Estates & Multi Generation Homes in Western North Carolina

MLS Number 1002690

• Residential
• Bedrooms 4
• Bathroom 4
• Acreage 1.05

Introducing a rare opportunity to own a custom mountain retreat by award-winning builder Loudermilk Custom Homes in the exclusive Saratay Falls community of Cashiers, North Carolina. Ideally situated on 2.29 private acres along Saratay Falls Drive, this thoughtfully designed residence blends refined craftsmanship with timeless mountain architecture. Designed for both comfort and sophistication, the home features 4 bedrooms, 3 full baths, and a powder room. The main-level owner's suite provides convenience and privacy, while expansive vaulted ceilings enhance the open-concept living spaces. The grand room flows seamlessly into the kitchen and breakfast area, all oriented toward covered outdoor living spaces-perfect for entertaining or relaxing in the cool mountain air. The spacious lower level offers three additional bedrooms along with a recreation room and flexible bonus space, ideal for guests, multi-generational living, or a private retreat. Architectural details include a welcoming covered entry, natural materials, layered rooflines, and a detached two-car garage connected by a breezeway-hallmarks of elevated mountain design. Buyers will have the opportunity to personalize interior selections in collaboration with Loudermilk's renowned design team, creating a home that reflects their individual vision. Saratay Falls is an intimate, upscale mountain enclave offering privacy, estate-sized homesites, and a serene natural setting just minutes from the heart of downtown Cashiers. Community amenities include a stunning boardwalk with viewing platforms overlooking the impressive Saratay Falls along Fowler Creek, a shared open green space with firepit, and gated access-all within minutes of fine dining, boutique shopping, golf, hiking, and waterfalls. Built by Loudermilk Custom Homes, an award-winning luxury builder known for exceptional craftsmanship and meticulous attention to detail, this residence represents a rare combination of location, design, and pedigree. A premier opportunity to build your legacy mountain home in one of Cashiers' most desirable new communities.

Listed by John Muir of Berkshire Hathaway HomeServices Meadows Mountain Realty - HF

MLS Number 103319

• Residential
• Bedrooms 3
• Bathroom 4
• Acreage 0.92

LOCATION! This Highlands landmark is one of the last great, walk-to-town parcels. Zoned B-4 (light commercial) and sits on .92 acre. Renovate or start over- anything can be duplicated- EXCEPT the location. The first time on the market and being offered AS-IS. The main level has wood floors and is paneled with clear Chestnut as the home was built just as the Chestnut blight came through town. The main level has a small kitchenette, storage, full bath and 4 rooms (The former living area is partitioned to allow for the reception area.) The attic is floored in, runs the entire length of the house and has great storage. This is a property full of memories for many local people. In the 1920s, this property was a 9-hole golf course as part of the Hall House property. Built in 1931 with chestnut paneling on the main level, this property has been a personal residence, home occupation, B&B, and is now zoned B-4. This property has been in the same family since the town was incorporated, and once took up the whole block. This is the only parcel left and contains .92 ac+/-. The home of Margaret and Tudor Hall and their extended family lived here from 1931 until the early 1990s when The Chambers Agency moved their real estate and vacation rentals office. Tudor and Margaret had a real estate office in town and were charter members of the Highlands Board of Realtors in 1956. In the mid-1990s, the garage was renovated into a one-bedroom/one-bath apartment and has been partially renovated. Prior to 1992, Mrs. Hall ran a boutique B&B, The Hall House, and the rooms upstairs that had been her children's bedrooms became weekend spots for tourists, and later became real estate offices for The Chambers Agency. In 2013, the four upper-level rooms were converted into two one-bedroom/one-bath apartments for workforce housing.

Listed by Jeannie Chambers of Chambers Realty & Vacation Rentals (8285263717)

MLS Number 1003463

• Residential
• Bedrooms 5
• Bathroom 5
• Acreage 3.01

Positioned just on the Glenville edge of Cashiers at 3,700 feet of elevation and only a few minutes' drive to the heart of town, this lovingly maintained mountain retreat in Josh's Trail offers the rare combination of privacy, usable land, and convenience. Custom-designed, owned, and loved by the same family since its creation, the five-bedroom, four-and-a-half-bathroom home is set on three gently rolling acres where a winding stream, native landscaping, and thoughtfully cleared outdoor spaces create an inviting setting for gathering, relaxing, and enjoying the natural beauty of the Plateau. The nearly level backyard - uncommon in a mountain setting - is designed for enjoying life outdoors, with mature native flora, expansive lawn space for recreation, a stone patio, and a fire pit tucked alongside the stream where evenings are best spent under cool mountain skies. Upper and lower rear decks, together with a screened porch connecting the two-car garage to the kitchen and main living area, create seamless indoor-outdoor living spaces built for every season. Inside, the open-concept main level centers around a grand stone, wood-burning fireplace that anchors the living and dining spaces with classic mountain character. Vaulted gathering spaces and generous windows invite the outdoors in, while the primary suite offers direct access to the screened porch and convenient main-level living alongside two additional bedrooms. Designed with hosting in mind, the lower level expands the living space with a spacious recreation room centered around a second fireplace, plus a kitchenette with bar seating for game days, holidays, and weekend guests. Two separate bunk rooms, a bonus room, laundry area, and two full bathrooms create exceptional flexibility for large gatherings, multi-generational living, or overflow accommodations. Located minutes from the shopping, dining, and community events of Cashiers, this property also provides convenient access to the boating, paddling, and recreation opportunities of Lake Glenville, extensive hiking trails, and the boutiques, restaurants, and cultural offerings of nearby Highlands. Whether envisioned as a full-time residence, mountain getaway, or legacy property to be enjoyed for years to come, this home delivers the setting, space, and mountain lifestyle buyers seek, with rental opportunities providing added flexibility for owners.

Listed by Daniel Allen of Silver Creek Real Estate Group,Inc.

MLS Number 1002529

• Residential
• Bedrooms 3
• Bathroom 6
• Acreage 2.82

Perched at a breathtaking 4,300 feet in elevation, this stunning mountain home in Glenridge offers sweeping panoramic views over miles of untouched national forest. Nestled beside the vibrant Chinquapin community and bordering the serene Panthertown National Forest, Glenridge is a small, private estate enclave just 8 easy miles from the Cashiers Crossroads - the perfect blend of privacy and convenience. This impeccably maintained, turnkey home is the epitome of mountain elegance, combining cozy cottage charm with high-end finishes and designer furnishings throughout. The inviting carport leads to a spacious mudroom with abundant storage and a seamless entry to the kitchen - ideal for storing hiking boots and easily unloading groceries. One of the standout features is the expansive three-season screened porch, which functions as a second living room. Complete with a wood-burning fireplace and custom screens, it's a warm and inviting space for year-round enjoyment. Just outside, an open porch leads to a beautifully landscaped and hardscaped fire pit area - perfect for gathering under the stars. All three bedrooms offer ensuite full bathrooms, and there's an additional private bonus room with its own bathroom - ideal for flexible use. Every finish throughout the home is custom, high-quality, and thoughtfully curated. Situated on just under three lush, beautifully landscaped acres with a flat driveway and easy access, the property is as practical as it is picturesque. Peaceful, private, and perched "on top of the world," this mountain sanctuary is truly a must-see to appreciate its beauty and craftsmanship.

Listed by Julia Banner of Silver Creek Real Estate Group,Inc.

MLS Number 1002677

• Residential
• Bedrooms 5
• Bathroom 6
• Acreage 85.67

Scenic, Serene, and Sustainable! Tucked away in the Highland Gap community just minutes from Dillard Road, this extraordinary log estate offers panoramic mountain views, unmatched privacy, and purposeful design. Built in 2001 by renowned Lupoli Construction, the five-bedroom residence showcases authentic log construction with soaring vaulted ceilings, rich natural wood interiors, and a dramatic floor-to-ceiling stone fireplace that anchors the great room - a true gathering place for family and friends. Designed with sustainability in mind, the property features a fully integrated solar power system while still offering access to traditional electricity, creating an impressive balance of self-sufficiency and modern convenience. Beyond the main residence, the land tells its own story. Two additional homesites have development potential, creating the opportunity for a future family compound or multi-generational retreat. With 70+ acres preserved in a land trust, your views, privacy, and peace of mind remain protected for generations to come. Surrounded by North Carolina wilderness yet conveniently located near both Highlands and Clayton, you'll enjoy access to fine dining, boutique shopping, outdoor recreation, country clubs, and excellent schools - all within easy reach. A remarkable combination of privacy, scale, craftsmanship, and conservation - this is mountain living at its finest!

Listed by Patrick Gleeson and Jessica Haberkern of Christie's International Real Estate Highlands-Cashiers

MLS Number 1003788

• Residential
• Bedrooms 4
• Bathroom 5
• Acreage 0.94

Welcome to 743 Hawk Mountain Road, a beautifully crafted brand-new UNDER CONSTRUCTION mountain home in Lake Toxaway Estates, designed to blend modern comfort with timeless style. Situated on 0.95 acres, this thoughtfully designed 4-bedroom, 4.5-bath residence offers 3,500+/- square feet of living space, wonderful lake and mountain views, exceptional craftsmanship, and an ideal location just minutes from the area's premier amenities. The home's open-concept living spaces are filled with natural light and showcase high-end finishes throughout, creating an inviting atmosphere for everyday living and effortless entertaining. With two levels of living, there is plenty of room for family and guests to gather while also providing private spaces to relax and unwind. Step outside to enjoy multiple outdoor living areas, perfect for morning coffee overlooking the mountains, afternoon gatherings, or cozy evenings by the fire while enjoying the cool mountain air. A two-car garage with room to park your golf cart, along with abundant storage, provides the convenience and functionality every mountain home needs. Ideally located with easy access to Highway 64, this home is just minutes from Lake Toxaway Country Club and the Lake Toxaway Marina, offering quick access to championship golf, dining, boating, and all the recreational opportunities that make Lake Toxaway one of Western North Carolina's most sought-after destinations. Whether you're looking for a full-time residence or a mountain retreat, 743 Hawk Mountain Road offers the perfect combination of luxury, comfort, and convenience in an exceptional Lake Toxaway setting. All pictures are conceptual renderings and will be updated when home is further along. *Home is under construction please use care when walking through job site and house.*

Listed by Ross Hyett of Lake Toxaway Company

MLS Number 1003200

• Residential
• Bedrooms 4
• Bathroom 7
• Acreage 1.03

Nestled on a private 1.03-acre wooded lot in an intimate gated community, this distinguished mountain estate offers sophisticated living just minutes from the heart of downtown Highlands. With soaring ten-foot ceilings throughout, spacious elegance welcomes you to every corner. The grand great room centers around a commanding masonry fireplace, creating an inviting setting for lively gatherings, spirited game days, or relaxed fireside evenings. The gourmet kitchen stands as a culinary masterpiece-featuring granite counters, a expansive island, top-tier built-in appliances including a propane cooktop, and ample space for a master chef and entertaining entourage. Step outside to the generous decks for al fresco dining, grilling, and breathtaking mountain views that define the Highlands experience. This well appointed residence boasts a luxurious primary suite on the main level, a sophisticated office for two, and a practical mudroom. A versatile bonus suite with full bath sits above the garage. The terrace level offers your guests a second expansive great room featuring a stylish wet bar, additional deck access with mountain vistas, three more bedrooms, three full baths, a bonus room, second laundry, and another two-car garage-delivering a total of four garage spaces plus abundant parking for the discerning collector. Thoughtful details abound: hardwood and terrazzo flooring, crown molding, chandeliers, dual primary closets, multiple living zones, and high-end finishes throughout. Outdoor highlights include a built-in grill and sweeping mountain views across the gently sloped, wooded grounds. Perfectly situated for privacy and convenience, this exceptional home in Highlands Point offers the rare combination of generous scale, luxury craftsmanship, and effortless access to the cultural charm, fine dining, and natural beauty of Highlands.

Listed by Dinah Davis of Christie's International Real Estate Highlands-Cashiers

MLS Number 1003921

• Residential
• Bedrooms 3
• Bathroom 4
• Acreage 2.23

Welcome to 72 Moonlight Lane, an extraordinary mountain sanctuary where timeless architecture, exceptional outdoor living, and more than two decades of thoughtfully cultivated landscaping create one of Highlands' most captivating properties. Set on 2.23 acres across two parcels, the estate features a breathtaking landscape designed and refined by renowned local landscape architect Jimmy Tate. Meandering paths wind beneath mature native trees and through vibrant gardens, while more than 300 feet of creek frontage flows through the property, feeding tranquil water features and a picturesque pond. The result is a private, serene setting with an exceptional connection to nature. The main residence blends timeless mountain character with warm, inviting spaces for gathering and entertaining. A dedicated office and separate TV room provide plenty of space for family and guests to relax and spread out. Downstairs, a versatile bonus room offers additional sleeping accommodations and is currently used as a fourth bedroom. The showpiece is the spectacular porch room. An indoor-outdoor living space surrounded by the gardens, creek, and pond. Filled with natural light, it is truly the heart of the home and an unforgettable setting for dining, entertaining, or relaxing to the sounds of the water. Elevated among the trees is the professionally constructed luxury treehouse, featuring sweeping views, a fireplace, wet bar, bathroom, dining area, and lounge. Whether entertaining friends or enjoying a quiet afternoon, it may be the most magical destination on the property. Blueprints are available to expand it into a full one-bedroom, one-bath retreat. The estate consists of two parcels-1.01 acres and 1.22 acres. The 1.01-acre parcel has access to available water and sewer connections, offering possibilities for an additional residence, expanded gardens, or potential future sale of the lot separately. 72 Moonlight Lane is a true Highlands legacy property, reflecting years of thoughtful care and stewardship. From its spectacular grounds and unforgettable porch room to its remarkable treehouse and flowing creek, every corner offers something special. The pictures only begin to tell the story. This property truly must be experienced to be fully appreciated. New flooring downstairs 2026 New roof & exterior paint 2025 Car port completed in 2024

Listed by Danny Gato and Andy Gato of Country Club Properties

MLS Number 1004074

• Residential
• Bedrooms 4
• Bathroom 4
• Acreage 1.59

Discover unparalleled mountain luxury in Holly Berry Estates, a serene 430-acre private community nestled at the base of Whiteside Mountain in the heart of North Carolina's Blue Ridge. This exceptional 4-bedroom, 4-bath home is perfectly positioned between the charming towns of Highlands and Cashiers, offering the ultimate blend of privacy, convenience, and authentic mountain living. The main level welcomes you with a premium open-concept design, showcasing rich Brazilian Cherry hardwood floors that flow throughout the expansive living spaces. The chef's kitchen impresses with beautiful granite countertops, while the spacious living area features a dramatic stone wood-burning fireplace beneath soaring vaulted ceilings accented with warm wooden beams. This level includes two primary suites for ultimate convenience and a versatile bonus room-ideal for a home office, den, or additional sleeping quarters. Step outside to the generous covered deck, where you can savor sweeping mountain and lake views of pristine Holly Berry Lake. Whether enjoying your morning coffee or hosting evening gatherings, this deck is the perfect vantage point to take in the beauty of the Blue Ridge Mountains. The lower level expands your living options with additional bonus rooms, a second full living room, a second kitchen, and a large recreation room-perfect for guests, multigenerational living, or entertaining. Additional highlights include a 2-car garage on the main level, plus an extra garage and shop on the lower level, providing ample space to store your UTV or side-by-side. The home sits on a private 1.59-acre lot with room to roam and enjoy cool mountain summers, plus access to your very own private dock on Holly Berry Lake. The property features a 22kW Generac generator, ensuring year-round comfort and peace of mind. Holly Berry Estates offers two private lakes ideal for swimming, fishing, canoeing, and picnicking, along with scenic hiking and biking trails. These trails wind through the community and connect to adjacent Nantahala National Forest lands, offering stunning views of Whiteside Mountain and access to its breathtaking rock face.

Listed by Collin Taylor of RE/MAX Summit Properties

MLS Number 1002696

• Residential
• Bedrooms 6
• Bathroom 7
• Acreage 4.45

Perfectly positioned in one of the Plateau's most established neighborhoods between Highlands and less than three miles to Cashiers, this private 4.45-acre estate presents a rare opportunity for a legacy family compound or multi-family vacation rental investment. Spectacular, unobstructed year-round views of Whiteside Mountain set the tone, with an oversized open deck designed to capture the iconic backdrop and cool mountain evenings. The main residence blends comfort and functionality. A covered breezeway flanks the attached 2 car garage and leads to a formal foyer and inviting living spaces with beautiful hardwood floors. The spacious kitchen offers an island, breakfast area, and access to a formal dining room overlooking the mountains. The living room features a brick fireplace with gas logs (can be wood-burning), while a cozy den or library with a wood stove provides a quiet retreat. A butler's pantry and powder room enhance the layout. Three en-suite bedrooms are located on the main level, including a generous primary suite with a cathedral ceiling, alcove sitting area, double vanities, walk-in tile shower, and its own washer and dryer, allowing for convenient one-level living. Flexibility defines this property. A two-bedroom, one-bath apartment with full kitchen, living room, and stack washer and dryer is located above a detached two-car garage, offering privacy from the main home. The lower level of the main home includes another fully equipped apartment accessible from the interior (with privacy door) or exterior entrance, complete with kitchen, washer and dryer, bedroom, bonus room, full bath, and a game room with a ping pong table. A separate studio apartment with exterior entrance features a kitchenette, full bath, and combined living/sleeping area-ideal for guests or rental income. Additional improvements include a detached two-car garage - perfect for a workshop- and a separate two-car carport with an additional storage room. A paved driveway with level entrance adds ease of access. Extensive storage, including a cedar closet, two Rinnai tankless water heaters, two central vacuum systems, three septic systems (no records on file with Jackson County), owned propane tanks, private well, and gas furnace support the estate's scale and versatility. With privacy, acreage, infrastructure, and one of the Plateau's most iconic views, this exceptional property offers rare potential as a generational retreat, income-producing investment, or both!

Listed by Lesley Howard of Landmark Realty Group - Frank Allen,Cashiers