165 Jack Wilcox
Highlands, NC 28741
- 2 Beds
- 3 Baths
2 Beds
3 Baths
(on 0.57 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1960
Lot Size
0.57 acres
About this House
This is a rare find where a classic "Joe Webb Cabin" intersects with a "Mountain Chic" restoration! This tasteful blend of styles creates charm, comfort, and move-in-readiness. Meticulously renovated and finished by the current owner, you'll discover a large primary bedroom and a guest bedroom both near updated full bathrooms. The sleeping quarters both flank the wide-open living spaces. An open chef-style kitchen with high-end appliances well-serves the living space which features a dining area, wet bar, and back-to-back fireplaces. 100% of the interiors access and open up to the views beyond thanks to a full-length deck/sunporch displaying the pasture, woods, and mountain views beyond. Outdoor living is exactly what the doctor ordered for this cottage! Natural light is an important purchase consideration, and this cottage has it by bringing the outside...in! A special opportunity presents itself to add that 3rd bedroom or studio/office on lower level. Steeped in history, this is the former site of the "Little Billy Cabin" created by Joe Webb himself. Chances are good that this cottage will check many of your boxes...including the bonus of being convenient to Downtown Highlands. If you're thinking peace, tranquility, and stillness in a property that's just minutes from downtown ...don't miss this one. Current rental history runs +/- $45K+ per year if you're inclined towards purchasing income property. Highlands is often referred to as the "Aspen of the East", we offer fine boutiques and shops, award-winning restaurants, cultural arts, festivals, music events. Abundant outdoor life includes fly fishing, hiking, kayaking, stand-up paddle-boarding, canoeing...all just minutes away. As we like to say here in Highlands..."come for the weekend, stay for a lifetime"!
165 Jack Wilcox, Highlands, NC 28741 is a 2 bedroom, 3 bathroom single-family home built in 1960. It last sold for $945,000 on Sep 15, 2023 (11% above the $849,000 asking price). It is currently off market. The Trulia Estimate rent is $3,727/month.
Home Details for 165 Jack Wilcox
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Interior Details Basement: Partial,Concrete,Partially Finished,Bath/Stubbed,Walk-Out AccessNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom 2, Bonus Room, Den, Dining Room, Family Room, Kitchen, Living RoomWet Bar |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Appliances & Utilities Utilities: Cable Available, High Speed Internet AvailableAppliances: Dryer, Dishwasher, Gas Oven, Refrigerator, WasherDishwasherDryerLaundry: Washer Hookup,Dryer HookupRefrigeratorWasher |
Heating & Cooling Heating: Central,GasHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central |
Fireplace & Spa Fireplace: Gas Log, Living Room, Masonry, Stone, Wood BurningHas a Fireplace |
Windows, Doors, Floors & Walls Window: Window TreatmentsFlooring: Carpet, Concrete, Tile, Wood |
Levels, Entrance, & Accessibility Stories: 1Levels: OneFloors: Carpet, Concrete, Tile, Wood |
View Has a ViewView: Mountain(s), Panoramic, Trees/Woods |
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Exterior Home Features Roof: ShinglePatio / Porch: Deck, Front Porch, Side Porch, Wrap Around |
Parking & Garage No CarportNo GarageParking: Gravel,Other,Paved,Parking Lot |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Year Built Year Built: 1960 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Bungalow,Log Home |
Building Construction Materials: Frame, Log, Log Siding, Wood SidingNot a New Construction |
Property Information Parcel Number: 7640195021 |
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Price List Price: $849,000 |
Status Change & Dates Off Market Date: Fri Sep 15 2023Possession Timing: Close Of Escrow |
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MLS Status: Closed |
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Direction & Address City: HighlandsCommunity: Billy Cabin |
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Association for this Listing: Highlands Cashiers Board of RealtorsNo HOA |
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Lot Area: 0.57 acres |
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Listing Terms: Cash |
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BasementMls Number: 102000Living Area Range Units: Square FeetAttribution Contact: 8285268300Universal Property Id: US-37113-N-7640195021-R-N |
Last check for updates: 13 minutes ago
Listed by Patrick Gleeson
Highlands Sotheby's International Realty - DT
Deborah Gleeson
Highlands Sotheby's International Realty - DT
Bought with: C. Dan Chapman, Country Club Properties
Originating MLS: Highlands Cashiers Board of Realtors
Source: HCMLS, MLS#102000
Price History for 165 Jack Wilcox
| Date | Price | Event | Source |
|---|---|---|---|
| 09/15/2023 | $945,000 | Sold | HCMLS #102000 |
| 08/18/2023 | $849,000 | Pending | HCMLS #102000 |
| 08/15/2023 | ListingRemoved | HCMLS #102000 | |
| 08/05/2023 | $849,000 | Contingent | HCMLS #102000 |
| 05/01/2023 | $849,000 | Listed For Sale | HCMLS #102000 |
| 03/19/2023 | ListingRemoved | HCMLS #100984 | |
| 10/13/2022 | $1,250,000 | Listed For Sale | HCMLS #100984 |
| 03/16/2015 | $210,000 | Sold | N/A |
Market trends in Highlands
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
186
25MoM
Property Tax and Assessment
| Year | 2014 |
|---|---|
| Tax | |
| Assessment | $1,636,700 |
Home facts updated by county records
Comparable Sales for 165 Jack Wilcox
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.37 | Single-Family Home | $874,000 | 03/23/26 | 3 | 3 | - | |
0.32 | Single-Family Home | $1,100,000 | 06/02/26 | 3 | 3 | - | |
0.32 | Single-Family Home | $825,000 | 08/27/25 | 3 | 3 | - | |
0.55 | Single-Family Home | $1,250,000 | 01/05/26 | 4 | 3 | - | |
0.60 | Single-Family Home | $955,000 | 09/12/25 | 3 | 3 | - | |
0.55 | Single-Family Home | $1,225,000 | 08/21/25 | 2 | 2 | - | |
0.47 | Single-Family Home | $1,270,000 | 07/21/26 | 3 | 3.5 | 1,966 | |
0.79 | Single-Family Home | $900,000 | 08/22/25 | 3 | 3 | - | |
0.89 | Single-Family Home | $1,130,000 | 10/27/25 | 2 | 2.5 | - | |
0.79 | Single-Family Home | $1,675,000 | 04/20/26 | 2 | 2.5 | - |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 165 Jack Wilcox.
What Locals Say about Highlands
At least 19 Trulia users voted on each feature.
95 % Say it's dog friendly
91 % Say it's quiet
89 % Say car is needed
89 % Say yards are well-kept
84 % Say people would walk alone at night
76 % Say there's holiday spirit
74 % Say parking is easy
74 % Say they plan to stay for at least 5 years
74 % Say there's wildlife
74 % Say there are community events
54 % Say neighbors are friendly
52 % Say streets are well-lit
46 % Say kids play outside
44 % Say it's walkable to grocery stores
30 % Say it's walkable to restaurants
25 % Say there are sidewalks
Sourced by Trulia users. Learn more about our methodology.
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Copyright Highlands-Cashiers Board of REALTORS. All rights reserved. Information is deemed reliable but not guaranteed.

