Winchester Homes with Pool

Winchester Homes with Pool

Welcome to Winchester, Virginia, a charming city nestled in the picturesque Shenandoah Valley. Known for its rich history, vibrant culture, and stunning natural landscapes, Winchester perfectly blends small-town charm with modern amenities. With its historic downtown, filled with quaint shops, delightful restaurants, and lively arts scenes, you'll find plenty to explore. The city is also home to numerous parks, walking trails, and outdoor recreational opportunities, making it a haven for nature lovers and adventure seekers alike.

One of the standout features of Winchester is its diverse real estate market, particularly the homes with pools that offer a luxurious lifestyle. Imagine coming home to your private oasis, where you can unwind and cool off during the warm Virginia summers. Whether you’re hosting a family barbecue, enjoying a quiet evening under the stars, or simply soaking in the sun, homes with pools in Winchester provide the perfect backdrop for relaxation and entertainment.

These properties range from charming single-family homes to stunning estates, each designed to complement the beautiful surroundings. With spacious backyards and expertly landscaped gardens, your poolside retreat will be the envy of friends and family. Additionally, the community is known for its excellent schools, friendly neighborhoods, and a welcoming atmosphere that makes it easy to settle in.

If you’re looking for a place that combines history, beauty, and a sense of community, Winchester, VA, with its delightful homes featuring pools, is the perfect choice for your next chapter. Come discover the magic of Winchester and make it your home!

Newest Winchester Homes with Pool

$525,000
5 Beds ⋅ 4 Baths ⋅ VAFV2043592 MLS
Nestled in the charming Apple Ridge community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Set on a generous 0.4-acre lot, the property backs onto serene open common areas and lush trees, providing a tranquil retreat right in your backyard. Enjoy the luxury of multiple balconies, a spacious deck, and a welcoming porch, ideal for relaxing or entertaining while soaking in the peaceful views of nature. With five spacious bedrooms and four full bathrooms, this home is designed for both relaxation and functionality. The fully finished basement with Kitchen adds extra living space. The main floor laundry adds convenience to your daily routine, while the attached front-entry garage ensures easy access and ample parking. The Apple Ridge neighborhood is known for its friendly atmosphere and community spirit. Excellent local schools are just a short drive away, making this location ideal for those seeking a nurturing environment. With a personal in-ground pool, this home invites you to create lasting memories during warm summer days. Experience the best of suburban living, where comfort meets community, and make this beautiful property your new home.

144 Morning Glory, Winchester
$586,900
4 Beds ⋅ 4 Baths ⋅ VAFV2043626 MLS
Gorgeous 4-Bedroom Colonial in Sought-After Sovereign Village! This beautifully maintained home is nestled on a large cul-de-sac, offering privacy, space, and comfort both inside and out. This home boasts a well-designed layout perfect for everyday living and entertaining. The bright, open main level with shining hardwood floors creates a warm and inviting atmosphere. Cozy up by the gas fireplace in the living area or enjoy meals in the spacious bay window style dining area overlooking the backyard. The chef's kitchen with large island, granite countertops and stainless steel appliances (brand new refrigerator!) opens seamlessly to the living spaces and offers plenty of room for meal prep and gatherings. Step outside to the fantastic private deck, patio and backyard, ideal for outdoor entertaining, gardening, or simply relaxing in your own peaceful oasis. On the second level, the spacious primary suite has a large walk-in closet, ensuite with a jacuzzi tub, and recessed high ceilings that add so much character. The two additional bedrooms are bright, generously sized and share a full hallway bathroom. The laundry room is right outside of the large 4th bedroom with its own private bathroom and walk in closet. The mostly finished basement has abundant storage space and the main area has so many possibilities! Additional highlights include: New Water Softener & New Water Heater and access to the Community Pool and Common Areas. (Pool membership for Sovereign Village residents is $210 as long as in good standing with the HOA. Senior Passes for those 55+ is $176.) Located on a cul-de-sac and walking distance to the elementary school.

104 Murphy Ct, Winchester
$399,990
4 Beds ⋅ 4 Baths ⋅ VAFV2043638 MLS
Brand-New 4-Bedroom Townhome | Late Summer Move-In! Enjoy stylish, low-maintenance living in Snowden Bridge's newest section. This thoughtfully designed home features a convenient entry-level bedroom, oak stairs with upgraded railings, and luxury vinyl plank flooring throughout the main level. The bright gourmet kitchen showcases greyhound cabinetry, quartz countertops, and stainless steel appliances, flowing seamlessly into the open living spaces. Upstairs, the spacious primary suite provides a private retreat. Located in a vibrant community with resort-style amenities including a pool, playgrounds, trails, and more to come. Ask about builder incentives! Photos are of a similar home.

132 Swansong Pl, Winchester
$349,990
3 Beds ⋅ 3 Baths ⋅ VAFV2043636 MLS
Enjoy low-maintenance living in this beautifully designed two-level villa in Hiatt Pointe! The main-level primary suite features two walk-in closets for exceptional storage, while the gourmet kitchen shines with two-tone white and burlap cabinetry, quartz countertops, and stylish finishes. Upstairs offers two spacious bedrooms, a full bath, and a convenient storage area, providing plenty of room for guests and hobbies. Ideally located near community amenities in Hiatt Pointe, a gated 55+ active adult community, residents enjoy a clubhouse, pool, fitness center, sports courts, and a vibrant lifestyle designed for active living. Ask about builder incentives!

117 Castaway Pl, Winchester
$482,990
2 Beds ⋅ 2 Baths ⋅ VAFV2043634 MLS
Under construction for late summer Move-In and Backing to Trees! This beautifully designed home offers easy, open-concept living with a stylish gourmet kitchen featuring quartz countertops, stone gray cabinetry, and stainless steel appliances. The kitchen flows seamlessly into the bright dining and family rooms, while the screened rear porch provides a peaceful retreat overlooking the wooded backdrop. The main-level primary suite includes a spacious walk-in closet and a spa-inspired bath with a seated frameless glass shower. A second bedroom and full bath offer comfort and flexibility for guests. Conveniently located near the two-car garage, the laundry room enhances everyday ease. Located in Hiatt Pointe at Snowden Bridge, a premier 55+ active adult community with exceptional amenities, social opportunities, and a vibrant lifestyle. Ask about builder incentives!

107 Lawford Way, Winchester
$3,500,000
3 Beds ⋅ 4 Baths ⋅ VAFV2043614 MLS
Be Sure to View the Video and 3D Tour to Fully Experience this Stunning Property <br><br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals.<br><br> For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership.<br><br> The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals.<br><br> The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional.<br><br> Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

450 Green Spring Rd, Winchester
$670,000
4 Beds ⋅ 4 Baths ⋅ VAFV2043524 MLS
Nestled in a private cul-de-sac and ideally located for commuters, this beautifully maintained Colonial offers the perfect blend of comfort, style, and privacy. The home features four spacious bedrooms and three and a half bathrooms, providing plenty of room for both relaxation and entertaining. Step inside to a warm and inviting atmosphere, complemented by thoughtful design and quality finishes throughout. The recently remodeled kitchen features quartz countertops and stainless steel appliances. The expansive living areas open onto a Trex deck overlooking the picturesque heated, saltwater gunite pool—perfect for enjoying summer days and entertaining family and friends. The fully fenced yard also includes a separate fenced area, ideal for gardening, pets, or a children’s play area. The full basement provides a private retreat for guests, complete with a separate living area, bathroom, and dry bar with refrigerator. Situated on a generous 0.65-acre lot, the property offers abundant privacy and a peaceful setting surrounded by nature. Parking is a breeze with an attached two-car garage and a spacious driveway with room for an RV, complete with exterior 220/120-volt electrical service. More than just a house, this exceptional property offers a wonderful place to call home and create lasting memories.

107 Dell Ct, Winchester
$3,500,000
3 Beds ⋅ 4 Baths ⋅ VAFV2042896 MLS
Be sure to see the video and 3D tour to fully explore this property! <br><br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals.<br><br> For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership.<br><br> The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals.<br><br> The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional.<br><br> Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

450 Green Spring Rd, Winchester
$599,990
4 Beds ⋅ 3 Baths ⋅ VAFV2043510 MLS
The Dover by D.R. Horton offers 1,958 square feet of thoughtfully designed, main floor living with 3 bedrooms, 2 full baths, and a 2-car garage. A private flex room with LVP flooring sits just off the foyer – ideal for a home office or craft room.<br><br> 9-foot ceilings lead into the open-concept kitchen, dining, and family room. The kitchen features quartz countertops, soft-close cabinet doors, a gas range, and modern island perfect for gathering. Sliding glass doors off the dining area fill the home with natural light and open to a covered patio – ideal for morning coffee or relaxed evenings outdoors.<br><br> The owner’s suite includes a spacious bath with split dual vanities, a large walk-in closet, and direct access to the laundry room for added convenience. This home also has 750 square feet of loft including an open living space, another bedroom, full bath, and extra storage.<br><br> Located in the serene and amenity-rich Willow Run community, residents will enjoy a clubhouse, outdoor pool, tennis and pickleball courts, and more. Move in this August/September and experience low-maintenance, active adult living at its best!

245 Hydrangea Way, Winchester
$889,900
5 Beds ⋅ 5 Baths ⋅ VAFV2043438 MLS
Opportunities of this caliber in the highly coveted Stonebrook Farms community are exceptionally rare. Positioned on a premium cul-de-sac lot backing directly to mature, private woods, this property is a true unicorn in today’s market: a sprawling, intelligently designed estate paired with a resort-style backyard and an exhaustive list of major capital improvements. ​The main level makes an immediate impact with soaring vaulted ceilings and an impeccable, flowing layout. Off the welcoming foyer, elegant French doors enclose a dedicated home office, complemented by formal living and dining spaces detailed with extensive, high-end trim work. Recent interior investments elevate the entire space. ​The kitchen is a masterpiece engineered for both daily living and high-capacity entertaining. It boasts crisp white cabinetry and counters, a Bosch electric cooktop, double ovens, and a massive walk-in pantry. Additional highlights include an expansive breakfast bar, a dedicated wall of extra cabinetry, and a highly practical secondary prep sink. This space transitions seamlessly into a substantial family room anchored by a gorgeous gas fireplace. Just off the kitchen, a bright sunroom with panoramic wooded views provides direct access to the newly constructed deck. A highly functional mudroom with built-in hooks, a dedicated laundry room, and a spacious half-bath complete the first floor. ​Upstairs, the layout is masterfully configured to accommodate family and guests with four bedrooms and three full bathrooms. The primary suite is a true private retreat with amgenerous walk-in closet space, and a fully appointed spa-like bathroom with dual vanities, a jetted soaking tub, and a separate walk-in shower. The secondary sleeping quarters are equally impressive, offering a private en-suite bedroom with its own dedicated bathroom, alongside two additional bedrooms that share a smartly designed Jack-and-Jill bathroom. ​The finished walk-out lower level serves as a massive secondary living space. It centers around a sprawling recreation and game room equipped with a built-in wet bar. Accommodations on this level include a private fifth bedroom with an egress window and a full bathroom. For logistics, the basement offers a large finished storage closet alongside an even larger utility storage room. ​Finding a private backyard oasis with a sprawling inground pool is rare; finding one where the heavy lifting has already been done is nearly impossible. The pool area is flanked by ample patio space, an adjacent fire pit, and a covered lower-level terrace perfect for shaded seating. ​Significant mechanical and structural investments have transformed this into a truly turnkey property. Key upgrades include a brand-new high-efficiency HVAC system, a new deck, a new pool pump, a new water heater and water softener, new garage doors and openers, and installed gutter guards. The property is also fully integrated with a Guardian security system. ​This home beautifully marries the convenience of Winchester city living with coming home to a private oasis. An incredible fleeting opportunity to secure a fully upgraded, resort-style property on one of the best lots in Stonebrook Farms.

102 Julie Ct, Winchester
$387,500
4 Beds ⋅ 3 Baths ⋅ VAFV2043432 MLS
WOW! 20K PRICE REDUCTION! PRICED TO SELL! MOTIVATED SELLER! Beautifully crafted and meticulously maintained 3-level townhome located in the highly desirable Sovereign Village community. Conveniently situated just minutes from Route 7 and I-81, this home offers an ideal location for commuters while providing a quiet neighborhood setting. The open-concept main level features hardwood flooring, abundant natural light, a spacious living room with a cozy gas fireplace, and a well-appointed kitchen complete with granite countertops, stainless steel appliances, and ample cabinetry. Granite countertops continue throughout the bathrooms, adding a touch of elegance. The spacious primary suite offers tray ceilings, a large walk-in closet, and a luxurious private bath. With 4 bedrooms, 2 full baths, and 1 half bath, there is room for everyone. The entry level includes a generous bonus room with a private exterior entrance and a rough-in for an additional bathroom, making it an excellent option for a home office, guest suite, secondary primary suite, or flex space. Additional highlights include a spacious 2-car garage with automatic opener, abundant storage throughout, and quality construction completed in November 2021. Residents also have the option to enjoy the community pool through membership. This exceptional home combines modern finishes, functional living spaces, and a prime location in one outstanding package.

126 Brockham Ct, Winchester
$599,000
4 Beds ⋅ 3 Baths ⋅ VAFV2043446 MLS
Nestled against a backdrop of mature trees, this nearly new 4-bedroom, 3-bath home offers beautiful finishes and modern comfort in the sought-after Raven Oaks community. Conveniently located with easy access to Routes 50 and I-81, this home is just minutes from Shenandoah University, Jim Barnett Park, shopping, restaurants, and everyday conveniences. Historic Old Town Winchester is only about three miles away, offering local dining, boutiques, entertainment, and community events. A fence and deck already in place for you. The thoughtfully designed floor plan features a main-level bedroom and full bath, perfect for guests or multi-generational living. The open-concept kitchen, dining, and living area showcases quartz countertops, stainless steel appliances, and an electric fireplace, creating a stylish and inviting gathering space. Luxury vinyl plank flooring extends throughout the main level. Upstairs, you'll find a spacious loft, a private primary suite with an attached bath, two additional bedrooms, a full hall bath, and the convenience of a bedroom-level laundry room. The unfinished basement offers plenty of storage and future expansion potential with rough-in plumbing for a full bath. Enjoy outdoor living on the deck overlooking the fenced backyard that backs to trees. Residents also have access to the community pool, making this home the perfect blend of comfort, convenience, and neighborhood amenities. Check out the 3-D Tour attached to this listing.

139 Poe Dr, Winchester
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