Highlands Single Family Listings

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Lt 105 Riverwalk Drive Highlands NC 28741

Highlands, NCLt 105 Riverwalk Drive

Price$2,850,000

Est. Mortgage: $/month

MLS Number 1003037

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acreage 1.12

Exceptional riverfront living opportunity in the highly sought-after Riverwalk community in Highlands, NC. This offering is a thoughtfully designed lot/home package positioned along the gentle waters of the Cullasaja River, providing a rare combination of privacy, natural beauty, and close proximity to downtown Highlands. The proposed residence features a well-designed floor plan with a main-level primary suite, expansive great room, and seamless indoor-outdoor living anchored by a large screened porch and outdoor entertaining areas. The layout also includes additional guest bedrooms, office space, and multiple gathering areas, creating an ideal setting for both full-time living and mountain retreat use. High-end finishes and selections elevate the home, including a premium Wolf and Sub-Zero appliance package, custom cabinetry, and thoughtfully curated materials throughout. Outdoor living is enhanced with infrared heaters on the porch, allowing for year-round enjoyment, while multiple fireplaces provide warmth and ambiance both inside and out. Set within Riverwalk, a boutique community known for its walkability and serene riverfront setting, this property offers direct access to the Cullasaja River and a peaceful mountain environment just minutes from the shops, dining, and amenities of Highlands.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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152 S Fairway Cottage Lane Highlands NC 28741
Pending

MLS Number 1002295

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.32

Charming Craftsman Home in Cullasaja Club with Main-Level Living. Located on the 10th Fairway with an expansive view of the golf course. Located inside the prestigious, gated Cullasaja Club, this beautifully designed craftsman-style home offers effortless main-level living and the rare opportunity to expand with an unfinished, plumbed lower level. Surrounded by mature trees and cool mountain breezes, this residence captures the relaxed elegance and outdoor lifestyle that define the Highlands-Cashiers Plateau. The main level features three comfortable bedrooms, including a welcoming primary suite, along with spacious living areas highlighted by warm finishes and classic architectural details. Large windows bring in natural light and views of the golf course from both the Livingroom/great room, outdoor deck or the screened in porch with fireplace, creating a peaceful mountain retreat. The unfinished basement provides outstanding potential-already plumbed for an additional bedroom and full bath, allowing you to customize the space for guests, hobbies, storage, or future expansion. Living in Cullasaja Club offers an exceptional lifestyle with access to world-class amenities (membership by invitation). The community features an Arnold Palmer golf course, clubhouse dining, tennis and pickleball, a fitness center, heated pool, and a warm, welcoming social environment loved by full-time and seasonal residents alike. Just minutes from the shopping, dining, and cultural offerings of Highlands, this home combines convenience with the tranquility of private mountain living. Enjoy cool summers, vibrant autumn colors, and the unique charm of one of the plateau's most sought-after clubs. A perfect blend of quality, comfort, and lifestyle - with room to grow. Let your mountain life??????????? begin.

Listed by Douglas Treadwell of Mountain Life Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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354 Flat Mountain Estates Road Highlands NC 28741

MLS Number 1002567

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.05

Step outside to the fully screened-in porch, complete with an outdoor kitchen which includes: a gas grill, a big green egg and a gas fire-pit; the perfect setting for sipping your morning coffee or for long evenings under the stars. Imagine sharing stories with your children or grandchildren, laughing around the fire-pit, and rediscovering the kind of simple fun that you cherished as a child and long for again as an adult. Set on a little over one acre of private, peaceful property with breathtaking long-range views. Designed with vaulted ceilings, 4 spacious bedrooms and 4 full baths, the layout blends light, comfort and elegance. At the heart of this home, is a REAL chef's kitchen, beautifully-appointed with premium Thermador appliances and wine refrigerator. Whether hosting holiday celebrations or preparing a quiet Sunday dinner, this kitchen provides you with culinary inspiration. The main level features a primary suite where the bathroom is complete with claw-foot tub and zero-entry shower. A second bedroom and full bath, are also on the main level-ideal for guests or multi-generational living. Custom metal railings lead you to the lower level. Designed for entertaining and unwinding. The lower level features: a pool table, wet bar, wine refrigerator, a movie room with a huge tv and surround sound, a microwave oven for cinematic nights at home. Plus two additional bedrooms and baths - all offering comfort and space for family and friends. Every inch of this home invites connection - to nature, to family and to friends. This beautiful property provides a nostalgic, welcoming spot to be handed down through generations. Come build a life that feels more grounded. Welcome to a home, where time slows down.

Listed by Andrea Gabbard of Highlands Sotheby's International Realty - DT

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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299 Oak Street Highlands NC 28741

Highlands, NC299 Oak Street, Unit 7

Price$2,700,000

Est. Mortgage: $/month

Active With Contract

MLS Number 1001729

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Acreage 0.14

In the heart of Downtown Highlands and tucked conveniently behind Main Street stands Eight on Oak, now under construction; An exclusive collection of eight luxury homes, Eight on Oak offers you the opportunity for Elevated Mountain Living with all the bells and whistles. Eight on Oak is where ease of living meets understated charm. Each residence is a blend timeless craftsmanship and creative spaces with a mountain-modern touch. Envision10-foot ceilings with exposed wood beams, designer kitchens, hardwood floors, ease of flow to indoor-outdoor spaces with private screened porches and stone fireplaces. With 3 bedrooms, 3.5 baths, two-car garages, HOA-maintained courtyards, and optional elevators, these homes are designed for lock-and-leave ease and/or full-time residency, take your pick. Your backyard is the splendor and scenic views of the Highlands Greenway and the Mill Creek watershed. Lifestyle is enhanced by being a short stroll to top-notch shops & boutiques, restaurants, and the cultural assets that define Highlands. Eight on Oak is where nature & neighborhood live in perfect balance with community & relationships. Eight on Oak…This is where you belong! PRICING NOTE: FINAL DELIVERED PRICE IS BASED UPON FINISHES SELECTED AND CUSTOMIZATION OF EACH UNIT. EXACT FINAL PRICING WILL BE PRESENTED TO BUYERS PRIOR TO CONTRACT.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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299 Oak Street Highlands NC 28741

Highlands, NC299 Oak Street, Unit 8

Price$2,700,000

Est. Mortgage: $/month

Pending

MLS Number 1001730

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Acreage 0.14

In the heart of Downtown Highlands and tucked conveniently behind Main Street stands Eight on Oak, now under construction; An exclusive collection of eight luxury homes, Eight on Oak offers you the opportunity for Elevated Mountain Living with all the bells and whistles. Eight on Oak is where ease of living meets understated charm. Each residence is a blend timeless craftsmanship and creative spaces with a mountain-modern touch. Envision10-foot ceilings with exposed wood beams, designer kitchens, hardwood floors, ease of flow to indoor-outdoor spaces with private screened porches and stone fireplaces. With 3 bedrooms, 3.5 baths, two-car garages, HOA-maintained courtyards, and optional elevators, these homes are designed for lock-and-leave ease and/or full-time residency, take your pick. Your backyard is the splendor and scenic views of the Highlands Greenway and the Mill Creek watershed. Lifestyle is enhanced by being a short stroll to top-notch shops & boutiques, restaurants, and the cultural assets that define Highlands. Eight on Oak is where nature & neighborhood live in perfect balance with community & relationships. Eight on Oak…This is where you belong! PRICING NOTE: FINAL DELIVERED PRICE IS BASED UPON FINISHES SELECTED AND CUSTOMIZATION OF EACH UNIT. EXACT FINAL PRICING WILL BE PRESENTED TO BUYERS PRIOR TO CONTRACT.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1135 Big Bear Pen Road Highlands NC 28741

Highlands, NC1135 Big Bear Pen Road

Price$2,700,000

Est. Mortgage: $/month

MLS Number 1002637

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.92

High atop the tranquil slopes of Highlands' prestigious Big Bear Pen Mountain lies an enchanting retreat at 1135 Big Bear Pen Road. Imagine waking each morning to the gentle whispers of mountain breezes drifting through lush, mature trees, the early sun painting gold across rolling hills and distant peaks. Recently transformed by a major renovation, this lovingly maintained home gracefully blends rustic elegance with sophisticated comfort. Rich wood accents create a warm, inviting atmosphere throughout, while expansive windows frame breathtaking vistas that evolve beautifully with each passing season. The generous living spaces, crowned by soaring ceilings, invite gatherings filled with laughter around the stone fireplace or peaceful afternoons enjoying the serenity from the spacious decks. Cooking becomes a delight in the thoughtfully designed kitchen, where modern amenities blend seamlessly with classic charm, offering both function and beauty to inspire your culinary creativity. The primary suite is a true sanctuary, highlighted by a luxurious tub and spa-like shower that will rival any exclusive retreat, providing ample space to rest and rejuvenate amid tranquil views. Rarely found, the property spans two flat lots just shy of an acre, completely fenced in, offering privacy, security, and abundant outdoor space. Outdoor enthusiasts will cherish the surrounding natural beauty, with opportunities for hiking, birdwatching, and simply reconnecting with nature just steps from your door. Yet, the convenience and charm of downtown Highlands, celebrated for its vibrant boutiques, fine dining, and cultural events, remain just moments away. 1135 Big Bear Pen Road is more than a home; it's a lifestyle, a personal retreat, and a timeless sanctuary awaiting its next chapter with you. Owner/broker listed.

Listed by Brenda Calcavecchia of Keller Williams Great Smokies

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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401 N Fifth Street Highlands NC 28741

Highlands, NC401 N Fifth Street

Price$2,700,000

Est. Mortgage: $/month

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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874 Foreman Road Highlands NC 28741

Highlands, NC874 Foreman Road

Price$2,650,000

Est. Mortgage: $/month

MLS Number 1002570

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.65

Located on a corner lot in the desirable Mirror lake area in town, this fully renovated 1930's home has a wonderful yard and lovely stream. Entry foyer opens to a living room that features a real stone fireplace. Old home charm is evident from the wood floors, the native stone, to the covered screened porch. Newly renovated cutting edge kitchen, with den/dining area adjacent. The kitchen opens onto a stone patio with stone steps to a usable yard with firepit, storage house, deluxe renovated garage and workshop. The additional main level has a bath, bedroom. Lower level has a sauna, and rec room- man cave. Upper level has a primary bedroom with huge suite baths. 3 additional bedrooms share a central bath. across Cullasaja drive, is an additional yard area to sit and enjoy the stream feeding Mirror Lake. Offered at $2,650,000. Some furnishings may be purchased outside of closing

Listed by W. Terry Potts of Country Club Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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299 Oak Street Highlands NC 28741

Highlands, NC299 Oak Street, Unit 1

Price$2,600,000

Est. Mortgage: $/month

Pending

MLS Number 1001706

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.14

In the heart of Downtown Highlands and tucked conveniently behind Main Street stands Eight on Oak, now under construction; An exclusive collection of eight luxury homes, Eight on Oak offers you the opportunity for Elevated Mountain Living with all the bells and whistles. Eight on Oak is where ease of living meets understated charm. Each residence is a blend timeless craftsmanship and creative spaces with a mountain-modern touch. Envision10-foot ceilings with exposed wood beams, designer kitchens, hardwood floors, ease of flow to indoor-outdoor spaces with private screened porches and stone fireplaces. With 3 bedrooms, 3.5 baths, two-car garages, HOA-maintained courtyards, and optional elevators, these homes are designed for lock-and-leave ease and/or full-time residency, take your pick. Your backyard is the splendor and scenic views of the Highlands Greenway and the Mill Creek watershed. Lifestyle is enhanced by being a short stroll to top-notch shops & boutiques, restaurants, and the cultural assets that define Highlands. Eight on Oak is where nature & neighborhood live in perfect balance with community & relationships. Eight on Oak…This is where you belong! PRICING NOTE: FINAL DELIVERED PRICE IS BASED UPON FINISHES SELECTED AND CUSTOMIZATION OF EACH UNIT. EXACT FINAL PRICING WILL BE PRESENTED TO BUYERS PRIOR TO CONTRACT.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

299 Oak Street Highlands NC 28741

Highlands, NC299 Oak Street, Unit 2

Price$2,600,000

Est. Mortgage: $/month

Pending

MLS Number 1001723

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.14

In the heart of Downtown Highlands and tucked conveniently behind Main Street stands Eight on Oak, now under construction; An exclusive collection of eight luxury homes, Eight on Oak offers you the opportunity for Elevated Mountain Living with all the bells and whistles. Eight on Oak is where ease of living meets understated charm. Each residence is a blend timeless craftsmanship and creative spaces with a mountain-modern touch. Envision10-foot ceilings with exposed wood beams, designer kitchens, hardwood floors, ease of flow to indoor-outdoor spaces with private screened porches and stone fireplaces. With 3 bedrooms, 3.5 baths, two-car garages, HOA-maintained courtyards, and optional elevators, these homes are designed for lock-and-leave ease and/or full-time residency, take your pick. Your backyard is the splendor and scenic views of the Highlands Greenway and the Mill Creek watershed. Lifestyle is enhanced by being a short stroll to top-notch shops & boutiques, restaurants, and the cultural assets that define Highlands. Eight on Oak is where nature & neighborhood live in perfect balance with community & relationships. Eight on Oak…This is where you belong! PRICING NOTE: FINAL DELIVERED PRICE IS BASED UPON FINISHES SELECTED AND CUSTOMIZATION OF EACH UNIT. EXACT FINAL PRICING WILL BE PRESENTED TO BUYERS PRIOR TO CONTRACT.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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299 Oak Street Highlands NC 28741

Highlands, NC299 Oak Street, Unit 3

Price$2,600,000

Est. Mortgage: $/month

MLS Number 1001726

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.14

In the heart of Downtown Highlands and tucked conveniently behind Main Street stands Eight on Oak, now under construction; An exclusive collection of eight luxury homes, Eight on Oak offers you the opportunity for Elevated Mountain Living with all the bells and whistles. Eight on Oak is where ease of living meets understated charm. Each residence is a blend timeless craftsmanship and creative spaces with a mountain-modern touch. Envision10-foot ceilings with exposed wood beams, designer kitchens, hardwood floors, ease of flow to indoor-outdoor spaces with private screened porches and stone fireplaces. With 3 bedrooms, 3.5 baths, two-car garages, HOA-maintained courtyards, and optional elevators, these homes are designed for lock-and-leave ease and/or full-time residency, take your pick. Your backyard is the splendor and scenic views of the Highlands Greenway and the Mill Creek watershed. Lifestyle is enhanced by being a short stroll to top-notch shops & boutiques, restaurants, and the cultural assets that define Highlands. Eight on Oak is where nature & neighborhood live in perfect balance with community & relationships. Eight on Oak…This is where you belong! PRICING NOTE: FINAL DELIVERED PRICE IS BASED UPON FINISHES SELECTED AND CUSTOMIZATION OF EACH UNIT. EXACT FINAL PRICING WILL BE PRESENTED TO BUYERS PRIOR TO CONTRACT.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

299 Oak Street Highlands NC 28741

Highlands, NC299 Oak Street, Unit 4

Price$2,600,000

Est. Mortgage: $/month

MLS Number 1001727

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.14

In the heart of Downtown Highlands and tucked conveniently behind Main Street stands Eight on Oak, now under construction; An exclusive collection of eight luxury homes, Eight on Oak offers you the opportunity for Elevated Mountain Living with all the bells and whistles. Eight on Oak is where ease of living meets understated charm. Each residence is a blend timeless craftsmanship and creative spaces with a mountain-modern touch. Envision10-foot ceilings with exposed wood beams, designer kitchens, hardwood floors, ease of flow to indoor-outdoor spaces with private screened porches and stone fireplaces. With 3 bedrooms, 3.5 baths, two-car garages, HOA-maintained courtyards, and optional elevators, these homes are designed for lock-and-leave ease and/or full-time residency, take your pick. Your backyard is the splendor and scenic views of the Highlands Greenway and the Mill Creek watershed. Lifestyle is enhanced by being a short stroll to top-notch shops & boutiques, restaurants, and the cultural assets that define Highlands. Eight on Oak is where nature & neighborhood live in perfect balance with community & relationships. Eight on Oak…This is where you belong! PRICING NOTE: FINAL DELIVERED PRICE IS BASED UPON FINISHES SELECTED AND CUSTOMIZATION OF EACH UNIT. EXACT FINAL PRICING WILL BE PRESENTED TO BUYERS PRIOR TO CONTRACT.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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 "Based on information submitted to HCBOR as of May 20, 2026 11:52 PM EDT. All data is deemed reliable but is not guaranteed accurate by the MLS. All information should be independently reviewed and verified for accuracy. IDX information is provided exclusively for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing."