Winters Landing Phase 2
Homes for Sale in Oakland, FL

Community in Oakland · Orange County
69 homesBuilt 1928–2024
Free · No obligation
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data19 years of closingsFL DOR public recordsUpdated twice daily
Live · Winters Landing Phase 2 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
80%
Owner-occupied · Winters Landing Phase 2
59 of 74 parcels homesteaded (FL DOR 2025)
20%
Non-owner-occupied · Winters Landing Phase 2
incl. 7% trust or LLC-held · 100% out-of-state
33%
Cash buyers · Winters Landing Phase 2
1 of 3 sales, 12 mo ending June 2018
69
Homes in the community
plus 5 vacant residential lots · 74 residential parcels (FL DOR 2025)
Track record · 19 years of records
Est. 1928
Community established
homes built 1928-2024, median 2006 (FL DOR 2025)
0
Failed listings · 2015
peaked at 6 in 2006

The market around Winters Landing Phase 2

Winters Landing Phase 2 is a small community — 26 recorded sales on file, most recently in 2015 — too few for its own price trend. Here is the market around it.

Across Orange County, 5,886 homes are active and 2,019 pending (26% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not Winters Landing Phase 2 specifically. Momentum Research analysis of MLS records.

If we were buying in Winters Landing Phase 2 today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Phase 2.

A closer look at the Winters Landing Phase 2 market

The housing stock is 69 homes built between 1928 and 2024, and 80% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.

The location and the amenities are priced into every listing in Winters Landing Phase 2. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

In short
  • Mandatory HOA — confirm current dues
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Winters Landing Phase 2 sales matched to your home.

What is your Winters Landing Phase 2 home worth?

Get a no-obligation home value based on real comparable sales in Winters Landing Phase 2, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.

See homes for sale in Winters Landing Phase 2 on the map →

Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Winters Landing Phase 2?
The Florida DOR 2025 assessment roll shows 69 homes plus 5 vacant residential lots in Winters Landing Phase 2 (public records).
What share of Winters Landing Phase 2 is owner-occupied?
80% of Winters Landing Phase 2 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Winters Landing Phase 2 built?
Homes in Winters Landing Phase 2 were built between 1928 and 2024, with a median year built of 2006 (FL DOR 2025 roll).
Do cash buyers compete in Winters Landing Phase 2?
Cash buyers took 33% of Winters Landing Phase 2 sales in the 12 months ending June 2018 (1 of 3 closings, Stellar MLS).
Who is the best real estate agent for Winters Landing Phase 2?
The best agent for Winters Landing Phase 2 is one who actively works Oakland and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Winters Landing Phase 2.
How do I find a top Oakland real estate agent who knows Winters Landing Phase 2?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Winters Landing Phase 2 and the wider Oakland area.
Can Momentum Realty connect me with an agent for Winters Landing Phase 2?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Winters Landing Phase 2 purchase or sale - no call center and no pressure.

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (5 streets, ZIP 34787))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-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 your area comps.

Looking to buy here? Search homes for sale →

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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.

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