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$495,000
4 Beds ⋅ 2 Baths ⋅ 4391674 MLS ⋅ ACTIVE Status
Character, charm, and opportunity come together at this beautifully maintained 1928 brick Tudor in the heart of Hendersonville. Just moments from downtown shops, restaurants, breweries, Hendersonville High School, and Pardee Hospital, this unique property offers the flexibility to fit your lifestyle and your future plans. Currently configured as both a residence and professional office, this dual-zoned property (Residential and MIC) opens the door to a variety of possibilities. Whether you're dreaming of a charming downtown home, a live work setup, or a professional office space with character, this property is ready to deliver. Inside, you'll find 1,769 square feet filled with timeless details, including original hardwood floors, abundant natural light, and classic Tudor architecture. The remodeled kitchen blends historic charm with modern convenience, featuring updated cabinetry, countertops, and stainless steel appliances. The flexible floor plan includes four bedrooms and two full bathrooms, with two bedrooms and a bath on the main level and a spacious primary suite, additional bedroom, and full bath upstairs. Enjoy the convenience of on site parking, a full basement for storage, and a low maintenance city lot. Sip your morning coffee on the porch, stroll downtown for dinner, or take advantage of the property's exceptional location near some of Hendersonville's most desirable destinations. Properties with this much character, versatility, and downtown convenience don't come along often. Come see what makes 831 Oakland Street such a special find.

831 Oakland Street, Hendersonville

Listing courtesy of Keller Williams Professionals. cres@yonderre.com
$5,900,000
9 Beds ⋅ 12 Baths ⋅ 4366582 MLS ⋅ ACTIVE Status
Teneriffe is one of Hendersonville’s extraordinary historic properties, an estate where history, architecture and opportunity converge in a rare and remarkable way. Originally constructed in 1855 as a Tudor Revival residence, the home was reimagined in 1903 by Richard Sharp Smith, supervising architect of the Biltmore Estate. With landscape input from the Olmsted firm, the property was shaped to complement its architectural beauty, establishing a setting steeped in provenance and timeless elegance. Set on 11.73 acres, the approach to Teneriffe winds along a leaf-canopied drive that opens to gardens, water features and the stately brick residence. The estate unfolds across rolling acreage, where pastures, walking trails and tranquil outdoor spaces form an enchanting natural setting. A historic barn recalls its agrarian heritage, while a separate log cabin offers endless possibilities for restoration, reinvention or flexible guest accommodations. Zoned for residential and commercial use, Teneriffe offers rare versatility. With a rich history as an active bed-and-breakfast, the property presents exceptional potential for a boutique hospitality venture, private retreat, event venue or simply as a legacy private residence. An additional 9.43-acre parcel (PIN 9567-20-4498) is also available, expanding the possibilities even further. The main residence is a showcase of grandeur and intimacy. A sweeping wraparound veranda welcomes you into a grand foyer, where light, scale and craftsmanship set the tone. Expansive entertaining spaces on the main level invite gracious gatherings and quiet reflection, with period details carefully preserved to honor the home’s heritage. The private primary wing is a sanctuary, complete with an executive home office, spa and the promise of seclusion. Two additional levels provide generous accommodations with multiple bedrooms and living spaces, offering flexibility for family, guests or creative repurposing. Each room reflects a chapter of the estate’s storied past yet stands ready to be reimagined for the future. Teneriffe is more than a property, it is a legacy. Rarely does such a distinguished estate, with architectural pedigree, historic significance and versatile potential, come to market. For those who value heritage while envisioning the future, Teneriffe offers an unparalleled opportunity to steward a landmark property and create a new chapter in its remarkable story.

2531 Little River Road, Hendersonville

Listing courtesy of Premier Sotheby’s International Realty. 828-279-3980
$1,295,000
4 Beds ⋅ 5 Baths ⋅ 4359040 MLS ⋅ ACTIVE Status
Welcome to the perfect spot for unparalleled in-town living at its finest. Located in the heart of Downtown Sylva, this meticulously restored 1939 French provincial home offers breathtaking views of the surrounding mountains and charming Sylva. Designed by the celebrated architect Charles N. Parker of Asheville's iconic Grove Arcade, this home is a rare opportunity to own a piece of history. Relax in the epic four-season outdoor living space, perfect for entertaining or unwinding, complete with living and dining spaces, a cozy fireplace, TV, grill station, and hot tub. The property also boasts a heated 4-car garage, 500 SF workshop, heated sidewalks, laundry on two levels, and a full terrace level with media room, home gym, and ample storage. Best of all, this exquisite home is just steps away from Sylva’s vibrant shops, restaurants, and breweries. Whether you're seeking an enchanting second home or a unique local residence steeped in history, this gem offers appeal and sophistication.

117 Jackson Street, Sylva

Listing courtesy of Howard Hanna Beverly-Hanks Biltmore Avenue. mills.coin@allentate.com

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