Side - 4424 HIGHLAND PARK #5, SARASOTA
Backyard - 4424 HIGHLAND PARK #5, SARASOTA
Side - 4424 HIGHLAND PARK #5, SARASOTA
ariel - 4424 HIGHLAND PARK #5, SARASOTA
ariel - 4424 HIGHLAND PARK #5, SARASOTA
Entry - 4424 HIGHLAND PARK #5, SARASOTA
Living area - 4424 HIGHLAND PARK #5, SARASOTA
Dining - 4424 HIGHLAND PARK #5, SARASOTA
Dining - 4424 HIGHLAND PARK #5, SARASOTA
wet bar - 4424 HIGHLAND PARK #5, SARASOTA
kitchen - 4424 HIGHLAND PARK #5, SARASOTA
kitchen - 4424 HIGHLAND PARK #5, SARASOTA
kitchen - 4424 HIGHLAND PARK #5, SARASOTA
kitchen - 4424 HIGHLAND PARK #5, SARASOTA
Primary bedroom entry - 4424 HIGHLAND PARK #5, SARASOTA
Primary bedroom - 4424 HIGHLAND PARK #5, SARASOTA
Primary shower/ toilet room - 4424 HIGHLAND PARK #5, SARASOTA
Primary bath - 4424 HIGHLAND PARK #5, SARASOTA
one of 2 Primary closets - 4424 HIGHLAND PARK #5, SARASOTA
laundry room - 4424 HIGHLAND PARK #5, SARASOTA
laundry room - 4424 HIGHLAND PARK #5, SARASOTA
second bedroom - 4424 HIGHLAND PARK #5, SARASOTA
courtyard - 4424 HIGHLAND PARK #5, SARASOTA
2 car garage - 4424 HIGHLAND PARK #5, SARASOTA
24 photos

$550,000

4424 HIGHLAND PARK #5
SARASOTA, FL 34235
Bedrooms
3
Bathrooms
2
Living area
2,120 sqft
Year built
1988

About this home

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

Highlights

Fireplace

Property details

MLS
Stellar MLS
MLS #
MFRA4692053
Property type
Villa
Subdivision
HIGHLAND PARK
Status
Active
Days on market
9
On market date
May 12, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
2
Parking spaces
N/A
Lot size
240,288 sqft
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
GOCIO ELEMENTARY SCHOOL
1.36 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
616
Student:teacher ratio
12.6:1
District
SARASOTA
Middle
BOOKER MIDDLE SCHOOL
2.7 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
911
Student:teacher ratio
14.2:1
District
SARASOTA
High
SARASOTA COUNTY ACCELERATION ACADEMIES
2.34 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
127
Student:teacher ratio
42.3:1
District
SARASOTA

Walkability

Blended score for SARASOTA's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

20
Car-dependent
out of 100
EPA National Walkability Index
4.0 / 20 -- Least walkable

Market position

How this listing compares to current activity in SARASOTA, from live MLS data.

On the market 9 days -- 160 fewer days than SARASOTA's current average of 169 days.
For reference, the median list price across 4,689 active listings in SARASOTA right now is $364,521.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$3,462/mo
$110,000 down
$440,000 loan
Principal & interest$2,854
Property tax (est.)$458
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated May 21, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.