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Under contract
    • $2,700,000

    1135 Big Bear Pen Road, Highlands, NC 28741

    4beds
    --sqft
    : 
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    Single Family Residence
    Built in 1961
    0.92 Acres Lot
    $-- Zestimate®
    $--/sqft
    $-- HOA

    What's special

    Stone fireplaceSpacious decksLush mature treesAbundant outdoor space
    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.
    99 days
    |
    281
    |
    16
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Brenda Calcavecchia,

    Keller Williams Great Smokies

    Source: HCMLS,MLS#: 1002637Originating MLS: Highlands Cashiers Board of Realtors

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: Main
      Bedroom 2
      • Level: Main
      Bedroom 3
      • Level: Main
      Bedroom 4
      • Level: Main
      Dining room
      • Level: Main
      Family room
      • Level: Main
      Kitchen
      • Level: Main
      Living room
      • Level: Main
      Heating
      • Gas, Heat Pump, Multi-Fuel
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Built-In Refrigerator, Double Oven, Dryer, Exhaust Fan, Freezer, Disposal, Gas Oven, Ice Maker, Microwave, Range, Refrigerator, Wine Cooler, Washer
      • Laundry: Washer Hookup, Dryer Hookup
      Features
      • Breakfast Bar, Eat-in Kitchen, Kitchen Island, Vaulted Ceiling(s), Walk-In Closet(s)
      • Flooring: Laminate, Tile, Wood
      • Basement: Crawl Space,Encapsulated
      • Number of fireplaces: 3
      • Fireplace features: Gas Log, Kitchen, Living Room, Stone, Wood Burning

      Property

      Parking
      • Total spaces: 1
      • Parking features: Additional Parking, Detached, Garage, One Car Garage, Gravel
      • Garage spaces: 1
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Rear Porch, Covered, Deck, Enclosed, Front Porch, Patio, Screened, Side Porch
      • Exterior features: Garden
      • Pool features: Community
      • Has view: Yes
      • View description: Mountain(s)
      • Waterfront features: None
      Lot
      • Size: 0.92 Acres
      • Features: Level, Rolling Slope, City Lot, Flat
      • Topography: Level
      Details
      • Additional structures: Guest House, Residence
      • Parcel number: 7540841262
      • Zoning description: Residential

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Bungalow,Contemporary,Ranch
      • Property subtype: Single Family Residence
      Materials
      • Frame, Wood Siding
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1961

      Utilities & green energy

      • Electric: Generator
      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Cable Available, Electricity Connected, High Speed Internet Available

      Community & HOA

      Community
      • Features: Clubhouse, Fitness Center, Pickleball, Pool, Tennis Court(s)
      • Security: Security System
      • Subdivision: Big Bear Pen
      HOA
      • Has HOA: No
      Location
      • Region: Highlands

      Financial & listing details

      • Tax assessed value: $889,790
      • Annual tax amount: $8,424
      • Date on market: 3/5/2026
      • Cumulative days on market: 106 days
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        $4,652/mo

        Price history

        DateEventPrice
        5/24/2026Contingent$2,700,000
        Source: HCMLS #1002637 Report a problem
        3/5/2026Listed for sale$2,700,000-1.8%
        Source: HCMLS #1002637 Report a problem
        1/13/2026Listing removed$2,750,000
        Source: HCMLS #103343 Report a problem
        11/23/2025Price change$2,750,000-5.2%
        Source: HCMLS #103343 Report a problem
        9/12/2025Price change$2,899,999-3.3%
        Source: HCMLS #103343 Report a problem
        7/2/2025Price change$2,999,999-6.1%
        Source: HCMLS #103343 Report a problem
        6/11/2025Price change$3,195,000-0.2%
        Source: HCMLS #103343 Report a problem
        4/15/2025Price change$3,200,000-6.4%
        Source: HCMLS #103343 Report a problem
        1/29/2025Price change$3,420,000-2.3%
        Source: HCMLS #103343 Report a problem
        10/15/2024Price change$3,500,000-2.8%
        Source: HCMLS #103343 Report a problem
        7/29/2024Price change$3,600,000-5.3%
        Source: HCMLS #103343 Report a problem
        6/30/2024Price change$3,800,000-2.6%
        Source: HCMLS #103343 Report a problem
        6/3/2024Price change$3,900,000-7.1%
        Source: HCMLS #103343 Report a problem
        4/30/2024Price change$4,200,000-4.5%
        Source: HCMLS #103343 Report a problem
        4/19/2024Listed for sale$4,399,000
        Source: HCMLS #103343 Report a problem
        3/9/2024Listing removed--
        Source: HCMLS #103343 Report a problem
        2/10/2024Price change$4,399,000-4.3%
        Source: HCMLS #103343 Report a problem
        11/14/2023Listed for sale$4,599,000+279%
        Source: HCMLS #103343 Report a problem
        1/29/2021Sold$1,213,500-6.6%
        Source: HCMLS #94975 Report a problem
        11/30/2020Pending sale$1,299,000
        Source: COUNTRY CLUB PROPERTIES #94975 Report a problem
        11/11/2020Price change$1,299,000-5.5%
        Source: COUNTRY CLUB PROPERTIES #94975 Report a problem
        10/13/2020Listed for sale$1,375,000+37.6%
        Source: COUNTRY CLUB PROPERTIES #94975 Report a problem
        10/6/2018Listing removed$999,000
        Source: HIGHLANDS SOTHEBYS INTL RLTY - DT OFFICE #87325 Report a problem
        10/6/2018Listed for sale$999,000
        Source: HIGHLANDS SOTHEBYS INTL RLTY - DT OFFICE #87325 Report a problem
        10/6/2018Pending sale$999,000+24.1%
        Source: HIGHLANDS SOTHEBYS INTL RLTY - DT OFFICE #87325 Report a problem
        10/5/2018Sold$805,000
        Source: HCMLS #87325 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2018$4,851 $889,790
        2017-- $889,790
        2016-- $889,790
        2015-- $889,790 -19%
        2014-- $1,097,850
        2013-- $1,097,850
        2012-- $1,097,850
        2011-- $1,097,850

        Find assessor info on the county website

        Monthly payment

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          Payment breakdown

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          All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
          HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
          Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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          Climate risks

          Neighborhood: 28741

          Getting around

          0 / 100
          Car-Dependent
          10 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating

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