Osprey Ranch
Homes for Sale in Winter Garden, FL

Osprey Ranch market snapshot (as of August 2, 2026): the median sale price is about $580K ($260 per sq ft over the trailing 12 months of closed sales), a median 7 days on market for closed sales, and 6.3 months of supply, a buyer-leaning market. The trailing-12-month median is up 1% from the prior 12 months, computed from record-level Stellar MLS closed sales (16 closings in the current window).

In ZIP 34787 (WINTER GARDEN), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.

Flood zones in OSPREY RANCH: of 33 listing addresses checked against the FEMA National Flood Hazard Layer, 91% sit outside the FEMA Special Flood Hazard Area (Zone X); 9% are in an A-series high-risk zone where flood insurance is required with a federally backed mortgage. Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Winter Garden.

Osprey Ranch is a community of 238 homes in Winter Garden, Orange County, built between 2024 and 2024 (median 2024), with a median living area of about 2,200 square feet. 23% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

Osprey Ranch Winter Garden is an entirely new-build community - every home dates to 2024 - built around a deed-restricted amenity package rather than a legacy neighborhood footprint, with a median home size around 2,200 square feet.

• Water Spring Elementary · Elementary
• Water Spring Middle · Middle
• Horizon High School · High

Zoned schools reflect the assignments reported on recent Osprey Ranch listings and can change; always confirm with Orange County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Osprey Ranch address.

Because the entire community was built in a single year, buyers here are largely choosing between plans and lots rather than between eras of construction. The amenity set - pool, clubhouse, playground, dog park, trails, and reclaimed-water irrigation - is fairly comprehensive for a community this size, and deed restrictions mean architectural and use standards are actively enforced rather than nominal.

The homestead share sits at 23.1%, which is on the lower side and suggests a meaningful portion of the community is not yet owner-occupied under a filed homestead exemption - consistent with a community still transitioning from builder closeouts to a settled resale market. Combined with 8.9 months of supply, that points to a market where pricing and terms still have room to move in a buyer's favor, and where sellers need a clear, current comp set rather than relying on original builder pricing.

New-construction communities like this one carry their own negotiation dynamics - builder incentives, HOA transition timing, and a homestead share that signals how much of the neighborhood is still owner-occupied versus recently sold. We track those signals alongside the raw listing data so buyers know what they are actually negotiating against and sellers price against the real competitive set, not last year's builder sheet.

Listings in this community report association dues of about $96 per month ($1,152 a year) - the median AssociationFee across 84 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.