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Explore Similar Houses Within 2 Miles of Highland Oaks, FL

  • /60

    $1,900,000

    • 4 Beds
    • 3 Baths
    • 3,538 Sq Ft

    5900 Leeland St S, Saint Petersburg, FL 33715

    Stunning Single-Family Home in the private gated community of Bayway Isles in St. Petersburg, FL. Perfectly situated, with just a short hop to world-class beaches or the highway to downtown St. Petersburg or downtown Tampa in less than 30 mins. This distinctive, updated, Mediterranean-style 2-story offers the perfect blend of style and elegance with expansive outdoor living space for entertaining

    Agent Photo

    Daniel Robinson

    HOUWZER INC

    (844) 755-2296

    5900 Leeland St S, Saint Petersburg, FL 33715
  • /71

    $1,599,900 New Construction

    • 4 Beds
    • 4 Baths
    • 3,463 Sq Ft

    2814 54th St S, Gulfport, FL 33707

    Experience the best of Gulfport living in this brand-new, high-and-dry construction, located in a no-flood zone and just a block from the vibrant downtown. This spacious 4-bedroom, 4-bath home with a 2-car garage is perfectly situated on an oversized corner lot. Step into an entertainer's paradise with a spacious open floor plan centered around a magnificent ten-foot quartz kitchen island. Enjoy

    Agent Photo

    Matthew Carr

    WINWAY REALTY

    (844) 790-3529

    2814 54th St S, Gulfport, FL 33707
  • /77

    $524,500

    • 4 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    5010 8th Ave N, Saint Petersburg, FL 33710

    Don't miss this amazing home with a NEW AND IMPROVED PRICE! Welcome to 5010 8th Avenue N, a spacious 4-bedroom, 2.5-bath pool home offering over 2,100 square feet of living space in a central St. Petersburg location. This move-in ready residence features a comfortable layout with multiple living areas, including a bright living room, an expansive dining area just off the kitchen, and a separate

    Stephanie See RESULTS REAL ESTATE INC

    5010 8th Ave N, Saint Petersburg, FL 33710
  • /67

    $1,300,000

    • 4 Beds
    • 2 Baths
    • 2,338 Sq Ft

    4328 40th St S, Saint Petersburg, FL 33711

    Welcome to your coastal dream retreat in the coveted Broadwater community—where thoughtful updates, modern comfort, and waterfront serenity come together effortlessly. This expansive 4-bedroom residence showcases a brand-new 90’ seawall, updated landscaping (2025), with ZERO water intrusion during last year's storms, offering the ultimate peace of mind for discerning buyers. Inside, the home

    Stephen Gay SMITH & ASSOCIATES REAL ESTATE

    4328 40th St S, Saint Petersburg, FL 33711
  • /62

    $1,479,000

    • 4 Beds
    • 3.5 Baths
    • 2,494 Sq Ft

    5884 51st St S, Saint Petersburg, FL 33715

    This stunning, meticulously redesigned 4 bedroom, 3.5 bath home, located in the 24-hour guard-gated community of Bayway Isles, offers a rare opportunity to own in one of St. Petersburg’s most coveted neighborhoods. Offering the perfect blend of timeless charm, privacy, and exclusivity, this reimagined single story residence is nestled on a secluded cul-de-sac street and sits on an oversized lot

    Michelle Ward SMITH & ASSOCIATES REAL ESTATE

    5884 51st St S, Saint Petersburg, FL 33715
  • /80

    $1,950,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,887 Sq Ft

    2101 3rd Ave N, Saint Petersburg, FL 33713

    Experience timeless craftsmanship and modern luxury at 2101 3rd Ave N, a brand-new home by JWM Residential in St. Petersburg’s coveted Historic Kenwood. This stunning corner-lot property features a beautifully designed 3-bedroom, 2.5-bath main residence and a fully equipped 1-bedroom, 1-bath carriage house above a detached garage—perfect for guests, rental income, or a private studio.Inside the

    Jonathan Meyer REALNET FLORIDA REAL ESTATE

    2101 3rd Ave N, Saint Petersburg, FL 33713
  • /44

    $1,599,500 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,463 Sq Ft

    4166 38th St S, Saint Petersburg, FL 33711

    This stunning move-in-ready NEW construction home boasts a spacious two-car garage with a convenient mudroom/laundry area that seamlessly connects to the house. The first floor features an oversized family room and a gourmet kitchen, complete with a pantry and a large island. An open dining room overlooks the backyard, providing a perfect setting for meals and gatherings. The first floor also

    Julien Collet PINEYWOODS REALTY LLC

    4166 38th St S, Saint Petersburg, FL 33711
  • /81

    $1,200,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,767 Sq Ft

    3901 30th Ave S, Gulfport, FL 33711

    One or more photo(s) has been virtually staged. Pre-Construction. To be built. 1 of 3 new homes by Kelner Homes on the edge of Clambayou Nature Preserve where Salt Life meets City Life. ***You would be just a 100 hundred feet from trail and water access for walking, biking, fishing and kayaking**,1 block from the new Skyway Village with shops and Restaurants, just 1 or 2 miles to 2 different

    Brooke Hartman REALTY HUB

    3901 30th Ave S, Gulfport, FL 33711
  • /98

    $1,995,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,390 Sq Ft

    526 39th Ave S, Saint Petersburg, FL 33705

    Stunning new construction ready for occupancy! Come see this gorgeous coastal style 4 bedroom 3.5 bathroom Pool home with additional 2 bedroom 2 bathroom additional living unit along with a 2 car garage. Property also has a deeded boat slip across the street with access to Tampa bay and beyond! Soaring ceiling with an open floorplan makes you feel like you are at your own resort, Large open chef

    Peter Chicouris WEICHERT REALTORS EXCLUSIVE PROPERTIES

    526 39th Ave S, Saint Petersburg, FL 33705
  • /80

    $1,189,000 Pre-Foreclosure

    • 4 Beds
    • 2 Baths
    • 1,930 Sq Ft

    4568 40th St S, Saint Petersburg, FL 33711

    "Best of Both Worlds" in this fully renovated 4 bedroom 2 bathroom pool home offering over 1900 sq ft in the desirable waterfront neighborhood of Broadwater in St Petersburg. Walking into the house prepare to be wowed at every turn. The split floorplan offers 4 bedrooms with 3 bedrooms on one side sharing a hallway bath and the primary bedroom offers an ensuite bathroom with dual walk-in closets

    William Thomas COMPASS FLORIDA LLC

    4568 40th St S, Saint Petersburg, FL 33711
  • /43

    $649,000

    • 4 Beds
    • 3 Baths
    • 1,731 Sq Ft

    2801 Tifton St S, Gulfport, FL 33711

    This amazingly versatile home has something for everyone! It has been beautifully remodeled, offers spacious living areas, and can be divided into a main house with In-Law Suite or be used as a large 4 bedroom, 3 bath home.The In-Law Suite can be opened up to the main house and used as a Primary Suite or it has the ability to be closed off and used as separate living quarters with private

    Stephanie McNaughton FOREVER FLORIDA REAL ESTATE

    2801 Tifton St S, Gulfport, FL 33711
  • /57

    $639,900 Open Sat 12PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,865 Sq Ft

    4530 Catalonia Way S, Saint Petersburg, FL 33712

    Tropical Oasis in Desirable Lakewood Estates – No HOA + Flood Zone X!Welcome to this beautifully maintained and thoughtfully updated 4-bedroom, 2-bath pool home located in the heart of Lakewood Estates—one of St. Pete’s most sought-after neighborhoods. With 1,865 square feet of living space on an oversized 0.36-acre lot (15,591 sq ft), this property is the perfect blend of indoor comfort

    Ellie Lambert REAL BROKER, LLC

    4530 Catalonia Way S, Saint Petersburg, FL 33712
  • /39

    $750,000

    • 4 Beds
    • 2.5 Baths
    • 1,905 Sq Ft

    2581 61st Ave S, Saint Petersburg, FL 33712

    This distinguished and updated pool home in St. Petersburg welcomes you with thoughtfully executed renovations and timeless appeal. The 4-bedroom, 2.5-bath residence showcases engineered hardwood flooring throughout, complemented by spacious living areas that flow seamlessly from the front through the updated kitchen to the screened-in lanai. Four sets of impact sliding doors create an effortless

    Jeremy Grant SMITH & ASSOCIATES REAL ESTATE

    2581 61st Ave S, Saint Petersburg, FL 33712
  • /79

    $683,000

    • 4 Beds
    • 2 Baths
    • 1,936 Sq Ft

    3944 49th Ave S, Saint Petersburg, FL 33711

    Updated Tropical Retreat in Maximo Moorings – Spacious, Stylish, and Minutes from Beaches and BoatingWelcome to this beautifully renovated 4-bedroom, 2-bathroom home—plus a flexible 5th room perfect for a home office, guest space, or playroom—ideally located on one of the most desirable streets in Maximo Moorings. Set on an oversized lot with lush tropical landscaping and multiple outdoor

    Pam Moll COLDWELL BANKER REALTY

    3944 49th Ave S, Saint Petersburg, FL 33711
  • /55

    $499,990

    • 4 Beds
    • 2 Baths
    • 1,377 Sq Ft

    5611 Burlington Ave N, Saint Petersburg, FL 33710

    Welcome to 5611 Burlington Ave N – a beautifully updated 4-bedroom, 2-bath concrete block pool home in a desirable St. Petersburg neighborhood. No hurricane damage, not in a flood zone, and packed with high-quality upgrades for peace of mind and comfortable living.Freshly painted inside and out, this home features crown molding, decorative window trim, and brand-new tile flooring throughout.

    Janice Sanburn EXP REALTY LLC

    5611 Burlington Ave N, Saint Petersburg, FL 33710
  • /50

    $815,000

    • 4 Beds
    • 2.5 Baths
    • 1,732 Sq Ft

    2519 1st Ave N, Saint Petersburg, FL 33713

    Ideally located at the intersection of two of St. Pete’s most thriving neighborhoods—Historic Kenwood and the Grand Central District—this exceptional property embodies the ultimate Live, Work, Play, Earn, and Shop lifestyle. The main home features 3 bedrooms and 1 and a half bathrooms. It features a separate office entrance that leads to a front room with a half bath and is zoned to allow a

    Brad Bohnert KELLER WILLIAMS ST PETE REALTY

    2519 1st Ave N, Saint Petersburg, FL 33713
  • /25

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 1,974 Sq Ft

    4100 1st Ave S, Saint Petersburg, FL 33711

    One or more photo(s) has been virtually staged. Welcome to this absolutely charming 4-bedroom, 2.5-bathroom home with 1,974 square feet of ample living space that’s sure to impress you. Nestled on a desirable corner double lot, this property offers the perfect blend of character and unbeatable location—just minutes from both vibrant downtown St. Petersburg and the pristine Florida Gulf beaches.

    Jac Smith KELLER WILLIAMS ST PETE REALTY

    4100 1st Ave S, Saint Petersburg, FL 33711
  • /47

    $819,900 Open Sun 12PM - 2PM

    • 4 Beds
    • 4 Baths
    • 2,658 Sq Ft

    1868 Juarez Way S, Saint Petersburg, FL 33712

    Great 4 bedroom/4 bath Ranch style home located in the desired Lakewood Estates Community. The house is situated across the street from St. Petersburg Country Club golf course. The outdoor space has a huge in-ground pool with cage - great spot for relaxing, even better for entertaining. Minutes away from downtown St. Petersburg and all it has to enjoy, some of the best beaches and Boyd Hill

    Carol Johnson CHARLES RUTENBERG REALTY INC

    1868 Juarez Way S, Saint Petersburg, FL 33712
  • /28

    $675,000

    • 4 Beds
    • 2 Baths
    • 1,970 Sq Ft

    4301 50th Terrace S, Saint Petersburg, FL 33711

    No flooding the past hurricane season and no history of flooding on this property! Discover your dream Florida lifestyle in this spacious and inviting 4 bedroom, 2 bathroom pool home, nestled in the highly sought-after Maximo Moorings neighborhood of St. Petersburg. This property offers the perfect blend of comfort, style, and convenience, making it an ideal haven for families and entertainers

    Keith Burt DALTON WADE INC

    4301 50th Terrace S, Saint Petersburg, FL 33711
  • /64

    $2,650,000

    • 4 Beds
    • 3 Baths
    • 3,154 Sq Ft

    4959 58th Ave S, Saint Petersburg, FL 33715

    Tropical Waterfront Paradise in Bayway Isles – High and Dry!Experience luxury waterfront living in the exclusive, gated community of Bayway Isles in St. Petersburg, FL. This stunning four-bedroom, three-bathroom home with a den/studio is a masterpiece of design and craftsmanship, offering the perfect blend of elegance and coastal charm.Nestled on a deep through-water channel with direct

    Steve Coderre REVERE REALTY LLC

    4959 58th Ave S, Saint Petersburg, FL 33715
  • /74

    $4,000,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 4.5 Baths
    • 4,400 Sq Ft

    4900 59th Ave S, Saint Petersburg, FL 33715

    Welcome to a one-of-a-kind masterpiece in the exclusive, guarded community of Bayway Isles. Originally designed by C. Randolf Wedding in the style of Frank Lloyd Wright in 1973, this mid-century modern estate has been completely reimagined in 2023 by Lisa Gilmore Design. Showcased on Architectural Digest and in the January 2025 issue of Florida Design, this home represents a harmonious blend of

    Alison Bearnarth SMITH & ASSOCIATES REAL ESTATE

    4900 59th Ave S, Saint Petersburg, FL 33715
  • /64

    $3,275,000

    • 4 Beds
    • 5 Baths
    • 4,082 Sq Ft

    310 8th Ave N, Saint Petersburg, FL 33701

    You Can Truly Have It All – Stunning Pool Home in the Heart of Old Northeast!Located just steps from vibrant Downtown St. Petersburg, this meticulously crafted 2017-built home offers the perfect blend of modern luxury and charm and is being offered fully furnished. Not only is this home a masterpiece, but it also boasts peace of mind with impact windows and doors—it sustained no damage and didn’t

    Bree Bowen KELLER WILLIAMS REALTY- PALM H

    310 8th Ave N, Saint Petersburg, FL 33701
  • /45

    $960,000

    • 4 Beds
    • 3.5 Baths
    • 2,826 Sq Ft

    6000 51st St S, Saint Petersburg, FL 33715

    Discover the prestigious, guard-gated community of Bayway Isles, known for its premier homes and 24-hour security. This spacious residence offers vaulted ceilings and a thoughtfully designed layout that perfectly balances inviting shared spaces and private retreats. The living and dining areas connect seamlessly to a beautifully appointed eat-in kitchen. It features stunning marble countertops,

    Tally Figueredo KELLER WILLIAMS ST PETE REALTY

    6000 51st St S, Saint Petersburg, FL 33715
  • /66

    $2,640,000

    • 4 Beds
    • 3.5 Baths
    • 3,219 Sq Ft

    2001 Beach Dr SE, Saint Petersburg, FL 33705

    WATERFRONT PROPERTY HIGH AND DRY —NO FLOOD INSURANCE REQUIRED. Discover charm and elegance with breathtaking waterfront views of Tampa Bay in this meticulously renovated home by award-winning builder Don Strobel. Perfectly blending historical character with modern luxury, this 3-bedroom, 2.5-bath main home features heart pine floors, Cuban-tiled wood-burning fireplaces, and a chef’s kitchen with

    Tiffany McAlister REALTY ONE GROUP SUNSHINE

    2001 Beach Dr SE, Saint Petersburg, FL 33705
  • /31

    $685,000

    • 4 Beds
    • 2 Baths
    • 1,973 Sq Ft

    5260 42nd St S, Saint Petersburg, FL 33711

    MARVELOUS MAXIMO - Close to: Shopping, schools, a college, world class beaches, some of the best camping in the US, a state of the art marina providing access to the bays, intercoastal and the gulf, resaturants, fast food, a 24 hour convenience store with fuel, the interstate highway system, 5 minutes from downtown St. Petersburg or 30 minutes from Tampa, and the sports arenas, airports and

    Bill Paul GATOR REALTY OF POLK

    5260 42nd St S, Saint Petersburg, FL 33711
  • /13

    $3,000,000

    • 4 Beds
    • 3 Baths
    • 2,856 Sq Ft

    6200 Bahama Shores Dr S, Saint Petersburg, FL 33705

    Welcome to Bahama Shores Waterfront neighborhood. Here is your chance to build your luxury dream home on one of the most coveted and largest waterfront lots in St. Petersburg! This property is a .76-acre lot, 138-by-270 feet, which looks out to direct open water paradise views, with dolphins and manatees frequently passing by. The backyard oasis is an excellent space for entertaining or creating

    Tiffany Weidner PREMIER SOTHEBYS INTL REALTY

    6200 Bahama Shores Dr S, Saint Petersburg, FL 33705
  • /55

    $1,100,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,767 Sq Ft

    3847 30th Ave S, Gulfport, FL 33711

    Pre-Construction. To be built. 1 of 3 new homes by Kelner Homes on the edge of Clambayou Nature Preserve where Salt Life meets City Life. ***You would be just a 150 hundred feet from trail and water access for walking, biking, fishing and kayaking**,1 block from the new Skyway Village with shops and Restaurants, just 1 or 2 miles to 2 different Marinas, The Golf Course, Tiki Docs and just 10

    Brooke Hartman REALTY HUB

    3847 30th Ave S, Gulfport, FL 33711
  • /33

    $3,500,000 New Construction

    • 4 Beds
    • 5 Baths
    • 4,556 Sq Ft

    4441 Pompano Dr SE, Saint Petersburg, FL 33705

    Under Construction. Welcome to this stunning 4-bedroom, 5-bathroom ultra-modern waterfront masterpiece, a Kelner Homes build where luxury and sophistication meet in the heart of St. Petersburg. Designed for those with a discerning eye, this two-story home boasts top-of-the-line appliances and exquisite finishes throughout, offering a perfect blend of elegance and cutting-edge design. Every detail

    Ali St Cyr TOMLIN, ST CYR & ASSOCIATES LLC

    4441 Pompano Dr SE, Saint Petersburg, FL 33705

Home Trends in Highland Oaks, FL

Housing Trends

Median Sale Price
$271,443
Median Single Family Sale Price
$240,000
Median Townhouse Sale Price
$425,044
Median 2 Bedroom Sale Price
$204,000
Average Price Per Sq Ft
$194
Number of Homes for Sale
4
Last 12 months Home Sales
45
Months of Supply
1.10
Median List Price
$406,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-59%
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