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$1,550,000
5 Beds 8 Baths 10016793 MLS CLOSED Status
All brick executive home with pristine 3.25 acre rolling estate nestled in Orange County. Spanning over 8,000 sqft this spacious home exudes elegance & all-inclusive living! INviting front porch welcomes your to a grand transitional floor plan with 2-story foyer and dual staircase welcomes you to a sophisticated main floorplan that leads to family room w/ soaring ceiling and fireplace. Off the foyer is the formal living room that leads to the large sunroom with plenty of natural lights. Plenty of room to host dinners at the formal dining room that leads to the massive breakfast area (can fit a 8 seater table!) and the gourmet kitchen w/ huge island. It has Yorktowne cabinetry & Monogram appliance suite, large pantry & built-in refirgerator. Off the ktichen is the screened porch, outdoor deck for outdoor grilling and large patio overlooking the vast private yard! Also on the 1st flr is the large office/study with built in bookcases and has full bath, perfect for a guest suite. Laundry room with built ins, 3 car garage with TESLA charging connection is also ont hemain level. Primary bedroom is on the 2nd flr & has sitting area.Primary bath has 2 walk in closets, large roman tub and dual vanity sinks. There are additional 4 bedrooms on the 2nd floor, all with private baths inside each bedroom. The walkout and daylight basement is an entertainment haven. It has recreation room, theater room complete with projector and surround sound, a kitchen, dining area and a full bath. Plenty of storage room as well. A whole houseback-up generator, Tesla wall charger and boundless options for future in-ground pool are just a few amenities this home has to offer. New roof and gutters. Serene location yet minutes to UNC, Wegmans & all conveniences.

101 Whirlaway Ln, Chapel Hill

$1,750,000
5 Beds 7 Baths 10083773 MLS CLOSED Status
Timeless Elegance in Triple Crown Estates A Masterpiece of Refined Living - 9,067 Square Feet of Uncompromising Luxury in the coveted Chapel Hill- Carrboro school system. Nestled on just over three meticulously manicured acres within the prestigious Triple Crown Estates, this magnificent all-brick manor stands as a testament to extraordinary craftsmanship and discerning taste. The residence commands attention with its intelligent yet cozy design, soaring 10-foot ceilings, exquisite architectural moldings, and sumptuous finishes that marry elegance with warmth throughout its 9,068 square feet of living space. The estate's grounds present a serene sanctuary, where a covered deck with graceful arbor and an expansive back patio illuminated by extensive landscape lighting overlook a verdant landscape. The park-like setting features countless specimen trees and shrubbery representing more than 30 botanical varieties, creating a seamless harmony between architectural grandeur and natural beauty. Upon crossing the threshold, guests are welcomed by a breathtaking double-height foyer with a sweeping dual staircase adorned with detailed wood and iron balustrades. The main level unfolds where formal living and dining areas flow effortlessly into an expansive family gathering space with convenient access to both the rear stairwell and outdoor entertaining areas. A secluded main-level guest suite offers the versatility of a secondary primary retreat, while a stately office showcases bespoke built-in cabinetry. The culinary heart of the home reveals GE Monogram and Miele appliances, complemented by an impressive center island with bar seating for four. Level 5 custom cabinetry with intuitive pull-out storage, a generous breakfast area, and a dedicated walk-in pantry define this gourmet kitchen designed for both everyday living and sophisticated entertaining. The upper level houses a magnificent owner's retreat featuring a private sitting room, trio of walk-in closets (one with integrated wall safe), and versatile flex space ideal for a nursery, second office, art studio, or meditation sanctuary. The lavish primary bath offers dual vanities, separate water closets, a therapeutic spa tub, and an oversized shower with dual fixtures. Three additional ensuite bedrooms with high end finishes and a generous bonus room which can function as a playroom, complete this level. Descending to the 3,000 square foot lower level reveals entertainment spaces of distinction—a game room with fireplace accommodating billiards, cards, and foosball; a theater room with luxurious theater-style seating for twelve; a fitness center with adjoining sauna; and a full bath. Practical considerations include a workshop/utility area and a security command center with interior and exterior monitoring systems. The residence's infrastructure reflects an unwavering commitment to excellence: whole house spray foam insulation, comprehensive drainage with dual sump pumps, Carrier furnaces, Rheem air conditioning, a Honeywell Total Dry whole-house dehumidification system, and programmable Nest climate controls. In addition, the house has been equipped with a 22kW Generac generator, ethernet cabling, and a ready-to-use Ubiquiti Unifi WiFi system. The oversized garage features an 8,000 lb. car lift expanding parking capacity to four vehicles, pristine epoxy flooring, custom storage solutions, and an electric vehicle charging station is installed adjacent to the garage at the top of the exposed aggregate concrete driveway. . This rare offering masterfully balances grandeur with intimacy, luxury with functionality—an ideal setting for multi-generational living and sophisticated entertaining. A legacy estate awaiting its next steward.

212 Whirlaway Ln, Chapel Hill

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Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .

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