Middleburg Homes with Pool

Middleburg Homes with Pool

Welcome to Middleburg, Virginia—an enchanting town nestled in the heart of Loudoun County, where history, charm, and natural beauty converge. Known as the "Nation's Horse and Hunt Capital," Middleburg boasts a rich equestrian heritage, scenic countryside, and a vibrant community spirit. With its picturesque streets lined with historic buildings, boutique shops, and delightful eateries, Middleburg offers a lifestyle that beautifully balances tranquility and sophistication.

For those seeking a serene retreat, Middleburg's real estate market features an array of stunning homes, many of which come complete with private pools. Imagine unwinding in your own backyard oasis, surrounded by lush landscapes and the gentle sounds of nature. Whether you're hosting summer barbecues, enjoying a quiet evening swim, or simply soaking up the sun, a home with a pool in Middleburg elevates your living experience.

The local area is rich in outdoor activities, from horseback riding along scenic trails to exploring the nearby vineyards and wineries that define Virginia’s wine country. With a strong sense of community and a calendar full of events, including art fairs and seasonal festivals, Middleburg is a place where neighbors become friends and every day feels like a celebration.

If you're looking to invest in a home that offers both elegance and leisure, consider the delightful properties with pools available in Middleburg. Here, you can enjoy the best of both worlds—a peaceful rural lifestyle with the convenience of modern amenities, all while being part of a community that embraces its heritage and welcomes new residents with open arms. Come discover your dream home in Middleburg, where every day feels like a getaway!

Newest Middleburg Homes with Pool

$1,950,000
3 Beds ⋅ 2 Baths ⋅ VALO2126668 MLS
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
$1,445,000
4 Beds ⋅ 4 Baths ⋅ VALO2125854 MLS
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
$2,700,000
3 Beds ⋅ 3 Baths ⋅ VALO2126254 MLS
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
$2,700,000
4 Beds ⋅ 5 Baths ⋅ VALO2124276 MLS
Canterwood presents a rare and compelling offering just moments from the heart of Middleburg—an exceptional 10.5-acre property that seamlessly blends refined living with a fully equipped equestrian lifestyle. The gracious home is thoughtfully sited to capture the beauty and tranquility of its surroundings. Inside, warm decor and hardwood floors, five fireplaces, and a notable elegant living room. The spacious kitchen flows easily into multiple indoor and outdoor gathering areas. The large finished lower level offers remarkable versatility, featuring a home office, recreation/media room with fireplace, bar, storage and an additional half bath. Outdoors, the property truly shines. Gorgeous, established gardens are complemented by stone walls, multiple patios and terraces—perfect for entertaining or quiet relaxation. The pool, peaceful pond with dock, and open land enhance the sense of retreat, while approximately two acres of woods add privacy and natural charm. Equestrian amenities are equally impressive: a four-stall stable with tack room, hayloft, and wash rack; 3 paddocks; two run-in sheds; and a bluestone riding ring. Additional features include a two-car garage, paved driveway, and high-speed Xfinity fiber internet. Canterwood is a rare opportunity to enjoy a peaceful, private lifestyle with close proximity to Middleburg’s shops, dining, and amenities—an ideal balance of elegance, comfort, and rural charm. Views to the east of the Bull Run Mountains. Live here, work here, swim her and ride here.

23559 Parsons Rd, Middleburg
$2,695,000
5 Beds ⋅ 5 Baths ⋅ VALO2117342 MLS
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
$5,500,000
4 Beds ⋅ 6 Baths ⋅ VALO2114350 MLS
Nestled within the prestigious Residences at Salamander, this newly constructed, custom-expanded Stables Deluxe floor plan occupies one of the most desirable settings in the community—a high-elevation corner lot in the Stables (Lot 38). Notably, it is one of the larger lots and positioned above many neighboring homes, offering enhanced privacy, presence, and long-range serenity among mature trees. This exceptional four-bedroom, four-bath, two half-bath residence spans approximately 7,900 square feet of total living and potential space and is currently the only move-in-ready home available in the Stables section of the community, a rare and compelling distinction. The striking stone façade and custom-designed two-car garage with porte cochère—an upgrade beyond the standard offering—create an elegant and substantial arrival. Inside, the home unfolds with effortless flow and inviting warmth, elevated by premium materials and finishes selected well above the builder’s baseline throughout. The main level has been thoughtfully expanded to include a side-load entry, service powder room, and enlarged mudroom, complemented by a spacious laundry room and a beautifully integrated wine cellar and pantry. Wide-plank French oak floors and refined custom millwork set the tone, while the chef’s kitchen anchors the home with Wolf, Sub-Zero, and Cove appliances, custom cabinetry, bespoke countertops, and a dramatic full-wall backsplash behind the island—perfectly balancing everyday functionality with elevated entertaining. The primary suite is a true retreat, generously enlarged to include a cozy sitting area with fireplace and direct access to the courtyard. Its spa-inspired bath showcases heated floors, custom cabinetry towers, designer wall coverings, a luxurious his-and-her wet room, and exquisite marble detailing. The primary closet, complete with a built-in wall safe, blends elegance with practicality. All additional bedrooms are spacious and feature their own ensuite luxury full baths, including two located on the upper level, ensuring comfort and privacy for family and guests alike. Beyond the home itself, this residence delivers a lifestyle that is both refined and convenient. Enjoy walking distance to the historic charm of Middleburg, easy proximity to Dulles Airport, and exclusive access to Salamander Resort’s world-class amenities, including acclaimed dining, spa and wellness experiences, equestrian offerings, and curated social events—all while enjoying the added distinction of a larger, elevated Stables lot that sets this home apart from the Vineyard section. This is a rare opportunity to own a bespoke, move-in-ready residence on one of the most premium lots within the Residences At Salamander, where elevated design, superior materials, and unmatched setting converge to offer not just a home—but a truly exceptional lifestyle.

1 Foxtrot Knoll Ln, Middleburg
$3,899,900
5 Beds ⋅ 4 Baths ⋅ VALO2110916 MLS
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
$2,950,000
5 Beds ⋅ 5 Baths ⋅ VALO2097614 MLS
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
$3,359,000
4 Beds ⋅ 5 Baths ⋅ VALO2097580 MLS
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
$4,995,000
5 Beds ⋅ 10 Baths ⋅ VALO2094274 MLS
Perched majestically in Virginia's prestigious Hunt Country, "The Looking Glass" estate offers an unparalleled living experience across 30 breathtaking acres. Named for its sweeping panoramic views of the mountains and neighboring vineyard, this Tuscan-inspired masterpiece seamlessly blends old-world charm with modern luxury. The magnificent main residence spans 17,000 square feet, with 11,000 square feet of meticulously designed living space on the first two levels and an additional 6,000 square feet on the lower level with room for further customization. Featuring five sumptuous bedrooms and ten elegant bathrooms, the estate creates an atmosphere of refined opulence through its exceptional construction and meticulous maintenance. The exterior showcases a harmonious blend of stone and stucco, complemented by distinctive arched doorways and windows that define its architectural character. Inside, rich hardwood, natural stone, and luxurious marble flooring extend throughout, while wrought iron staircases add to the estate's old-world ambiance. Outdoor entertaining reaches new heights with a heated pool and spa adjacent to an inviting pavilion featuring a stone terrace and outdoor fireplace—all overlooking the estate's stunning grounds and breathtaking vistas. The property is further enhanced by a spacious 2,500-square-foot guest house offering four bedrooms, generous living spaces, and a full kitchen. Equestrian enthusiasts will appreciate the connecting eight-stall stable with its grand ceiling, convenient wash stall, and well-appointed tack room. "The Looking Glass" represents an extraordinary opportunity to own one of Hunt Country's most distinguished estates.

38793 Chelten Ln, Middleburg
$3,550,000
4 Beds ⋅ 4 Baths ⋅ VALO2087682 MLS
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
$2,700,000
2 Beds ⋅ 2 Baths ⋅ VALO2087514 MLS
**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
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