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

$634,900
5 Beds ⋅ 4 Baths ⋅ VAFV2044776 MLS
Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining — all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. This impressive 5-bedroom, 4-bathroom, three-level Colonial, with new roof (2026), delivers the kind of versatile space today’s buyers are looking for, with room to work from home, host friends, grow your household, or create the ultimate hangout zone. Start with the front wraparound porch, the perfect spot for morning coffee or winding down at the end of the day. Out back, the fun really begins: multiple composite decks with a pergola overlook a private, fully fenced yard backed by mature trees, creating your own outdoor retreat. The 20' x 30' saltwater above-ground pool takes summer entertaining to the next level. Inside, beautiful hardwood floors run throughout the main and upper levels. The main level offers an easy-flowing layout with a welcoming family room featuring a gas fireplace, separate dining and living rooms, plus a spacious kitchen with upgraded countertops, breakfast bar, and breakfast room. The first floor also includes a bedroom and full bathroom — ideal for guests, a home office, or flexible living arrangements. Upstairs, the spacious primary suite feels like a private escape, complete with double sinks, jetted tub, walk-in shower, and walk-in closet. Three additional bedrooms, a full bathroom, and conveniently located laundry complete the upper level. And then there’s the lower level — a huge bonus space ready for whatever your lifestyle demands. The large family room with wet bar is made for movie nights, game days, parties, or a dedicated entertainment space. An additional room plus a full bathroom offers incredible flexibility for a home gym, office, guest suite, teen hangout, or potential in-law setup. Outside your front door, you're conveniently located near Winchester Country Club, shopping, restaurants, and schools, giving you the best of both convenience and neighborhood living. This isn't just a house — it's the space to live the way you want now, with room for whatever comes next.

314 Huntersridge Rd, Winchester
$595,390
3 Beds ⋅ 3 Baths ⋅ VAFV2044520 MLS
NEW BUILD, move in ready single-family home at Hiatt Pointe, 55+ community at Snowden Bridge by Van Metre Homes! The Sierra 39-F2 at Hiatt Pointe is stunning! This home offers 3 bedrooms, 3 full bathrooms, a 2-car front load garage, a finished basement and much more! As you enter the home you are greeted with 9' ceilings, luxury vinyl plank flooring, recessed lighting throughout, programmable thermostat, tankless gas water heater, solar panel ready, open floor plan, huge rec room on the lower level, all spanning over 3200 sq ft. The kitchen is a chef's dream with all stainless-steel appliances, white quartz counters, a spacious island and a walk-in pantry with solid shelving. Off the great room is your 20x12 deck, making it easy to entertain your family and friends! Cozy up by your electric fireplace to unwind or enjoy a good book. The primary suite offers a large bath with quartz counters, dual vanities, soaking tub and a roll -in frameless tile shower. On the lower level of the home, you will find a finished rec room, the third bedroom and the third full bath. Don't miss your opportunity to live in Hiatt Pointe at Snowden Bridge, a gated 55+ active adult community! Enjoy all the amenities to include a full clubhouse, fitness center, pickleball, outdoor pool and hot tub, fire tables and outdoor kitchens! Located near restaurants, shopping and downtown Winchester. Close to Rt 7, I-81 and I-66, making it a great commuter location. Schedule your showing today!

116 Magpie Ln, Winchester
$645,000
4 Beds ⋅ 4 Baths ⋅ VAFV2044488 MLS
Come and discover this impressive beauty where easy main-level living meets exceptional indoor-outdoor entertaining. This beautifully appointed Cape Cod offers the convenience of a spacious main-level primary suite, while the heart of the home flows seamlessly from the well-appointed kitchen to a covered rear porch overlooking the sparkling inground pool and hot tub. With ceiling fans and a TV, the covered porch is an inviting gathering space for morning coffee, lazy summer afternoons, or movie night—truly an extension of the home all year long. Inside, the main level offers an ideal blend of an open floorplan and defined rooms with gleaming hardwood floors, soaring ceilings, crown molding, beautiful fresh paint, and an abundance of natural light. The kitchen features generous cabinet storage and prep space,a gas cook top, double ovens, built in microwave, a center island, and breakfast nook with direct access to the covered porch and expansive patio & pool area, making indoor-outdoor entertaining effortless. From the kitchen flow into the spacious living room with charming built-ins to find a warm and inviting place to relax and watch TV while being part of the action. This home also has a formal dining and living room (currently used as office) that flank the welcoming and generously sized foyer. The large main-level primary suite offers a private retreat with a relaxing en-suite bath featuring a soaking tub, step in shower, and huge walk-in closet. The main level is also home to laundry room and gorgeous powder room. Upstairs, three generously sized bedrooms share a full bath, providing comfortable accommodations for family and guests along with a loft area perfect as play area or reading nook. The versatile lower level expands the living space with ceramic tile throughout, a spacious recreation area, full bath, and finished room with closet that could serve as a fifth bedroom, home office, guest space, gym, media room, or game room. Outside, the covered rear porch, expansive patio, inground pool, and hot tub create a backyard designed for enjoying home to the fullest. The inviting front porch adds another charming outdoor space, perfect for morning coffee or winding down at the end of the day. A two-car garage, newer roof (2025), two-zone HVAC, and desirable corner-lot setting add to the home's appeal. Meaningful updates include new pool cover (3 years old), pool pump (2 years old) and brand new sand filter. Located in the quiet, Oakdale Crossing neighborhood, this home offers convenient access to Jim Barnett Park, Shenandoah University, Schools, Costco, Apple Blossom Mall, Winchester Country Club, and everyday amenities. Whether you're looking for the ease of main-level living, a comfortable home for entertaining, or your own private backyard retreat, 200 Fairfield Drive offers a wonderful combination of comfort, convenience, and lifestyle.

200 Fairfield Dr, Winchester
$585,659
3 Beds ⋅ 3 Baths ⋅ VAFV2044426 MLS
Find Homesite 1035, a brand new SINGLE FAMILY HOME designed for Active Adult (55+) living. This never lived-in before, MOVE-IN READY 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! -----Offering three bedrooms, three full bathrooms, and a two-car front-load finished garage, this home spans across 3,200 finished square feet between two levels. A welcoming covered front porch, 9 ft. ceilings, and Luxury Vinyl Plank (LVP) flooring throughout the main living areas and primary bedroom make this home a standout. At the heart of the home, the kitchen features white quartz countertops, soft-close cabinetry, an oversized island, a walk-in pantry with solid shelving, and stainless steel appliances. 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 spa-inspired primary bath offers dual vanities with quartz countertops, a roll-in frameless shower with floor-to-ceiling tile, and a soaking tub. A second full bath, family foyer with access to the laundry room with a utility sink, walk-in pantry, and two-car garage, complete the main level. The attached finished 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). -----NterNow self-touring is available on select homesites at Hiatt Pointe, no agent or appointment required. Buyers may visit independently during daylight hours. For access instructions and availability, contact Van Metre Homes directly or visit our website. -----*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.

108 Magpie Ln Unit #HOMESITE 1035, Winchester
$624,990
4 Beds ⋅ 3 Baths ⋅ VAFV2044230 MLS
Welcome to 101 Poe Dr! Offering 2,793 sq. ft. ABOVE GRADE, plus a finished basement office/flex room and substantial additional basement space ready for future expansion, this beautifully maintained 4-Bedroom, 2.5 Bath Craftsman style home offers space, flexibility, and modern finishes throughout. The Open-Concept main level features LVT flooring, a private home office, and a spacious kitchen with a large island, Quartz countertops, stainless steel appliances, and a walk-in pantry. The kitchen flows seamlessly into the dining and family rooms, creating an ideal layout for everyday living and entertaining. Upstairs, a large loft provides additional flexible living space alongside 4 generously sized bedrooms and convenient upper-level laundry. The spacious primary suite features a spa-like bath with an oversized walk-in shower and large walk-in closet. The basement offers even more potential, with a finished room perfect for an additional office, gym, playroom or flex space, plus a large unfinished area ready to customize. Plumbing for a future full bath and an egress window are already in place. Situated on a desirable corner lot with an expansive yard, the home backs toward a cul-de-sac, providing an open feel and added privacy. Enjoy the welcoming front porch, 2-zone heating and cooling, water softener, and community amenities including a clubhouse, pool, tennis/basketball courts, and 2 playgrounds. Conveniently located near Costco, Target, I-81, shopping, restaurants, and downtown Winchester, this home combines nearly 2,800 sq. ft. above grade with even more room to grow in the basement--all in a convenient Winchester location!

101 Poe Dr, Winchester
$456,639
3 Beds ⋅ 3 Baths ⋅ VAFV2044288 MLS
Discover a new MOVE-IN READY and thoughtfully designed home for active 55+ living. This BRAND NEW END VILLA gives you more time to enjoy what matters most. Main-level living and a low-maintenance design means less time on upkeep and more time enjoying Hiatt Pointe's RESORT-STYLE AMENITIES and active social calendar events. From pickleball and the pool to water aerobics, Mahjong nights, and Friday happy hours, every day offers a new opportunity to stay active, connected, and engaged—all within a gated community. -----Explore Homesite 1090, the final move-in ready end villa home at Hiatt Pointe (55+). Offering a two-car front-load finished garage, with three bedrooms, two full bathrooms, and one half bathroom. With 9 ft. ceilings on both levels, Luxury Vinyl Plank (LVP) flooring, oak main stairs, and expertly selected finishes, this villa feels effortlessly unique. The kitchen, central to the entire home, is complete with white soft-close cabinetry, white quartz countertops, a large island, Samsung® stainless steel appliances, and a pantry with solid shelving. The great room has an electric fireplace and connects to a spacious outdoor patio for seamless outdoor living. This home has an entry level primary suite which includes a private full bathroom with dual vanities, soft-close cabinets, quartz countertops, a roll-in frameless shower with floor-to-ceiling tile, and elongated comfort-height toilets. Upstairs, enjoy a flexible retreat space, two secondary bedrooms, and a full bathroom. The two-car finished garage with electric opener and exterior keypad adds extra storage and convenience. 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). -----NterNow self-touring is available on select homesites at Hiatt Pointe, no agent or appointment required. Buyers may visit independently during daylight hours. For access instructions and availability, contact Van Metre Homes directly or visit our website. -----*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.

100 Keystone Ln Unit #HOMESITE 1090, Winchester
$424,990
3 Beds ⋅ 4 Baths ⋅ VAFV2044202 MLS
BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS QUICK MOVE IN HOME!! Brand-New Dual Primary Townhome—Late Summer Move-In! Step into modern living with this beautifully designed dual primary bedroom home, ideally located just steps from Snowden Bridge’s newest amenities. The entry-level bedroom with a full bath offers flexible space for guests, multigenerational living, or a private office. Upstairs, the light-filled open-concept layout features a stylish kitchen that flows seamlessly into the spacious family room—perfect for entertaining or everyday comfort. The top level showcases two spacious primary suites, each with a walk-in closet and private en suite bath, plus a conveniently located laundry area. Enjoy resort-style living at Snowden Bridge with a pool, pirate-themed water park, indoor sportsplex, trails, dog park, and more—all just minutes from Winchester shopping and dining. Secure your new home now for a late summer move-in! Note - Photos are similar while home is under construction.

110 Coriander Dr, Winchester
$425,000
3 Beds ⋅ 2 Baths ⋅ VAWI2011370 MLS
This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous mature trees. A large deck spans the back of the home and incorporates a charming stock-tank plunge pool with liner and filtration system, creating a fantastic space for relaxing and entertaining. Inside, the beautifully renovated kitchen is a standout, while the primary suite offers a walk-in closet and a stylishly remodeled en suite full bath with walk-in shower. The lower level adds even more living and entertaining space, with over half of the basement finished, a wet bar, and convenient walk-up access to the backyard. A carport and high-speed internet round out the home's practical features. Tucked into an established Winchester neighborhood with incredible convenience, you’re just minutes from shopping, dining, Shenandoah University, Winchester Medical Center and historic Old Town, with easy access to I-81 and Route 37.

413 Superior Ave, Winchester
$2,599,000
4 Beds ⋅ 6 Baths ⋅ VAFV2044082 MLS
This upscale custom home blends clean, modern comfort with rustic charm—and does it sublimely with nearly 5,000 finished square feet on one level, including a separate in-law suite. Resting on 5.38 pastoral acres, the handsome façade includes charming details like exposed beams, stonework, classic exterior barn lighting, a metal roof, and a grand covered porch with stunning details that preview the craftsmanship inside. The entry welcomes you to a great room with some delineations for the dining and kitchen areas. Plank hardwood floors, high ceilings, and pleasing neutral colors combine with fetching built-ins, exposed beams, and lighting that create an environment that’s cozy, elegant, and inviting. The dining area to the left has a handy built-in bar and wine cooler. The roomy kitchen is a chef’s dream with its pristine white cabinetry, upscale appliances, and a four-seat wooden island with a quartz countertop that matches the rest of the kitchen counters and backsplash. The crown jewel is the main living area with its luxurious lounge space, anchoring stone fireplace, and beams overhead, adding to the seamless ease of this floorplan. The main home has three bedrooms and 3.5 baths, along with a sizeable laundry room with counterspace and storage galore plus another room perfectly suited for a den, library, or office. The bedrooms are thoughtfully designed, all with attached baths, and the owner’s suite can only be described as resplendent. With its location on one end of the home, the suite provides picturesque views of the outdoors not only from the generous bedroom itself, but also in the bright sitting area, offset by glass barn doors. In addition to a deluxe walk-in closet, the ensuite offers a stylish double vanity, standalone soaking tub, and walk-in shower. The in-law suite is separated by a breezeway with its own entrance and contains the same high-end features in terms of floors, color scheme, and vibe. The common area is both practical and comforting with natural light in the kitchen, dining, and living rooms, the latter getting a dose of ambiance from the stone fireplace. A large bedroom and attached bath sit adjacent, along with a laundry room, and a screened-in porch overlooks the backyard. And let’s talk about the attractive pool and patio area. It’s the icing on the cake—spacious with covered and open seating and dining and a rectangular heated pool at its center. An pool house provides a bar/kitchenette and entertainment center (with TV!) with a pull-out awning for extra shade plus a half-bath and changing room. The area is fenced and landscaped as thoughtfully as the rest of the home and surrounded by lush lawn with a backdrop of mature hardwoods, making for an idyllic setting. There’s also a three-car garage (with bonus room), and a separate outbuilding to use as you like that are both fully heated and cooled. Built with craft and care three years ago, this is arguably the best lot in Frederick County, and with a Winchester address, it’s close to amenities and main arteries, while still offering a quiet, private enclave that is seriously swoon-worthy.

144 Robinson Dr, Winchester
$339,999
3 Beds ⋅ 3 Baths ⋅ VAFV2044152 MLS
Why rent when you can own? This spacious townhome has everything you are looking for. Located steps away from Route 7 & I Interstate 81, with grocery stores, pharmacy and restaurants. Who needs to go out when you can entertain at home. LARGE rooms, well equipped Kitchen w/ walk-in Pantry & Island, Microwave & Glass Top cooking Range & durable easy to clean Corian Countertops. Kitchen flows to wooden Deck w/ Stairs that lead to FULLY FENCED Yard. Huge Family Rm w/ Gas FP & 1/2 BA on Main level. Huge MASTER w/ Private full Bath & walk-in closet, 2 good size bedrooms for family guest or gaming/office space. Home features 2 Full Baths and one half. Washer and Dryer in home making staying in feel like an escape .

113 Windmill Ln, Winchester
$665,000
4 Beds ⋅ 3 Baths ⋅ VAFV2044100 MLS
NEW PRICE — NOW $665,000! An exceptional opportunity to make 158 Old Forest your new home. With a $10,000 price improvement, this property offers even more value. If you've been waiting to take a second look, now is the time! SELLER OFFERING ONE-YEAR STONEBROOK CLUB MEMBERSHIP! Offering approximately 4,000 square feet of living space, welcome to 158 Old Forest Circle, a spacious and inviting Colonial nestled among mature trees in the desirable Stonebrook Farms community. This classic home features four bedrooms, two full baths and one half bath, along with a partially finished lower level offering additional living space and the potential for a fifth bedroom. Inside, hardwood floors and abundant natural light create a warm and welcoming feel. The spacious living room offers plenty of room to gather and relax, while the separate formal dining room provides a beautiful setting. The kitchen features white cabinetry, granite countertops, stainless steel appliances, generous workspace, and a convenient breakfast bar. Upstairs, four generously sized bedrooms provide plenty of room for family, guests, or a home office. The partially finished lower level adds even more flexibility, with space that can be used for a recreation room, home gym, office, hobby area, or future fifth bedroom. One of the home's most appealing features is its peaceful outdoor setting. Step outside onto the spacious rear deck, perfect for morning coffee, outdoor dining, grilling, or entertaining while surrounded by mature trees and the privacy of the wooded lot. A lower-level garage and extended driveway provide convenient off-street parking. Additionally, seller-provided home warranty offers additional peace of mind. SPECIAL SELLER INCENTIVE: The seller is offering the new owner a one-year membership to the Stonebrook Club, where you can enjoy swimming, tennis, pickleball, a fitness/weight room, and a variety of other recreational and social activities—a wonderful way to begin enjoying the Stonebrook lifestyle from day one.

158 Old Forest Cir, Winchester
$329,900
3 Beds ⋅ 3 Baths ⋅ VAFV2044088 MLS
Welcome home to 103 Trade Wind Lane, a beautifully updated townhome offering low-maintenance living on Winchester’s desirable east side! Perfectly situated near top schools, shopping, dining, and major commuter routes, this turn-key residence delivers both comfort and ultimate convenience. Natural light pours into the bright living room, where modern flooring lead you straight into the open kitchen and dining area designed for easy everyday living. Outfitted with brand-new granite countertops, a center island, plentiful cabinetry, and a new dishwasher, this space effortlessly opens to the rear deck for peaceful outdoor relaxation. Rounding out the main level are a conveniently located half bath and main-level laundry setup. Upstairs, retreat to the primary suite featuring a spacious layout, a walk-in closet, and a private ensuite bath. Two additional well-proportioned bedrooms share a second full bath, perfect for family, guests, or a flexible work space. The upper level shines with brand-new carpet and stylishly refreshed bathroom fixtures and lighting. Outside, the freshly pressure-washed exterior is highlighted by a private back deck with a handy built-in storage shed, all overlooking a quiet grassy common area. Beyond the home itself, enjoy community living with an inground pool and an all-inclusive HOA that handles lawn care, road upkeep, and snow removal. With two assigned parking spots right at your front step, you can leave the stress of exterior maintenance behind. Don't miss out on this rare opportunity to enjoy updated, turn-key living in one of Winchester’s most convenient locations.

103 Trade Wind Ln, Winchester
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