Windermere Landings
Homes for Sale in Windermere, FL

All 255 homes for sale in Windermere, FL · median $930,000 · 176 homes for sale in 34786 · Orange County homes for sale

Community in Windermere · Orange County · ZIP 34786
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Built fromLive Stellar MLS data12 years of closingsUpdated twice daily

As of September 2026, the MLS records 25 closed sales in Windermere Landings Ph 2 in Windermere, FL since 2014, the most recent in May 2026. Across Windermere as a whole, 426 homes closed in the last 12 months at a median of $640,000, 37 median days on market, with 100 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,670 ($10,000 with the full homestead exemption).

Live · Windermere Landings Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
1
Sold · last 12 mo
10-yr average: about 1 a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Windermere Landings Ph 2 is a tight build cluster — every home went up between 2011 and 2017, with a median year built of 2012. That narrow construction window means the housing stock reads as one generation: similar systems, similar ages on roofs and HVAC, similar layouts near the 2,139-square-foot median. Differentiation here comes down to how well each individual owner has maintained or updated the home, not lot size or architectural era.

Closings have been thin in the most recent window, which is common in a community this size and tells you more about pacing than demand. With only 171 homes total and homestead share sitting at 46.2%, a meaningful share of inventory turns over as non-primary or investment product, so pricing conversations should be handled deal-by-deal rather than off a headline number. Anyone active here right now — buying or selling — needs comps pulled tight to the same build years, not the wider Windermere market.

Nearby homes for sale

No active listings inside Windermere Landings Ph 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.

6152 GOLDEN DEWDROP TRAIL
$1.13M · 0.1 mi away
8 bd · 5 ba · 4,830 sqft
6152 GOLDEN DEWDROP TRAIL
Listed by VESTI LLC
6412 GOLDEN DEWDROP TRAIL
$520K · 0.1 mi away
3 bd · 2.5 ba · 1,984 sqft
6412 GOLDEN DEWDROP TRAIL
Listed by URBAN-O REAL ESTATE SOLUTIONS
17526 BLACK RAIL STREET
$1.50M · 0.2 mi away
5 bd · 4 ba · 3,656 sqft
17526 BLACK RAIL STREET
Listed by CHARLES RUTENBERG REALTY ORLANDO
6631 CRESTMONT GLEN LANE
$809K · 0.3 mi away
4 bd · 3.5 ba · 3,068 sqft
6631 CRESTMONT GLEN LANE
Listed by IRM INVEST., REAL EST.& MGMT.
12102 MONTALCINO CIRCLE
$3.10M · 0.3 mi away
4 bd · 4.5 ba · 4,296 sqft
12102 MONTALCINO CIRCLE
Listed by EXP REALTY LLC
11768 HAMPSTEAD STREET
$1.32M · 0.3 mi away
6 bd · 4 ba · 3,900 sqft
11768 HAMPSTEAD STREET
Listed by COMPASS FLORIDA, LLC

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

Windermere Landings Ph 2 is a compact, single-era neighborhood of 171 homes built between 2011 and 2017, with living space clustered around 2,139 square feet. No community amenities are currently identified in MLS listings, which puts the emphasis on the home itself rather than a shared clubhouse or recreation package.

Stellar MLS sales records identify 23 homes in Windermere Landings that have changed hands since 2011, built between 2011 and 2012 (median 2012), with a median living area of about 2,176 sq ft and a typical 3-bedroom, 2.5-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.

Best for

  • Buyers who want a home built within a tight, identifiable construction era and are comfortable evaluating condition property by property.
  • Buyers focused on square footage near the 2,139 sq ft median without paying into a large shared amenity package.
  • Investors comfortable with a market where a notable share of homes are already held as non-primary residences.

Probably not for

  • Buyers who want a clubhouse, pool, or other structured community amenity as part of the purchase decision.
  • Buyers who need deep historical closing data to price with confidence — recent transaction volume here has been limited.
  • Buyers seeking varied architectural eras or lot styles rather than a single, consistent build period.

The market around Windermere Landings

Windermere Landings is too small for its own price trend, so here is the market around it.

In ZIP 34786, 336 homes are on the market and 26% are under contract — a steady corner of Windermere.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

In ZIP 34786 (Windermere), 784 homes closed in the last 12 months at a median of $622K ($262/sq ft), down 1.5% year over year, with a median 38 days on market. Right now 113 active and 37 pending listings put supply at about 3.0 months — a balanced market. See the live ZIP 34786 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Windermere Landings specifically. Momentum Research analysis of MLS records.

If we were buying in Windermere Landings 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 Windermere Landings.

Best Buy
Buyers seeking a single-generation home in a small, defined pocket of Windermere without a bundled amenity fee.
Biggest Risk
Thin recent closing volume and a near-even homestead split mean pricing data needs careful, deal-specific verification.
Sweet Spot
A move-in-ready home near the 2,139 sq ft median that's had systems updated since original construction.
Avoid If
You want resort-style community amenities as part of the purchase — none are currently listed here.

A single-era pocket of Windermere

The defining trait of this community is its build consistency. A six-year construction span (2011–2017) means most homes share a similar structural age — now entering the stage where roofs, water heaters, and HVAC systems are due for a first or second replacement cycle. That makes an inspection and a clear-eyed look at update history more decisive here than in a neighborhood with mixed construction eras.

Homestead share at 46.2% suggests a meaningful portion of the 171 homes are held as second homes, rentals, or investment property rather than primary residences. That can loosen up inventory turnover compared to communities with near-universal homestead filing, but it also means buyers should ask direct questions about occupancy and maintenance history rather than assuming owner-occupied upkeep. With no community amenities identified from current MLS listings, this reads as a straightforward residential build — value here is tied to the home and lot, not a shared amenity package.

The location and the amenities are priced into every listing in Windermere Landings. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a community this size with a single-era build and thin recent closing activity, pricing off broad Windermere averages is a mistake. We pull comps strictly within Windermere Landings Ph 2's own build years and square footage band, and we push past MLS amenity fields to confirm what — if anything — actually comes with the home before you write an offer.

Windermere Landings in 15 seconds.

Best forBuyers seeking a single-generation home in a small, defined pocket of Windermere without a bundled amenity fee.
Biggest advantageConsistent construction era simplifies comparing homes on condition rather than vintage.
Biggest riskThin recent closing volume and a near-even homestead split mean pricing data needs careful, deal-specific verification.
Sweet spotA move-in-ready home near the 2,139 sq ft median that's had systems updated since original construction.
Avoid ifYou want resort-style community amenities as part of the purchase — none are currently listed here.

HOA, CDD & Fees

In short
  • 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.

The takeaway

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

What is your Windermere Landings home worth?

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Real comps, not an automated estimate.
Buyers who want a home built within a tight, identifiable construction era and are comfortable evaluating condition property by property.Excellent fit
Buyers focused on square footage near the 2,139 sq ft median without paying into a large shared amenity package.Excellent fit
Investors comfortable with a market where a notable share of homes are already held as non-primary residences.Excellent fit
Buyers who want a clubhouse, pool, or other structured community amenity as part of the purchase decision.Probably not
Buyers who need deep historical closing data to price with confidence — recent transaction volume here has been limited.Probably not
Buyers seeking varied architectural eras or lot styles rather than a single, consistent build period.Probably not

Data sources & freshness

Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-sale records back to 2014 (25 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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CallFree valuation →
Thinking of selling in Windermere Landings Ph 2? 1 recorded closings (window ending 2026-09-12). See the Orange County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.

Common questions about Windermere Landings

Where is Windermere Landings?

Windermere Landings is a community in Windermere, Orange County, Florida, ZIP 34786.

Are there homes for sale in Windermere Landings right now?

No active listings inside Windermere Landings at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.

Does Windermere Landings have an HOA or CDD?

No HOA is on record for Windermere Landings 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 Windermere Landings with Momentum Realty’s local guides.

WLWindermere Lndgs0.0 mi away · median $520K, 4 sales/12 moWindermere Lndgs Fd 10.1 mi away · 1 for saleWLWindermere Landing0.1 mi awayEnclave0.2 mi away · median $1.25M, 5 sales/12 moEAEnclave At Windermere Landing0.2 mi away

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