Winterpark
Condos for Sale in Naples, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Florida Gulf Coast MLS
As of November 2026, Winterpark in Naples, FL has 23 homes for sale and 1 pending, asking from $199,500 to $329,900 (median $249,900). Over the 12 months ending 2026-11-11, 5 recorded sales closed at a median of $210,000, $162 per square foot, a median 108 days on market, sellers accepting 85% of original asking. Homes listed or recently sold were built 1985–1989; 4 of 24 report an HOA (median $568/mo); 16 of the 24 geocoded homes sit in a FEMA special flood hazard zone (median elevation 7 ft). At the median price and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $2,320 ($1,880 with the full homestead exemption).
| Location | Naples, Collier County, FL · ZIP 34112 |
|---|---|
| Home types (current listings and sales) | condos 100% |
| Sale prices, last 12 months | $210,000 median across 5 closed sales · $162 per sq ft |
| Days on market (closed sales) | 108 median |
| For sale right now | 23 active, 1 pending · median asking $249,900 · 55.2 months of supply |
Data as of November 11, 2026. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winterpark key facts,” movewithmomentum.com/neighborhoods/winterpark, data as of November 11, 2026.
Last 30 days in Winterpark: 11 new listings (median asking $250,000), 1 under contract right now. As of November 11, 2026, Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate.
Homes For Sale Right Now in Winterpark
Live MLS inventory for Winterpark. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 138 daysTop listing
Active · 31 days
Active · 15 days
Active · 0 days
Active · 101 days
Active · 43 days
Active · 8 days
Active · 24 days
Active · 0 days
Active · 141 days
Active · 0 days
Active · 13 days
Active · 49 days
Active · 92 daysActive and pending Winterpark listings as of 2026-11-11, priced high to low. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Tap any home to ask about it.
Every Home for Sale in Winterpark Right Now (24)
All 24 active and pending Winterpark listings with a detail page, newest first, refreshed twice a day from the MLS.
- 4100 Looking Glass Ln 7 · $239,900 · 2 bd / 2 ba · listed Nov 8, 2026 · listed by Realty One Group MVP
- 4200 Looking Glass Ln 4207 · $229,000 · 2 bd / 2 ba · listed Nov 5, 2026 · listed by William Raveis Real Estate
- 4230 Jack Frost Ct 7 · $259,900 · 2 bd / 2 ba · listed Oct 28, 2026 · listed by Premier Sotheby's Int'l Realty
- 4065 Northlight Dr 1807 · $250,000 · 2 bd / 2 ba · listed Oct 27, 2026 · listed by Coldwell Banker Realty
- 4001 Ice Castle Way 3605 · $265,000 · 2 bd / 2 ba · listed Oct 11, 2026 · listed by Premiere Plus Realty Company
- 4030 Northlight Dr · $309,900 · 2 bd / 2 ba · listed Oct 9, 2026 · listed by Premier Property Management
- 4079 Northlight Dr 2 · $220,000 · 2 bd / 2 ba · listed Oct 3, 2026 · listed by Downing Frye Realty Inc.
- 4096 Northlight Dr 1709 · $239,000 · 2 bd / 2 ba · listed Sep 29, 2026 · listed by Blue Lighthouse Realty Inc
- 3400 Frosty Way 5 · $299,000 · 2 bd / 2 ba · listed Sep 24, 2026 · listed by Realty One Group MVP
- 4073 Northlight Dr 1803 · $249,000 · 2 bd / 2 ba · listed Sep 19, 2026 · listed by Brodersen LLC
- 4100 Looking Glass Ln 3008 · $255,000 · 2 bd / 2 ba · listed Sep 11, 2026 · listed by Naples Homes and Rentals Inc
- 4038 Northlight Dr 1506 · $249,900 · 2 bd / 2 ba · listed Sep 11, 2026 · listed by Marzucco Real Estate
- 4001 Ice Castle Way 1 · $215,000 · 2 bd / 2 ba · listed Sep 11, 2026 · listed by Premiere Plus Realty Company
- 4230 Jack Frost Ct 4402 · $230,000 · 2 bd / 2 ba · listed Aug 30, 2026 · listed by William Raveis Real Estate
- 4027 Northlight Dr 4 · $259,900 · 2 bd / 2 ba · listed Aug 28, 2026 · listed by Coffey Real Estate Agency LLC
- 3574 Antarctic Cir 2107 · $255,000 · 2 bd / 2 ba · listed Aug 17, 2026 · listed by KW Elevate Luxury
- 4140 Looking Glass Ln 7 · $329,900 · 2 bd / 2 ba · listed Aug 13, 2026 · listed by Keller Williams Realty Naples
- 3420 Frosty Way 4902 · $262,000 · 2 bd / 2 ba · listed Aug 13, 2026 · listed by Premiere Plus Realty Company
- 4031 Ice Castle Way 3306 · $250,000 · 2 bd / 2 ba · listed Aug 13, 2026 · listed by Realty World Top Producers Rlt
- 3532 Antarctic Cir 2216 · $248,000 · 2 bd / 2 ba · listed Aug 13, 2026 · listed by Re/Max Alliance Group
- 4050 Ice Castle Way 2812 · $239,000 · 2 bd / 2 ba · listed Aug 13, 2026 · listed by Waterfront Realty Group Inc
- 3816 Snowflake Ln 1303 · $199,999 · 2 bd / 2 ba · listed Aug 13, 2026 · listed by Broker Brothers LLC
- 4200 Looking Glass Ln 4204 · $199,500 · 2 bd / 2 ba · listed Aug 13, 2026 · listed by Portside Property Group
- 4100 Looking Glass Ln 3002 · $240,000 · 2 bd / 2 ba · pending · listed Aug 13, 2026 · listed by Saggio Realty, Inc
Winterpark's numbers describe a small, older condo/villa-scale product rather than a single-family subdivision — a median living area of 1,246 square feet and a build window clustered between 1985 and 1990 tells you this is compact, established housing stock, not new construction. At a median price of $236,250 and median price per square foot of $189.61, the math works out to modest, straightforward units where condition and updates likely explain most of the spread buyers will see listing to listing.
The posture right now is soft. A year-over-year change of -9.1% alongside a median days on market of just over 80 and a market heat score of 10 all point the same direction: this is a buyer's market with time to negotiate. Sellers here should price to the current data, not last year's comps, and buyers can afford to be patient and specific about what they want before writing an offer.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
Winterpark market snapshot (as of November 11, 2026): the median sale price is about $210K ($162 per sq ft over the trailing 12 months of closed sales), and a median 108 days on market for closed sales.
Winterpark is a modest, older Naples community of 470 homes built mostly in the second half of the 1980s, with a homestead share of 28.1% suggesting a meaningful share of non-primary ownership among current owners.
The setting & the homes.
Aerial and on-site photos of Winterpark. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
WinterparkWinterparkWinterparkWinterparkWinterparkWinterparkWinterparkWinterparkPhotos from Florida Gulf Coast MLS listings in Winterpark; content deemed reliable but not guaranteed.
Who Winterpark is best for.
Best for
- Buyers prioritizing a lower purchase price in Naples over unit size or amenities
- Investors or secondary-home buyers comfortable with a market where a large share of owners are non-homestead
- Buyers with flexibility on timeline who can use a slower market to negotiate on price or terms
Probably not for
- Buyers who want a community clubhouse, pool, or organized recreational amenities included
- Buyers seeking larger living space, given the median size runs near 1,246 square feet
- Sellers expecting quick turnaround, given a median days-on-market running past 80
Winterpark on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Florida Gulf Coast MLS. Map data © OpenStreetMap contributors.
The Winterpark buying strategy.
If we were buying in Winterpark today, this is the order of operations we would run for our clients.
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.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
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 Winterpark.
An older, compact community finding its price
With a median year built of 1986 and living areas centered around 1,246 square feet, Winterpark reads as an entry point into Naples rather than a move-up community. The 24 closings in the current window is a thin enough sample that any single sale — a well-updated unit or a distressed one — can swing the visible median, so buyers and sellers should treat the $236,250 figure as a directional marker, not a hard ceiling or floor.
No community amenities are identified from current MLS listings, which means whatever draws a buyer here is likely the price point, the location within Naples, or the unit itself rather than a clubhouse or recreational package. That absence is worth confirming directly with any HOA documents rather than assuming, since MLS listing data does not always capture every amenity a community may have.
The location and the amenities are priced into every listing in Winterpark. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A market with a heat score this low and days on market stretching past 80 rewards buyers who negotiate from real data rather than list price, and rewards sellers who price precisely to move within that window — we track both sides of that line in Winterpark and price accordingly.
Winterpark in 15 seconds.
Tools for a Winterpark buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Winterpark sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winterpark, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winterpark home worth?
Get a no-obligation home value based on real comparable sales in Winterpark, 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 all homes for sale in Naples →
Recently off market in Winterpark
Homes in Winterpark that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 8 on record.
- 3420 Frosty Way 12 · off market
- 3420 Frosty Way 4910 · off market
- 4027 Northlight Dr 4 · off market
- 4070 Looking Glass Ln 3101 · off market
- 4079 Northlight Dr 1802 · off market
- 4150 Looking Glass Ln 3903 · off market
- 4180 Looking Glass Ln 4102 · off market
- 4240 Jack Frost Ct 6 · off market
Frequently Asked Questions
What is the median home price in Winterpark?
How long do homes in Winterpark take to sell?
Who is the best real estate agent for Winterpark?
How do I find a top Naples real estate agent who knows Winterpark?
Can Momentum Realty connect me with an agent for Winterpark?
Should you buy in Winterpark?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Winterpark with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Florida Gulf Coast MLS, refreshed twice daily (last: November 11, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending November 11, 2026 |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-11-11 |
| Historical depth | Closed-sale records back to 2026 (5 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 Florida Gulf Coast 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. A Momentum agent can price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Winterpark fits the bigger picture — live prices, inventory, and Momentum Scores: