Neighborhood · Lakeland, Florida
Winston
West Lakeland value between Tampa and Orlando
27
Homes for sale
$227,000
Median list price
$189
Avg price / sqft
85
Median days on market
Winston sits on the west side of Lakeland, a practical, workaday pocket of Polk County where the pace is easy and the commute options run in two directions. It's close to the Lakeland Municipal Airport and a short hop from established neighborhoods like Sandpiper and the lakefront draws of Lake Hollingsworth, with Gibsonia and Lake Bentley rounding out the area to the north and south. It's the kind of place where you can own a home without stretching, and still reach downtown Tampa in about 38 minutes.
For a buyer today, Winston reads as an affordable entry point. The median list price is $219,950 with active listings running from $79,900 to $375,000, and homes are selling at a median of $210,000 — right in line with what's being asked. With 26 homes on the market and a median 76.5 days on market, there's room to negotiate and time to make a considered decision rather than a rushed one.
Winston is a community in Lakeland, Florida.
Quick facts
$79,999 – $849K price range
1,200 sqft median home
$483/mo median HOA
$1,500/mo median rent
75 sold in 12 months
Drive times
On the market now
Homes for sale in Winston
View all 27 →
$315,000
1028 S TERRY AVENUE, LAKELAND
4 bd · 2 ba · 1,705 sqft
$170,000
915 N WABASH AVENUE, LAKELAND
3 bd · 1 ba · 746 sqft
$325,000
725 STRAIN BOULEVARD, LAKELAND
4 bd · 3 ba · 2,186 sqft
$250,000
1123 S TERRY AVENUE, LAKELAND
3 bd · 2 ba · 1,539 sqft
$849,000
451 LONE PALM DRIVE, LAKELAND
4 bd · 3.5 ba · 2,929 sqft
$219,900
709 HEMLOCK LANE, LAKELAND
2 bd · 2 ba · 1,120 sqft
$195,000
3539 COLLEEN DRIVE, LAKELAND
3 bd · 1.5 ba · 1,064 sqft
$79,999
1138 S NOKOMIS AVENUE, LAKELAND
1 bd · 1 ba · 624 sqft
$120,000
1111 S TERRY AVENUE, LAKELAND
2 bd · 1 ba · 624 sqft
$280,000$299,000
2921 CRUTCHFIELD ROAD, LAKELAND
4 bd · 3 ba · 2,898 sqft
$180,000$190,000
835 MEMPHIS ROAD, LAKELAND
2 bd · 2 ba · 896 sqft
$85,000$97,000
2536 CANNON STREET, LAKELAND
3 bd · 2 ba · 924 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
75
Sold, last 12 months
$209,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
22 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
▼ 3.6% 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
≈ $2,071/mo
$227,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$483/mo
Median HOA
From current listings inside the boundary
$1,500/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
Straight answers
Winston FAQs
Is Winston a good place to live?+
Winston works well for buyers who want an affordable west-side Lakeland base with real commute flexibility — downtown Tampa is about 38 minutes and Walt Disney World roughly 51. It's a settled, practical area near the Lakeland Municipal Airport, and homes are assigned to Kathleen Middle and Kathleen Senior High School.
Is Winston expensive?+
No — it's one of Lakeland's more affordable neighborhoods, with a median list price of $219,950 and active homes ranging from $79,900 up to $375,000. At an average of $181 per square foot, your dollar goes further here than in many nearby lakefront pockets like Lake Hollingsworth.
What do homes cost in Winston?+
The median list price is $219,950 and the median home that sold over the past year went for $210,000. With a median size around 1,216 square feet, most listings here are compact, functional homes rather than sprawling estates.
How is the market in Winston right now?+
There are 26 active listings and homes are taking a median of 76.5 days to sell, so this is a measured market rather than a frenzy. Over the last 12 months 75 homes closed, with sellers netting about 96% of their asking price on average — meaning offers should be realistic but there's usually room to talk.
What about HOA fees and property taxes?+
The median property tax runs about $2,086 a year, which is modest for the price point. Some communities carry an HOA — the median is $450 per month — so confirm the fee and what it covers on any specific listing, since not every home in Winston has one.
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.
Never miss a listing
New Winston homes, in your inbox
A daily digest of new Lakeland listings — straight from the MLS. Unsubscribe anytime.