mud room for coats and boots and a half bath are off the kitchen. A hall featuring a wet bar, mini refrigerator and half bath leads to the family room, again with a fireplace, which also connects to the living room and opens to a long covered patio with fireplace, and a back staircase that leads up to the children's wing offering a playroom, 3 bedrooms and 2 baths. Also on this level is a fourth bedroom with bath, sitting room, a child's library and second laundry room. From this level, one can access the 3rd level which can be a home office, studio, bonus room, etc. with a full bath. At the other side of the house on the second level is the guest suite featuring a sitting room with wet bar and refrigerator, access to a private, covered porch overlooking the grounds, 2 bedrooms and 2 baths. Where one enters the home there are two formal staircases - one on the right leads to the guest suite and on the left, to the children's quarters. At the top of the steps there is an open hall leading from one side to the other. The lower level features a 135 bottle climate-controlled wine cellar, a media room, full bath and an exercise room. The heart-shaped heated swimming pool and spa includes a cabana, an outdoor shower, and a pool bath is available. The upstairs of the 3 car garage is an all-purpose space with kitchenette. The 31 acres offers long frontage on Goose Creek (considered a river by Virginia). A wonderful and historic 20 foot wide waterway offering opportunities to fish, kayak and swim. For more information on Goose Creek, visit Goose Creek Association. Access to the river is by well maintained grassy trails through the forest. There is also a 4 stall stable with paneled tack room, lounge, wash stall and lots of equipment storage. The house is well equipped with two propane gas furnaces on the first floor with electric air conditioning and the rest of the house has four heat pumps. There is also a heat pump for the garage second floor. There is a generator for the house and a generator for the garage. There are 3 fresh air ventilator systems that serve the house. The house has a full security system. Starlink is available. The roof is copper and the floors are elegantly appointed with tile, ash, oak and old pine. The property is in the land use tax program. Interested parties should verify dimensions and square footage. Covenants are in documents.

35387 Creek Ridge Ln, Middleburg

Listing courtesy of Allen Real Estate. Contact: (540) 229-1770

$1,950,000

3 Beds ⋅ 2 Baths

The Jacob Mann House, circa 1817 and once home to Middleburg’s local tanner, is a charming fieldstone residence ideally located on the eastern edge of the historic village. Rich in character and thoughtfully updated, the home offers three bedrooms and two full baths including a main level primary suite. Step inside to find original hardwood floors, two fireplaces, built-ins, custom cabinetry, and abundant natural light throughout. The designer kitchen features high-end appliances and looks out over a bright enclosed back porch overlooking a deck, the private gardens and a swimming pool. The finished walk-out lower level includes a spacious Tavern Room upgraded with exposed beams, custom cabinetry, a gas fireplace, and a mini-split system, along with a private office space and a Butler’s Pantry with more custom cabinetry and an exposed stone wall. Just steps from the main house, the restored Smoke House provides exceptional flexibility with a full bath, heated hardwood floors and a fireplace making it ideal as a guest suite, home office, artist’s studio or workout room. The fully fenced grounds offer rare privacy within town limits and are enhanced by mature landscaping, including more than 50 boxwoods, laurels, arborvitae, hollies, and pines. Other improvements include pool renovations, updated fencing, a tar-based pea gravel driveway, three mini-split systems, a retractable pool cover and a hot tub. Savor the privacy of a secluded in-town setting, while enjoying an easy walk to Middleburg’s shops, restaurants, library, and post office along with quick access to local wineries, breweries, and nearby walking trails through the Salamander Resort. Unique corner parcel on .48 acres fronts three streets and has subdivision potential. A rare opportunity to own a beautifully preserved historic home in Middleburg. Don't miss!

406 E Washington St, Middleburg

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact: 5406876500

$1,445,000

4 Beds ⋅ 4 Baths

Proudly presenting an exceptional property located in the Town of Middleburg, situated within walking distance to many ethnic restaurants, several world class museums, a plethora of unique boutiques and the renown, 5-star, Salamander Resort and Spa. This end-unit residence is in pristine condition and masterfully blends artistic design with 'Hunt Country' style. Enjoy private parking, a generous yard, no HOA and hi-speed internet! The French-influenced landscaping features impressive topiary urns, pea gravel trim, copper gutters, and solar lighting. The interior offers 11-foot ceilings, solid hardwood floors, and exquisite details including crystal chandeliers plus hand-carved newel posts. The upgraded kitchen boasts hardwood cabinets, an induction range, a soapstone farm sink, LG appliances and offers a generous eat-in area which can easily accommodating your guest. The primary suite includes a luxurious spa-inspired bathroom punctuated by an Arabesque-style marble floor, a jetted tub, marble shower, private toilet closet and cosmetic, fog-free mirrors. In addition to two, generous upper-level bedrooms sharing a dual vanity bathroom and a fourth floor spacious loft, this home offers a sunny bedroom and full bathroom on the main level too! A significant highlight is the "Showcase" lower level which features an impressive, fully equipped bar accented by Turkish marble flooring, a custom-designed iron railing, a camouflaged mechanical room, recessed lighting and a full bathroom. This soundproof space which includes an extensive waterproofing system is ideal for the ultimate in entertaining friends and family! The baby grand piano including the rug may be purchased separately. You can find additional information at the Town site: www.middleburgva.gov

12 Orange Dr, Middleburg

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500

$2,499,999

3 Beds ⋅ 3 Baths

New price for this Special home and property set in Virginia’s famed Hunt Country just west of Middleburg, this exceptional estate is the first property on the left in the sought-after Atoka Chase community. Enter through the private security gate and follow the tree-lined drive past the horse barn to a beautifully constructed Cape-style stone residence set on 18 fully fenced acres overlooking an amazing pond and manicured fenced pastures. Designed for both elegant country living and equestrian pursuits, the property features copper roofs and gutters on the house, cottage and garage, extensive landscaping and hardscaping, horse barn with heated office tack room, fenced paddocks, a machine barn, and thoughtfully designed outdoor spaces that capture the beauty of the surrounding Virginia countryside. The main residence offers three bedrooms and two-and-a-half baths with warm, timeless interiors and picturesque views from nearly every room. Sought after primary bedroom suite on the main level. The stone work was done by a local master craftsman in 1990. A separate guest house includes one bedroom and one full bath and half bath. All new SS appliances, redone kitchen and bathrooms, providing ideal accommodations for guests, extended family, or a farm manager. Propane heating for the main house and heat pump for the cottage. Additional amenities include an indoor heated spa/lap pool, oversized two-car garage, horse barn, and multiple outbuildings supporting both recreational and working farm use. Stone duck house building overlooking the pond with fountain. Multiple paddocks and 3 automatic waterers. This 18 acre gem combines privacy, beauty, and functionality, and this rare Atoka Chase offering presents an extraordinary opportunity to enjoy refined country living just minutes from historic Middleburg. Property has potential to build another home on the property per counsel opinion for the estate. Subject to the covenants in the Deed of Dedication dated October 20th, 1980 and the approval of the ARC.

34520 Atoka Chase Ln, Middleburg

Listing courtesy of Washington Fine Properties, LLC. Contact:

$3,899,900

5 Beds ⋅ 4 Baths

A completely reimagined estate designed in collaboration with renowned Middleburg architect Timothy Clites. This modern farmhouse is a breathtaking fusion of refined luxury and timeless equestrian elegance, set on 12 acres in the coveted Atoka Chase community with paved roads. An entry framed by original historic stone walls leads to a home and barn cottage that has been completed to the highest standard, surrounded by expansive stone porches capturing panoramic views of rolling pastures and the Blue Ridge Mountains on all sides. Every room was intentionally positioned to frame the intensely beautiful sunrises and sunsets, offering panoramic views from every window and filling the home with natural light from dawn to dusk. Inside, the thoughtful floorplan blends traditional craftsmanship and contemporary sophistication with oak hardwood flooring, shiplap walls and ceilings, vaulted spaces featuring exposed antique beams sourced from local barns, custom closets, designer lighting, heated tile floors and ceiling fans throughout. The main-level primary suite offers incredible western sunset views, a private outdoor screened porch and a bath with heated floors and towel racks. A study with a wood stove and an adjacent office/guest suite is equipped with high-speed fiber internet for seamless remote work and access to an additional full bath all on the main level. The chef’s kitchen is both striking and efficient, featuring heated floors, a gas range, two dishwashers, ice maker and stainless-steel appliances. French doors off the mud room open to the rear covered porch and outdoor kitchen offering a one and only outdoor entertaining space. The living room centers around a dramatic stone wood-burning fireplace, pool views to one side and mountain views out the other. The upper level includes three additional bedrooms and two full baths, each with hardwood flooring, heated tile floors and towel warmers. Large dormer windows provide abundant natural sunlight and mountain views. Every mechanical and electrical system is updated, reflecting the level of detail and investment poured into this property. There is a large unfinished basement with a bathroom rough-in and fireplace. The outdoor living experience rivals a private resort, with a heated saltwater infinity pool and spa overlooking the pastures, Sonos surround sound system, a flagstone patio, gas firepit, a fully equipped outdoor kitchen with gas grill, refrigerator, and a dedicated ice maker. The property is a turnkey horse facility with board-fenced pastures, automatic waterers, electric fencing, run-in sheds with electric and individual two-stall barns—all lined with oak milled from Middleburg trees and clad to match the main residence for perfect visual harmony—as well as a dedicated tack room, covered parking/equipment storage, and a comprehensives smart home security system with exterior cameras for full remote monitoring and peace of mind. Every detail was curated to balance beauty, efficiency, and the ease of a true horse lifestyle. This property is more than a home; it is a masterwork of architecture, design, and lifestyle—an unparalleled Middleburg estate where luxury, privacy, and function meet.

34642 Atoka Chase Ln, Middleburg

Listing courtesy of Douglas Elliman of Metro DC, LLC. Contact: 7035524180

$2,950,000

5 Beds ⋅ 5 Baths

Elegant Vineyard Hunt Box at the Residences at Salamander completed and ready for move-in on very-convenient-to-town Lot 19! Be among the first to own a thoughtfully designed Vineyard Hunt Box in the exclusive Residences at Salamander—a luxury community set adjacent to the Salamander Resort & Spa in the heart of Middleburg��s iconic Wine and Hunt Country. This spec home begins construction in June 2025 with an anticipated completion in 8–10 months.<> Situated on a deep, sought-after lot, this home features four bedrooms and four full baths. A flexible library/bedroom with full bath on the main level offers versatility for guests, work-from-home needs, or additional sleeping quarters. Main level features include: Spacious primary suite with ensuite bath Flex library/bedroom with full bath Light-filled open-concept great room and kitchen with expansive rear glass doors and clerestory windows Oversized two-cook kitchen with a 48” Wolf/Sub-Zero range, 36” Sub-Zero refrigerator, Cove dishwasher, Wolf microwave drawer, and upgraded countertop and backsplash Full walk-in pantry and large mudroom/laundry Wide board European oak flooring throughout Coffered tray ceilings in the primary, flex space, and foyer 10’ ceilings on the main floor Lower level features: Three bedrooms all ensuite Family/media room ideal for gathering and entertaining 9’ ceilings and view-out windows for ample natural light Additional features include: Over 1,100 sq ft of covered bluestone slate porches for year-round outdoor living Standing seam metal roof with black half-round gutters Low-E, floor-to-ceiling insulated windows and doors Prepped garage foundation for future build-out (with or without pool bath) Designer lighting and plumbing packages with dimming capabilities Irrigation and farmhouse-style landscape package Clean, neutral interior finishes that blend Hunt Country charm with modern simplicity As a resident of the Residences at Salamander, you’ll enjoy a serene lifestyle within walking distance to resort amenities, fine dining, boutique shopping, and vibrant community experiences—all set against the backdrop of Virginia’s rolling hills and equestrian heritage. Secure your place in one of Middleburg’s most prestigious addresses.

505 Martingale Ridge Dr, Middleburg

Listing courtesy of Corcoran McEnearney. Contact: 5406876321

$3,359,000

4 Beds ⋅ 5 Baths

100% COMPLETE AND READY TO MOVE-IN! This home is the only Salamander Residence offered well below $1000 per square foot and it's on THE PREMIUM LOT in the neighborhood! Property is currently rented for $20,000 per month and available to be shown. Lease is assumable and will produce instant income! When Sheila Johnson, one of America’s foremost business leaders, created Salamander Middleburg in Middleburg, Virginia, her vision included a community of residents fully connected with the vibrant life of the resort. Thoughtful amenities, impeccable service, and a truly creative approach to the guest experience have established the resort as a standout destination. Nestled in the heart of horse and wine country, Residences at Salamander is a curated collection of estate homes set within the grounds of the acclaimed 340-acre Salamander Middleburg. Homes at Residences at Salamander, boast exceptionally private settings and 606 Martingale Ridge sits on the PREMIUM LOT, backing to a 200-acre conservation preserve – an oasis of woodlands, streams, walking, riding, and biking trails. 606 Martingale Ridge is the largest of The Vineyards model and is 100% COMPLETE and ready for your immediate enjoyment. This coveted home showcases true luxury resort living with multiple high-end upgrades set within a pastoral landscape and a Blue Ridge Mountain backdrop. Some of the luxury upgrades include: automatic privacy blinds installed; automatic screens on the covered porch; state-of-the-art AV system; top-of-the-line appointments throughout. At the Salamander Residences, you will find a fabulous array of amenities just beyond your doorstep and the village charms of historic Middleburg a mere stroll away. You’ll enjoy daily access to all the resort has to offer, as well as a collection of perks and benefits further afield designed to ease and enhance the ownership experience. A concierge team can facilitate everything from dining, spa and equestrian reservations to tee times at the nearby Creighton Farms golf course. Every day ease is the goal at Salamander Residences. All you have to do is ask!

606 Martingale Ridge Dr, Middleburg

Listing courtesy of TTR Sotheby's International Realty. Contact:

$3,550,000

4 Beds ⋅ 4 Baths

Elegant Stables Hunt Box Premiere at the Residences at Salamander — Ready for immediate delivery! Be among the first to own a thoughtfully designed Stables Hunt Box Premiere in the exclusive Residences at Salamander—a luxury community set adjacent to the Salamander Resort & Spa in the heart of Middleburg’s iconic Wine and Hunt Country. <> Situated on a large, private, sought-after lot (42), this home features four bedrooms and four full baths. A flexible library/bedroom with full bath on the main level offers versatility for guests, work-from-home needs, or additional sleeping quarters. Main level features include: Spacious primary suite with ensuite bath Flex library/bedroom with full bath Light-filled open-concept great room and kitchen with expansive rear glass doors and clerestory windows Oversized two-cook kitchen with a 48” Wolf/Sub-Zero range, 36” Sub-Zero refrigerator, Cove dishwasher, Wolf microwave drawer, and upgraded countertop and backsplash Full walk-in pantry and large mudroom/laundry Wide board European oak flooring throughout Coffered tray ceilings in the primary, flex space, and foyer 10’ ceilings on the main floor Lower level features: Three bedrooms all ensuite Family/media room ideal for gathering and entertaining 9’ ceilings and view-out windows for ample natural light Additional features include: Over 1,100 sq ft of covered bluestone slate porches for year-round outdoor living Standing seam metal roof with black half-round gutters Low-E, floor-to-ceiling insulated windows and doors 2 Car detached garage Designer lighting and plumbing packages with dimming capabilities Irrigation and farmhouse-style landscape package Clean, neutral interior finishes that blend Hunt Country charm with modern simplicity As a resident of the Residences at Salamander, you’ll enjoy a serene lifestyle within walking distance to resort amenities, fine dining, boutique shopping, and vibrant community experiences—all set against the backdrop of Virginia’s rolling hills and equestrian heritage. This home is ready for delivery end of January. Secure your place in one of Middleburg’s most prestigious addresses.

4 Foxtrot Knoll Ln, Middleburg

Listing courtesy of Corcoran McEnearney. Contact: 5406876321

$2,700,000

2 Beds ⋅ 2 Baths

**To-be Built** Situated adjacent to the acclaimed Salamander Middleburg in the historic town of Middleburg, Virginia, the Residences at Salamander offer an exceptional opportunity to enjoy refined living in the heart of Wine and Hunt Country. Blending timeless elegance with modern comfort, this community provides a lifestyle that is as luxurious as it is serene. Lot 1 can accommodate the Huntbox floor plan, this residence is over 2,000 square feet on the main level, highlighted by a welcoming covered front porch, a foyer with soaring 10-foot ceilings, a fireplace, and custom built-ins. The open-concept main living area captivates with 20-foot vaulted ceilings and expansive windows and doors that frame stunning views while leading to a wide, covered bluestone terrace. The elegant main level primary suite includes a to-die-for primary bath with wet room and spacious walk-in closet. The lower level, consists of an additional 1875 square feet of finished living space with two additional bedrooms, a large rec room, and an office/fitness space. It is also fully walk-out on the eastern exposure and bathed in natural light through well-placed windows and doors. Whether as a permanent residence or a tranquil retreat, this home offers the perfect blend of town, country, and resort living. Just a short walk from Middleburg’s charming shops and fine dining along Washington Street, it allows you to immerse yourself in the town’s vibrant culture while enjoying the serenity of Blue Ridge Mountain views. *** Artistic renderings and photos of previously completed homes are provided for illustrative purposes only and may not reflect the final design, construction, or finishes of the residence.

400 Martingale Ridge Dr, Middleburg

Listing courtesy of Corcoran McEnearney. Contact: 5406876321

Browse All Middleburg VA Properties with Pool for Sale

Middleburg Homes with Pool