Winter Park Pines
Homes for Sale in Winter Park, FL
All 394 homes for sale in Winter Park, FL · median $636,250 · 158 homes for sale in 32792 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, winter park pines in Winter Park, FL has 4 homes for sale and 5 pending, asking from $619,500 to $724,900 (median $667,000). Over the 12 months ending 2026-11-13, 13 recorded sales closed at a median of $588,000, $325 per square foot, a median 25 days on market, sellers accepting 99% of original asking. Homes listed or recently sold were built 1963 - 1970; 6 of 21 report an HOA (median $5/mo); none of the 21 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 $9,800 ($9,130 with the full homestead exemption).
Last 30 days in Winter Park Pines: 5 under contract right now, 3 closed sales (median $535,000). As of November 12, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
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 · 46 daysTop listing
Active · 163 days
Active · 36 days
Active · 419 days
Under Contract · 89 days
Under Contract · 69 days
Under Contract · 54 days
Under Contract · 9 days
Under Contract · 39 daysActive and pending Winter Park Pines listings as of 2026-11-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2024 through 2026. Tap any home to ask about it.
Price here is driven by condition and lot, not square footage alone. Homes date from 1960 through 2007 with a median build around 1965 and a median footprint near 1,813 square feet, so you are buying into an established, mid-century housing stock where renovated interiors command a real premium over dated ones. At a $600,000 median and roughly $324 per square foot, expect a wide spread between updated and original homes carrying the same address.
The current posture is seller-leaning but not frantic. With 2.9 months of supply, only 8 active listings against 289 homes, and a median 19 days on market, well-prepared listings move quickly, while anything overpriced or deferred sits. Buyers should come ready to act on the right house and underwrite renovation costs honestly; sellers have leverage but still need condition and pricing to line up.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Winter Park Pines right now
🔴 Seller-leaning market. 1.5 months of supply and 56% 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 November 13, 2026. Confidence: High (9 active and pending listings, 13 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 14, 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 November 13, 2026): the median sale price is about $588K ($325 per sq ft over the trailing 12 months of closed sales), a median 25 days on market for closed sales, and 1.5 months of supply, a seller-leaning market.
County records show 34 qualified sales in winter park pines across 2024 - 2025 (16 in 2024, 18 in 2025), median $598,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
In ZIP 32792 (Winter Park), 236 homes closed in the last 12 months at a median of $447K ($264/sq ft), down 7.0% year over year, with a median 32 days on market. Right now 9 active and 11 pending listings. See the live ZIP 32792 housing market and the Orange County market.
Flood zones in Winter Park Pines: of 19 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 342 homes in Winter Park, Orange County, built between 1960 and 2007 (median 1965.0), with a median living area of about 1,814 square feet. 79% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Winter Park Pines is an established, low-turnover pocket in Winter Park where mid-century homes anchor the stock and a near-79% homestead share signals an owner-occupied, hold-oriented street rather than a churn of rentals.
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
Winter Park PinesWinter Park PinesWinter Park PinesWinter Park PinesWinter Park PinesWinter Park PinesWinter Park PinesWinter Park PinesPhotos from Stellar MLS listings in Winter Park Pines; content deemed reliable but not guaranteed.
Who Winter Park Pines is best for.
Best for
- Buying to hold long term in an established, owner-occupied part of Winter Park
- Buyers who want tennis, pickleball, trails, and golf access close to home
- Buyers willing to renovate a mid-century home to build in value
Probably not for
- Needing recent or new construction rather than 1960s-era housing stock
- Requiring large square footage well above the roughly 1,813-foot median
- Shopping on a tight timeline with little inventory and fast-moving listings
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 contributors.
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.
An established mid-century enclave
The amenity list reported across MLS listings is unusually deep for a neighborhood of this vintage: pool, park, playground, tennis and pickleball courts, trails, and golf, plus golf-cart access and secured garage/parking. Verify current access and any HOA terms before you count on them, but the spread points to a community built for people who want to stay outside and stay put.
The numbers tell a long-hold story. Values are up 13.2% year over year and 265% since 2012, and with 23 closings in the window against 289 total homes, turnover is thin. That scarcity supports the seller-leaning band, but it also means patience: the right floor plan or updated kitchen may not come up often, and when it does it tends to clear fast.
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 3 factors (8.6). Basis: Liquidity & Demand 1.5 months of supply; Owner Commitment 79% owner-occupied; Pricing Power 99.3% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a thin, condition-driven market like this, the margin is in reading each house honestly. We help buyers separate a true renovation from cosmetic lipstick and underwrite the work before the offer, and we help sellers hit the narrow window where a well-prepped home moves inside the median 19 days instead of lingering. With only a handful of listings active at any time, knowing what is coming matters as much as what is listed.
Winter Park Pines in 15 seconds.
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. 12 on record.
- 2708 Lion Heart Road · off market
- 2715 Prince John Road · off market
- 274 N Ranger Boulevard · off market
- 2803 Banchory Road · off market
- 2833 Prince John Road · off market
- 333 Cornwall Road · off market
- 410 Saint Dunstan Way · off market
- 505 Cornwall Road · off market
| Location | Winter Park, Orange County, FL · ZIP 32792 |
|---|---|
| Homes in the community | 342 (FL DOR 2025 assessment roll) |
| Years built | 1960–2007 (median 1965.0) |
| Typical living area | 1,814 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Pool, Park, Playground, Tennis Court(s), Golf Course, Pickleball Court(s) |
| Sale prices, last 12 months | $588,000 median across 13 closed sales · $325 per sq ft |
| Days on market (closed sales) | 25 median |
| For sale right now | 4 active, 5 pending · median asking $667,000 · 1.5 months of supply |
| Owner-occupied (homestead) share | 79% |
Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2024 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winter Park Pines key facts,” movewithmomentum.com/neighborhoods/winter-park-pines-winter-park, data as of November 13, 2026.
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 November 2026 through November 2026. Deemed reliable but not guaranteed.
Every Home for Sale in Winter Park Pines Winter Park Right Now (9)
All 9 active and pending Winter Park Pines Winter Park listings with a detail page, newest first, refreshed twice a day from the MLS.
- 257 Lincolnshire Road · $550,000 · 3 bd / 2 ba · pending · listed Oct 29, 2026 · listed by Keller Williams Winter Park
- 518 Gilbert Road · $639,000 · 3 bd / 2 ba · listed Oct 8, 2026 · listed by Palmano Group Re Brokerage Llc
- 266 N Ranger Boulevard · $724,900 · 4 bd / 3 ba · listed Sep 28, 2026 · listed by Elite Property Real Estate Llc
- 433 Gilbert Road · $669,900 · 3 bd / 2 ba · pending · listed Sep 9, 2026 · listed by Keller Williams Winter Park
- 2824 Prince John Road · $475,000 · 2 bd / 2 ba · pending · listed Aug 23, 2026 · listed by Bhhs Florida Realty
- 724 Monmouth Way · $759,675 · 5 bd / 3.5 ba · pending · listed Aug 23, 2026 · listed by Central Tower Properties
- 722 S Ranger Boulevard · $775,000 · 4 bd / 3 ba · pending · listed Aug 16, 2026 · listed by Charles Rutenberg Realty Orlando
- 715 S Ranger Boulevard · $695,000 · 4 bd / 3 ba · listed Aug 15, 2026 · listed by Dahlia Realty Group
- 2758 Banchory Road · $619,500 · 3 bd / 2.5 ba · listed Aug 15, 2026 · listed by Mr Vargas Property Management Llc
Recently sold in Winter Park Pines Winter Park
- 333 Cornwall Road · sold $535,000
- 2833 Prince John Road · sold $629,000
- 410 Saint Dunstan Way · sold $525,000
- 744 Cornwall Road · sold $610,000
- 2803 Banchory Road · sold $430,000
- 275 N Ranger Boulevard · sold $759,000
- 528 Saint Dunstan Way · sold $536,000
- 729 Monmouth Way · sold $793,500
- 505 Cornwall Road · sold $670,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
More Winter Park home searches
- All homes for sale in Winter Park, FL
- Homes for sale in Orange County, FL
- Gated communities in Winter Park
- Homes under $300K in Winter Park
- 4-bedroom homes for sale in Winter Park
- Winter Park home values: what is my house worth?
- ZIP 32792 housing scorecard
Winter Park guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
- New construction
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
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What it really costs to own in Winter Park Pines
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | MLS listings here mostly enter dues as billed annually, but the median entry is only $60/year across 5 listings (2026-11-14), which usually means a quarterly or monthly amount was entered as annual. Ask the association for the current dues. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Orange County is $1,409/yr (4,204 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 19 listing addresses checked against the FEMA flood map, 100% sit outside the high-risk zone. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 1965 across 16 listings. An original roof here would be about 61 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Winter Park Pines
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.
Ask an agent about Winter Park Pines
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Winter Park Pines will answer, and the answer is published on this page for the next buyer.
21% of homes for sale in ZIP 32792 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 (2026-11-14).
Winter Park Pines Market Scorecard
Winter Park Pines is currently a strong seller's market. About 1.5 months of supply, a median asking price of $667,000, and homes go under contract in about 104 days.
Typical home value in the 32792 ZIP is $394,707, about 19.8% 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.
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?
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?
Should you buy in Winter Park Pines?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: November 12, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending November 13, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (6 streets, ZIP 32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-11-13 |
| Historical depth | Closed-sale records back to 2024 (14 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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