Windermere Ridge
Homes for Sale in Orlando, FL

Community in Orlando · Orange County
91 homesBuilt 2001–2004
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Built fromLive Stellar MLS data20 years of closingsFL DOR public recordsUpdated twice daily
Live · Windermere Ridge Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
87%
Owner-occupied · Windermere Ridge
79 of 91 parcels homesteaded (FL DOR 2025)
13%
Non-owner-occupied · Windermere Ridge
incl. 8% trust or LLC-held · 100% out-of-state
0%
Cash buyers · Windermere Ridge
0 of 3 sales, 12 mo ending June 2019
91
Homes in the community
91 residential parcels (FL DOR 2025)
Track record · 20 years of records
Est. 2001
Community established
homes built 2001-2004, median 2002 (FL DOR 2025)
0
Failed listings · 2020
peaked at 10 in 2006
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Windermere Ridge is a small, single-phase community built out over a tight window in the early 2000s, with a median year built of 2002. That consistency in age matters more than any single listing headline: the homes were built to similar specifications in the same era, so condition and updates since then are what actually separate one sale from another, not lot size or floor plan variety.

With only 91 homes in the community and no shared amenities identified in current MLS listings, this is not a market driven by clubhouse fees or resort-style extras. It trades on the house itself and its lot. A high homestead share of roughly 87% points to a base of owner-occupied households rather than a rotating investor pool, which tends to mean fewer distressed or flip-driven listings hitting the market at any given time.

Best for

  • Buyers who want a larger single-family home and are comfortable evaluating original-build systems against two-plus decades of age.
  • Buyers prioritizing a small, defined community over clubhouse or resort-style amenities.
  • Long-term owner-occupant buyers, consistent with the community's high owner-occupancy share.

Probably not for

  • Buyers who want a newly built home with systems and finishes under original warranty.
  • Buyers whose primary criterion is a community pool, clubhouse, or other shared recreational amenity.
  • Investors seeking a large inventory pool to choose from, given the community's total of only 91 homes.

The market around Windermere Ridge

Windermere Ridge is a small community — 55 recorded sales on file, most recently in 2020 — 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 Windermere Ridge specifically. Momentum Research analysis of MLS records.

If we were buying in Windermere Ridge 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 Ridge.

Best Buy
Buyers who want a larger floor plan in an established, small-footprint community without shared amenity fees.
Biggest Risk
Homes are now over two decades old, so system and finish updates vary listing to listing and should be verified directly.
Sweet Spot
Move-up buyers prioritizing square footage over community-provided recreation or common space.
Avoid If
You are searching specifically for a clubhouse, pool, or programmed amenity as part of the purchase.

One generation of homes, one story at a time

Every home in Windermere Ridge was built within a narrow four-year span, 2001 to 2004, which gives the community an unusual degree of structural consistency. Roofs, systems, and original finishes are aging on a similar timeline across the neighborhood, so a buyer evaluating any single listing should weigh how much of that original build-out has already been updated versus what is still original to the house.

The living space itself is the standout data point: a median of roughly 3,450 square feet is large for a single-family community of this size, at just 91 homes total. That combination, sizable floor plans with no clubhouse, pool, or other shared amenity currently listed against the community, suggests buyers here are paying for square footage and a defined enclave rather than for programmed common areas.

The location and the amenities are priced into every listing in Windermere Ridge. 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 only 91 homes and no recurring amenity story to lean on, the real work is in the details: matching a specific home's age-related condition against what similar early-2000s builds nearby have needed in updates. We track that history closely so you are pricing the actual house, not a generic assumption about the neighborhood.

Windermere Ridge in 15 seconds.

Best forBuyers who want a larger floor plan in an established, small-footprint community without shared amenity fees.
Biggest advantageA tight construction window means consistent build quality and era across the community, simplifying comparisons.
Biggest riskHomes are now over two decades old, so system and finish updates vary listing to listing and should be verified directly.
Sweet spotMove-up buyers prioritizing square footage over community-provided recreation or common space.
Avoid ifYou are searching specifically for a clubhouse, pool, or programmed amenity as part of the purchase.

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 Windermere Ridge sales matched to your home.

What is your Windermere Ridge home worth?

Get a no-obligation home value based on real comparable sales in Windermere Ridge, 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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Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Windermere Ridge?
The Florida DOR 2025 assessment roll shows 91 homes in Windermere Ridge (public records).
What share of Windermere Ridge is owner-occupied?
87% of Windermere Ridge parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Windermere Ridge built?
Homes in Windermere Ridge were built between 2001 and 2004, with a median year built of 2002.0 (FL DOR 2025 roll).
Do cash buyers compete in Windermere Ridge?
Cash buyers took 0% of Windermere Ridge sales in the 12 months ending June 2019 (0 of 3 closings, Stellar MLS).
Who is the best real estate agent for Windermere Ridge?
The best agent for Windermere Ridge is one who actively works Orlando 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 Windermere Ridge.
How do I find a top Orlando real estate agent who knows Windermere Ridge?
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 Windermere Ridge and the wider Orlando area.
Can Momentum Realty connect me with an agent for Windermere Ridge?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Windermere Ridge purchase or sale - no call center and no pressure.
Buyers who want a larger single-family home and are comfortable evaluating original-build systems against two-plus decades of age.Excellent fit
Buyers prioritizing a small, defined community over clubhouse or resort-style amenities.Excellent fit
Long-term owner-occupant buyers, consistent with the community's high owner-occupancy share.Excellent fit
Buyers who want a newly built home with systems and finishes under original warranty.Probably not
Buyers whose primary criterion is a community pool, clubhouse, or other shared recreational amenity.Probably not
Investors seeking a large inventory pool to choose from, given the community's total of only 91 homes.Probably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (3 streets, ZIP 32835))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2006 (7 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.

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