Dubsdread Heights
Homes for Sale in Winter Park, FL
All 394 homes for sale in Winter Park, FL · median $636,250 · 169 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of November 2026, Dubsdread Heights in Winter Park, FL has 2 homes for sale. Over the 12 months ending 2026-11-13, 3 recorded sales closed at a median of $622,000, $295 per square foot, a median 18 days on market, sellers accepting 99% of original asking. Homes listed or recently sold were built 1925 - 2010; none of the 9 geocoded homes sit in a FEMA special flood hazard zone (median elevation 99 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,370 ($9,700 with the full homestead exemption).
Price here is driven by condition and lot more than square footage. The median home is right around 1,408 square feet and the housing stock spans roughly a century, from 1920 to 2023, with a median build year of 1955. That mix means you are often paying for a renovated older home or a newer infill rebuild, and the median of $414,000 at about $294.51 per square foot reflects a wide spread by condition rather than a tidy tier of comparable homes.
The posture is seller-leaning but not frantic. With 1.5 months of supply, a single active listing at the snapshot, and a median of 23 days on market, well-prepared homes move. Prices are up 4.6% year over year and have tripled since 2012 (up 200%). Buyers should expect to compete on the better-prepped homes; sellers should not assume the market does the work for a dated, as-is listing.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Dubsdread Heights right now
🔴 Seller-leaning market. 1.5 months of supply and 0% 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: Medium (1 active and pending listings, 7 closed sales in 12 months).
🟡 Still climbing. The trailing-12-month median ($414K) is up 4.6% from the prior 12 months ($396K) and up 200% 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 September 20. Confidence: Medium (7 and 10 sales in the two windows).
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
Dubsdread Heights market snapshot (as of September 20, 2026): the median sale price is about $414K ($295 per sq ft over the trailing 12 months of closed sales), a median 23 days on market for closed sales, and 1.5 months of supply, a seller-leaning market. The trailing-12-month median is up 5% from the prior 12 months and up 200% since 2012, computed from record-level Stellar MLS closed sales (7 closings in the current window).
In ZIP 32789 (Winter Park), 111 homes closed in the last 12 months at a median of $627K ($396/sq ft), down 21.6% year over year, with a median 42 days on market. Right now 34 active and 4 pending listings put supply at about 3.7 months - a buyer's market. See the live ZIP 32789 housing market and the Orange County market.
County records show 20 qualified sales in Dubsdread Heights across 2024 - 2025 (7 in 2024, 13 in 2025), median $435,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Dubsdread Heights: of 8 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.
Dubsdread Heights is a community of 263 homes in Winter Park, Orange County, built between 1920 and 2023 (median 1955.0), with a median living area of about 1,408 square feet. 56% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Dubsdread Heights is a small, golf-adjacent pocket of Winter Park in Orange County where older bungalows sit beside newer rebuilds, and inventory stays thin.
The setting & the homes.
Aerial and on-site photos of Dubsdread Heights. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Dubsdread HeightsPhotos from Stellar MLS listings in Dubsdread Heights; content deemed reliable but not guaranteed.
Who Dubsdread Heights is best for.
Best for
- Buying to hold in a tightly held, golf-adjacent Winter Park pocket
- Buyers who want a modest-footprint home and will move quickly when one lists
- Buying a renovation or newer rebuild and valuing condition over raw size
Probably not for
- Needing a broad set of listings to tour and compare at once
- Wanting a large-square-footage floor plan as the baseline
- Expecting a buyer's-market posture with room to negotiate down
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 ($414K) IS the median in the snapshot above, and the move from 2025 ($396K) IS the +4.6% one-year change.
Windows contain 0 to 13 sales each (7 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 2008 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.
19% of homes for sale in ZIP 32789 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).
DUBSDREAD HEIGHTS Market Scorecard
DUBSDREAD HEIGHTS is currently a seller's market. About 3.4 months of supply, a median asking price of $407,450, and homes go under contract in about 120 days.
Typical home value in the 32789 ZIP is $817,354, about 60.9% 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.
Homes For Sale Right Now in Dubsdread Heights
Live MLS inventory for Dubsdread Heights. 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 Dubsdread Heights listings as of 2026-11-02, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2008 through 2026. Tap any home to ask about it.
Dubsdread Heights 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 Dubsdread Heights
- Golf Carts OK · 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.
The Dubsdread Heights buying strategy.
If we were buying in Dubsdread Heights 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 Dubsdread Heights.
Old bones, new builds, one street at a time
With 263 homes and a build range from 1920 to 2023, this is a community defined by its range. You will find original-era cottages next to ground-up 2020s construction, which makes condition the single biggest variable in what you pay. The median living area of 1,408 square feet keeps footprints modest, so the delta between a tired original and a full renovation shows up clearly in price per foot.
A homestead share of 56.3% suggests a core of owner-occupants, which tends to support steady upkeep over time. Golf Carts OK is the reported community amenity across MLS listings; verify current access and any HOA details directly, since this is a reported note rather than a guarantee.
The location and the amenities are priced into every listing in Dubsdread Heights. 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 Dubsdread Heights 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 (8.0). Basis: Long-Term Appreciation +200% since 2012; Recent Direction +4.6% year-over-year; Liquidity & Demand 1.5 months of supply; Owner Commitment 56% owner-occupied; Pricing Power 98.4% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a market this thin, with one active listing at the snapshot and a 23-day median, pricing and prep decide the outcome. We read condition against the median honestly, tell you when an as-is home is overpriced, and help sellers spend renovation dollars where they actually return value in this specific pocket of Winter Park.
Dubsdread Heights in 15 seconds.
Tools for a Dubsdread Heights 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 Dubsdread Heights sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Dubsdread Heights, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Dubsdread Heights home worth?
Get a no-obligation home value based on real comparable sales in Dubsdread Heights, 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 Dubsdread Heights
Homes in Dubsdread Heights 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.
- 846 Driver Avenue · off market
| Location | Winter Park, Orange County, FL · ZIP 32789 |
|---|---|
| Homes in the community | 231 (FL DOR 2025 assessment roll) |
| Years built | 1920–2020 (median 1955.0) |
| Typical living area | 1,349 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Golf Carts OK, Security System |
| Sale prices, last 12 months | $622,000 median across 3 closed sales · $295 per sq ft |
| Days on market (closed sales) | 18 median |
| For sale right now | 2 active, 0 pending · median asking $407,450 · 3.4 months of supply |
| Owner-occupied (homestead) share | 54% |
Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2026 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Dubsdread Heights key facts,” movewithmomentum.com/neighborhoods/dubsdread-heights-winter-park, data as of November 13, 2026.
Housing distress & ownership in Dubsdread Heights, 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.
Just listed in Dubsdread Heights
The newest homes for sale in Dubsdread Heights right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 712 Baffie Avenue $419,900 · 3 bd · 1 ba · 1,304 sq ft · listed Sep 30, 2026 Courtesy of RP INVESTMENT REALTY LLC
- 811 Overspin Drive $395,000 · 2 bd · 1 ba · 749 sq ft · listed May 1, 2026 Courtesy of RICK SINGH REAL ESTATE
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Dubsdread Heights Right Now (2)
All 2 active and pending Dubsdread Heights listings with a detail page, newest first, refreshed twice a day from the MLS.
- 712 Baffie Avenue · $419,900 · 3 bd / 1 ba · listed Sep 30, 2026 · listed by Rp Investment Realty Llc
- 811 Overspin Drive · $395,000 · 2 bd / 1 ba · listed Sep 10, 2026 · listed by Rick Singh Real Estate
More Winter Park home searches
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- Winter Park home values: what is my house worth?
- ZIP 32789 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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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Minnesota Avenue (3 homes on record)
Email me new listings in Dubsdread Heights
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 Dubsdread Heights
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Dubsdread Heights will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
What is the median home price in Dubsdread Heights?
How long do homes in Dubsdread Heights take to sell?
Is Dubsdread Heights a buyer's or seller's market right now?
How many homes are in Dubsdread Heights?
What share of Dubsdread Heights is owner-occupied?
When were the homes in Dubsdread Heights built?
Have Dubsdread Heights home prices gone up?
Who is the best real estate agent for Dubsdread Heights?
How do I find a top Winter Park real estate agent who knows Dubsdread Heights?
Can Momentum Realty connect me with an agent for Dubsdread Heights?
Where is Dubsdread Heights, and what county is it in?
Should you buy in Dubsdread Heights?
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 2, 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 (9 streets, ZIP 32789/32804)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2008 (82 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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See how Dubsdread Heights fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Dubsdread Heights
- Home values · What homes in Dubsdread Heights actually sell for