Winters Landing
Homes for Sale in Oakland, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 12 closed sales in Winters Landing Phase 2 in Oakland, FL since 2007, the most recent in August 2025. Across Oakland as a whole, 51 homes closed in the last 12 months at a median of $560,000, 53 median days on market, with 11 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,340 ($8,660 with the full homestead exemption).
Winters Landing Phase 2 is a small pocket of 69 homes in Oakland, and the story here is spread, not sameness. The recorded year-built range runs from 1928 to 2024, nearly a century of construction, while the median year built lands at 2006. That combination tells you this is not a single-builder, single-era subdivision — it is a mix of legacy structures and newer builds sharing a name and a boundary, which means condition and construction era do more to set value than location alone.
Median living area here is large at 3,349 square feet, well above what you'd find in a typical starter subdivision, and homestead share sits high at just under 80%, pointing to a base of owner-occupied primary residences rather than a market dominated by short-term rentals or flips. For a buyer, that means less competitive noise from investor turnover, but it also means fewer homes cycle onto the market at any given time — patience and a clear read on each individual property's age and condition will matter more than chasing a 'typical' comp.
Nearby homes for sale
No active listings inside Winters Landing Phase 2 right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
A compact enclave of 69 homes in Oakland where construction dates span nearly a century, from 1928 to 2024, sitting alongside a median build year of 2006 and a median home size over 3,300 square feet.
Stellar MLS sales records identify 55 homes in Winters Landing that have changed hands since 2006, built between 2005 and 2007 (median 2006), with a median living area of about 3,133 sq ft and a typical 4-bedroom, 3-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Winters Landing is best for.
Best for
- Buyers wanting a larger home footprint (median near 3,349 sq ft) rather than a compact or entry-level layout.
- Buyers who prioritize a low-turnover, largely owner-occupied setting over a high-volume resale market.
- Buyers willing to do property-specific diligence on age and condition given the wide 1928–2024 build range.
Probably not for
- Buyers who want a community with defined shared amenities, since none are identified from current listings.
- Buyers seeking a uniform, single-era architectural look across the neighborhood.
- Buyers who want a large, frequently turning inventory pool to choose from, given the small 69-home count.
The market around Winters Landing
Winters Landing is too small for its own price trend, so here is the market around it.
In ZIP 34787, 957 homes are on the market and 30% are under contract — a steady corner of Oakland.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 34787 (Oakland), 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.
ZIP and county figures describe the wider market, not Winters Landing specifically. Momentum Research analysis of MLS records.
The Winters Landing buying strategy.
If we were buying in Winters Landing today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Winters Landing.
A Wide Age Spread, A Narrow Pool
With only 69 homes total, Winters Landing Phase 2 is not a high-volume market, and the year-built range is the detail that deserves attention before anything else. Homes here date as far back as 1928 and as recently as 2024, with the median landing at 2006. That spread means two houses on the same street can carry very different construction standards, systems, and maintenance histories, so buyers should evaluate each property on its own age and condition rather than assuming a community-wide build standard.
Size is more consistent than age: the median living area of 3,349 square feet suggests larger-format homes are the norm rather than the exception. Combined with a homestead share near 80%, this reads as a community built around larger, owner-occupied residences rather than smaller or investment-oriented product. No community amenities are identified from current MLS listings, so any recreational or common-area features would need to be confirmed property by property rather than assumed as part of the package.
The location and the amenities are priced into every listing in Winters Landing. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, age-diverse pool like this, the details that separate a 1928-era structure from a 2024 build matter more than the address itself. We walk buyers through the construction era, condition, and systems of each specific home in Winters Landing Phase 2 rather than leaning on community-wide assumptions, and we help sellers position an individual property clearly against neighbors that may look nothing alike on paper.
Winters Landing in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Winters Landing buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Winters Landing sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winters Landing, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winters Landing home worth?
Get a no-obligation home value based on real comparable sales in Winters Landing, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Should you buy in Winters Landing?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2007 (12 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Winters Landing Phase 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Winters Landing
Where is Winters Landing?
Winters Landing is a community in Oakland, Orange County, Florida, ZIP 34787.
Are there homes for sale in Winters Landing right now?
No active listings inside Winters Landing at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Winters Landing have an HOA or CDD?
No HOA is on record for Winters Landing in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Winters Landing with Momentum Realty’s local guides.