For sale

$565,000

Est. $3,978/mo

•

1,446

sq ft

4986 Woodland Dr, Saint Petersburg, FL 33708

About this home

FULLY RENOVATED POOL HOME with NO RENTAL RESTRICTIONS offering the perfect blend of lifestyle and investment potential * This is an ACTIVE Short-Term RENTAL * . This move-in ready 2 BEDROOM, 2 BATH home also features a FLEX/OFFICE that can easily function as a 3RD BEDROOM. Situated on an OVERSIZED LOT at the end of a QUIET DEAD-END STREET people rately move away from, you'll enjoy exceptional privacy surrounded by lush tropical landscaping. Recent updates include a NEW KITCHEN, RENOVATED BATHROOMS, NEW FLOORING, NEW HVAC DUCTWORK, MODERN LIGHTING, FRESH INTERIOR & EXTERIOR PAINT, EXPANDED C-SHAPED DRIVEWAY with room for multiple vehicles, * * * RV and BOAT PARKING * * * , PLUS ALL NEW WINDOWS and a NEWLY SCREENED LANAI completed in 2025. The sparkling pool creates your own private backyard retreat, while the property's SUCCESSFUL SHORT-TERM RENTAL HISTORY and NO RENTAL RESTRICTIONS provide incredible flexibility for personal use or income generation. Centrally located just 5 MINUTES TO MADEIRA BEACH, 20 MINUTES TO DOWNTOWN ST. PETERSBURG, 30 MINUTES TO CLEARWATER, and approximately 30 MINUTES TO BOTH TAMPA (TPA) and PIE (ST. PETE/CLW) AIRPORTS. Quick 5 Min Drive to SEminole City Center for Movies, Dining, and Shopping for guests and easy straight shot to the Beach. This one isn't just style, it's THE Florida Lifestyle — Priced to Sell Quickly. Schedule your private showing today! (Only Availabe During Vacancies)

Single-familyProperty Type

1960Year Built

0.34 acresLot Size

$391Price/Sq.Ft.

1 car garageParking

Listed by Amber Heddleson • FUTURE HOME REALTY INC

Contact: 813-855-4982

Listing updated: Aug 10, 2026 at 01:23pm

Redfin checked: 4 minutes ago

•Source:Stellar MLS as Distributed by MLS Grid #TB8530083

Payment calculator

$3,978 per month

Principal and interest$2,932

Property taxes

$642

HOA dues

Home insurance

$405

Utilities

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This home is unavailable to tour on this day.

Next available date: Thursday, August 13

Open houses

No upcoming open houses.

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Around this home

Schools

K - 12
Preschool & daycare

Orange Grove Elementary School

Public PreK-5 • Assigned • 1.0mi

10/10

Osceola Middle School

Public 6-8 • Assigned • 2.8mi

5/10

Seminole High School

Public 9-12 • Assigned • 3.0mi

4/10

Provided by GreatSchools

About South

Pinellas

South Pinellas, located between Boca Ciega Bay and the Intracoastal Waterway, is a coastal and suburban Bay Pines neighborhood with a salt-air shoreline and a patchwork of marinas. The neighborhood’s character concentrates around the Bay Pines Boulevard and 100th Way North corridor, where boat ramps, tackle shops, and low-key waterfront eateries set a working-coastal tone. Mid-century ranch homes and condo communities sit along palms and canal edges, with pockets of mangroves framing the streetscape. War Veterans’ Memorial Park adds a broad green pause for walks and picnics. The Bay Pines VA Healthcare System campus anchors a civic presence and steady daytime rhythm. Nearby beaches and causeways keep the geography front and center.

Provided by Walk Score and Local Logic

Offer insights

4986 Woodland Dr · $565,000

Strong offer

$565K and above

75% chance or better to win

Why $565K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 38 days.

SALE-TO-LIST

Most homes are selling 3% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Ceiling fans
Kitchen/family room combo
Living room/dining room combo
Open floorplan
Stone counters
Thermostat

Bedrooms
2 bedrooms

Bathrooms
2 full bathrooms

Kitchen
Built-in oven
Range
Range hood
Microwave
Dishwasher
Disposal
Exhaust fan
Refrigerator

Laundry & utility
Washer hookup
Electric dryer hookup
Laundry area in garage

Flooring
Vinyl flooring

Heating & cooling
Central heating (electric)
Central air conditioning

Sale and tax history for 4986 Woodland Dr

Sale History
Tax History

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #TB8530083

Aug 10, 2026

Relisted

—

Jul 16, 2026

Listed

$565,000

$391/sq ft

Public Records

Oct 21, 2024

Sold

$530,000

$367/sq ft

Stellar MLS as Distributed by MLS Grid #U8253868

Oct 28, 2024

Listing Removed

—

Oct 24, 2024

Sold

$530,000

$367/sq ft

Sep 20, 2024

Pending

—

Aug 13, 2024

Listed

$559,000

$387/sq ft

Welcome to a private oasis! This beautifully renovated 2-bed, 2-bath home features a stunning pool surrounded by lush, mature tropical landscaping that fills the oversized lot with natural beauty and light; it also has an office which could be used as a 3rd bedroom. Enjoy serene views from nearly every window, offering a true retreat feel. There are no rental restrictions, so this property could be utilized as a short-term rental. This property is move-in ready with a recent full renovation including a new kitchen, new bathroom, new flooring, new ventilation ducts, new modern lighting, fresh paint inside and out, a new c-shape driveway with ample parking for many guests, an RV, and a Boat. Nestled in a secluded neighborhood in the heart of Pinellas County, this home is centrally located with privacy as the last house on a peaceful dead-end street with ample parking for guests. Close proximity to VA hospital, shopping, restaurants, and several Gulf beaches. Many attractions within a short drive include: Madeira Beach in 5 minutes, St Pete in 20 minutes, Clearwater in 30 minutes, two international airports in 30 minutes, Busch Gardens 1 hour, and Disney World and Universal Studios are about a ~2.5 hour drive. Owner is a Licensed Real Estate Agent.

Public Records

Jun 7, 2024

Sold

$384,000

$266/sq ft

Public Records

May 20, 2024

Sold

$349,200

$241/sq ft

Stellar MLS as Distributed by MLS Grid #T3402036

Oct 15, 2022

Listing Removed

—

Sep 12, 2022

Listed

$499,000

$345/sq ft

Stellar MLS as Distributed by MLS Grid #T2550963

Mar 22, 2013

Sold

$120,007

$83/sq ft

Jan 14, 2013

Listed

$116,980

$81/sq ft

Stellar MLS as Distributed by MLS Grid #U7168740

Jul 28, 2006

Sold

$247,500

$171/sq ft

Jan 24, 2006

Listed

$249,900

$173/sq ft

Public Records

May 3, 2004

Sold

$165,000

$114/sq ft

Public Records

Dec 27, 1995

Sold

$83,000

$57/sq ft

Public Records

Mar 22, 1989

Sold

$72,400

$50/sq ft

Public record

Public record
Zoning

Beds

—

Baths

Stories

Lot width

95 ft.

Lot depth

100 ft.

Lot size

0.34 Acres

Year renovated

2007

Finished Sq. Ft.

1,446

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,446

Year built

1960

Style

Single Family Residential

County

Pinellas County

APN

153103057960000080

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 16, 2026.

R-3

Single-Family Residential District

The R-3, Single-Family Residential District provides for areas of single-family residential development located where higher density single-family uses are desirable. It provides for the highest density of all the traditional single-family residential zoning districts.

Permitted uses

Include but are not limited to:

Garden center
Day care facility
Housing-Group
Housing-Single unit
Infrastructure
Recreation
Communications tower
Housing-Mobile home park
Park & open space

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

10/10 Heat Factor

7 days above 107° expected this year, 26 days in 30 years

10/10 Wind Factor

99% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Saint Petersburg, FL • 33708

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

88/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.3 hrs

5.8 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 4986 Woodland Dr

$546,360

$19K under list price of $565K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $467K to $652K.

SOLD JUN 5, 2026
$540,000 Last sold price
3 beds2 baths1,464 sq ft
5135 101st St N, St Petersburg, FL 33708
$22/sq ft
smaller lot
3 years older
SOLD JUL 14, 2026
$525,000 Last sold price
3 beds2 baths1,498 sq ft
5576 Williamsdale Ct, Seminole, FL 33772
$41/sq ft
smaller lot
6 years newer
SOLD JUN 25, 2026
$565,000 Last sold price
3 beds2 baths1,301 sq ft
11124 60th Ave, Seminole, FL 33772
$43/sq ft
smaller lot
9 years newer
SOLD JUL 24, 2026
$547,000 Last sold price
4 beds2 baths1,822 sq ft
9836 52nd Ter N, St Petersburg, FL 33708
$91/sq ft
smaller lot
1 year older
SOLD JUN 9, 2026
$652,000 Last sold price
3 beds2 baths1,794 sq ft
5010 109th Way N, St Petersburg, FL 33708
$28/sq ft
smaller lot
2 years newer
SOLD MAY 27, 2026
$467,000 Last sold price
3 beds2.5 baths2,466 sq ft
5041 Myrtle Ln, Saint Petersburg, FL 33708
$202/sq ft
smaller lot
3 years older

Rental earnings

Est. $3,833 per month, based on comparable rentals

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Details provided by Stellar MLS as Distributed by MLS Grid and may not match the public record. Learn more.

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