Winter Park Pines
Homes for Sale in Winter Park, FL
All 356 homes for sale in Winter Park, FL · median $697,000 · 124 homes for sale in 32792 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of October 2026, winter park pines in Winter Park, FL has 9 homes for sale and 4 pending, asking from $494,900 to $798,000 (median $669,900). Over the 12 months ending 2026-09-20, 23 recorded sales closed at a median of $600,000, $324 per square foot, a median 19 days on market, sellers accepting 98% of original asking (+13% versus the prior year). Homes listed or recently sold were built 1963 - 1971; 5 of 25 report an HOA (median $5/mo); none of the 25 geocoded homes sit in a FEMA special flood hazard zone (median elevation 92 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,000 ($9,330 with the full homestead exemption).
Homes For Sale Right Now in Winter Park Pines
Live MLS inventory for Winter Park Pines. 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 and pending Winter Park Pines listings as of 2026-10-04, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026. Tap any home to ask about it.
Every Home for Sale in Winter Park Pines Winter Park Right Now (13)
All 13 active and pending Winter Park Pines Winter Park listings with a detail page, newest first, refreshed twice a day from the MLS.
- 266 N Ranger Boulevard · $724,900 · 4 bd / 3 ba · listed Sep 28, 2026 · listed by Elite Property Real Estate Llc
- 739 Roughbeard Road · $780,000 · 5 bd / 3 ba · listed Sep 24, 2026 · listed by Serhant
- 274 N Ranger Boulevard · $659,900 · 3 bd / 2 ba · listed Sep 10, 2026 · listed by Explore Florida Realty Services Llc
- 410 Saint Dunstan Way · $500,000 · 3 bd / 2 ba · pending · listed Aug 28, 2026 · listed by Coldwell Banker Realty
- 724 Monmouth Way · $798,000 · 5 bd / 3.5 ba · listed Aug 23, 2026 · listed by Central Tower Properties
- 2824 Prince John Road · $475,000 · 2 bd / 2 ba · pending · listed Aug 23, 2026 · listed by Bhhs Florida Realty
- 2833 Prince John Road · $669,000 · 4 bd / 2 ba · pending · listed Aug 12, 2026 · listed by Networth Realty Of Orlando, Llc
- 433 Gilbert Road · $669,900 · 3 bd / 2 ba · listed Aug 3, 2026 · listed by Keller Williams Winter Park
- 2715 Prince John Road · $494,900 · 3 bd / 2 ba · listed Jul 29, 2026 · listed by Via Properties Llc
- 722 S Ranger Boulevard · $775,000 · 4 bd / 3 ba · pending · listed Jul 10, 2026 · listed by Charles Rutenberg Realty Orlando
- 715 S Ranger Boulevard · $695,000 · 4 bd / 3 ba · listed Jul 6, 2026 · listed by Dahlia Realty Group
- 2708 Lion Heart Road · $612,500 · 3 bd / 2 ba · listed Jul 6, 2026 · listed by Equitypro Llc
- 2758 Banchory Road · $619,500 · 3 bd / 2.5 ba · listed Jul 6, 2026 · listed by Mr Vargas Property Management Llc
Winter Park Pines right now
🔴 Seller-leaning market. 2.9 months of supply and 33% of the inventory already under contract give sellers the pressure advantage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: Very High (12 active and pending listings, 23 closed sales in 12 months).
🟢 Still climbing. The trailing-12-month median ($600K) is up 13.2% from the prior 12 months ($530K) and up 265% since 2012. With about 20 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: High (23 and 29 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 5, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Winter Park Pines market snapshot (as of September 20, 2026): the median sale price is about $600K ($325 per sq ft over the trailing 12 months of closed sales), a median 19 days on market for closed sales, and 2.9 months of supply, a seller-leaning market. The trailing-12-month median is up 13% from the prior 12 months and up 265% since 2012, computed from record-level Stellar MLS closed sales (23 closings in the current window).
In ZIP 32792 (Winter Park), 617 homes closed in the last 12 months at a median of $408K ($256/sq ft), down 1.9% year over year, with a median 28 days on market. Right now 49 active and 13 pending listings put supply at about 3.4 months - a balanced market. See the live ZIP 32792 housing market and the Orange County market.
County records show 29 qualified sales in winter park pines across 2024 - 2025 (12 in 2024, 17 in 2025), median $575,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Winter Park Pines: of 21 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Winter Park.
Winter Park Pines is a community of 289 homes in Winter Park, Orange County, built between 1960 and 2007 (median 1965), with a median living area of about 1,813 square feet. 79% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Winter Park Pines. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Winter Park Pines; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($600K) IS the median in the snapshot above, and the move from 2025 ($530K) IS the +13.2% one-year change.
Windows contain 0 to 44 sales each (23 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026. Deemed reliable but not guaranteed.
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.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
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.
31% of homes for sale in Winter Park Pines are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-05).
Winter Park Pines Market Scorecard
Winter Park Pines is currently a seller's market. About 3.5 months of supply, a median asking price of $669,900, and homes go under contract in about 42 days.
Typical home value in the 32792 ZIP is $394,153, about 20.1% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in winter park pines, Winter Park
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
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.
Winter Park Pines on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Winter Park Pines
- Pool · reported on 8 of 17 listings
- Park · reported on 6 of 17 listings
- Playground · reported on 6 of 17 listings
- Tennis Court(s) · reported on 6 of 17 listings
- Trail(s) · reported on 4 of 17 listings
- Golf Carts OK · reported on 2 of 17 listings
- Golf · reported on 2 of 17 listings
- Golf Course · reported on 2 of 17 listings
- Pickleball Court(s) · reported on 2 of 17 listings
- Secured Garage/Parking · reported on 1 of 17 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Aloma Elem · Elementary
- Glenridge Middle · Middle
- Winter Park High · High
Zoned schools reflect the assignments reported on recent Winter Park Pines listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winter Park Pines address.
Shop the zone: Homes zoned for Winter Park High High School
The Winter Park Pines buying strategy.
If we were buying in Winter Park Pines 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 Winter Park Pines.
A closer look at the Winter Park Pines market
At a median of $325 per square foot, Winter Park Pines prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 2.9 months of supply, a seller-leaning market and the trailing-12-month median up 13% year over year. Homes that do trade take a median 19 days on market, useful leverage on any listing that has lingered.
The housing stock is 289 homes built between 1960 and 2007, and 79% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Winter Park Pines. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Winter Park Pines buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 5 factors (8.5). Basis: Long-Term Appreciation +265% since 2012; Recent Direction +13.2% year-over-year; Liquidity & Demand 2.9 months of supply; Owner Commitment 79% owner-occupied; Pricing Power 97.6% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $5/month · median of 95 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $5 per month - the median AssociationFee across 95 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Winter Park Pines 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 Winter Park Pines sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winter Park Pines, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winter Park Pines home worth?
Get a no-obligation home value based on real comparable sales in Winter Park Pines, 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 Winter Park →
Recently off market in winter park pines
Homes in winter park pines 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. 6 on record.
- 2803 Banchory Road · off market
- 333 Cornwall Road · off market
- 505 Cornwall Road · off market
- 528 Saint Dunstan Way · off market
- 729 Monmouth Way · off market
- 744 Cornwall Road · off market
Frequently Asked Questions
What is the median home price in Winter Park Pines?
How long do homes in Winter Park Pines take to sell?
Is Winter Park Pines a buyer's or seller's market right now?
How many homes are in Winter Park Pines?
What share of Winter Park Pines is owner-occupied?
When were the homes in Winter Park Pines built?
Have Winter Park Pines home prices gone up?
Who is the best real estate agent for Winter Park Pines?
How do I find a top Winter Park real estate agent who knows Winter Park Pines?
Can Momentum Realty connect me with an agent for Winter Park Pines?
Where is Winter Park Pines, and what county is it in?
Is Winter Park Pines in a flood zone?
Is Winter Park Pines a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 4, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2005 (350 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?
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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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See how winter park pines fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Winter Park Pines
- Home values · What homes in Winter Park Pines actually sell for
- Find an agent · How to choose the best real estate agent in Winter Park Pines
Nearby Communities
Explore more neighborhoods near Winter Park Pines with Momentum Realty’s local guides.