Neighborhood · Winter Park, Florida
Hidden Oaks
An affordable foothold in one of Orlando's best towns
7
Homes for sale
$180,000
Median list price
$179
Avg price / sqft
41
Median days on market
Hidden Oaks is a compact, low-key pocket of Winter Park homes for sale that sits within easy reach of the town's most recognizable corners — from Lake Killarney to the shops and restaurants around Hannibal Square. It's a practical, right-sized neighborhood where you're 16 minutes from downtown Orlando and 26 from MCO, with the Winter Park High attendance zone attached to it. Homes here tend to be modest in footprint, which keeps day-to-day living simple and the price of entry reasonable.
For buyers, this is one of the few places in Winter Park where the numbers stay grounded. The median list price sits at $179,900 across just 7 active listings, and homes are selling in about 41 days at roughly 97% of asking. If you've been priced out of pricier corners like Kenilworth or Winter Park Pines, Hidden Oaks is worth a serious look.
Hidden Oaks is a community in Winter Park, Florida.
Quick facts
$169,900 – $229K price range
1,031 sqft median home
$450/mo median HOA
$1,825/mo median rent
12 sold in 12 months
Drive times
On the market now
Homes for sale in Hidden Oaks
$229,000
7454 WYNNEWOOD SQUARE UNIT 188, WINTER PARK
3 bd · 2.5 ba · 1,151 sqft
$185,000
7450 WYNNEWOOD SQUARE UNIT 189, WINTER PARK
2 bd · 2.5 ba · 1,031 sqft
$179,900
3381 CEDAR SPRINGS PLACE UNIT 151, WINTER PARK
2 bd · 2.5 ba · 1,031 sqft
$172,000$175,000
3243 FOREST OAKS COURT UNIT 117, WINTER PARK
2 bd · 1.5 ba · 990 sqft
$169,900$179,900
7336 FOREST HILL COURT UNIT 240, WINTER PARK
2 bd · 1.5 ba · 990 sqft
$180,000$185,000
7327 FOREST HILL COURT UNIT 223, WINTER PARK
2 bd · 2.5 ba · 1,031 sqft
$185,000$189,000
3370 CEDAR SPRINGS PLACE UNIT 156, WINTER PARK
2 bd · 2.5 ba · 1,031 sqft
Every active listing inside the Hidden Oaks boundary
Open full map search →Find your fit
Browse Hidden Oaks
By feature — on the live map
Where the market lives
The numbers that matter
The Hidden Oaks market
12
Sold, last 12 months
$181,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
76 days
Median time to sell
Hidden Oaks vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 28.2% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Hidden Oaks boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Hidden Oaks is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Hidden Oaks home
≈ $1,824/mo
$180,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$450/mo
Median HOA
From current listings inside the boundary
$1,825/mo
Median rent
Homes for rent inside the boundary
Population
750
Median age
29
Median income
$44,732
Median home value
$226,600
Beyond the listings
Living in Hidden Oaks
Active
Top 2% in the U.S.Fitness Obsession
Passionate about strength training, this population relies heavily on the encouragement of the exercise community. While these people seek the latest fitness techniques, they're also interested in supplements and equipment.
Active
Top 4% in the U.S.Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
Food & Drink
Top 4% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Appearance oriented
Top 5% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Relationships
Top 5% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Culture
Top 5% in the U.S.Hip Hop Culture
Dropping the beat and raising the roof, this population enjoys everything hip hop culture has to offer, including music, dance moves, and fashion.
People who close here
Our Winter Park experts
Straight answers
Hidden Oaks FAQs
Is Hidden Oaks a good place to live?+
It's a solid fit if you want a Winter Park address without a Winter Park price tag. You're minutes from spots like Lake Killarney and downtown Orlando is a 16-minute drive, while the neighborhood is zoned for Winter Park High, Glenridge Middle, and Aloma Elementary.
Is Hidden Oaks expensive?+
Not by Winter Park standards — the median list price is $179,900 and active listings run from $154,500 to $229,000. That makes it one of the more accessible ways into the area, especially compared with pricier pockets nearby.
What do homes cost in Hidden Oaks?+
Expect to pay around $176 per square foot, with a median home size near 1,031 sqft. Over the last 12 months, 12 homes sold at a median price of $181,000, so list and sold values are tracking closely.
How is the market in Hidden Oaks right now?+
It's a small, steady market with just 7 active listings and a median of 41 days on market. Sellers are getting about 97% of their asking price, which points to fair, realistic pricing rather than bidding wars.
What about HOA fees and property taxes?+
The median HOA here runs about $450 per month and median property taxes are around $2,723 per year. If you're weighing renting first, the median rent in the area is about $1,900 per month.
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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