Westover Club Ph 01 44/139
Homes for Sale in Windermere, FL

Community in Windermere · Orange County
108 homesBuilt 2000–2003
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Built fromLive Stellar MLS data11 years of closingsFL DOR public recordsUpdated twice daily
Live · Westover Club Ph 01 44/139 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
2
Sold · last 12 mo
10-yr average: about 1 a year
Ownership and context
83%
Owner-occupied · Westover Club Ph 01 44/139
90 of 108 parcels homesteaded (FL DOR 2025)
17%
Non-owner-occupied · Westover Club Ph 01 44/139
incl. 3% trust or LLC-held · 100% out-of-state
0%
Cash buyers · Westover Club Ph 01 44/139
0 of 3 sales, 12 mo ending June 2023
108
Homes in the community
108 residential parcels (FL DOR 2025)
Track record · 11 years of records
Est. 2000
Community established
homes built 2000-2003, median 2001 (FL DOR 2025)
0
Failed listings · 2019
peaked at 3 in 2015
1.9%/yr
Turnover rate
about 2 of 108 homes trade a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Westover Club is a built-out enclave of 108 homes in Windermere, all delivered in a tight window between 2000 and 2003. That uniformity matters: you are shopping a single generation of construction, and price here is driven less by vintage than by what an owner has done with the house since. With a median living area north of 3,400 square feet, the story is condition and updates — original-finish homes and renovated ones can sit far apart on price despite similar bones.

This is a low-turnover, owner-occupied community — roughly 83% carry a homestead exemption — so inventory is thin and listings are episodic rather than constant. For sellers, that scarcity works in your favor when a well-prepared home hits the market. For buyers, patience and readiness to move on the right listing count more than waiting for a wide selection to compare.

Best for

  • Buyers seeking substantial square footage in an established Windermere setting and prepared to act on limited inventory
  • Buyers comfortable budgeting for updates on an original-condition home in exchange for a strong footprint
  • Long-hold owners who value a stable, built-out community over new construction

Probably not for

  • Buyers who want many active listings to compare side by side at once
  • Buyers unwilling to evaluate roof, systems, and finish age before committing
  • Buyers looking for a smaller or lower-maintenance home than the large plans here

The market around Westover Club Ph 01 44/139

Westover Club Ph 01 44/139 is a small community — 14 recorded sales on file, most recently in 2019 — 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 Westover Club Ph 01 44/139 specifically. Momentum Research analysis of MLS records.

If we were buying in Westover Club Ph 01 44/139 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 Westover Club Ph 01 44/139.

Best Buy
Buyers who want a large early-2000s home in Windermere and will move when the right one lists.
Biggest Risk
Similar-looking homes can price very differently depending on deferred maintenance.
Sweet Spot
An updated home near the 3,400-square-foot median where the improvements are documented.
Avoid If
You need broad selection or move-in-ready certainty without vetting condition.

One vintage, many conditions

Because every home dates to a three-year build window, the honest variable here is upkeep and updating, not floor plan era. Kitchens, baths, roofs, and mechanical systems are all reaching the age where an owner has either invested or deferred, and that split is what you will feel most when you tour. Read the improvements carefully — the spread in value tracks the work done, not the square footage on paper.

The homestead share tells you this is a place people stay, which keeps the neighborhood stable but also keeps supply tight. Expect to act decisively rather than to browse; when a home that matches your list appears, the comparison set is small and the decision window is short.

The location and the amenities are priced into every listing in Westover Club Ph 01 44/139. 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 low-turnover community where condition drives price, the value is in reading the house, not the listing photos. We help sellers position updated homes so the work is fully credited, and we help buyers separate a well-maintained property from one carrying deferred costs — the difference that actually sets price in Westover Club.

Westover Club Ph 01 44/139 in 15 seconds.

Best forBuyers who want a large early-2000s home in Windermere and will move when the right one lists.
Biggest advantageTight supply and long-term ownership give well-prepared sellers real leverage.
Biggest riskSimilar-looking homes can price very differently depending on deferred maintenance.
Sweet spotAn updated home near the 3,400-square-foot median where the improvements are documented.
Avoid ifYou need broad selection or move-in-ready certainty without vetting condition.

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 Westover Club Ph 01 44/139 sales matched to your home.

What is your Westover Club Ph 01 44/139 home worth?

Get a no-obligation home value based on real comparable sales in Westover Club Ph 01 44/139, 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 Westover Club Ph 01 44/139?
The Florida DOR 2025 assessment roll shows 108 homes in Westover Club Ph 01 44/139 (public records).
What share of Westover Club Ph 01 44/139 is owner-occupied?
83% of Westover Club Ph 01 44/139 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Westover Club Ph 01 44/139 built?
Homes in Westover Club Ph 01 44/139 were built between 2000 and 2003, with a median year built of 2001 (FL DOR 2025 roll).
Do cash buyers compete in Westover Club Ph 01 44/139?
Cash buyers took 0% of Westover Club Ph 01 44/139 sales in the 12 months ending June 2023 (0 of 3 closings, Stellar MLS).
Who is the best real estate agent for Westover Club Ph 01 44/139?
The best agent for Westover Club Ph 01 44/139 is one who actively works Windermere 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 Westover Club Ph 01 44/139.
How do I find a top Windermere real estate agent who knows Westover Club Ph 01 44/139?
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 Westover Club Ph 01 44/139 and the wider Windermere area.
Can Momentum Realty connect me with an agent for Westover Club Ph 01 44/139?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Westover Club Ph 01 44/139 purchase or sale - no call center and no pressure.
Buyers seeking substantial square footage in an established Windermere setting and prepared to act on limited inventoryExcellent fit
Buyers comfortable budgeting for updates on an original-condition home in exchange for a strong footprintExcellent fit
Long-hold owners who value a stable, built-out community over new constructionExcellent fit
Buyers who want many active listings to compare side by side at onceProbably not
Buyers unwilling to evaluate roof, systems, and finish age before committingProbably not
Buyers looking for a smaller or lower-maintenance home than the large plans hereProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (3 streets, ZIP 34786))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2015 (16 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.

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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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