WINFIELD
Homes for Sale in MAITLAND, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
WINFIELD right now
🟡 Balanced market. 3.3 months of supply and 25% of the inventory already under contract put buyers and sellers on roughly even footing.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 August 2, 2026. Confidence: Medium (4 active and pending listings, 9 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($415K) is down 10.3% from the prior 12 months ($462K) and up 246% since 2012. With about 5 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 August 2. Confidence: Medium (9 and 6 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 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
WINFIELD market snapshot (as of August 2, 2026): the median sale price is about $415K ($227 per sq ft over the trailing 12 months of closed sales), a median 14 days on market for closed sales, and 3.3 months of supply, a balanced market. The trailing-12-month median is down 10% from the prior 12 months and up 246% since 2012, computed from record-level Stellar MLS closed sales (9 closings in the current window).
WINFIELD is a community of 224 homes in MAITLAND, Orange County, built between 1995 and 1999 (median 1997), with a median living area of about 1,751 square feet. 65% 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 WINFIELD. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WINFIELDPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($415K) IS the median in the snapshot above, and the move from 2025 ($462K) IS the -10.3% one-year change.
Windows contain 0 to 14 sales each (9 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.
WINFIELD Market Scorecard
WINFIELD is currently a strong seller's market. About 2.2 months of supply, a median asking price of $464,950, and homes go under contract in about 54 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in WINFIELD, MAITLAND
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 August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in WINFIELD
Live MLS inventory for WINFIELD. 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 · 119 daysTop listing
Active · 1 days
Pending · 30 days
Pending · 13 days
Pending · 5 daysActive and pending WINFIELD listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026. Tap any home to ask about it.
WINFIELD 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 WINFIELD
- Playground · reported on 4 of 9 listings
- Deed Restrictions · reported on 3 of 9 listings
- Community Mailbox · reported on 1 of 9 listings
- Vehicle Restrictions · reported on 1 of 9 listings
- No Truck/RV/Motorcycle Parking · reported on 1 of 9 listings
- Park · reported on 1 of 9 listings
- Dog Park · reported on 1 of 9 listings
- Security Lights · reported on 1 of 9 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
- Lake Sybelia Elem · Elementary
- Lockhart Middle · Middle
- Edgewater High · High
Zoned schools reflect the assignments reported on recent WINFIELD 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 WINFIELD address.
The WINFIELD buying strategy.
If we were buying in WINFIELD 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 WINFIELD.
A closer look at the WINFIELD market
At a median of $227 per square foot, WINFIELD 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 3.3 months of supply, a balanced market and the trailing-12-month median down 10% year over year. Homes that do trade take a median 14 days on market, useful leverage on any listing that has lingered.
The housing stock is 224 homes built between 1995 and 1999, and 65% 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 WINFIELD. 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 WINFIELD 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 (6.9). Basis: Long-Term Appreciation +246% since 2012; Recent Direction -10.3% year-over-year; Liquidity & Demand 3.3 months of supply; Owner Commitment 65% owner-occupied; Pricing Power 96.5% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- 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 WINFIELD 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 WINFIELD sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WINFIELD, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your WINFIELD home worth?
Get a no-obligation home value based on real comparable sales in WINFIELD, 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 homes for sale in WINFIELD on the map →
Frequently Asked Questions
What is the median home price in WINFIELD?
How long do homes in WINFIELD take to sell?
Is WINFIELD a buyer's or seller's market right now?
How many homes are in WINFIELD?
What share of WINFIELD is owner-occupied?
When were the homes in WINFIELD built?
Do cash buyers compete in WINFIELD?
Have WINFIELD home prices gone up?
Who is the best real estate agent for WINFIELD?
How do I find a top MAITLAND real estate agent who knows WINFIELD?
Can Momentum Realty connect me with an agent for WINFIELD?
Nearby Communities
Explore more neighborhoods near WINFIELD with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2006 (86 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?
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. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.
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