Windsong Preserve Point in Winter Park

Windsong Preserve Point
Homes for Sale in Winter Park, FL

All 394 homes for sale in Winter Park, FL · median $636,250 · 169 homes for sale in 32789 · Orange County homes for sale

Community in Winter Park · Orange County · ZIP 32789
25 homesBuilt 2002–2015
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Built fromLive Stellar MLS dataFL DOR public recordsUpdated twice daily

As of November 2026, the MLS records 1 closed sale in Windsong Preserve Point in Winter Park, FL, the most recent in August 2026. Across Winter Park as a whole, 887 homes closed in the last 12 months at a median of $499,000, 37 median days on market, with 326 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,320 ($7,650 with the full homestead exemption).

Live · Windsong Preserve Point Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
Ownership and context
74%
Owner-occupied · Windsong Preserve Point
20 of 27 parcels homesteaded (FL DOR 2025)
26%
Non-owner-occupied · Windsong Preserve Point
incl. 15% trust or LLC-held · 100% out-of-state
25
Homes in the community
plus 2 vacant residential lots · 27 residential parcels (FL DOR 2025)
Track record · 0 years of records
2002–2015
Years homes were built
median 2008 · county roll (FL DOR 2025)
Jon Brooks, Co-Founder of Momentum Realty
Jon's Read · written October 26, 2026

Windsong Preserve Point is a small, gated enclave of just 25 homes in Winter Park, built between 2002 and 2015. What sets price here is square footage and condition, not location novelty - with a median living area north of 5,500 square feet, these are substantial houses, and the spread between an updated home and a dated one will be wide. Expect price to be driven by how move-in ready a given house is far more than by any published range.

As of September 2026, there are no active listings. That is the headline for both sides: this is a hold-and-stay community with low turnover, reinforced by a homestead share near three-quarters. For a buyer, patience and readiness matter - when a home does come up, you need to be positioned to move. For a seller, scarcity works in your favor, but only if the home is priced and presented to the standard the square footage implies.

Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.

Nearby homes for sale

No active listings inside Windsong Preserve Point 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.

620 VIRGINIA DRIVE
$3.89M · 0.4 mi away
6 bd · 5 ba · 4,677 sqft
620 VIRGINIA DRIVE
Listed by ONE LUXURY INTERNATIONAL LLC
541 VIRGINIA DRIVE
$5.70M · 0.4 mi away
4 bd · 3.5 ba · 4,725 sqft
541 VIRGINIA DRIVE
Listed by EXP REALTY LLC
1735 DEMETREE DRIVE
$1.05M · 0.4 mi away
4 bd · 3 ba · 2,787 sqft
1735 DEMETREE DRIVE
Listed by EXP REALTY LLC
609 S PHELPS AVENUE
$2.80M · 0.4 mi away
5 bd · 4.5 ba · 4,018 sqft
609 S PHELPS AVENUE
Listed by ONE LUXURY INTERNATIONAL LLC
555 E LAKE SUE AVENUE
$2M · 0.4 mi away
4 bd · 4 ba · 3,776 sqft
555 E LAKE SUE AVENUE
Listed by KELLER WILLIAMS Winter Park
1825 WHITEHALL DRIVE
$3.19M · 0.5 mi away
4 bd · 5 ba · 4,311 sqft
1825 WHITEHALL DRIVE
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

A gated, 25-home community of large houses built across roughly a decade and a half, with most owners occupying as primary residences and essentially no inventory changing hands right now.

Stellar MLS sales records identify 8 homes in Windsong Preserve Point that have changed hands since 2010, built between 2001 and 2012 (median 2006), with a median living area of about 7,160 sq ft and a typical 5-bedroom, 6-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

  • Buying to settle in for the long term in a gated, low-turnover enclave
  • Needing substantial living space well above average square footage
  • Buyers who can stay ready and move quickly when a rare listing appears

Probably not for

  • Needing to close on a fixed or near-term timeline
  • Looking for a smaller or lower-maintenance home
  • Wanting active inventory and several options to compare right now

The market around Windsong Preserve Point

Windsong Preserve Point is too small for its own price trend, so here is the market around it.

In ZIP 32789, 239 homes are on the market and 23% are under contract — a steady corner of Winter Park.

Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).

In ZIP 32789 (Winter Park), 111 homes closed in the last 12 months at a median of $627K ($396/sq ft), down 21.6% year over year, with a median 42 days on market. Right now 34 active and 4 pending listings put supply at about 3.7 months - a buyer's market. See the live ZIP 32789 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Windsong Preserve Point specifically. Momentum Research analysis of MLS records.

Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.

If we were buying in Windsong Preserve Point 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 Windsong Preserve Point.

Best Buy
Buyers who want a large home in a small, gated Winter Park enclave and can wait for inventory.
Biggest Risk
With no active listings, you may wait a long time for the right home to appear.
Sweet Spot
An updated, move-in-ready home where the square footage is matched by condition.
Avoid If
You need to buy on a fixed timeline or want a smaller, lower-maintenance house.

A small, stay-put enclave

The scale here is the story. A median living area of about 5,500 square feet puts these firmly in the large-home category, and the 2002 - 2015 build window means construction is relatively current - not new, but past the oldest systems-and-finishes concerns. Because the community is only 25 homes, no two sales are truly comparable; condition, updates, and lot will swing value more than any neighborhood average.

Amenities reported across MLS listings include a park, playground, pool, and a security gate with security lights. For a gated community this small, that is a reasonable package, but access and current status should be confirmed directly with the HOA. The high homestead share tells you this is a community people buy into and keep, which is why active inventory sits at zero.

“

The location and the amenities are priced into every listing in Windsong Preserve Point. 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 25-home community with no active listings, the deals happen before they hit the open market or in the narrow window when one appears. We track this enclave closely, know how to read condition against the large median footprint, and can tell you honestly whether a specific home is priced to its finish level. For sellers, we build the pricing and presentation case that scarcity rewards; for buyers, we keep you ready for the rare opening.

Windsong Preserve Point in 15 seconds.

Best forBuyers who want a large home in a small, gated Winter Park enclave and can wait for inventory.
Biggest advantageScarcity and low turnover - most owners stay, so quality homes rarely sit.
Biggest riskWith no active listings, you may wait a long time for the right home to appear.
Sweet spotAn updated, move-in-ready home where the square footage is matched by condition.
Avoid ifYou need to buy on a fixed timeline or want a smaller, lower-maintenance house.
The takeaway

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

What is your Windsong Preserve Point home worth?

Get a no-obligation home value based on real comparable sales in Windsong Preserve Point, 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.
Windsong Preserve Point key facts
LocationWinter Park, Orange County, FL · ZIP 32789
Homes in the community25 (FL DOR 2025 assessment roll)
Years built2002–2015 (median 2008.0)
Typical living area5,500 sq ft (median)
Amenities listed by sellersPark, Playground, Pool, Security Gate, Security Lights, Security System
For sale right now0 active, 0 pending
Owner-occupied (homestead) share74%

Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2026 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windsong Preserve Point key facts,” movewithmomentum.com/neighborhoods/windsong-preserve-point-winter-park, data as of November 13, 2026.

Housing distress & ownership in Windsong Preserve Point, Winter Park

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
0.0%
0 of 1 listings
Distress share trend - 0.0% now (2026-08-12 → 2026-10-25)

Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.

Email me new listings in Windsong Preserve Point

One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.

Equal Housing Opportunity. Every community is open to everyone; alerts are about homes, never about who lives here.

Ask an agent about Windsong Preserve Point

Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windsong Preserve Point will answer, and the answer is published on this page for the next buyer.

Property facts only: homes, fees, rules, commute. Every community is open to everyone; agents do not answer questions about who lives here.

The real cost & risk here

Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.

$2,537/mo
Orange County typical true cost to own
$117/mo
Orange County typical home insurance
Check CDD
Confirm before you offer

County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.

Frequently Asked Questions

How many homes are in Windsong Preserve Point?
The Florida DOR 2025 assessment roll shows 25 homes plus 2 vacant residential lots in Windsong Preserve Point (public records).
What share of Windsong Preserve Point is owner-occupied?
74% of Windsong Preserve Point parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Windsong Preserve Point built?
Homes in Windsong Preserve Point were built between 2002 and 2015, with a median year built of 2008.0 (FL DOR 2025 roll).
Who is the best real estate agent for Windsong Preserve Point?
The best agent for Windsong Preserve Point is one who actively works Winter Park 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 Windsong Preserve Point.
How do I find a top Winter Park real estate agent who knows Windsong Preserve Point?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Windsong Preserve Point and the wider Winter Park area.
Can Momentum Realty connect me with an agent for Windsong Preserve Point?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Windsong Preserve Point purchase or sale - no call center and no pressure.
Where is Windsong Preserve Point, and what county is it in?
Windsong Preserve Point is in Winter Park, Orange County, FL, ZIP 32789.
Buying to settle in for the long term in a gated, low-turnover enclaveExcellent fit
Needing substantial living space well above average square footageExcellent fit
Buyers who can stay ready and move quickly when a rare listing appearsExcellent fit
Needing to close on a fixed or near-term timelineProbably not
Looking for a smaller or lower-maintenance homeProbably not
Wanting active inventory and several options to compare right nowProbably not

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: October 26, 2026)
Housing stock & ownershipFlorida DOR assessment roll (street-list match (1 streets, ZIP 32789))
Under-contract sharesStellar MLS records, as of 2026-09-20
Historical depthClosed-sale records back to 2026 (1 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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Nearby Communities

Explore more neighborhoods near Windsong Preserve Point with Momentum Realty’s local guides.

WLWindsong Lookout Landing0.3 mi awayTimberlane Shores0.4 mi away · 193 homes, built 1925–24, 1 for saleLake Virginia0.4 mi awayWindsong Elizabeths Walk 43 810.4 mi away · 69 homes, built 2000–16Windsong Knowles Place0.4 mi away · 23 homes, built 2008–16SEStonehurst Estates0.5 mi away · 59 homes, built 1947–24WWaterbridge0.5 mi away · 28 homes, built 1980–86, 2 for sale

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