Neighborhood · St Petersburg, Florida
Highland Oaks
Approachable St Pete living with room to grow
12
Homes for sale
$317,500
Median list price
$265
Avg price / sqft
67
Median days on market
Highland Oaks sits in the heart of St Petersburg, a neighborhood of modest, well-scaled homes that appeals to buyers who want to be part of the city without paying waterfront premiums. You're within easy reach of neighboring pockets like Greater Pinellas Point and Shore Acres, and the broader mix of St Petersburg homes for sale means there's usually something to compare against nearby. It's a practical, everyday corner of the city rather than a resort enclave.
For buyers today, the math is friendly: a median list price of $330,000 and 15 active listings give you real choices without a bidding frenzy. Homes here sit for a median of 68 days and sellers are getting about 97% of asking, so there's room to negotiate if you come prepared. Compare that against a spot like Winston Park and you'll see Highland Oaks holds its own on value.
Highland Oaks is a community in St Petersburg, Florida.
Quick facts
$169,900 – $520K price range
1,142 sqft median home
$2,195/mo median rent
18 sold in 12 months
Drive times
On the market now
Homes for sale in Highland Oaks
$269,900
2410 18TH AVENUE S, ST PETERSBURG
4 bd · 1 ba · 927 sqft
$305,000
2112 25TH STREET S, ST PETERSBURG
3 bd · 1 ba · 1,094 sqft
$179,900
2226 27TH STREET S, ST PETERSBURG
2 bd · 1 ba · 672 sqft
$509,000
2321 25TH AVENUE S, ST PETERSBURG
4 bd · 2 ba · 1,805 sqft
$450,000$465,000
1821 27TH STREET S, ST PETERSBURG
3 bd · 2 ba · 1,584 sqft
$169,900$179,900
1924 30TH STREET S, ST PETERSBURG
2 bd · 1 ba · 918 sqft
$338,000$347,000
2443 26TH AVENUE S, ST PETERSBURG
4 bd · 2 ba · 1,249 sqft
$199,990$224,900
2210 20TH AVENUE S, ST PETERSBURG
3 bd · 1 ba · 754 sqft
$269,000
1922 23RD STREET S, ST PETERSBURG
3 bd · 1 ba · 930 sqft
$330,000$335,000
1900 25TH STREET S, ST PETERSBURG
3 bd · 2 ba · 1,190 sqft
$474,000
2459 25TH AVENUE S, ST PETERSBURG
4 bd · 2 ba · 1,665 sqft
$520,000$529,000
2035 28TH STREET S, ST PETERSBURG
4 bd · 3 ba · 2,480 sqft
Every active listing inside the Highland Oaks boundary
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Browse Highland Oaks
By feature — on the live map
Where the market lives
The numbers that matter
The Highland Oaks market
18
Sold, last 12 months
$277,500
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
52 days
Median time to sell
Highland Oaks vs St Petersburg
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 7.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Highland Oaks boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Highland Oaks is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Highland Oaks home
≈ $2,043/mo
$317,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$2,195/mo
Median rent
Homes for rent inside the boundary
Population
2,072
Median age
41
Median income
$80,090
Median home value
$220,256
Beyond the listings
Living in Highland Oaks
Active
Top 14% 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.
Relationships
Top 18% 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.
Culture
Top 21% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Lifestyles
Student Life
There's more to student life than academics. It's about the experience - from classes and homecoming, to making lifetime friends and alumni events. These are students at school, taking classes online, or finding other ways to be students in their daily lives.
Beliefs
Mindfulness & Spirituality
Seeking peace and well-being through meditation, gratitude and spirituality.
Hobbies & Interests
Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
People who close here
Our St Petersburg experts
Straight answers
Highland Oaks FAQs
Is Highland Oaks a good place to live?+
It's a practical, everyday St Petersburg neighborhood with modest, well-scaled homes and easy access to the rest of the city. Assigned schools include Maximo Elementary, Bay Point Middle and Gibbs High. With Tampa International Airport about 30 minutes out, it works well for buyers who want city convenience without the waterfront price tag.
Is Highland Oaks expensive?+
Not by St Petersburg standards. The median list price is $330,000 and recent sales closed at a median of $283,000, well below the premiums you'd pay in waterfront pockets like Shore Acres.
What do homes cost in Highland Oaks?+
Current active listings run from $179,900 to $529,000, with a median list price of $330,000 and an average of $264 per square foot. The median home size is about 1,249 square feet, so expect compact, affordable footprints.
How is the market right now?+
There are 15 active listings and 19 homes have sold in the past year, with the median sale at $283,000. Homes sit a median of 68 days and sellers get about 97% of asking, so buyers have some negotiating room without a frantic pace.
What about HOA fees and property taxes?+
There's no meaningful HOA data reported for Highland Oaks, so most homes here aren't burdened by monthly association dues. The median property tax runs about $2,836 per year, and if you're weighing renting, the median rent is around $2,395 per month.
Keep exploring
More St Petersburg 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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