Winter Run
Homes for Sale in Orlando, FL
All 4,060 homes for sale in ORLANDO, FL · median $384,945 · 146 homes for sale in 32839 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-09-12, 5 recorded sales closed at a median of $303,500, $281 per square foot, a median 18 days on market, sellers accepting 100% of original asking (-2% versus the prior year). Homes listed or recently sold were built 1980 - 1985; 1 of the 8 geocoded homes sit in a FEMA special flood hazard zone (median elevation 95 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $5,060 ($4,390 with the full homestead exemption).
Winter Run right now
🟡 Off the recent peak. The trailing-12-month median ($304K) is down 2.1% from the prior 12 months ($310K) and up 390% since 2012. With about 4 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 12. Confidence: Low (5 and 10 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside Winter Run 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.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Winter Run market snapshot (as of September 12, 2026): the median sale price is about $304K ($281 per sq ft over the trailing 12 months of closed sales), and a median 18 days on market for closed sales. The trailing-12-month median is down 2% from the prior 12 months and up 390% since 2012, computed from record-level Stellar MLS closed sales (5 closings in the current window).
In ZIP 32839 (ORLANDO), 286 homes closed in the last 12 months at a median of $350K ($240/sq ft), down 11.2% year over year, with a median 46 days on market. Right now 69 active and 24 pending listings put supply at about 3.5 months - a balanced market. See the live ZIP 32839 housing market and the Orange County market.
Winter Run is a community of 78 homes in Orlando, Orange County, built between 1980 and 1983 (median 1980.0), with a median living area of about 1,119 square feet. 60% 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 Run. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Winter RunPhotos from Stellar MLS listings in Winter Run; 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 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($304K) IS the median in the snapshot above, and the move from 2025 ($310K) IS the -2.1% one-year change.
Windows contain 0 to 12 sales each (5 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 2006 through 2026. Deemed reliable but not guaranteed.
WINTER RUN Market Scorecard
WINTER RUN is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32839 ZIP is $233,712, about 7.8% below 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 Run Orlando, ORLANDO
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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Winter Run 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.
Recent Developments in Winter Run
Development, infrastructure, retail, and school activity affecting Winter Run, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.
- July 2026Development
Capstone begins construction on The Gateway luxury apartments
Capstone Building Corp began construction on The Gateway, a 270-unit apartment community at 7250 Shadowridge Drive in Orlando, developed by JBL Development. The five-story gated project spans more than 417,000 square feet and is expected to be completed in late 2027. Amenities include a saltwater pool, fitness center, pickleball court, and a clubhouse with a restaurant and bar.
What it may mean for the marketAdds 270 market rate apartments in a five story building with resort style amenities, expanding the local rental housing stock in the Airport Lakes area of south Orlando. The project is about 7 miles southeast of Winter Run, elsewhere in Orange County.
Source: Construction Owners - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The site is about 1 mile east of Winter Run.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 6 miles northwest of Winter Run, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The project is about 6 miles northeast of Winter Run, elsewhere in Orange County.
Source: Florida YIMBY - June 2026Development
Planning board approves zoning for 37-story tower at 170 East Washington Street
Orlando's Municipal Planning Board voted to approve a Planned Development amendment for a 37-story, 425-foot mixed-use tower at 170 East Washington Street across from Lake Eola Park. The project would include 252 residential units, a 221-room hotel, a three-story restaurant, and structured parking. It still requires City Council consideration before construction.
What it may mean for the marketWould add a 37 story tower with 252 residences and a hotel to the downtown skyline, replacing a prior approval for a 7 story hotel and increasing high density housing and parking supply. The project is about 5 miles northeast of Winter Run, elsewhere in Orange County.
Source: Florida YIMBY - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 11 miles southeast of Winter Run.
Source: ClickOrlando
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in the Orlando Metro.
The Winter Run buying strategy.
If we were buying in Winter Run 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 Winter Run.
A closer look at the Winter Run market
At a median of $281 per square foot, Winter Run prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The trailing-12-month median down 2% year over year. Homes that do trade take a median 18 days on market, useful leverage on any listing that has lingered.
The housing stock is 78 homes built between 1980 and 1983, and 60% 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 Run. 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 Run 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 4 factors (7.9). Basis: Long-Term Appreciation +390% since 2012; Recent Direction -2.1% year-over-year; Owner Commitment 60% owner-occupied; Pricing Power 100.0% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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.
Tools for a Winter Run 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 Run sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winter Run, 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 Run home worth?
Get a no-obligation home value based on real comparable sales in Winter Run, 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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Frequently Asked Questions
What is the median home price in Winter Run?
How long do homes in Winter Run take to sell?
How many homes are in Winter Run?
What share of Winter Run is owner-occupied?
When were the homes in Winter Run built?
Have Winter Run home prices gone up?
Who is the best real estate agent for Winter Run?
How do I find a top Orlando real estate agent who knows Winter Run?
Can Momentum Realty connect me with an agent for Winter Run?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 32839)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2006 (85 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 Winter Run with Momentum Realty’s local guides.