Conwill Estates
Homes for Sale in Winter Park, FL
All 337 homes for sale in WINTER PARK, FL · median $664,900 · 150 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of September 2026, Conwill Estates in Winter Park, FL has 3 homes for sale. Over the 12 months ending 2026-09-12, 9 recorded sales closed at a median of $1,875,000, $528 per square foot, a median 16 days on market, sellers accepting 93% of original asking (+109% versus the prior year). Homes listed or recently sold were built 1957 - 2026 with 3 new construction; 3 listings state no HOA; none of the 11 geocoded homes sit in a FEMA special flood hazard zone (median elevation 87 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $31,260 ($30,590 with the full homestead exemption).
Homes For Sale Right Now in Conwill Estates
Live MLS inventory for Conwill Estates. 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 · 1 daysTop listing
Active · 11 days
Active · 22 daysActive and pending Conwill Estates listings as of 2026-09-14, 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.
Conwill Estates right now
🟡 Balanced market. 4.0 months of supply and 0% 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 September 12, 2026. Confidence: Medium (3 active and pending listings, 9 closed sales in 12 months).
🟢 Still climbing. The trailing-12-month median ($1.88M) is up 108.6% from the prior 12 months ($899K). 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 (9 and 3 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
The 60-Second Overview
Conwill Estates market snapshot (as of September 12, 2026): the median sale price is about $1.88M ($528 per sq ft over the trailing 12 months of closed sales), a median 16 days on market for closed sales, and 4.0 months of supply, a balanced market. The trailing-12-month median is up 109% from the prior 12 months, computed from record-level Stellar MLS closed sales (9 closings in the current window).
In ZIP 32789 (WINTER PARK), 394 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.4% year over year, with a median 40 days on market. Right now 88 active and 21 pending listings put supply at about 4.9 months - a balanced market. See the live ZIP 32789 housing market and the Orange County market.
Flood zones in Conwill Estates: of 10 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.
Conwill Estates is a community of 145 homes in Winter Park, Orange County, built between 1926 and 2024 (median 1971), with a median living area of about 2,394 square feet. 67% 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 Conwill Estates. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Conwill EstatesPhotos from Stellar MLS listings in Conwill Estates; 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 ($1.88M) IS the median in the snapshot above, and the move from 2025 ($899K) IS the +108.6% one-year change.
Windows contain 0 to 9 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.
CONWILL ESTATES Market Scorecard
CONWILL ESTATES is currently a balanced market. About 4.0 months of supply, a median asking price of $1,900,000, and homes go under contract in about 12 days.
Typical home value in the 32789 ZIP is $809,773, about 61.9% 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 Conwill Estates Winter Park, 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Conwill Estates 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 Conwill Estates
- Golf Carts OK · reported on 1 of 4 listings
- Park · reported on 1 of 4 listings
- Playground · reported on 1 of 4 listings
- Tennis Court(s) · reported on 1 of 4 listings
- Security Lights · reported on 1 of 4 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
- Lakemont Elem · Elementary
- Maitland Middle · Middle
- Winter Park High · High
Zoned schools reflect the assignments reported on recent Conwill Estates 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 Conwill Estates address.
Shop the zone: Homes zoned for Winter Park High High School
The Conwill Estates buying strategy.
If we were buying in Conwill Estates 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 Conwill Estates.
A closer look at the Conwill Estates market
At a median of $528 per square foot, Conwill Estates 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 4.0 months of supply, a balanced market and the trailing-12-month median up 109% year over year. Homes that do trade take a median 16 days on market, useful leverage on any listing that has lingered.
The housing stock is 145 homes built between 1926 and 2024, and 67% 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 Conwill Estates. 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 Conwill Estates 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 (7.0). Basis: Recent Direction +108.6% year-over-year; Liquidity & Demand 4.0 months of supply; Owner Commitment 67% owner-occupied; Pricing Power 92.9% 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 Conwill Estates 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 Conwill Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Conwill Estates, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Conwill Estates home worth?
Get a no-obligation home value based on real comparable sales in Conwill Estates, 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 Conwill Estates
Homes in Conwill Estates 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. 1 on record.
- 1750 Walnut Avenue · off market
Frequently Asked Questions
What is the median home price in Conwill Estates?
How long do homes in Conwill Estates take to sell?
Is Conwill Estates a buyer's or seller's market right now?
How many homes are in Conwill Estates?
What share of Conwill Estates is owner-occupied?
When were the homes in Conwill Estates built?
Who is the best real estate agent for Conwill Estates?
How do I find a top Winter Park real estate agent who knows Conwill Estates?
Can Momentum Realty connect me with an agent for Conwill Estates?
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 (4 streets, ZIP 32789/32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2006 (57 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 local comps.
Looking to buy here? Search homes for sale →
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See how Conwill Estates fits the bigger picture — live prices, inventory, and Momentum Scores:
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