Neighborhood · Lakeland, Florida
Winston
West Lakeland living with easy Tampa access
22
Homes for sale
$227,450
Median list price
$192
Avg price / sqft
67
Median days on market
Winston sits on the west side of Lakeland in Polk County, a practical, unassuming pocket of the city where the pace stays relaxed and you're never far from the everyday things that matter. It's close to established neighbors like Sandpiper and the lakeside stretches around Lake Hollingsworth and Lake Bentley, and it keeps you within a short drive of downtown Lakeland's shops and services.
For buyers, Winston is one of Lakeland's more attainable entry points. There are currently 22 active listings with a median list price of $227,450, which lands well below what you'll find in more polished corners of the city like Grasslands. If you're comparing it against the wider pool of Lakeland homes for sale, Winston reads as a value play worth a serious look.
Winston is a community in Lakeland, Florida.
Quick facts
$85,000 – $375K price range
1,216 sqft median home
$450/mo median HOA
$1,450/mo median rent
71 sold in 12 months
Drive times
On the market now
Homes for sale in Winston
View all 22 →
$225,000
408 HOWARD AVENUE UNIT B, LAKELAND
3 bd · 3 ba · 2,074 sqft
$189,000
2638 SEA OATS CIRCLE S, LAKELAND
3 bd · 2 ba · 960 sqft
$178,500
1835 W GREENWOOD STREET, LAKELAND
2 bd · 1 ba · 520 sqft
$195,000
2594 MCINTOSH DRIVE, LAKELAND
3 bd · 2 ba · 1,232 sqft
$237,000
400 S HOWARD AVENUE, LAKELAND
3 bd · 3 ba · 1,844 sqft
$209,900$212,900
2135 ELIZABETH STREET, LAKELAND
2 bd · 1 ba · 1,086 sqft
$299,000$315,000
907 N WABASH AVE, LAKELAND
4 bd · 2 ba · 1,480 sqft
$229,900$235,000
608 PINEVILLE LANE, LAKELAND
3 bd · 2 ba · 1,386 sqft
$299,000$320,000
1215 EL CAMINO ROAD, LAKELAND
4 bd · 3 ba · 1,471 sqft
$245,000
2530 CRESAP STREET, LAKELAND
3 bd · 2 ba · 1,200 sqft
$169,000$173,000
1106 MILNER DRIVE W, LAKELAND
3 bd · 1.5 ba · 1,026 sqft
$85,000$89,900
829 NASHVILLE ROAD, LAKELAND
3 bd · 2 ba · 672 sqft
Every active listing inside the Winston boundary
Open full map search →Find your fit
Browse Winston
By feature — on the live map
Where the market lives
The numbers that matter
The Winston market
71
Sold, last 12 months
$209,900
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
21 days
Median time to sell
Winston vs Lakeland
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 23.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winston boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winston is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winston home
≈ $2,041/mo
$227,450 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
$1,450/mo
Median rent
Homes for rent inside the boundary
Population
10,023
Median age
47
Median income
$45,211
Median home value
$79,754
Beyond the listings
Living in Winston
Entertainment
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.
Entertainment
Late-night Leisure
Ready to turn up when the sun goes down, this population is looking for nighttime entertainment at home or out on the town.
Lifestyles
Nerd Culture
These people aren't afraid to nerd out. Common activities include comic books, video games, and often intellectual pursuits.
Active
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.
Entertainment
Live Experiences
When it comes to entertainment, this population is looking for the ultimate experience. Whether it's a charity fundraiser or a concert, elements such as lights, sounds, and merchandise are critical for a good time.
Beliefs
Spiritual Practices
Making it to church on Sunday, this population is drawn together by their devotion to, primarily Christian, religion. Common activities include worship services and bible studies.
People who close here
Our Lakeland experts
Yordanka Sanchez Quillen
REALTOR®
Brittany Huey
REALTOR®
Kevin Johnson
CEO & Managing Broker
Iain Robinson
Broker Associate
Straight answers
Winston FAQs
Is Winston a good place to live?+
Winston is a low-key west Lakeland neighborhood that trades flash for convenience, with quick access to downtown Lakeland and a 38-minute drive to downtown Tampa. It's close to established areas like Sandpiper and the lakes on the south side of town. If you want an affordable base that still keeps Tampa and Orlando in reach, it fits.
Is Winston expensive?+
No — it's one of Lakeland's more attainable neighborhoods, with a median list price of $227,450 across the current 22 active listings. That sits below many of Lakeland's higher-end enclaves, so your budget stretches further here.
What do homes cost in Winston?+
The median list price is currently $227,450, based on 22 homes actively for sale. Detailed price-per-square-foot and sold data aren't available for this pocket right now, so it's worth touring a few listings with an agent to get a feel for value against the broader Lakeland homes for sale market.
How is the market in Winston?+
Inventory is on the leaner side, with 22 active listings at the moment and a median around $227,450. There were no recorded sales in the neighborhood over the last 12 months in the data, so pricing and pace are best confirmed through a live comparison with nearby areas like Lake Bentley.
What about HOA fees and property taxes in Winston?+
HOA and property-tax figures aren't reported for Winston in the current data, and none of the active listings fall into gated or 55+ segments. Because costs vary house by house here, ask your agent to pull the specific HOA and millage details on any home before you make an offer.
Keep exploring
More Lakeland 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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