$139,900
5 Vintage Oaks Way
Simpsonville, SC 29681
2 mo ago
Vintage Oaks is one of the smallest and most tightly controlled neighborhoods in Simpsonville: a 14-lot gated enclave off Jonesville Road where estate-scale spacing matters as much as the houses themselves.
Listing summary: 1 Active1 Pending19 Recently Sold
$139,900
Simpsonville, SC 29681
2 mo ago
$129,900
Simpsonville, SC 29681
9 yr ago
$139,500
Simpsonville, SC 29681
DOM: 98 d
$139,900
Simpsonville, SC 29681
DOM: 902 d
$1,419,000 $303/sqft
Simpsonville, SC 29681
4 bd · 3 ba · 4,681 sqft · 2023 · DOM: 28 d
$1,347,624 $340/sqft
Simpsonville, SC 29681
5 bd · 4 ba · 3,960 sqft · 2022 · DOM: 54 d
$1,347,624 $340/sqft
Simpsonville, SC 29681
5 bd · 4 ba · 3,960 sqft · DOM: 55 d
$1,500,000 $357/sqft
Simpsonville, SC 29681
4 bd · 3 ba · 4,199 sqft · 2023 · DOM: 229 d
$127,000
Simpsonville, SC 29681
DOM: 170 d
southeastern Greenville County
$1,150,000 $263/sqft
Simpsonville, SC 29681
5 bd · 4 ba · 4,380 sqft · 2021 · DOM: 254 d
$119,900
Simpsonville, SC 29681
DOM: 1663 d
$125,900
Simpsonville, SC 29681
DOM: 1595 d
AI-assisted overview based on MLS listing data for Vintage Oaks, Simpsonville
Vintage Oaks is one of the smallest and most tightly controlled neighborhoods in Simpsonville: a 14-lot gated enclave off Jonesville Road where estate-scale spacing matters as much as the houses themselves. Most homesites sit around 0.57 acres, and the largest cul-de-sac parcel reaches nearly 0.87 acres, giving the street a noticeably lower-density feel than many suburban subdivisions.
The finished homes establish the neighborhood's tone. Completed residences closed from $806,000 to $1.48 million between 2021 and 2025, with construction from 2020 to 2023 and repeated ties to custom builders Chanticleer Custom Home Builders and Intercon Construction. The architectural direction leans European-inspired rather than formulaic production design: lot marketing repeatedly references Old European styling, while completed homes bring in painted brick or brick-and-stone exteriors, vaulted or beamed ceilings, stacked-stone or gas fireplaces, large quartz islands, professional-grade appliances, walk-in pantries, and main-level primary suites. Three-car garages, bonus rooms, home offices, walk-in attic storage, and covered or screened porches show up again and again, reinforcing a custom-home profile built for scale and flexibility.
Vintage Oaks is not an amenity-centered subdivision, and that is part of its identity. There is no long roster of shared recreation in the MLS narrative; instead, the neighborhood trades on gated entry, architectural consistency, and roomy homesites that keep houses visually separated. Lot marketing emphasizes private half-acre-plus parcels, green terrain, and groves of mature oaks, while completed homes add outdoor living through vaulted porches, stone patios, screen porches, and in one case an in-ground pool. Even where pools are not installed, several remarks position the lots and backyards as pool-ready, which speaks to the amount of usable yard space.
The neighborhood sits off Jonesville Road in Simpsonville's southeastern Greenville County corridor, a setting repeatedly tied to quick access to Five Forks, downtown Simpsonville, Highway 14, and I-385. That makes it easier to reach everyday shopping, dining, and commuter routes without pushing the community toward a higher-density pattern. The most common school assignment in the community record is Simpsonville Elementary, Hillcrest Middle, and Hillcrest High.
Vintage Oaks stands out for what it limits as much as what it offers: only 14 lots, large parcels, newer custom construction, and a gated streetscape with a clear design agenda. Compared with larger amenity-driven neighborhoods, it reads more like a compact estate-lot enclave.
Talk to a local agent about homes in Vintage Oaks, Simpsonville
Communities similar to Vintage Oaks
19 recently sold in Vintage Oaks, Simpsonville
| Property | Sold | List Price | DOM | Size | List $/SF |
|---|---|---|---|---|---|
| | Apr 17 2026 | $139,500 | 98 | — | — |
| | Dec 19 2025 | $139,900 | 902 | — | — |
| | Jul 3 2025 | $1,419,000 | 28 | 4,681 sq ft | $303 |
| | Jun 11 2025 | $1,347,624 | 54 | 3,960 sq ft | $340 |
| | Jun 11 2025 | $1,347,624 | 55 | 3,960 sq ft | $340 |
| | Mar 28 2024 | $1,500,000 | 229 | 4,199 sq ft | $357 |
| | Oct 30 2023 | $127,000 | 170 | — | — |
| | Mar 11 2022 | $1,150,000 | 254 | 4,380 sq ft | $263 |
| | Mar 8 2022 | $119,900 | 1663 | — | — |
| | Dec 30 2021 | $125,900 | 1595 | — | — |
| | Nov 15 2021 | $125,900 | 1550 | — | — |
| | Aug 6 2021 | $129,900 | 1449 | — | — |
| | Aug 5 2021 | $119,900 | 1448 | — | — |
| | Jul 15 2021 | $114,900 | 1427 | — | — |
| | Apr 9 2021 | $119,900 | 1330 | — | — |
| | Mar 8 2021 | $109,900 | 1298 | — | — |
| | Feb 4 2021 | $796,500 | 74 | 4,001 sq ft | $199 |
| | Feb 5 2020 | $119,900 | 901 | — | — |
| | Jan 31 2020 | $114,900 | 896 | — | — |
Aggregated from MLS listing history for Vintage Oaks, Simpsonville
The Vintage Oaks real estate market shows buyer's market conditions. Homes typically sell within 902 days. With 2 active listings and 5 homes sold in the past year, buyers have more negotiating power and time to decide.
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