Date
Details
Price
Change
Source
5/12/2026
Listed
$550,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$550,000 Just Listed
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Property Description
Beautifully remodeled villa-style home in the premier Sarasota community of The Meadows. Recent updates include fresh interior paint, new flooring, tile, and appliances, creating a clean, move-in-ready feel throughout. Spacious Great Room featuring a wood burning fireplace and built in wet bar. This free-standing residence is in the charming Highland Park enclave, offering privacy with no adjoining walls and a generously sized two-car garage. High ceilings with molding and eight-foot sliding glass doors fill the home with natural light while framing beautiful views. The floor plan flows exceptionally well, creating a sense of openness, comfort, and privacy. Enjoy the exceptional lifestyle of The Meadows, known for its 85 lakes and waterways, 14 miles of walking and biking trails, majestic oak trees, preserved open spaces, and commitment to wildlife and ecology. Community amenities include golf, 15 Har-Tru tennis courts, eight new pickleball courts, a lifestyle center, and a Junior Olympic-size pool. Ideally situated between UTC and downtown Sarasota, this location offers convenient access to world-renowned restaurants, exclusive shopping, vibrant arts and culture, Nathan Benderson Park, the newly opened Mote Marine Aquarium, and Sarasota's sparkling Gulf Coast beaches. A wonderful opportunity to enjoy comfort, convenience, and the natural beauty of one of Sarasota's most established communities
Full Property Details
Full Property Details for 4424 Highland Park #5
General
- Price: $550,000
- HOA FEE: $171/month
- HOA FEE FREQ.: Annually
- Taxes: $3,107 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4692053
- Updated: Today (5/12/2026)
- Added to Site: Today
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 9
- Interior Features: Crown Molding, Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Free Standing, Living Room, Masonry, Wood Burning
- Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Luxury Vinyl, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room, Same Floor As Condo Unit
Additional Information
- Shared Amenities: Fitness Center, Golf Course, Pickleball Court(s)
- Pool Description: Auto Cleaner, Child Safety Fence, Gunite
- Spa: Yes
- Spa Description: In Ground
Exterior
- Exterior Features: Courtyard, Private Entrance, Sliding Doors
- Deck/Patio: Enclosed, Patio, Rear Porch
- Porch/Patio/Deck: Enclosed, Patio, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener, Garage Faces Side, Ground Level, Off Street
Location
- Area: 34235 - Sarasota
- County: Sarasota
- Development Name: 34235 - Sarasota
- Subdivision: HIGHLAND PARK
- Driving Directions: From Longmeadow and Hadfield, turn on Hadfield. Right on Highland Oaks Dr., Right into Highland Park and turn into 4424 on right.
- Direction Faces: North
School Information
- Elementary School: Gocio Elementary
- Middle School: Booker Middle
- High School: Booker High
Community
- Community Name: 34235 - Sarasota
- Community Features: Buyer Approval Required, Deed Restrictions, Dog Park, Fitness Center, Golf Carts OK, Pool, Tennis Court(s)
- Optional Amenities: Fitness Center, Golf Course, Pickleball Court(s)
- Association: Yes
- Assoc. Name: Stokes Property Management
- Assoc. Fees Include: Cable TV, Common Area Taxes, Community Pool, Insurance, Maintenance Grounds, Maintenance Repairs, Pest Control, Pool Maintenance, Private Road
- Number of Pets: 2
- Management Type: Full Time
- Mgmt. Company: Full Time
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: None
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Sewer Connected, Underground Utilities
Structural Information
- Architectural Info: Coastal, Contemporary, Florida, Patio
- Architectural Style: Coastal, Contemporary, Florida, Patio
- Exterior Const.: Block, Stucco
- Roof: Concrete, Tile
- Stories/Levels: One
- Square Feet: 2,120
- Sq. Ft. Source: Public Records
- Year Built: 1988
Lot Features
- Property View: Garden, Pool
- Lot Size (Sq. Ft.): 240,288
- Lot Size: 5.5163
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Green Features
- Energy Efficient: Appliances
Financial Considerations
- Association Fee: $2,049
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Required
- Condo Fee: $2,624
- Condo Fee Freq: Quarterly
- Tax Amount: $3,107
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: UNIT 5 HIGHLAND PARK
- Flood Zone Info: AE
- APN: 33051005
- Property ID: 33051005
Listed by Morgan Johnson Realty Llc
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 4424 Highland Park #5 —
Morgan Johnson Realty Llc
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 4424 Highland Park #5
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Gocio Elementary School 3450 Gocio Road, Sarasota, FL 34235 | PK-5 | 1.3 mi |
Booker Middle School 2250 Myrtle Street, Sarasota, FL 34234 | 6-8 | 2.7 mi |
Booker High School 3201 North Orange Avenue, Sarasota, FL 34234 | 9-12 | 3.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 4424 Highland Park #5
Tax History
Tax History for 4424 Highland Park #5
Year
Property Taxes
Change
Tax Assessment
Change
2024
$2,961
—
$239,728
3%
2024
$2,961
6%
$232,972
3%
2023
$2,784
6%
$226,186
6%
2021
$2,637
-2%
$213,202
-3%
2022
$2,696
2%
$219,598
4%
2021
$2,637
4%
$210,258
2%
2019
$2,538
3%
$205,531
2%
2018
$2,472
1%
$201,699
2%
2017
$2,458
1%
$197,550
2%
2016
$2,443
-2%
$193,487
1%
2015
$2,483
—
$192,142
1%
2014
$2,472
—
$190,617
2%
2013
$2,461
—
$187,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 4424 Highland Park #5
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4424 Highland Park #5, Sarasota, FL 34235 (MLS# A4692053) is a Single Family property with 3 bedrooms and 2 full bathrooms. 4424 Highland Park #5 is currently listed for $550,000 and was received on May 12, 2026. Want to learn more about 4424 Highland Park #5? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.