
$324,900 $278/sqft
2805 Chester Highway
York, SC 29745
3 bd · 2 ba · 1,168 sqft · 1 ac · 1997 · 27 d ago
Whipoorwill Estates in York has the feel of a country-address community that still keeps daily life within easy reach.
Community overview based on MLS listing data for Whipoorwill Estates, York
Whipoorwill Estates in York has the feel of a country-address community that still keeps daily life within easy reach. The setting is defined by generous lots, single-level ranch homes, and a relaxed, open landscape that gives each property room to breathe. Many homes here lean into front porches, back decks, and broad yards, so the neighborhood reads as lived-in and practical rather than polished and formal.
"A spacious, low-key setting where porch living and open yards do most of the talking."
The housing stock is refreshingly consistent: mostly single-family ranch homes built in the late 1990s and early 2000s. Inside, updates show up often in the places buyers notice first—flooring, paint, kitchens, and baths—while outside, the appeal comes from level or gently rolling lots, fenced yards, storage buildings, and workshop space. A few homes add detached garages or carports, but the larger draw is the amount of usable land, with lot sizes commonly around an acre or more. The overall impression is practical and flexible, with enough space for gardening, hobbies, and outdoor living without feeling overdeveloped.
This is the kind of place where the day naturally spills outdoors. Rocking-chair front porches, screened back porches, decks, and fire-pit areas are common touches, and they suit the setting well. Storage sheds and detached outbuildings add another layer of utility, especially for buyers who want room for tools or projects. The streets themselves are simple and residential, with a calm, rural rhythm that still feels connected to everyday needs in York and nearby towns.
"Country character, updated interiors, and room to spread out define the everyday experience here."
Whipoorwill Estates sits in York near the York and McConnells area, with Rock Hill also called out as a convenient nearby destination for shopping, dining, and commuting. Public remarks place the community just minutes from downtown York, and the location is described as close to schools, shopping, and dining while still feeling set apart from busier corridors. The community is served by Jefferson Elementary, York Middle, and York Comprehensive High, placing the schools squarely within the York district. For buyers who want a straightforward York County location with access to local errands and regional travel, this pocket offers an appealing middle ground between open land and town convenience.
Palmetto Park Realty Team · York
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27 recently sold in Whipoorwill Estates, York
| Property | Sold | Sold Price | Days on Market | Size | Sold to Ask | Sold $/SF |
|---|---|---|---|---|---|---|
| | Jan 23 2026 | $275,000 | 63 | 1,200 sq ft | 88.7% | $229 |
| | Oct 6 2025 | $278,000 | 49 | 1,200 sq ft | 94.6% | $232 |
| | Sep 29 2025 | $299,900 | 24 | 1,410 sq ft | 100.0% | $213 |
| | Jul 26 2024 | $315,000 | 29 | 1,271 sq ft | 100.0% | $248 |
| | Sep 28 2022 | $254,000 | 40 | 1,200 sq ft | 97.7% | $212 |
| | Dec 16 2021 | $259,900 | 66 | 1,410 sq ft | 100.0% | $184 |
| | Aug 17 2021 | $255,000 | 32 | 1,261 sq ft | 104.1% | $202 |
| | Oct 6 2020 | $205,000 | 48 | 1,200 sq ft | 103.0% | $171 |
| | Feb 11 2020 | $174,000 | 68 | 1,127 sq ft | 97.5% | $154 |
| | Sep 27 2019 | $169,000 | 39 | 1,166 sq ft | 99.5% | $145 |
| | Jun 21 2019 | $169,900 | 58 | 1,200 sq ft | 100.0% | $142 |
| | May 23 2019 | $180,000 | 51 | 1,261 sq ft | 102.9% | $143 |
| | May 23 2019 | $180,000 | 51 | 1,261 sq ft | 102.9% | $143 |
| | Sep 24 2018 | $160,000 | 49 | 1,200 sq ft | 100.3% | $133 |
| | Aug 30 2018 | $154,000 | 58 | 1,204 sq ft | 97.0% | $128 |
| | May 30 2018 | $162,000 | 47 | 1,200 sq ft | 100.6% | $135 |
| | May 30 2018 | $162,000 | 47 | 1,200 sq ft | 100.6% | $135 |
| | Apr 27 2018 | $163,000 | 58 | 1,386 sq ft | 101.9% | $118 |
| | Apr 27 2018 | $163,000 | 58 | 1,386 sq ft | 101.9% | $118 |
| | Mar 21 2018 | $153,300 | 41 | 1,248 sq ft | 102.2% | $123 |
| | Feb 14 2018 | $165,000 | 35 | 1,267 sq ft | 100.1% | $130 |
| | Jun 2 2016 | $115,000 | 170 | 1,200 sq ft | 85.8% | $96 |
| | Jun 2 2016 | $115,000 | 170 | 1,200 sq ft | 85.8% | $96 |
| | Jan 20 2016 | $134,500 | 119 | 1,248 sq ft | 99.7% | $108 |
| | Jul 29 2014 | $90,000 | 42 | 1,158 sq ft | 100.1% | $78 |
| | Jul 29 2014 | $90,000 | 42 | 1,158 sq ft | 100.1% | $78 |
| | Mar 14 2013 | $107,000 | 237 | 1,203 sq ft | 97.4% | $89 |
Closed sales from MLS history for Whipoorwill Estates, York
Below trend-line threshold — city median shown for context
The Whipoorwill Estates real estate market shows balanced market conditions. Homes typically sell within 49 days. With 2 active listings and 3 homes sold in the past year, a healthy balance exists between buyers and sellers.
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