Neighborhood · Winter Park, Florida
The Stratford
Small-scale Winter Park living close to everything
5
Homes for sale
$155,000
Median list price
$211
Avg price / sqft
55
Median days on market
The Stratford is a compact residential pocket in Winter Park, Orange County, with the kind of quiet, established feel that draws buyers who want to be near the city without living in the middle of it. It sits within easy reach of neighboring communities like Lake Killarney, Winter Park Pines, and the walkable energy of Hannibal Square, so you get variety without going far. Downtown Orlando is about 23 minutes away and Orlando International Airport roughly 34, which makes the location practical for commuters and travelers alike.
For buyers today, this is a small, focused market — there are just 6 active listings with a median list price of $153,950, which puts The Stratford at the accessible end of the Winter Park spectrum. With no recorded sales in the past 12 months, pricing here rewards buyers who do their homework and lean on local guidance. If you're weighing options across Winter Park homes for sale, this neighborhood is worth a close look for its entry price and location.
The Stratford is a community in Winter Park, Florida.
Quick facts
$144,000 – $249K price range
678 sqft median home
$351/mo median HOA
$1,800/mo median rent
8 sold in 12 months
Drive times
On the market now
Homes for sale in The Stratford
$155,000
189 LEWFIELD CIRCLE UNIT 189, WINTER PARK
1 bd · 1 ba · 678 sqft
$248,900
193 LEWFIELD CIRCLE, WINTER PARK
2 bd · 2.5 ba · 1,300 sqft
$152,900$154,900
262 LEWFIELD CIRCLE UNIT 262, WINTER PARK
1 bd · 1 ba · 678 sqft
$144,000
291 LEWFIELD CIRCLE UNIT 291, WINTER PARK
1 bd · 1 ba · 678 sqft
$182,900$220,000
205 LEWFIELD CIRCLE UNIT 205, WINTER PARK
2 bd · 2 ba · 927 sqft
Every active listing inside the The Stratford boundary
Open full map search →Find your fit
Browse The Stratford
By feature — on the live map
Where the market lives
The numbers that matter
The The Stratford market
8
Sold, last 12 months
$157,750
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
79 days
Median time to sell
The Stratford vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 12.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the The Stratford boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools The Stratford is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median The Stratford home
≈ $1,538/mo
$155,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$351/mo
Median HOA
From current listings inside the boundary
$1,800/mo
Median rent
Homes for rent inside the boundary
Population
370
Median age
39
Median income
$75,362
Median home value
$287,000
Beyond the listings
Living in The Stratford
Hobbies & Interests
Top 2% in the U.S.Dog Lovers
Pups are just another member of the family. Dog lovers adore their tail-wagging friends and are looking for new ways to make them happy.
Emotional
Top 4% in the U.S.Happy Place
Expressing feelings of safety, comfort and happiness - especially with loved ones.
Hobbies & Interests
Top 4% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Active
Top 6% in the U.S.Yoga Advocates
Improving flexibility, strength, and overall well-being is the yogi's aim. This population is looking for the right community, instruction, and accessories.
Hobbies & Interests
Top 6% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Relationships
Top 7% in the U.S.Connected Motherhood
Motherhood is a unique journey for every woman. There are highs, lows,and lots to celebrate. These moms seek to share their experiences and engage with a community of moms.
People who close here
Our Winter Park experts
Straight answers
The Stratford FAQs
Is The Stratford a good place to live?+
It's a small, established residential pocket in Winter Park with quick access to the city — downtown Orlando is about 23 minutes away and the airport roughly 34. You're also close to established neighbors like Winter Park Pines and Kenilworth, which gives you options for dining, parks, and errands nearby. For buyers who want a low-key location with strong connectivity, it fits well.
Is The Stratford expensive?+
No — it sits at the accessible end of the Winter Park market, with a median list price of $153,950. That's notably lower than much of the surrounding area, which makes it appealing for first-time buyers or anyone wanting a Winter Park address without a premium price. Compared with nearby Kenilworth, it offers a more budget-friendly entry point.
What do homes cost in The Stratford?+
There are currently 6 active listings with a median list price of $153,950. Price-per-square-foot and size data aren't available for this small market right now, so it's worth reviewing individual listings closely with an agent who knows the area.
How is the market in The Stratford?+
It's a small and quiet market — 6 homes are active today and there were no recorded sales in the past 12 months. That means limited comparable data, so working with a local agent to interpret pricing and timing is especially valuable here. Buyers who move deliberately and understand the surrounding Winter Park homes for sale will have an edge.
What about HOA fees and property taxes?+
Current HOA and property tax figures aren't available for The Stratford in the active data. Because these can vary meaningfully by property, confirm the specifics on any home you're considering before making an offer.
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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