Winding Creek Real Estate

Winding Creek Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winding Creek and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

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Newest Listings in Winding Creek

14326 Bookcliff Ct, Hillsborough
$1,425,000
5 Beds ⋅ 5 Baths
EXCEPTIONAL WESTERN LOUDOUN ESTATE ON 3 ACRES WITH BREATHTAKING MOUNTAIN VIEWS FRONT & BACK, NEARLY 6,000 TOTAL SQFT + NO HOA**RESORT-STYLE LANDSCAPED OUTDOOR LIVING FEATURES ELEGANT 38-FT IN-GROUND POOL W/ 9-FT DEPTH & NEW LINER ('23), HOT TUB, PAVILION W/ WORKING FIREPLACE + EXPANSIVE FRONT & REAR STONE PATIOS ('22)—AN INCREDIBLE SETTING FOR RELAXING, GATHERING & TAKING IN THE SCENERY**IMPRESSIVE INTERIOR FEATURES SOARING 2-STORY GREAT ROOM W/ MAJESTIC UPPER-LEVEL OVERLOOK, FLOOR-TO-CEILING STONE FIREPLACE W/ PELLET STOVE + ABUNDANT NATURAL LIGHT**GOURMET KITCHEN FEATURES QUARTZ COUNTERS, SS APPLIANCES (GAS COOKING), NEW FARMHOUSE SINK, DOUBLE OVENS, TILE BACKSPLASH, LARGE WALK-IN PANTRY + SUNROOM JUST OFF KITCHEN**ENJOY MULTIPLE INDOOR/OUTDOOR LIVING SPACES INCL SCREENED-IN PORCH W/ TREX DECKING & 2 LIGHTED CEILING FANS + SEPARATE DECK FOR GRILLING**EXCEPTIONALLY VERSATILE FLOOR PLAN INCL MAIN-LEVEL OFFICE + OPTIONAL 5TH BEDROOM/2ND PRIMARY W/ FULL BATH—EXCELLENT FLEXIBILITY FOR MULTI-GENERATIONAL LIVING & GUESTS**UPPER LEVEL FEATURES 3 FULL BATHS (INCL JACK & JILL) & 4 BEDROOMS** EXPANSIVE PRIMARY SUITE W/ GENEROUS SITTING ROOM, EXCEPTIONALLY LARGE WALK-IN CLOSET + EN SUITE BATH W/ LARGE SOAKING TUB**LARGE ATTIC SPANS THE UPPER LEVEL FOR ABUNDANT ADDITIONAL STORAGE**FINISHED WALKOUT LOWER LEVEL OFFERS OUTSTANDING IN-LAW/AU-PAIR POTENTIAL W/ FULL BATH, REC/FAMILY ROOM, GAME ROOM + ADDITIONAL BONUS ROOM & 6TH BEDROOM POTENTIAL W/EGRESS WINDOW**CUSTOM WINE ROOM W/ ABUNDANT BOTTLE STORAGE + RUSTIC WOOD DETAILING**GAME ROOM (AIR HOCKEY TABLE & TV CONVEY) + 2 LARGE WORKSHOP/TOOL/STORAGE AREAS PROVIDE EXCEPTIONAL FUNCTIONALITY**WHOLE-HOME GENERATOR + UV WATER FILTRATION SYSTEM, OWNED 1,000-GAL IN-GROUND PROPANE TANK & EXTERIOR ELECTRIC HOOKUP FOR EV OR RV ADD COMFORT, CONVENIENCE & SELF-SUFFICIENCY** NUMEROUS THOUGHTFUL DETAILS THROUGHOUT INCL CUSTOM SHELVING, CEILING FANS IN ALL BEDROOMS & MOST MAIN-LEVEL ROOMS + REMOTE-CONTROL LOUVER BLIND ON DRAMATIC PALLADIAN FOYER WINDOW**NEWER ROOF ('21) & PAID SOLAR PANELS ('22) OFFER SIGNIFICANT ENERGY-SAVINGS (ABOUT $500/MONTH) + POSSIBLE REVENUE-GENERATING OPPORTUNITIES** +3-CAR GARAGE W/ 2 INDIVIDUAL DOORS + TRANSITION/MUDROOM PROVIDES ABUNDANT PARKING & EVERYDAY FUNCTIONALITY**FENCED BACKYARD + SHED COMPLETES THIS PRIVATE WESTERN LOUDOUN RETREAT**POTENTIAL FOR 2.25% ASSUMABLE LOAN** EXPERIENCE THE BEST OF HILLSBORO & LOUDOUN WINE COUNTRY WITH SEVERAL NEARBY WINERIES, FARM BREWERIES, HISTORIC HILLSBORO, APPALACHIAN TRAIL, SHENANDOAH RIVER & HARPERS FERRY + CONVENIENT ACCESS TO PURCELLVILLE & LEESBURG**PRIME LOCATION NEAR RT 9/CHARLES TOWN PIKE & RT 7 FOR ACCESS THROUGHOUT NORTHERN VA, MARYLAND & WEST VIRGINIA**COMING SHORTLY...SEE MATTERPORT 360 TOUR, VIDEO & AERIAL PHOTOGRAPHY!

14326 Bookcliff Ct, Hillsborough

Listing courtesy of Real Broker, LLC - Gaithersburg. Contact:

609 Pinnacle Ridge Dr, Annville
$608,400
2 Beds ⋅ 2 Baths
UNDER CONSTRUCTION - AVAILABLE EARLY 2027. Located in the 55+ community of Winding Creek in Annville, PA, this Perry quick move-in home offers convenient one-story living with thoughtfully selected finishes and inviting spaces. A welcoming front porch leads into a home with 9’ ceilings and luxury vinyl plank flooring in the living areas. Two secondary bedrooms and a full bathroom are located near the front of the home, while an entry bench provides a convenient place to settle in. Decorative beams add character to the open kitchen and great room. The kitchen features stainless steel appliances, quartz countertops, a tile backsplash, a large island, and a pantry. The great room is warmed by a gas fireplace with stone and shiplap detailing and a box beam mantel. A screened-in porch, accessible from the dining area, extends the living space outdoors. Tucked quietly toward the back of the home, the spacious owner’s suite includes an expansive closet and a private bathroom with a tile shower and double-bowl vanity. A 2-car garage with mudroom entry completes this thoughtfully designed new construction home. Enjoy an active, low-maintenance lifestyle at Winding Creek 55+, with a clubhouse, outdoor pool, pickleball and bocce courts, putting green, and scenic walking trails. The Annville location also offers convenient access to local shops and dining, Hershey, golf, recreation, and regional attractions.

609 Pinnacle Ridge Dr, Annville

Listing courtesy of Today's Realty. Contact:

14254 Bookcliff Ct, Hillsboro
$1,395,000
5 Beds ⋅ 6 Baths
Gorgeous, 3 private acres in Winding Creek and there is no HOA! This beautiful home offers five bedrooms, six full bathrooms, an in-ground pool, a detached two-bay garage, and a fully finished walk-out lower level. The entire home was recently painted, and all major inspections were completed in Spring 2026. Significant improvements include Hardie Plank and stone exterior, new windows and frames, HVAC systems and condensers, and attic insulation, all completed in 2024. New roof in 2022. Inside, the main level features the 5th bedroom in the house and full bathroom, office, laundry room, hardwood flooring, a two-story foyer, formal dining room and a family room with a wood-burning fireplace and open floorplan`. The kitchen includes granite countertops, stainless steel appliances less than two years old, gas cooking, double wall oven, a pantry with a second refrigerator, and a spacious breakfast area with direct access to the deck and pool. Upstairs, each of the four bedrooms includes a private en-suite bath. The primary suite features a sitting area, expansive walk-in closet, dual vanities, and a walk-in shower. The finished walk-out lower level also has a full bathroom, wet/dry bar, bonus room, daylight windows and flexible space for recreation, entertaining, or working from home. Outside, the property features an in-ground pool, established gardens, an electric- and water-equipped greenhouse added in 2022, and an electric-equipped shed. The heated and insulated 29' x 29' detached garage offers epoxy flooring, two bays, and 10' x 10' doors. Additional features include an attached garage with EV charging, whole-house water filtration, and smart garage systems. Located on a private corner lot, this extensively updated home offers exceptional flexibility, storage, and outdoor living space.

14254 Bookcliff Ct, Hillsboro

Listing courtesy of EXP Realty, LLC. Contact:

208 Pinnacle Ridge Dr, Annville
$637,900
2 Beds ⋅ 2 Baths
UNDER CONSTRUCTION – AVAILABLE THIS WINTER. Located in the 55+ community of Winding Creek in Annville, this new construction Cooper quick move-in home offers the ease of single-story living with thoughtfully selected upgrades and open-concept design. The inviting front porch leads into a welcoming foyer accented by luxury vinyl plank flooring, a craftsman bench seat, and decorative wainscoting. The front of the home features a private study, secondary bedroom, and full bath, providing flexible space for work, guests, or hobbies. At the heart of the home, the open kitchen showcases stainless steel appliances, quartz countertops, a tile backsplash, attractive cabinetry, and seamless flow into the sunny dining area. The spacious family room is highlighted by a gas fireplace featuring dramatic floor-to-ceiling stone and a box beam mantel, creating a warm and inviting focal point for everyday living and entertaining. A screened-in deck extends the living space outdoors and provides the perfect setting to relax and enjoy the surroundings. Privately situated at the rear of the home, the owner’s suite offers an expansive closet and a luxurious bath with a tile shower and double bowl vanity. Additional highlights include 9' first-floor ceilings, a daylight basement with outdoor access, convenient laundry room access from the mudroom, and upgraded finishes throughout. Enjoy an active, low-maintenance lifestyle at Winding Creek 55+, where resort-style amenities include a clubhouse with outdoor pool, pickleball and bocce courts, a putting green, and scenic walking trails. Ideally located in Annville, residents are just minutes from charming local shops and dining, Hershey attractions, golf, recreation, and regional destinations.

208 Pinnacle Ridge Dr, Annville

Listing courtesy of Today's Realty. Contact:

212 Pinnacle Ridge Dr, Annville
$652,100
2 Beds ⋅ 2 Baths
UNDER CONSTRUCTION – AVAILABLE THIS WINTER. Located in the 55+ community of Winding Creek in Annville, PA, this Ashton quick move-in home offers charming one-story living with a second-floor loft and storage area, elevated design details, and comfortable spaces for everyday living. A welcoming front porch opens to a bright entry with a built-in bench seat and accent wall. Beautiful luxury vinyl plank flooring flows throughout the main living areas, where 9’ ceilings and a shared cathedral ceiling in the great room and kitchen create an open, airy feel. The well-appointed kitchen features stainless steel appliances, quartz countertops, tile backsplash, a spacious pantry, and a large center island that opens to the great room. A gas fireplace with floor-to-ceiling stone and a box beam mantel adds warmth and character. Enjoy outdoor living from the screened-in deck, easily accessed from the sunny dining area. The owner’s suite is tucked to the rear of the home with an expansive closet and private bath featuring a tile shower and double bowl vanity. A second bedroom, full bathroom, and flex room are located toward the front of the home. At Winding Creek 55+, homeowners enjoy a low-maintenance lifestyle with resort-style amenities, including a clubhouse with outdoor pool, pickleball and bocce courts, putting green, scenic walking trails, and convenient access to Annville, Hershey, golf, local dining, and regional attractions.

212 Pinnacle Ridge Dr, Annville

Listing courtesy of Today's Realty. Contact:

536 Stone Gate Blvd, Annville
$549,900
3 Beds ⋅ 3 Baths
UNDER CONSTRUCTION - AVAILABLE FALL. Located in the 55+ community of Winding Creek in Annville, this Bella floor plan offers easy, single-story living with an open-concept layout and thoughtfully selected upgrades throughout. A welcoming entry opens to a bright foyer and a secondary bedroom, ideal for guests or a home office. The main living area features 9’ ceilings and luxury vinyl plank flooring throughout the entry, kitchen, dining area, and great room, creating a seamless and inviting space. The kitchen is beautifully appointed with quartz countertops, tile backsplash, stainless steel appliances, and a central island that flows into the dining area and great room. The great room is highlighted by a vaulted ceiling, accent wall, and a gas fireplace with floor-to-ceiling stone and a painted mantel, creating a warm focal point. Step outside to enjoy the rear deck, offering additional space for relaxation or entertaining. Tucked to the back of the home, the owner’s suite features a spacious closet and a private bath with a tile shower. A basement with outdoor access provides additional storage and future possibilities to finish. Enjoy an active, low-maintenance lifestyle at Winding Creek 55+, where resort-style amenities like a clubhouse with outdoor pool, pickleball and bocce courts, putting green, and scenic walking trails create endless opportunities for recreation and connection. Ideally located in Annville, PA, residents are just minutes from charming local shops and dining to popular nearby destinations like Hershey, golf and recreation, and regional attractions.

536 Stone Gate Blvd, Annville

Listing courtesy of Today's Realty. Contact:

532 Stone Gate Blvd, Annville
$504,500
2 Beds ⋅ 2 Baths
UNDER CONSTRUCTION - AVAILABLE FALL. Located in the 55+ community of Winding Creek in Annville, this Bella floor plan offers low-maintenance, single-story living with elevated finishes and an open-concept design. A welcoming entry opens to a bright foyer and a secondary bedroom, ideal for guests or a home office. The main living areas feature 9’ ceilings and luxury vinyl plank flooring throughout the kitchen, dining area, great room, and entry, creating a seamless and inviting space. The kitchen is beautifully appointed with quartz countertops, tile backsplash, stainless steel appliances, and a central island overlooking the dining area and great room. A vaulted ceiling with exposed beams, accent wall, and gas fireplace with stone and shiplap create a warm and visually striking focal point. Sliding glass doors provide access to the rear deck, perfect for relaxing or entertaining. The owner’s suite is tucked quietly to the back of the home and features a spacious closet and private bath with a tile shower. A basement with outdoor access offers additional storage and future possibilities to finish. Enjoy an active, low-maintenance lifestyle at Winding Creek 55+, where resort-style amenities like a clubhouse with outdoor pool, pickleball and bocce courts, putting green, and scenic walking trails create endless opportunities for recreation and connection. Ideally located in Annville, PA, residents are just minutes from charming local shops and dining to popular nearby destinations like Hershey, golf and recreation, and regional attractions.

532 Stone Gate Blvd, Annville

Listing courtesy of Today's Realty. Contact:

720 Longwood Mnr, Annville
$665,900
2 Beds ⋅ 2 Baths
UNDER CONSTRUCTION - AVAILABLE FALL. Located in the 55+ community of Winding Creek, this charming Northfield home offers thoughtfully designed single-story living with elevated finishes throughout. A welcoming front porch and 9’ ceilings create an inviting first impression, while the open layout enhances comfort and functionality. The 2-car garage opens to a convenient mudroom featuring built-in lockers and a spacious pantry. Luxury vinyl plank flooring flows through the main living areas, adding both durability and style. At the heart of the home, the kitchen impresses with stainless steel appliances, quartz countertops, a tile backsplash, and a large center island—perfect for everyday living and entertaining. The kitchen and family room share a vaulted cathedral ceiling, creating a bright and airy atmosphere. A gas fireplace with a striking stone surround serves as a cozy focal point in the family room. The adjoining dining area opens to an outdoor living space that includes both a deck and screened-in porch, ideal for relaxing or entertaining in any season. Tucked quietly at the rear of the home, the owner’s suite offers a peaceful retreat complete with an expansive closet and a private bathroom featuring a beautifully tiled shower. A secondary bedroom and full bathroom are located at the front of the home, along with a private study enhanced by glass French doors—perfect for a home office or flex space. A conveniently located laundry room sits just off the owner’s suite for ease of daily living.

720 Longwood Mnr, Annville

Listing courtesy of Today's Realty. Contact:

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