Neighborhood · St Petersburg, Florida
Highland Oaks
Approachable St Pete living close to the water
14
Homes for sale
$293,950
Median list price
$270
Avg price / sqft
43
Median days on market
Highland Oaks sits in the southern reach of St Petersburg, a pocket of single-family homes surrounded by established neighborhoods like Greater Pinellas Point and Winston Park. It's the kind of spot where homes stay right-sized and the pace is quiet, with easy access to the bay-side character that defines this part of Pinellas County. Assigned schools include Maximo Elementary, Bay Point Middle, and Gibbs High.
For buyers, the market here is refreshingly attainable — the median list price is $299,900, well below much of the St Pete waterfront. There are 13 active listings ranging from $210,000 to $535,000, homes are moving in a median of 44 days, and sellers are pulling in about 98% of asking. If you've been priced out of nearby Shore Acres or Bayway Isles, this is a realistic entry point.
Highland Oaks is a community in St Petersburg, Florida.
Quick facts
$189,900 – $535K price range
1,228 sqft median home
$2,698/mo median rent
16 sold in 12 months
Drive times
On the market now
Homes for sale in Highland Oaks
View all 14 →
$275,000
2055 29TH STREET S, ST PETERSBURG
3 bd · 1 ba · 1,266 sqft
$249,000
2210 20TH AVENUE S, ST PETERSBURG
3 bd · 1 ba · 754 sqft
$189,900
1924 30TH STREET S, ST PETERSBURG
2 bd · 1 ba · 918 sqft
$210,000
1905 24TH STREET S, ST PETERSBURG
2 bd · 1 ba · 612 sqft
$269,000
1922 23RD STREET S, ST PETERSBURG
3 bd · 1 ba · 930 sqft
$299,900$325,000
2211 22ND AVENUE S, ST PETERSBURG
4 bd · 2 ba · 1,400 sqft
$469,900$475,000
3069 19TH AVENUE S, ST PETERSBURG
3 bd · 2 ba · 1,770 sqft
$459,000$469,000
1844 AUBURN STREET S, ST PETERSBURG
3 bd · 2 ba · 1,506 sqft
$345,000$350,000
1900 25TH STREET S, ST PETERSBURG
3 bd · 2 ba · 1,190 sqft
$535,000$550,000
2335 MURILLA WAY S, ST PETERSBURG
4 bd · 3 ba · 1,840 sqft
$474,000
2459 25TH AVENUE S, ST PETERSBURG
4 bd · 2 ba · 1,665 sqft
$255,000$265,000
2351 25TH AVENUE S, ST PETERSBURG
3 bd · 1 ba · 1,088 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
16
Sold, last 12 months
$278,500
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
64 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
≈ $1,957/mo
$293,950 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$2,698/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 quiet, established residential pocket in southern St Petersburg, close to bay-side neighborhoods and assigned to Maximo Elementary, Bay Point Middle, and Gibbs High. Homes tend to be modest and single-family, and both Tampa International Airport and Downtown Tampa are around a 30-minute drive. It suits buyers who want an approachable St Pete address without the waterfront premium.
Is Highland Oaks expensive?+
Not by St Pete standards — the median list price is $299,900, with active homes ranging from $210,000 to $535,000. That's a notable step down from waterfront enclaves like Bayway Isles, making it one of the more realistic entry points in the area.
What do homes cost in Highland Oaks?+
Expect a median around $299,900 on the list side and $278,500 for homes that actually sold over the past year. Prices average about $275 per square foot on a median home size of roughly 1,266 square feet, so most properties here are compact single-family homes.
How is the market in Highland Oaks?+
There are 13 active listings and 16 homes sold in the last 12 months, with a median of 44 days on market. Sellers are averaging about 98% of their asking price, which points to a steady, balanced market rather than a frenzy. Compared with tighter nearby areas like Greater Pinellas Point, buyers have room to negotiate.
What about HOA fees and property taxes?+
Property taxes run a median of about $2,291 per year, which is manageable at these price points. There's no significant HOA data on file for the neighborhood, so most homes here are likely fee-free. If renting the numbers instead, the median rent sits around $2,698 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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