Neighborhood · Cutler Bay, Florida
Winston Park
Southern Miami-Dade living with room to grow
13
Homes for sale
$720,000
Median list price
$361
Avg price / sqft
73
Median days on market
Winston Park sits in Cutler Bay, in the quieter southern reaches of Miami-Dade where single-family living and space still feel attainable. It's the kind of neighborhood where families put down roots close to schools like Martin Luther King Elementary School and Ethel F. Beckford/Richmond Primary Learning Center, with a mix of established homes and a few standouts with private pools.
For buyers, the current market rewards patience. There are 13 active listings with a median list price of $720,000, but the median home actually sold over the past year at $272,000 — a wide spread that tells you the asking prices skew high while real closings land far lower. With homes taking a median 73 days to sell and sellers getting about 97% of asking, there's room to negotiate; browse the full picture on the live map or across Cutler Bay homes for sale.
Winston Park is a community in Cutler Bay, Florida.
Quick facts
$210,000 – $999K price range
1,362 sqft median home
$2,200/mo median rent
56 sold in 12 months
On the market now
Homes for sale in Winston Park
View all 13 →
$265,000
8400 SW 133rd Ave Rd # 424, Miami FL 33183, MIAMI
2 bd · 2 ba · 965 sqft
$720,000$760,000
8014 SW 133rd Ct, Miami FL 33183, MIAMI
3 bd · 2 ba · 1,362 sqft
$899,000
13611 SW 77th St, Miami FL 33183, MIAMI
4 bd · 3 ba · 1,796 sqft
$249,900$259,900
8760 SW 133rd Ave Rd # 107, Miami FL 33183, MIAMI
3 bd · 2 ba · 1,040 sqft
$799,000$820,000
13391 SW 78th St, Miami FL 33183, MIAMI
4 bd · 2 ba · 1,684 sqft
$230,000$240,000
8600 SW 133rd Ave Rd # 410, Miami FL 33183, MIAMI
2 bd · 2 ba · 965 sqft
$759,900
7344 SW 135th Ct, Miami FL 33183, MIAMI
4 bd · 2.5 ba · 2,047 sqft
$210,000
8700 SW 133rd Ave Rd # 109, Miami FL 33183, MIAMI
1 bd · 1.5 ba · 705 sqft
$810,000
7434 SW 129th Ct, Miami FL 33183, MIAMI
3 bd · 2 ba · 2,052 sqft
$999,000
, MIAMI
4 bd · 2 ba · 1,914 sqft
$779,000
7354 SW 135th Ct, Miami FL 33183, MIAMI
4 bd · 2 ba · 2,050 sqft
$225,000
8420 SW 133rd Ave Rd # 317, Miami FL 33183, MIAMI
2 bd · 2 ba · 965 sqft
Every active listing inside the Winston Park boundary
Open full map search →Find your fit
Browse Winston Park
By feature — on the live map
Where the market lives
The numbers that matter
The Winston Park market
56
Sold, last 12 months
$272,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
48 days
Median time to sell
Winston Park vs Cutler Bay
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 34.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winston Park boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winston Park is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winston Park home
≈ $4,304/mo
$720,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$2,200/mo
Median rent
Homes for rent inside the boundary
Population
7,488
Median age
49
Median income
$76,489
Median home value
$418,567
Beyond the listings
Living in Winston Park
Lifestyles
Top 4% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Relationships
Top 11% 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.
Entertainment
Top 14% in the U.S.Party Life
The party don't stop until the sun comes up. Loud music, crowds, and shots are a recipe for a great night out for these people.
Hobbies & Interests
Top 21% in the U.S.Engine Enthusiast
This population loves working on and showing off their cars, trucks and motorcycles. You can find them researching car shows and the hottest models on the lot.
Appearance oriented
Top 21% in the U.S.All About Hair
Passionate about all things hair, this population is talking about hair tutorials or the hottest celebrity blowout.
Entertainment
Top 23% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Straight answers
Winston Park FAQs
Is Winston Park a good place to live?+
It's a solid fit for buyers who want a settled, family-oriented pocket of Cutler Bay with access to schools like George T. Baker Aviation Technical College and other assigned programs. The neighborhood leans residential and quiet, with a handful of pool homes among its listings.
Is Winston Park expensive?+
It depends on which end of the market you look at. Active listings show a median list price of $720,000 and range from $210,000 up to $999,000, but homes actually closed over the past year at a median of $272,000 — so real transaction prices are far more accessible than the current asking prices suggest.
What do homes cost in Winston Park?+
Sold prices over the last 12 months centered on $272,000 across 56 closings, while active listings average about $361 per square foot on a median home size of 1,362 square feet. Renters can expect a median around $2,200 a month.
How is the market in Winston Park?+
There are 13 homes on the market now, and the median listing takes about 73 days to sell. Sellers are getting roughly 97% of their asking price, which points to a market where well-priced homes move but buyers still have negotiating room.
What about HOA fees and taxes?+
There's no typical HOA fee reported for Winston Park, which keeps monthly costs simpler than in many South Florida communities. Median annual property tax comes in around $3,599, a manageable figure for the price points here.
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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