Whippoorwill Hollow Charlottesville Homes For Sale

No properties found

Recently Sold Whippoorwill Hollow Homes For Sale

HUGE PRICE REDUCTION! FABULOUS IVY LOCATION, JUST OVER 6 MILES TO CHARLOTTESVILLE, VIA GARTH ROAD. WESTERN SCHOOL DISTRICT, including Meriwether Elementary just 5 minutes away. The home has over two acres, and is quietly situated on a cul-de-sac. The main level floor plan is an open concept, and includes one of the four bedrooms, and a full renovated bath. Upstairs is freshly painted and carpeted, and includes the primary bedroom with a large renovated bath, walk in closet, plus two more bedrooms and another renovated bath. There is also a walk out full basement with large rec room (that includes a stove and second fireplace), another fully renovated bath, laundry, utility room, large unfinished workshop, and lots of storage. Lots of recent maintenance and upgrades. $575,000 Closed

2601 Cardinal Ridge Rd Charlottesville, Virginia

4 Beds 4 Baths 3,062 SqFt 2.21 Acres

This classic Ivy home, minutes to Meriwether Lewis Elem & Garth Rd (for an easy commute to Charlottesville) is in the desirable Whippoorwill neighborhood, on 2 gorgeous acres w/a distant peek of the Blue Ridge. With graciously proportioned rooms, a great flow & super outdoor living space, this home has warmth, appeal & wonderful functionality. Off the entry are the roomy formal dining & living rooms, the latter of which opens to an enormous screen porch. A cozy den w/fp, built-ins & wetbar is to the rear of the home & opens to the huge, recently rebuilt rear deck overlooking the rolling yard, mature trees & winter mtn views. The large, sunny kitchen has extensive workspace, a nice work triangle & is adjacent to both the high ceilinged breakfast room & the side entry/mud room with cabinetry & laundry. Rounding off the main floor is a stylish powder room, recently renovated (as are all the home’s bathrooms). Upstairs is an oversized owners suite with a jumbo walk in closet & extra storage in an attic space, plus 2 good sized family bedrooms which share a renovated full bathroom. The terrace level has 2 large family/flex spaces, one with a fireplace & kitchenette, plus the 4th bedroom & last full bath, ideal for guests or teens! $675,000 Closed

2584 Cardinal Ridge Rd Charlottesville, Virginia

4 Beds 4 Baths 3,255 SqFt 2.02 Acres

Well-maintained, spacious home in sought-after Garth Road area! Situated on an impressive, 2-acre corner lot in a quiet neighborhood, you’ll be delighted by the privacy & outdoor living spaces this beautiful property provides. Step inside & find hardwood floors & plantation shutters throughout the main level. A large formal dining room, cozy sitting room, powder room, & updated kitchen w/ granite countertops & additional dining area. The open concept family room includes coffered ceilings, a gas fireplace & access to the screened porch, perfect for cooking while entertaining guests. Off the kitchen, is the laundry closet, access to the garage, & access to the oversized deck. The 2nd level features a unique master suite that includes a private tucked away office, a sitting room w/ cedar closet & access to the private balcony, & two separate bathrooms for the shower & jetted soaking tub. Down the hall are 3 additional bedrooms w/ large closets & another full bath. You’ll find plenty of desirable features such as multiple skylights & storage space throughout. The landscaped, fenced backyard is open & flat, allowing plenty of space for entertaining & play! A short drive to shopping & dining at Barracks Road and UVa. No HOA dues! $725,000 Closed

2595 Cardinal Ridge Rd Charlottesville, Virginia

4 Beds 3 Baths 3,500 SqFt 2.15 Acres

A charming and well-maintained home privately tucked off Owensville Road in the sought after neighborhood of Whippoorwill Hollow. Situated on two acres, this oasis is protected by mature trees yet offers plenty of yard to garden, to play, and/or to simply enjoy nature. The welcoming circular driveway is complemented by a detached garage with a concrete sport court behind. Inside, an open kitchen flows seamlessly into a breakfast nook with French doors that lead to an expansive and welcoming screened porch. A cozy living room features a wood burning fireplace with an adjacent dining room. A bedroom, currently used as a home office, and a full bath complete the main floor. The second floor hosts a primary bedroom suite, along with two additional bedrooms and a full bath. All bathrooms were remodeled in 2020, along with new exterior paint, new carpet, and additional paint inside. Please see associated documents for details on renovation and maintenance over the years, including a 16kW generator. A wonderful offering in the heart of the western school district and less than ten miles to most everything Charlottesville. $755,000 Closed

2110 Whippoorwill Rd Charlottesville, Virginia

4 Beds 3 Baths 2,360 SqFt 2 Acres

Fabulous home in Ivy...lovingly cared for and updated over the past 40 years by the current owners...Beautifully landscaped yard...The screened porch and rear deck extend the living space...great backyard leads toward the woods... Family room (with stone fireplace) opens to the deck and kitchen...Terrific terrace level recreation room features a fireplace and sliding doors to the back yard...Hardwood floors throughout...large driveway...peaceful and quiet.. $781,000 Closed

2033 Bobwhite Ct Charlottesville, Virginia

4 Beds 3 Baths 3,418 SqFt 2.47 Acres

Charming home on an incredible lot on one of Ivy's most coveted streets. Enter the property and be enchanted with mature trees, green lawns, and surprising privacy. Curb appeal galore with hardiplank siding, copper roofing and half round gutters on the front porch, and classic architectural lines. Main floor features a formal dining room and living room with wood burning fireplace which flows to the kitchen and lightfilled sun room currently used as an office. Second entrance off the driveway conveniently leads to the kitchen via mudroom offering wonderful amenities including storage benches, laundry, and powder room. Gas Wolf range, dishwasher, butcher block island, and dedicated pantry cabinets are highlights of the eat in kitchen. Heading upstairs you'll find the generous owner's suite with large tub, slate tile shower, and streaming natural light. Two more bedrooms and full bathroom in the hall complete the second floor. Walkout basement includes den with wood stove and ample storage space. Room to run and play or even add on in the future if you need more space. Get into the neighborhood at an approachable pricepoint and make it your own. Shown by appointment. $765,000 Closed

2051 Whippoorwill Rd Charlottesville, Virginia

3 Beds 3 Baths 2,904 SqFt 2.1 Acres

This move-in ready newer home in Ivy has been impeccably maintained & features all of the modern features of a newer home in a well established neighborhood. Main level highlights include open concept living, kitchen w/ gorgeous granite counters, stainless appliances & ample cabinet space. The entry greets you w/ a two story foyer, off of which is a flex room w/ built-in shelving that is currently used as an office but could also be a formal sitting room or playroom and on the other side a formal dining room. The backside of the home is full of windows exposing the mountain views & letting in tons of natural light. Family room includes a gas fireplace w/ a stone facade that extends to the ceiling. Upstairs, the primary bedroom has a gorgeous en-suite bath w/ a tile surround shower, large soaking tub, granite counter, & huge windows to take in the mountain views. There are three secondary bedrooms, laundry, & a hall bath w/ dual vanities & a sliding door to the tub/shower. Lower level includes a spacious mudroom coming in from the driveway or garage, a finished rec room w/ sliders to a back patio, and a full bath. The lot backs to the Mechums River and owners built steps all the way down from the house to the river. $800,000 Closed

2648 Cardinal Ridge Rd Charlottesville, Virginia

4 Beds 4 Baths 3,110 SqFt 2.59 Acres

Sited on over 2 private acres in a popular Ivy neighborhood the current owners transformed this home with interior and exterior renovations including a first floor primary suite addition with access to an outdoor shower and private courtyard, new front porch and three season porch fitted with heater, fan and TV, rear deck with composite rails, bluestone patio, fully renovated kitchen with heated floors, new well pump, tank and water filtration system, tesla car charger and extensive finish upgrades. The covered porch with ipe floors and metal roof opens into the home's foyer which leads into a dining room with wood burning fireplace. The owners converted an area off the dining room and kitchen to a cozy den with built-ins and desk area. The renovated kitchen has soft grey painted cabinetry, new appliances, soapstone island and sunny breakfast room and opens to a large vaulted great room with wood burning fireplace and built-ins. The first floor primary suite addition includes vaulted ceilings, walk-in closets and a beautiful bathroom with designer finishes. The second floor includes a second primary suite and 2 additional bedrooms and bath plus den. A detached garage with new doors offers additional storage. $1,300,000 Closed

2205 Whippoorwill Rd Charlottesville, Virginia

4 Beds 4 Baths 3,338 SqFt 2.5 Acres

Just in time for summer! This is the one you've been waiting for! Located in the charming neighborhood of Whippoorwill Hollow, this home is spacious and well appointed with the best yard in the whole community. Four large bedrooms accommodate the whole family with two full baths on the second floor in addition to the main level primary suite. There is a large living/family room plus a basement rec room so there is space for everyone to find their place. But the best part is outside! This home is on a corner lot with each road ending in a cul-de-sac, so there is little traffic and lots of space! The yard is a combination of woods and flat grassy play area. The deck wraps two sides of the house and has built in seating and a spot to enjoy every view. Between the sunsets and the amazing show of Rhododendron lining the drive there is always something beautiful to see. Schedule your visit today. $850,000 Pending

2034 Bobwhite Ct Charlottesville, Virginia

4 Beds 4 Baths 3,443 SqFt 2 Acres

Nestled on 2.53 wooded acres with winter mountain vistas and a walking path to the Mechums River this Western Albemarle contemporary offers the ultimate private retreat. The open-concept design features a vaulted living and dining area with stunning wood beams and skylights, while the custom kitchen and cozy family room with a wood-burning fireplace and heat circulator provide comfort and warmth. Adjacent to the living room is a sunroom that leads to a spacious rear deck, perfect for enjoying nature. The custom kitchen with cherry cabinetry and soapstone counters opens into a versatile combination room with a Japanese soaking tub and cast iron woodstove. The main floor is completed with a primary suite and two additional bedrooms. Upstairs is a 500+ square-foot bonus room ideal for a home office or playroom. Recent upgrades in 2024 and 2025 include new paint throughout interior and exterior, renovated bathrooms and new deck. $965,000 Closed

2664 Cardinal Ridge Rd Charlottesville, Virginia

3 Beds 2 Baths 3,491 SqFt 2.53 Acres

Whippoorwill Hollow Charlottesville homes are highly sought after due to their wonderful location in a small, attractive neighborhood in Ivy, Virginia.

Whippoorwill Hollow Charlottesville, consists of 48 homes set back off private roads in a lovely, wooded setting.

Lot Sizes: 2-acres+

Whippoorwill Hollow HOA Fees: None, nor road maintenance fees.

Years Built: 1978 to 2013

Builders: Craig Builders, Gercke Construction, Winn Homes, and Randy Rinehart.

Architectural Styles: Cape Cod, Colonial, Queen Anne, saltbox, and traditional.

Amenities: none.

2025 Recent Sales: 5 homes

2025 Median Sales Price: $873,000

Median Days on the Market: 5

Note: The first home built in Whippoorwill Hollow was 2295 Whippoorwill Rd, and the last home built was 2648 Cardinal Ridge Rd.

Albemarle Public Schools serving Whippoorwill Hollow are Ivy Elementary (3 minutes away), Henley Middle, and Western Albemarle High Schools.

Location: Ivy, Virginia,, off Owensville Road.

Whippoorwill Hollow Charlottesville homes for sale map

Directions: Take Garth Road out of Charlottesville. Left on Owensville and right on Whippoorwill Rd.

Toby Beavers, an Ivy VA realtor since 2003, may be reached by text or phone at 434-327-2999

toby beavers, Ivy VA realtor since 2003

Discovering Serenity: Whippoorwill Hollow Charlottesville Homes for Sale

As a seasoned Charlottesville realtor with 22 years of experience specializing in the area’s most desirable neighborhoods, I’ve had the privilege of working with discerning buyers who seek more than just a house, they want a lifestyle.

Among the many exceptional communities I represent, Whippoorwill Hollow stands out as one of the most coveted residential enclaves in the greater Charlottesville area. The current selection of Whippoorwill Hollow Charlottesville homes for sale represents an extraordinary opportunity for buyers seeking privacy, luxury, and natural beauty in one of Virginia’s most prestigious neighborhoods.

Located in the charming Ivy area of western Albemarle County, Whippoorwill Hollow offers an unparalleled combination of rural tranquility and urban convenience. The Whippoorwill Hollow homes for sale currently available showcase the neighborhood’s commitment to preserving its natural character while providing residents with spacious, well-appointed properties that exemplify quality construction and thoughtful design.

The Distinguished Character of Whippoorwill Hollow

What sets Whippoorwill Hollow apart from other neighborhoods in the Charlottesville area is its unique blend of privacy, acreage, and architectural diversity. The Whippoorwill Hollow Charlottesville real estate market is characterized by generous lot sizes, typically featuring two-plus acres that provide homeowners with remarkable privacy and space for outdoor enjoyment. This commitment to preserving open space and natural beauty makes each property feel like a private retreat while maintaining the benefits of neighborhood living.

The current inventory of Whippoorwill Hollow Charlottesville homes for sale reflects the community’s architectural diversity, featuring everything from classic colonial designs to Dutch colonial masterpieces, charming Cape Cod styles, and even some contemporary homes with modern flair. This variety ensures that buyers with different aesthetic preferences can find their perfect home within this exclusive community.

The neighborhood’s location just off Owensville Road (A common practice in naming streets and settlements is to honor early settlers or prominent families in the area), close to Garth Road, provides residents with easy access to Charlottesville’s amenities while maintaining the peaceful, wooded atmosphere that defines rural living. The mature trees and careful landscaping throughout the community create a sense of established elegance that new developments simply cannot replicate.

Whippoorwill Hollow Charlottesville homes for sale

Current Whippoorwill Hollow Neighborhood Market Opportunities

The market for homes for sale in Whippoorwill Hollow reflects the broader strength of Charlottesville’s luxury real estate sector. Properties in this neighborhood consistently command premium prices due to their desirable location, generous acreage, and high-quality construction.

Recent listings have showcased the diversity of options available, from meticulously maintained traditional homes to thoroughly renovated properties that blend historic charm with modern conveniences.

One of the most appealing aspects of Whippoorwill Hollow Charlottesville homes for sale is the consistency of quality throughout the neighborhood. The community’s development guidelines and the natural selectivity of the location have created a cohesive environment where property values remain strong and the neighborhood character is preserved.

This stability makes Whippoorwill Hollow an excellent choice for both primary residences and investment properties.

The current market conditions favor serious buyers who understand the unique value proposition of Whippoorwill Hollow luxury homes Charlottesville. With limited inventory and strong demand, properties in this neighborhood tend to move quickly when priced appropriately.

My experience with this market allows me to help buyers navigate the competitive landscape and identify the best opportunities as they become available.

Whippoorwill Hollow Charlottesville homes for sale

Architectural Excellence and Design Features

The homes for sale in Whippoorwill Hollow showcase a remarkable attention to architectural detail and quality construction. Many properties feature custom millwork, hardwood floors, stone fireplaces, and other premium finishes that reflect the discriminating taste of their original builders and subsequent owners. The generous room sizes and thoughtful floor plans common throughout the neighborhood accommodate both intimate family living and large-scale entertaining.

Several recent Whippoorwill Hollow Charlottesville homes for sale have featured extensive renovations that demonstrate how classic architectural styles can be updated for contemporary living without losing their essential character. These renovations often include gourmet kitchens with high-end appliances, luxurious master suites, and family rooms designed for casual living while maintaining the formal entertaining spaces that define gracious Virginia living.

The outdoor spaces associated with Whippoorwill Hollow properties are equally impressive. Large lots provide opportunities for swimming pools, tennis courts, extensive gardens, and other recreational amenities.

The mature landscaping throughout the neighborhood creates natural privacy screens and seasonal beauty that enhance the value and enjoyment of every property.

Location Benefits and Lifestyle Advantages

The strategic location of Whippoorwill Hollow provides residents with the perfect balance of privacy and convenience. The neighborhood’s position in western Albemarle County offers easy access to Charlottesville’s cultural attractions, shopping, dining, and business districts while maintaining the peaceful atmosphere of country living. The University of Virginia, downtown Charlottesville Mall, and major employment centers are all within a reasonable commuting distance.

For families considering Whippoorwill Hollow Charlottesville real estate, the area’s proximity to excellent schools adds significant value. Albemarle County’s public school system is highly regarded, and several prestigious private schools are located nearby.

The neighborhood’s quiet streets and spacious lots provide an ideal environment for raising children while maintaining the sophisticated atmosphere that appeals to empty nesters and young professionals alike.

The recreational opportunities available to Whippoorwill Hollow residents extend far beyond their individual properties. The nearby Blue Ridge Mountains offer hiking, skiing, and other outdoor activities, while the region’s numerous vineyards, historic sites, and cultural attractions provide endless options for weekend exploration.

Investment Potential and Market Trends

The long-term investment potential of Whippoorwill Hollow luxury homes Charlottesville remains strong due to several key factors. The neighborhood’s established character, limited development potential, and desirable location create natural barriers to oversupply that help protect property values. The quality of construction and the generous lot sizes typical of the area ensure that homes retain their appeal over time.

Recent market analysis shows that properties in exclusive neighborhoods like Whippoorwill Hollow tend to outperform the broader real estate market during both rising and declining cycles. The unique characteristics that make these homes desirable, privacy, acreage, quality construction, and prestigious location—continue to appeal to buyers regardless of broader economic conditions.

The current selection of Whippoorwill Hollow Charlottesville homes for sale includes properties at various price points, allowing buyers with different budgets to find opportunities within this prestigious community.

From homes requiring some updating that offer excellent value for renovation-minded buyers to move-in-ready properties that showcase the neighborhood’s full potential, the current inventory provides options for diverse preferences and investment strategies.

Working with a Whippoorwill Hollow Neighborhood Specialist

My extensive experience with homes for sale in Whippoorwill Hollow provides clients with insights that generic real estate agents simply cannot offer. I understand the subtle differences between properties, the neighborhood’s development history, and the factors that influence value in this unique market. This specialized knowledge allows me to help buyers identify the best opportunities and negotiate effectively in competitive situations.

The process of purchasing Whippoorwill Hollow Charlottesville real estate often involves considerations that don’t apply to more typical residential transactions. Issues such as well and septic systems, easements, and zoning regulations require careful attention and expert guidance.

My relationships with local contractors, inspectors, and other professionals ensure that clients receive comprehensive support throughout the buying process.

For sellers considering listing their Whippoorwill Hollow Charlottesville homes for sale, my marketing approach emphasizes the unique characteristics that set these homes apart from ordinary real estate. Professional photography, detailed property descriptions, and targeted marketing to qualified buyers help ensure that Whippoorwill Hollow Charlottesville homes for sale receive the attention they deserve from serious buyers.

The Future of Whippoorwill Hollow Charlottesville Real Estate

The future prospects for Whippoorwill Hollow Charlottesville homes for sale remain exceptionally bright. The neighborhood’s established character, combined with Charlottesville’s continued growth and development, creates a favorable environment for long-term property appreciation.

The limited supply of similar properties in the area ensures that Whippoorwill Hollow will continue to attract buyers seeking the unique combination of privacy, luxury, and convenience that defines this exceptional community.

Whether you’re seeking a primary residence, a weekend retreat, or an investment property, the current selection of Whippoorwill Hollow Charlottesville homes for sale offers opportunities that are increasingly rare in today’s real estate market. The combination of architectural quality, natural beauty, and prestigious location makes these properties not just homes, but legacies that can be enjoyed for generations.

For those ready to explore the exceptional opportunities available in this remarkable neighborhood, I invite you to contact me at 434-327-2999 to discuss the current Whippoorwill Hollow Charlottesville homes for sale and discover how this special community might be the perfect setting for your next chapter.

Toby Beavers has been helping discerning buyers discover exceptional properties in Charlottesville’s most desirable neighborhoods for 22 years.

Contact Toby to explore current opportunities in Whippoorwill Hollow and other prestigious Ivy VA real estate.

Toby Beavers, an Ivy VA realtor since 2003, may be reached by text or phone at 434-327-2999

toby beavers, Ivy VA realtor since 2003