Neighborhood · Winter Park, Florida
Dubsdread Heights
Golf-course living with a downtown Orlando commute
2
Homes for sale
$388,500
Median list price
$391
Avg price / sqft
92
Median days on market
Dubsdread Heights sits at the edge of Winter Park near the historic Dubsdread golf course, a pocket of walkable streets and older bungalow-scale homes where you're 11 minutes from downtown Orlando. Neighbors here trade big-lot sprawl for location — Lake Killarney is close, Orwin Manor and Eastbrook sit nearby, and the whole area feels like a quieter extension of the Winter Park homes for sale market. Kids are zoned for Edgewater High, College Park Middle, and Princeton Elementary.
The market reality is tight: just 2 homes are active right now, with a median list price of $398,500 and a range from $349,000 to $448,000. Homes here move fast — the median days on market is essentially half a day — and over the last 12 months 7 homes sold at a median of $414,000, with sellers collecting 98% of asking. If you want in, come pre-approved and ready to decide, because inventory near Hannibal Square and this stretch of Winter Park doesn't sit.
Dubsdread Heights is a community in Winter Park, Florida.
Quick facts
$329,000 – $448K price range
1,027 sqft median home
7 sold in 12 months
Drive times
On the market now
Homes for sale in Dubsdread Heights
$448,000
712 BAFFIE AVENUE, WINTER PARK
3 bd · 1 ba · 1,304 sqft
$329,000$349,000
811 OVERSPIN DRIVE, WINTER PARK
2 bd · 1 ba · 749 sqft
Every active listing inside the Dubsdread Heights boundary
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Browse Dubsdread Heights
Where the market lives
The numbers that matter
The Dubsdread Heights market
7
Sold, last 12 months
$414,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
23 days
Median time to sell
Dubsdread Heights vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 56.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Dubsdread Heights boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Dubsdread Heights is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Dubsdread Heights home
≈ $2,625/mo
$388,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
261
Median age
44
Median income
$123,097
Median home value
$379,300
Beyond the listings
Living in Dubsdread Heights
Relationships
Top 3% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Active
Top 5% in the U.S.Organized Sports
From tryouts and casual pick-up games, to varsity tournaments and intramural matches, this population includes people who participate in organized athletics. Often through schools or public recreational areas.
Lifestyles
Top 9% in the U.S.Student Life
There's more to student life than academics. It's about the experience - from classes and homecoming, to making lifetime friends and alumni events. These are students at school, taking classes online, or finding other ways to be students in their daily lives.
Entertainment
Top 10% in the U.S.Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Entertainment
Top 11% in the U.S.Competitive Nature
These folks have their head in the game. Whether it's creating a card game tournament with friends or cheering on the home team, these people want to win.
Attitudes
Top 12% in the U.S.Volunteering & Giving
Expressing a desire to give back and do good for the community, this behavior emphasizes charity. Common activities include volunteering, fundraisers, and donations.
People who close here
Our Winter Park experts
Straight answers
Dubsdread Heights FAQs
Is Dubsdread Heights a good place to live?+
It's a strong fit if you want Winter Park proximity with a quick downtown Orlando commute — about 11 minutes — and a walkable, established feel near the Dubsdread golf course. Homes are zoned for Edgewater High, College Park Middle, and Princeton Elementary, and you're close to Lake Killarney and Orwin Manor. It suits buyers who value location over lot size.
Is Dubsdread Heights expensive?+
It sits in a mid-range band for the Winter Park area, with a median list price of $398,500 and homes running from $349,000 to $448,000. At roughly $405 per square foot, you're paying for location and character rather than square footage. There are currently no listings above $1 million here.
What do homes cost in Dubsdread Heights?+
The 2 active listings have a median list price of $398,500, and over the past 12 months 7 homes sold at a median of $414,000. With a median size near 1,027 square feet, expect right-sized bungalow-scale homes rather than large estates in nearby Eastbrook.
How is the market right now?+
It's fast and competitive — the median days on market is about half a day, and sellers are getting 98% of asking on average. With only 2 homes active, buyers need to move quickly and come pre-approved to compete.
What about HOA fees and property taxes?+
There's no meaningful HOA data reported for this neighborhood, so most homes here trade without significant association fees. Property taxes run around $4,418 per year at current values, which is typical for this part of Orange County.
Keep exploring
More Winter Park neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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