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Active

106 Winding Stream Circle

Simpsonville, SC 29681

Active Total est. Days on Market: 154 Listing ID GVL 1607962

$499,000
Est. $3,001/mo20% down · 7.125% · 30-yrAdjust
  • P&I$2,689
  • Taxes$47
  • Insurance$166
  • HOA$99

Principal, interest, property tax, insurance & HOA. Estimate only — not a loan offer.

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$176/Sq Ft

5 bd · 2.5 ba · 2,831 sqft · $176/sqft

5 Beds
2.5 Baths
2,831 Sq Ft
$176/Sq Ft
2025 Built
.14 acres Single Family Residence Woodcrest Hills Listed Oct 28, 2026 Updated Nov 1, 2026 HOA $99/mo

HOA & Association

Dues$99/mo
Includes
  • Street Lights
  • Restrictive Covenants

About This Home

OVER $40,000 IN SELLER-ADDED UPGRADES! BETTER THAN NEW AND OFFERED AT $499,000! Welcome to 106 Winding Stream Circle, a stunning Toll Brothers home in the desirable Woodcrest Hills community of Simpsonville!

Offering approximately 2,831 square feet of beautifully designed living space, this home combines the appeal of newer construction with exceptional custom finishes and thoughtful upgrades throughout. Why wait to build and spend thousands more when the work has already been done for you? From the moment you arrive, you'll appreciate the enhanced landscaping, decorative rock accents, solar lighting, and beautiful three-quarter glass front door.

Step inside to discover a home filled with character and craftsmanship, featuring extensive custom millwork including picture frame molding, crown molding, beadboard, chair rail accents, designer wallpaper, upgraded interior paint, and custom cordless Roman window shades. Beautiful hardwood stairs with a custom runner add another touch of elegance. The gorgeous kitchen is the heart of the home, showcasing beautiful quartz countertops, abundant cabinetry, and an open layout that flows effortlessly into the dining and living areas.

The spacious living room features a cozy gas fireplace surrounded by custom built-in cabinetry, creating a beautiful focal point. An oversized storage area off the living space offers incredible versatility, whether used for seasonal storage, hobbies, or even a dedicated pet room! A main-level bedroom, currently used as a home office, offers flexibility for guests or working from home.

The adjacent half bathroom includes a generously sized closet offering potential for a future shower addition and conversion to a full bathroom, subject to necessary approvals. Upstairs, a spacious loft at the top of the stairs provides the perfect additional living area, media space, or playroom. The beautiful primary suite offers a relaxing retreat with upgraded bathroom mirrors, lighting, and shower fixtures, along with custom closets.

You'll love the convenient flow directly from the primary closet into the laundry room! Three additional generously sized bedrooms complete the upper level, offering plenty of space for family and guests. THE BACKYARD IS A PRIVATE RETREAT!

Fully fenced and surrounded by a peaceful backdrop of mature trees with no homes directly behind, this outdoor space is truly special. The sellers have invested in extensive landscaping throughout the front, side, and rear yard, decorative rock features, solar lighting, an additional concrete patio, a concrete walkway along the right side of the home, and a custom trash can enclosure. The covered, screened-in back porch is perfect for morning coffee or entertaining, while the additional patio and HOT TUB SPA create the ultimate outdoor escape!

Additional highlights include a two-car attached garage and the refrigerator, washer, dryer, and hot tub spa ALL REMAINING with the home! Conveniently located just a short drive from the popular Five Forks area, with easy access to shopping, dining, and everyday conveniences. Currently zoned for Rudolph Gordon School (K4-8) and Fountain Inn High School.

With over $40,000 invested in seller-added improvements, this home offers an incredible opportunity to enjoy the beauty of newer construction without the expense and hassle of completing upgrades yourself. Beautifully maintained, thoughtfully enhanced, and priced at just $499,000, this exceptional home is ready for its next owners. Schedule your private showing today!

Property history

  1. Oct 28, 2026
    Listed for sale $499,000 Active
    Total est. Days on Market: 154 2 MLS regions
  2. Oct 22, 2026
    Status changed to Off Market $499,106 Off Market
    Active -> Off Market
  3. Oct 2, 2026
    Status changed to Off Market $499,999 Off Market
    Active -> Off Market
Show 13 more Show less
  1. Oct 2, 2026
    Previously listed $499,106 Off Market
  2. Sep 4, 2026
    Status changed to Off Market $525,000 Off Market
    Active -> Off Market
  3. Sep 4, 2026
    Previously listed $499,999 Off Market
  4. Aug 17, 2026
    Status changed to Off Market $537,000 Off Market
    Active -> Off Market
  5. Aug 17, 2026
    Previously listed $525,000 Off Market
  6. Aug 3, 2026
    Price reduced $537,000 Active
    Was $549,999
  7. Jul 21, 2026
    Previously listed $537,000 Off Market
  8. Jul 20, 2026
    Status changed to Off Market $549,999 Off Market
    Active -> Off Market
  9. Jul 7, 2026
    Price reduced $549,999 Active
    Was $559,000
  10. Jun 26, 2026
    Status changed to Off Market $575,000 Off Market
    Active -> Off Market
  11. Jun 26, 2026
    Previously listed $549,999 Off Market
  12. Jun 16, 2026
    Price reduced $575,000 Active
    Was $589,000
  13. May 28, 2026
    Previously listed $575,000 Off Market

Property Details

Property Overview

County
Greenville
Levels
  • Two
Architectural Style
  • Craftsman

Interior Details

Flooring
  • Carpet
  • Ceramic Tile
  • Luxury Vinyl
Appliances
  • Gas Cooktop
  • Dishwasher
  • Disposal
  • Oven
  • Microwave
  • Range Hood
  • Gas Water Heater
  • Tankless Water Heater
Laundry Features
  • Sink
  • 2nd Floor
  • Walk-in
  • Electric Dryer Hookup
  • Stackable Accommodating
  • Washer Hookup
  • Laundry Room
Interior Features
  • Bookcases
  • Ceiling Fan(s)
  • Ceiling Smooth
  • Open Floorplan
  • Countertops – Quartz
  • Pantry
  • Radon System
Fireplace Features
  • Gas Log

Parking And Garage

Garage Spaces
2
Parking Features
  • Attached
  • Concrete
  • Garage Door Opener

Exterior Features

Roof
  • Architectural
Driveway
  • Attached
  • Concrete
  • Garage Door Opener
Foundation
  • Slab
Patio Porch
  • Screened
  • Patio
  • Front Porch
Construction
  • Hardboard Siding
  • Stone

Lot And Land

Lot Features
  • 1/2 Acre or Less
  • Sidewalk
  • Few Trees
  • Sprklr In Grnd-Full Yard
Lot Size Acres
0.14

Utilities And Systems

Sewer
  • Public Sewer
Cooling
  • Central Air
  • Electric
Heating
  • Natural Gas
Utilities
  • Cable Available
Water Source
  • Public

Tax Information

Annual Tax
569.28

Community

Community Features
  • Common Areas
  • Street Lights
  • Sidewalks

Primary Suite

Features
  • Double Sink
  • Full Bath
  • Primary on 2nd Lvl
  • Shower Only
  • Walk-in Closet

Listed by Jolene T Peddicord of Belle Haven Realty Group

Location

Address
106 Winding Stream Circle
City
Simpsonville, SC 29681
County
Greenville
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Schools

Elementary
Rudolph Gordon
Middle
Rudolph Gordon
High
Fountain Inn High

School assignments may change. Contact the school district to confirm.

The information is being provided by Greater Greenville MLS. Information deemed reliable but not guaranteed. Information is provided for consumers’ personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Greater Greenville MLS. All Rights Reserved.

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106 Winding Stream Circle, Simpsonville, SC, 29681

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