Highlands Single Family Listings

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42 High Gate Drive Highlands NC 28741

Highlands, NC42 High Gate Drive

Price$3,100,000

Est. Mortgage: $/month

MLS Number 1002714

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acreage 1.01

Discover 1875, Highlands' newest luxury neighborhood-an exclusive enclave of 15 custom residences located on the desirable Atlanta side of town, only minutes from Highlands Country Club and downtown. This modern and sleek farmhouse offers a striking blend of timeless style and contemporary sophistication. A grand architectural statement begins at the expansive stone-clad entry terrace, where precision masonry and elegant lines set the tone for what lies within. Guests are welcomed through a custom wall of steel clad windows and door into a soaring space defined by 18-foot ceilings, wide-plank white oak floors, and an oversized granite fireplace that serves as a striking sculptural focal point-masterfully blending form, function, and mountain elegance. A stunning indoor wood-burning fireplace anchors the living space, while a covered patio with an additional fireplace invites relaxation year-round. Floor-to-ceiling windows bring the outdoors in, filling the home with natural light and capturing the beauty of the Highlands landscape. The thoughtfully designed floor plan includes a luxurious primary suite with a paneled ceiling and a spa-inspired bath featuring luxurious tiling, heated floors, soaking tub, and a lavish shower with six Brizo body sprays and dual shower heads. Two additional en suite guest rooms also enjoy heated floors, and a full laundry room makes cleanup simple. The kitchen is a masterpiece in itself-equipped with a 60” Wolf gas range/oven combo, an oversized vent hood, paneled Thermador and Cove appliances, counter-to-ceiling tiling, and custom steel windows with marble window sills. A stylish scullery adds extra storage, ice maker, wine cooler and character. A mudroom connects to the grilling terrace and a generously sized two-car garage, above which sits a full guest suite with bath, kitchenette, and closet-perfect for visitors or a private office. Every detail in this exceptional home showcases craftsmanship, intention, and the best of elevated mountain living. Come experience life in Highlands and coveted 28741-a luxurious lifestyle unlike any other-founded in 1875.

Listed by Julie Osborn of Pat Allen Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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86 High Gate Drive Highlands NC 28741

Highlands, NC86 High Gate Drive

Price$2,999,999

Est. Mortgage: $/month

MLS Number 1002744

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.85

The second offering at 1875 is underway on Lot 5, a beautifully crafted multi-textured stone flanked modern 4,197 square foot residence that artfully blends rustic character with refined mountain elegance. Masterful craftmanship, care and meticulous detailing abound throughout, incorporating the architectural landscape and natural surroundings. Hand-hewn, rough-sawn reclaimed beams frame the entry to the grand living room, where a trussed ceiling and a dramatic wall of custom floor-to-ceiling windows draw the surrounding natural beauty indoors. A striking floor-to-ceiling stone fireplace anchors the space, creating a warm and inviting focal point. The thoughtfully designed floor plan centers around an entertaining chef's kitchen and dining area, creating an ideal gathering space for family and friends. A 60” Wolf Dual Fuel Oven/Range with massive hood above will anchor the kitchen with a built-in Sub-Zero refrigerator/freezer and built-in Cove dishwasher that will seamlessly flow with the kitchen cabinetry. A dedicated scullery and grilling porch will enhance both everyday living and entertaining and the covered stone terrace with its own fireplace will provide year-round outdoor enjoyment. Designed for both comfort and effortless privacy, the home features a main-level primary suite, tucked away for a calm space, complete with a rough-sawn beamed ceiling and a lavishly tiled bath will feature heated floors, free-standing soaking tub and an expansive walk-in closet. Upstairs, spacious guest accommodations include three additional bedrooms, two bathrooms, a loft retreat for relaxation or office, and a versatile bonus room for reading, media, or recreation. Additional highlights include a two-car garage for convenience during inclement weather and beautifully landscaped grounds with native plantings and sculptural boulder accents. Privately gated and tucked into a serene setting, the property is just minutes from vibrant downtown Highlands and is close to Highlands Country Club, offering an exceptional balance of privacy, natural beauty, and convenience. Architectural plans and finishes are subject to changes at the builder's discretion prior to completion. Estimated Completion Date June 2026.

Listed by Julie Osborn and Patricia Allen of Pat Allen Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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159 Highlands Point Highlands NC 28741

Highlands, NC159 Highlands Point

Price$2,995,000

Est. Mortgage: $/month

MLS Number 1003200

  • Residential
  • Bedrooms 4
  • Bathroom 12
  • 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 and Steve Castellaw of Christie's International Real Estate Highlands-Cashiers

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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656 Big Bearpen Road Highlands NC 28741

Highlands, NC656 Big Bearpen Road

Price$2,990,000

Est. Mortgage: $/month

MLS Number 1002403

  • Residential
  • Bedrooms 4
  • Bathroom 7
  • Acreage 0.76

This highly desirable home is loaded with Highlands Charm and has great curb appeal. The main house has 4 bedrooms, 4 bathrooms, there is a free-standing guest quarters with one bedroom, one bath. The dwellings are completely renovated and ready to move in. Updated with the old Highlands Charm of real stone fireplaces, wood floors and wood walls. The kitchen was professionally designed, and it has a wonderful exterior Carolina room with a fireplace. Lower level has additional storage and utility/Mechanical space. This one has rental income and is grandfathered for rental with the city, has ample parking and a usable yard.

Listed by W. Terry Potts of Country Club Properties, John Muir of Berkshire Hathaway HomeServices Meadows Mountain Realty - HF

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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656 Big Bear Pen Road Highlands NC 28741

Highlands, NC656 Big Bear Pen Road

Price$2,990,000

Est. Mortgage: $/month

MLS Number 1002404

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Acreage 0.76

Nestled on the slopes of Big Bear Pen Mountain and just a stone's throw from the bustling heart of downtown Highlands, NC, lies a gem of a property that's recently undergone a complete makeover. Introducing 656 Big Bear Pen Road: a stunningly renovated and professionally decorated haven (courtesy of Spruce Interiors) that promises comfort, style, and unparalleled mountain living. This exquisite property boasts a spacious four bedroom, five bath main home along with a charming one bedroom guest cottage, making it perfect for entertaining guests or indulging in some quiet time. The main residence is a marvel of modern design and rustic charm, featuring a grand great room with a large stone fireplace that invites cozy evenings and warm conversations. The heart of the home is undoubtedly the chef's kitchen, complete with a large island for gathering. The main level also houses the owner's suite, a guest bathroom, a cozy study/den for quieter moments, and a dining room for memorable meals. But the allure doesn't stop there. Step outside to the large covered porch with its own stone fireplace, or enjoy the tranquility from the deck off the back of the house. Upstairs, guests can enjoy their own private retreats in three beautifully appointed bedrooms, each with its own bathroom. The separate guest house offers additional space and independence; it has a living room with a kitchenette, bedroom, and a full bathroom. This property has not only been a beloved home but also a successful vacation rental, grandfathered by the town of Highlands, adding to its appeal as a wise investment or a personal escape. Don't miss your chance to own a piece of paradise at 656 Big Bear Pen Road.

Listed by John Muir of Berkshire Hathaway HomeServices Meadows Mountain Realty - HF, W. Terry Potts of Country Club Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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: 6.53% last updated on May 28, 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

Active With Contract

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: 6.53% last updated on May 28, 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: 6.53% last updated on May 28, 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: 6.53% last updated on May 28, 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 (8285263717)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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: 6.53% last updated on May 28, 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: 6.53% last updated on May 28, 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 June 3, 2026 11:44 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."