Pioneer Heights Real Estate

Pioneer Heights Real Estate

Welcome to Pioneer Heights, a charming subdivision nestled in the heart of Winchester, Virginia. This delightful community offers the perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Pioneer Heights boasts a variety of well-designed homes, each reflecting the warmth and character of the community. With tree-lined streets and beautifully landscaped yards, this subdivision creates an inviting atmosphere that encourages outdoor activities and neighborly interactions. Residents can enjoy leisurely strolls through the neighborhood or gather in community parks, where children can play and families can picnic under the shade of mature trees.

Located in Frederick County, Pioneer Heights provides easy access to the vibrant city of Winchester, known for its rich history and cultural attractions. Explore the charming downtown area, where you’ll find an array of shops, restaurants, and local markets. History enthusiasts will appreciate the nearby Civil War battlefields and museums that offer a glimpse into the past.

For those who enjoy the great outdoors, Pioneer Heights is conveniently situated near numerous parks and recreational areas, including the scenic Shenandoah National Park, perfect for hiking, biking, and enjoying nature’s beauty.

With its friendly community spirit, excellent schools, and proximity to major highways, Pioneer Heights is more than just a place to live; it’s a place to thrive. Come discover the warmth and charm of Pioneer Heights, where your dream home awaits!

Newest Listings in Pioneer Heights

$539,900
5 Beds ⋅ 4 Baths ⋅ VAFV2044852 MLS
Welcome to 114 Settlers Circle, a spacious 5-bedroom, 3.5-bathroom home nestled on a quiet street in a prime east-side Winchester location. Classic curb appeal greets you with a timeless brick front, framed by gorgeous mature trees that offer natural shade, privacy, and lush beauty. Step inside to an elegant two-story foyer flanked by formal living and dining rooms, setting the stage for easy entertaining. The main level shines with gleaming hardwood floors throughout most of the living areas and flows effortlessly into a sun-filled kitchen. Outfitted with a convenient breakfast bar and pantry, the kitchen centers around a bright eat-in nook surrounded by wall-to-wall windows, seamlessly opening to a family room complete with a cozy gas fireplace. A convenient half bath rounds out the main floor. Upstairs, you will find a spacious primary suite featuring a large walk-in closet and a beautifully appointed attached bath with dual/split vanities and a relaxing corner soaking tub. The upper level also includes three additional bedrooms, another full bath, and convenient upper-level laundry. Brand-new carpet flows across both sets of stairs and three of the upper bedrooms—including the primary—while the fourth bedroom features classic hardwood flooring. The mostly finished basement features fresh carpet and offers endless possibilities for versatile living. A large recreation room provides the perfect layout for movie nights, an extra living area, a playroom, home office, or a dedicated workout space. It also boasts a private fifth bedroom alongside a full bathroom, ideal for extended family or overnight visitors. Practical functionality continues with an unfinished storage room and a fantastic workshop complete with built-in cabinetry and framed pegboard for tool organization. The outdoor setting is a true standout, featuring a covered deck off the main level where you can unwind rain or shine. Tucked seamlessly into a canopy of mature trees, the backyard offers exceptional privacy in a peaceful, serene environment. Lower-level access leads directly out to a covered patio and open deck, creating an ideal layout for outdoor entertaining or quiet mornings surrounded by nature. Complete with an attached 2-car garage for easy parking and extra storage, this move-in ready home delivers space, comfort, and character in an unbeatable location.

114 Settlers Cir, Winchester
$552,000
4 Beds ⋅ 3 Baths ⋅ VAFV2044754 MLS
Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone wood fireplace, new natural gas upstairs furnace and a/c, upgraded insulation in attic, oversized garage and large deck. New paint, LVPk flooring in baths and kitchen. Must see.

100 Winns Cir, Winchester
$549,900
5 Beds ⋅ 4 Baths ⋅ VAFV2044748 MLS
“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy commuter access. Offering five bedrooms and 3.5 baths, this spacious home has been thoughtfully updated and improved over the years, providing a comfortable blend of classic character and modern convenience. The heart of the home is the updated kitchen, featuring custom cabinetry, granite countertops, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Throughout the home, you'll find updated bathrooms, newer carpeting, and numerous additional improvements that make this home truly move-in ready. The finished basement adds valuable living space and versatility, complete with a walkout, comfortable living area, fifth bedroom, and full bathroom. Ample storage space provides plenty of room for seasonal items, hobbies, or household needs. Step outside and enjoy multiple spaces designed for relaxing and entertaining. A rear porch leads to a deck and backyard patio, creating an easy flow for outdoor gatherings, morning coffee, or quiet evenings. The meticulously manicured front yard is a standout, featuring lush green grass, thoughtfully maintained mulch beds, and beautiful flower gardens—all complemented by an underground sprinkler system for easy lawn care. With generous living space, numerous updates, attractive outdoor amenities, and a convenient location close to Route 7, this Pioneer Heights home offers the space, comfort, and accessibility you've been looking for. Schedule your appointment to see it today!

223 Asbury Rd, Winchester
$565,000
4 Beds ⋅ 3 Baths ⋅ VAFV2042094 MLS
Welcome home to this beautifully updated 4-bedroom Colonial situated on a large corner lot in a highly desirable commuter location just off Route 7. From top to bottom, this home has been thoughtfully improved, offering the perfect blend of modern updates and timeless charm. The newly updated kitchen features brand-new quartz countertops, all-new stainless steel appliances, including a gas range with built-in air fryer functionality, making meal preparation a delight. New flooring has been installed throughout the main and upper levels, with the exception of the elegant hardwood foyer that warmly welcomes guests. All bathrooms have been refreshed with new flooring (1/2 bath on main has new counters and fixtures), providing a clean, contemporary feel throughout. Relax year-round in the inviting sunroom complete with a cozy wood stove, perfect for chilly evenings. The spacious family room features a wood-burning fireplace that creates a warm and inviting atmosphere for gatherings and everyday living. Major system updates provide peace of mind, including a brand-new roof (May 2026), HVAC systems replaced within the last five years, a gas furnace installed in 2024, and a water heater replaced in 2025. Filled with character and charm, this move-in ready home offers exceptional value with no maintenance worries. Conveniently located for commuters and close to everyday amenities, this is a rare opportunity to own a beautifully updated Colonial that's truly ready for its next chapter.

109 Artillery Rd, Winchester
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