Neighborhood · St Petersburg, Florida
Highland Oaks
Approachable St Pete living close to the water
13
Homes for sale
$325,000
Median list price
$276
Avg price / sqft
40
Median days on market
Highland Oaks sits in the southern reaches of St Petersburg, a part of Pinellas County where neighborhoods like Shore Acres, Greater Pinellas Point and Coquina Key trade on easy access to Tampa Bay and a relaxed, residential pace. It's the kind of pocket where you can settle into everyday St Pete life without paying the premiums of the marquee waterfront enclaves like Bayway Isles.
For buyers, the appeal right now is price. With 12 active listings and a median list price of $337,500, Highland Oaks reads as one of the more attainable entries into St Petersburg homes for sale, especially compared with the county's coastal segments. Inventory is modest, so the right home tends to move, and it pays to be ready when something fits.
Highland Oaks is a community in St Petersburg, Florida.
Quick facts
$210,000 – $535K price range
1,266 sqft median home
$2,698/mo median rent
17 sold in 12 months
Drive times
On the market now
Homes for sale in Highland Oaks
View all 13 →
$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
$325,000
2211 22ND AVENUE S, ST PETERSBURG
4 bd · 2 ba · 1,400 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
$469,900$475,000
3069 19TH AVENUE S, ST PETERSBURG
3 bd · 2 ba · 1,770 sqft
$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
$288,000$309,000
1826 30TH STREET S, ST PETERSBURG
2 bd · 1 ba · 986 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
17
Sold, last 12 months
$272,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
72 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
≈ $2,113/mo
$325,000 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 solid choice if you want an everyday St Petersburg neighborhood on the city's south side, near established communities like Disston Heights and Coquina Key. You get proximity to Tampa Bay and a residential feel, with Tampa about 30 minutes away for work or travel.
Is Highland Oaks expensive?+
Not by St Petersburg standards. The median list price of $337,500 is notably lower than the city's waterfront-heavy segments, and there are currently no listings above $1M, which keeps the area accessible for first-time and move-up buyers.
What do homes cost in Highland Oaks?+
Right now the median list price is $337,500 across 12 active listings. That's the practical center of the market here, giving buyers a clear sense of where competitive offers should land.
How is the market in Highland Oaks?+
Inventory is tight at 12 active listings, so choices are limited and well-priced homes tend to move. Recorded sales data over the past 12 months is thin, so leaning on the current list price of $337,500 and comparable St Petersburg homes for sale is the best way to gauge value.
What about HOA fees and property taxes?+
We don't have reliable HOA or property-tax figures specific to Highland Oaks in the current data, and many homes here are traditional single-family properties without heavy association costs. Ask your agent to pull the exact HOA and tax numbers on any home before you write an offer.
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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