Winchester Homes with Pool

Winchester Homes with Pool

Welcome to Winchester, Virginia—a charming city steeped in history and brimming with Southern hospitality. Nestled in the picturesque Shenandoah Valley, Winchester offers a perfect blend of small-town charm and modern conveniences. With its rich Civil War heritage, you can stroll through beautifully preserved historic districts, explore the renowned Museum of the Shenandoah Valley, or take a leisurely walk in one of the many serene parks.

Winchester is not just a place to live; it’s a community where families thrive and friendships blossom. The city boasts excellent schools, vibrant local shops, and a variety of dining options that cater to every palate. For outdoor enthusiasts, the stunning Blue Ridge Mountains provide ample opportunities for hiking, biking, and enjoying nature’s beauty.

For those seeking a slice of paradise right in their own backyard, Winchester offers a fantastic selection of homes with pools. Imagine relaxing on a warm summer day, splashing in your private oasis, or hosting unforgettable gatherings with friends and family around the poolside. These homes not only provide a refreshing escape but also enhance your lifestyle, making every day feel like a vacation.

Whether you’re a first-time homebuyer or looking to upgrade, Winchester’s real estate market has something for everyone. With its friendly atmosphere, rich culture, and beautiful homes with pools, Winchester is the perfect place to call home. Experience the charm and warmth of this delightful city—your dream home awaits!

Newest Winchester Homes with Pool

5 Beds ⋅ 4 Baths

A rare opportunity to live on Lake Serene - Welcome to your private waterfront retreat on Lake Serene, where resort-style outdoor living meets timeless modern craftsmanship. Rarely does an opportunity like this come along. Tucked among the trees on one of Frederick County's most sought-after private lakes, this beautifully renovated waterfront home offers the perfect balance of luxury, recreation, and everyday comfort. Completely transformed in 2016 with a 2-story addition along with thoughtful updates & remodeling, the home features a stunning custom Chef's kitchen with rich cherry cabinetry, elegant soapstone countertops, and quality finishes include KitchenAid gas range and Viking range hood. Designed for gathering with family and friends we have 5 bedrooms and 3.5 beautifully remodeled bathrooms, numerous living areas on two spacious levels making this THE gathering place! Offering one level living for all daily activity the main level is host to gorgeous family room with soaring ceilings, kitchen, dining room, living room with fireplace, laundry, 3 bedrooms & 2.5 baths. The lower level offers additional space to spread out with game room, recreation room, wet bar and two additional bedrooms and storage. Step outside and discover your own private retreat. Extensive hardscaping, an oval in-ground heated pool, multiple outdoor entertaining spaces, and mature landscaping create a resort-like setting that's perfect for summer afternoons or evening sunsets with views of the lake. A detached 2-bay garage also has a finished area w/ fireplace which was originally utilized as an office now acts as a pool house. Life at Lake Serene is about more than the home itself. Enjoy boating, kayaking, fishing, paddleboarding, or simply relaxing by the water. Inventory on Lake Serene is exceptionally limited, with many properties remaining in the same families for generations. Even more uncommon is finding a home that has already been tastefully updated—allowing you to begin enjoying the lake lifestyle immediately instead of planning years of renovations. Whether you're searching for a full-time residence or the ultimate weekend escape, this exceptional waterfront property offers a rare opportunity to own one of the area's most desirable lake homes. Come experience why life is simply better at Lake Serene.

485 Lake Serene Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

3 Beds ⋅ 3 Baths

Welcome to 109 Nootka Way, a beautifully maintained end-unit townhome offering the perfect blend of modern style, comfort, and low-maintenance living. Built just a year and a half ago, this like-new home features 3 spacious bedrooms, 2.5 baths, and 1,509 square feet of thoughtfully designed living space. The open-concept main level is filled with natural light and provides an inviting space for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and living areas, creating a functional and welcoming layout. Upstairs, you’ll find a generous primary suite with an en-suite bath, two additional bedrooms, a full hall bath, and convenient upper-level laundry. As an end unit, the home enjoys added privacy, extra windows, and abundant natural light throughout. A rear-entry one-car garage provides secure parking and additional storage. Located in a desirable Winchester community with easy access to shopping, dining, commuter routes, and everyday conveniences, this move-in-ready home offers the benefits of newer construction without the wait.

109 Nootka Way, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

3 Beds ⋅ 4 Baths

Rare Dual Primary Suites on the Main Level! Backing to trees, this stunning new Matisse at Hiatt Pointe at Snowden Bridge offers the perfect blend of comfort and flexibility for active adults 55+. Personalize your finishes and move in this spring! Enjoy a gourmet kitchen with SS appliances including hood, quartz countertops, an oversized island, and walk-in pantry. The open layout features 10' ceilings, a gas fireplace, and a screened porch overlooking the wooded homesite. The finished lower level adds a rec room, third bedroom, and full bath. Enjoy resort-style amenities including a gated entrance, clubhouse, fitness center, pickleball, bocce, pool, and hot tub. Ask about builder incentives!

3168 Ruby Royce Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

3 Beds ⋅ 3 Baths

MOVE-IN READY and designed for Active Adult (55+) living, this never lived-in before SINGLE FAMILY HOME offers main-level living and low-maintenance design at Hiatt Pointe, a gated community in Winchester, VA. Experience a true RESORT-STYLE lifestyle with exceptional onsite community amenities including a clubhouse, fitness center, pickleball and bocce courts, pool and hot tub, yoga studio, outdoor kitchen, fireside lounge, wine lockers, walking trails, and more. A full calendar of resident activities, from water aerobics and Mahjong game nights to Friday happy hours, creates endless opportunities to stay active, socialize, and enjoy everything Hiatt Pointe by Van Metre Homes has to offer! -----Spanning 3,200 finished square feet, this two-level single family home welcomes you with a covered front porch, 9ft. ceilings, and Luxury Vinyl Plank (LVP) flooring throughout the entire main level. Homesite 1014 features three bedrooms, three full bathrooms, and a finished two-car front-load garage. At the heart of the home, the kitchen features granite countertops, soft-close cabinetry, an oversized island, a walk-in pantry with solid shelving, and Samsung® stainless steel appliances. Enjoy a walkout deck off the great room for seamless outdoor living. The open-concept main level includes a spacious great room with an electric fireplace, a dedicated dining area, a secondary bedroom, and a luxurious primary suite. The primary bath has dual vanities and a roll-in frameless shower with floor-to-ceiling tile. A second full bath, family foyer with access to the laundry room, pantry, and two-car garage, complete the main level. The finished attached garage includes an electric opener and exterior keypad, while the home is solar-ready for future energy upgrades. The walkout finished basement adds a bedroom, full bath, and spacious rec room ideal for guests, entertaining, or flexible living. Being a new build, your home is constructed to the highest energy efficiency standards and comes with a post-settlement warranty. This home offers available closing cost assistance when financing with Intercoastal Mortgage and closing with Walker Title. -----Hiatt Pointe (55+) is located in Frederick County with convenient access to historic Downtown Winchester, Route 7, I-81, and I-66. Nearby shopping and dining includes Rutherford Crossing (4 mins away), Apple Blossom Mall (11 mins away), Downtown Winchester (13 mins away), and Winchester Commons (14 mins away). -----This home is available for self-guided touring through NterNow, no agent or appointment required. Buyers may visit independently during daylight hours. Scan the QR code at the door for instant access and follow a few quick prompts to let yourself in. For more information, visit our website or call Van Metre Homes. -----*Other homesites and delivery dates may be available. Pricing, offers, and availability are subject to change without notice. Images, renderings, and site plans are for illustrative purposes only and may not reflect actual homes or features. Some images and renderings may depict interior designs created in collaboration with AI or may represent a similar home. Additional terms and conditions may apply. Please see a Van Metre New Home Advisor for details.

134 Wagtail Ln Unit #HOMESITE 1014, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com

6 Beds ⋅ 6 Baths

6-bedroom, 5.5-bath Monroe sits on a desirable cul-de-sac in Snowden Bridge and is still under construction, giving you time to select your own cabinets, countertops, and flooring. The main level features a convenient guest suite. The kitchen boasts Gourmet Stainless Steel Appliances with hood, quartz counters and a farmhouse style sink. Oak stairs lead to the 2nd level. The primary suite has 2 walk in closets, and the ensuite offers dual vanities and shower with frameless door. 3 secondary bedrooms and 2 additional baths are found on the upper level along with the convenient laundry room. Walkout lower level with 9' foundation walls, comes finished with recreation room, bedroom and full bath, making this the perfect place to call home. Snowden Bridge is a premier master-planned community with exceptional amenities including a swimming pool, pirate water park, indoor sportsplex, community park, fenced in dog park, and playground. In addition, there is a bike track, walking trails, and a picnic pavilion. You won’t have to leave to have fun, but when you do you’re just minutes from all the convenience and entertainment around Winchester. Ask about builder incentives! Please note the photos are of a similar home while under construction.

2484 Scotch Bonnet Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

4 Beds ⋅ 4 Baths

Welcome to this exceptional 4-bedroom, 3.5-bath Colonial in the sought-after Raven Pointe subdivision, where luxury living extends well beyond the front door. The backyard is a true showstopper, featuring a one-year-old 20' x 40' heated Hayward OmniLogic saltwater pool with a tanning ledge, sunken spa, and Coverstar automatic safety cover. A covered Trex deck with a porch swing overlooks the private backyard, creating the perfect space for relaxing or entertaining. Inside, the main level offers a private home office with custom built-ins, a formal dining room, a spacious family room with a gas fireplace, and a beautifully appointed kitchen featuring a large center island, butler's pantry, stainless steel appliances, gas cooking, and a bright breakfast room. Upstairs, the spacious primary suite includes luxury vinyl plank flooring, a walk-in closet, and a spa-like bath with a jetted tub, walk-in shower, and dual vanities. Three additional bedrooms, a versatile bonus room, and an upper-level laundry room complete the second floor. The finished walk-up basement is made for entertaining with a large recreation room, wet bar with a built-in ice maker, full bath, storage room, and a flexible bonus room that can serve as a fifth bedroom, home gym, or office. Located in Raven Pointe with sidewalks and streetlights, this home is just minutes from shopping, dining, schools, and commuter routes. Offering an incredible combination of elegant living spaces and a resort-style backyard, this is a home you won't want to miss.

107 Cahille Dr, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

5 Beds ⋅ 4 Baths

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. Plus, Solar panels provide a renewable source of energy and much lower electricity bills. Home also includes a whole house water filtered system. Schedule your showing online today. Photos will be done early this week.

144 Morning Glory, Winchester

Listing courtesy of RE/MAX Supercenter. Contact:

4 Beds ⋅ 4 Baths

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

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

3 Beds ⋅ 3 Baths

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

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

2 Beds ⋅ 2 Baths

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

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

3 Beds ⋅ 4 Baths

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

Listing courtesy of Keller Williams Realty. Contact: 7036690099

3 Beds ⋅ 4 Baths

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

Listing courtesy of Keller Williams Realty. Contact: 7036690099

Start Your Search