Neighborhood · Winter Park, Florida
The Stratford
Compact condo living minutes from downtown Winter Park
5
Homes for sale
$182,900
Median list price
$202
Avg price / sqft
47
Median days on market
The Stratford is a small-scale condo community that puts you inside one of Central Florida's most walkable, tree-lined pockets. You're close to Lake Killarney and the dining and shopping around Hannibal Square, with easy connections to the rest of Winter Park and neighborhoods like Winter Park Pines. It's the kind of address that trades square footage for location, and the trade lands in your favor if you want low-maintenance living near the center of it all.
For buyers today, this is a genuinely accessible entry point into Winter Park. With just five active listings and a median list price of $182,900, inventory is tight but priced well below the surrounding single-family market, and homes are moving at a measured pace — a median of 75 days on market. If you're patient and ready to negotiate, there's room to work: sellers over the past year have averaged 95% of asking.
The Stratford is a community in Winter Park, Florida.
Quick facts
$140,000 – $249K price range
927 sqft median home
$457/mo median HOA
$1,700/mo median rent
10 sold in 12 months
Drive times
On the market now
Homes for sale in The Stratford
$140,000
302 LEWFIELD CIRCLE UNIT 302, WINTER PARK
1 bd · 1 ba · 678 sqft
$189,900
222 LEWFIELD CIRCLE, WINTER PARK
2 bd · 2 ba · 953 sqft
$147,000
285 LEWFIELD CIRCLE UNIT 285, WINTER PARK
1 bd · 1 ba · 678 sqft
$248,900
193 LEWFIELD CIRCLE, WINTER PARK
2 bd · 2.5 ba · 1,300 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
10
Sold, last 12 months
$146,250
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
▼ 33.5% 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
≈ $1,793/mo
$182,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$457/mo
Median HOA
From current listings inside the boundary
$1,700/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 solid fit if you want a walkable, low-maintenance Winter Park address without a single-family price tag. You're close to Lake Killarney, Hannibal Square dining, and downtown Winter Park, with downtown Orlando about 23 minutes away. The compact condo footprint suits buyers who prioritize location over square footage.
Is The Stratford expensive?+
By Winter Park standards, no — the median list price is $182,900, with active listings ranging from $147,000 to $248,900. That's a meaningful discount to the surrounding single-family market in neighborhoods like Eastbrook. It's one of the more accessible ways to buy in the area.
What do homes cost at The Stratford?+
Active listings run from $147,000 to $248,900 with a median of $182,900, and average about $205 per square foot on a median home size of 927 square feet. Over the past 12 months, 10 homes sold at a median price of $157,750. Expect efficient, condo-scale layouts at this price.
How is the market at The Stratford?+
It's a small, steady market with five active listings and a median of 75 days on the market. Ten homes have sold in the past year, and sellers are averaging 95% of asking — so there's typically room to negotiate. Patience and a strong offer both pay off here.
What about HOA fees and property taxes?+
The median HOA is $457 a month, which reflects the shared maintenance that comes with condo living. Property taxes run a median of about $1,942 per year. If you're weighing a rental instead, the median rent in the area is around $1,700 a 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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