Longleaf at Oakland Homes for Sale
Town of Oakland · Winter Garden 34787
Longleaf at Oakland Homes for Sale in Oakland, FL
A Pulte neighborhood of single-family homes and townhomes built in 2019 and 2020, off Oakland Avenue in the Town of Oakland, with a community pool, park, playground, and walking trails, across the street from the West Orange Trail.
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Live listings
Current Longleaf at Oakland homes on the market.
$500,000Median sold price (12 months · 13 sales)
39 daysMedian days on market (CDOM)
2019 to 2020Typical year built (middle 50% of sales)
Stellar MLS sold data, closings Oct 3, 2025 through Oct 2, 2026.
| Fact | Figure |
|---|---|
| Closed sales (last 12 months) | 13 |
| Median sold price (last 12 months) | $500,000 (13 sales) |
| Median price per sq ft | $276 |
| Median days on market | 39 days (CDOM) |
| Single-family median (sold) | $519,000 (9 sales) |
| Townhome median (sold) | $369,500 (4 sales) |
| Typical year-built range | 2019 to 2020 (middle 50% of sales) |
| Legal subdivision names | Longleaf at Oakland; Longleaf at Oakland, A Replat; Longleaf/Oakland Rep |
| ZIP | 34787 |
Sources: Stellar MLS (sold closings 2025-10-03 to 2026-10-02); Stellar MLS listing records for Longleaf at Oakland (community features and builder, Oct 2026).
Where is Longleaf at Oakland?
Longleaf at Oakland sits in the Town of Oakland in west Orange County, off Oakland Avenue, a short drive north of SR 50. The West Orange Trail runs directly across the street, the Oakland Nature Preserve and Lake Apopka are close by, and Downtown Winter Garden is about 3 miles away. Florida’s Turnpike and SR 429 connect the area to Orlando and Clermont. MLS records list these homes with an Oakland city name and ZIP 34787.
Location snapshot
- ZIP: 34787
- Town: Oakland, Orange County
- Access: Oakland Avenue, north of SR 50
- Highways: SR 50, Florida’s Turnpike, SR 429
- Trail: West Orange Trail across the street
What’s around
- Nature: Oakland Nature Preserve, Lake Apopka
- Dining and shops: Downtown Winter Garden (Plant Street)
- Mall: Winter Garden Village
- Bike and walk: West Orange Trail
- Schools: check Orange County Find My School by address
What amenities does Longleaf at Oakland include?
Longleaf at Oakland has a mandatory HOA. Listing records describe a community pool, a park, a playground, walking trails, green spaces, sidewalks, and street lights. Several recent listings note that grounds maintenance is part of the HOA dues. Fees vary by home type, so ask us for the current figure and what it covers on any address you like.
PoolCommunity pool for residents
Parks & playPark, playground, green spaces
Walking trailsPaths through the community
West Orange TrailDirectly across the street
StreetscapeSidewalks and street lights
HOAMandatory HOA; we pull current fees per address
What do Longleaf at Oakland homes typically look like?
Pulte Homes built Longleaf at Oakland, and the community mixes single-family homes and townhomes. Of the 13 sales in the last 12 months, 9 were single-family homes and 4 were townhomes, all built in 2019 or 2020. The single-family homes ran 1,554 to 2,473 square feet with 3 or 4 bedrooms and sold from $450,000 to $600,000, and one had a private pool. The townhomes, on Gopher Tortoise Terrace and Painted Bunting Avenue, ran 1,472 to 1,809 square feet with 2 or 3 bedrooms and sold from $332,500 to $415,000. Treat these ranges as a guide to the sample, not a promise for a specific listing.
How does Longleaf at Oakland compare to nearby Oakland and Winter Garden options?
Longleaf at Oakland is a newer neighborhood in the Town of Oakland, so buyers often weigh it against other small Oakland communities along the West Orange Trail and against established Winter Garden neighborhoods. Start with the Oakland, FL Guide 2026 for the town itself. For an established Winter Garden community to compare on price and home size, see Stoneybrook West homes for sale, then use this page for active Longleaf at Oakland inventory.
Frequently asked questions
Is Longleaf at Oakland in Oakland or Winter Garden?
Longleaf at Oakland is in the Town of Oakland in west Orange County, off Oakland Avenue. It shares ZIP 34787 with Winter Garden, and Downtown Winter Garden is about 3 miles away.
What do Longleaf at Oakland homes sell for?
Across 13 closed sales from October 3, 2025 through October 2, 2026, the median sold price was $500,000, or $276 per square foot, with a median of 39 days on market. Single-family homes had a median of $519,000 and townhomes a median of $369,500.
Who built Longleaf at Oakland?
Pulte Homes built Longleaf at Oakland. The homes sold in the last 12 months were built in 2019 or 2020, so most resales here are still well under 10 years old.
What amenities does Longleaf at Oakland have?
Listing records describe a community pool, park, playground, walking trails, green spaces, sidewalks, and street lights, all covered by a mandatory HOA. The West Orange Trail runs directly across the street from the community.
How do I see current Longleaf at Oakland homes for sale?
Use the live listings block on this page for active inventory, or call or text the Jared Jones Team at 407-706-5000. We can also set a custom alert for new Longleaf at Oakland homes and townhomes, plus nearby Oakland listings that match your budget.
Sources
- Stellar MLS: Longleaf at Oakland sold closings, 2025-10-03 to 2026-10-02 (13 sales; median $500,000; $276/sf; 39 CDOM)
- Stellar MLS listing records: Longleaf at Oakland community features, builder, and HOA (Oct 2026)
- Orange County Public Schools Find My School: school assignment by address
Browse nearby
Thinking about a home in Longleaf at Oakland?
Call or text the Jared Jones Team at 407-706-5000. We will pull current comps, get HOA details on the addresses you like, and set up showings.