Welcome Home to 4415 Highland Oak - 4415 HIGHLAND OAKS CIR, SARASOTA
New tile roof , Refreshed landscaping. - 4415 HIGHLAND OAKS CIR, SARASOTA
Birds eye view of golf course backyard. - 4415 HIGHLAND OAKS CIR, SARASOTA
Double glass front doors,wide foyer, high ceilings. - 4415 HIGHLAND OAKS CIR, SARASOTA
Split living quaters gives you more privacy. - 4415 HIGHLAND OAKS CIR, SARASOTA
Formal dinning room adjacent to oversized livingroom. - 4415 HIGHLAND OAKS CIR, SARASOTA
Cut out wall space creates a flowing living space. - 4415 HIGHLAND OAKS CIR, SARASOTA
Open concept from every space , perfect for creating lasting memories, and easy entertaining gatherings. - 4415 HIGHLAND OAKS CIR, SARASOTA
Beautiful luxury flooring ,13 foot ceilings in the living room.Bright and filled with sunshine. - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 10 of 54
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 11 of 54
Living space with views of the outdoor pool and golf course. - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 13 of 54
Oversized granite peninsula 12ft long . - 4415 HIGHLAND OAKS CIR, SARASOTA
Blackend stainless steel appliances. - 4415 HIGHLAND OAKS CIR, SARASOTA
Additional bar seating area. - 4415 HIGHLAND OAKS CIR, SARASOTA
Glass pendant lighting over the peninsula gives you designer touchesand flair. - 4415 HIGHLAND OAKS CIR, SARASOTA
Plenty of cabient space throughout the kitchen for all your storge needs. - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 19 of 54
Soaring columns offers a distinguish and stylish appearance. - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 21 of 54
Spacious living room , with 13 foot ceilings. - 4415 HIGHLAND OAKS CIR, SARASOTA
Breakfast nook perfect for quick meals , or enjoying your morning coffee. - 4415 HIGHLAND OAKS CIR, SARASOTA
Built in wine cabient storage with lite glass cabients. - 4415 HIGHLAND OAKS CIR, SARASOTA
Living room with sliding doors leading to a private backyard tranquil pool and golf course oasis. - 4415 HIGHLAND OAKS CIR, SARASOTA
Primary Bedroom with large sliding glass doors . - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 27 of 54
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 28 of 54
Primary closet filled with custom cabinets. - 4415 HIGHLAND OAKS CIR, SARASOTA
Walk in closet. - 4415 HIGHLAND OAKS CIR, SARASOTA
Primary Bathroom with oversized shower . - 4415 HIGHLAND OAKS CIR, SARASOTA
Double sliding doors leading to outdoor enclosed area. - 4415 HIGHLAND OAKS CIR, SARASOTA
Large double vanity in primary bathroom. - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 34 of 54
Rich wood paneling with a danity claw foot tub. - 4415 HIGHLAND OAKS CIR, SARASOTA
Bedroom #2 - 4415 HIGHLAND OAKS CIR, SARASOTA
Bedroom #2 - 4415 HIGHLAND OAKS CIR, SARASOTA
Bedroom #2 walk in closet. - 4415 HIGHLAND OAKS CIR, SARASOTA
Bedroom #2 walk in closet. - 4415 HIGHLAND OAKS CIR, SARASOTA
Bathroom #2 Frameless glass shower, tiled flooring. - 4415 HIGHLAND OAKS CIR, SARASOTA
Bathroom #2 Granite counterr top vanity, plantion window shades. - 4415 HIGHLAND OAKS CIR, SARASOTA
Bathroom # 2nd View adjacent to bedrooms - 4415 HIGHLAND OAKS CIR, SARASOTA
Bathroom #2 - 4415 HIGHLAND OAKS CIR, SARASOTA
Bathroom #2 Access to outdoor pool area very convenient. - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 45 of 54
Bedroom #3 Double closet space. - 4415 HIGHLAND OAKS CIR, SARASOTA
Bedroom #3 - 4415 HIGHLAND OAKS CIR, SARASOTA
Plantation window treatments, ceiling fan for warm days. - 4415 HIGHLAND OAKS CIR, SARASOTA
Laundry room with lots of storage space. - 4415 HIGHLAND OAKS CIR, SARASOTA
Easy access to the 2 car garage. - 4415 HIGHLAND OAKS CIR, SARASOTA
Powder room . - 4415 HIGHLAND OAKS CIR, SARASOTA
Single Family Residence at 4415 HIGHLAND OAKS CIR, SARASOTA, photo 52 of 54
Picture swimming in the privacy of your pool and views of the golf course . - 4415 HIGHLAND OAKS CIR, SARASOTA
Picture swimming in the privacy of your pool and views of the golf course . - 4415 HIGHLAND OAKS CIR, SARASOTA
54 photos

$813,000

4415 HIGHLAND OAKS CIR
SARASOTA, FL 34235
Listed by Marilyn Gioffre
Bedrooms
3
Bathrooms
2.5
Living area
2,046 sqft
Year built
1988

About this home

Virtually Staged. Welcome to an elevated Sarasota lifestyle in The Highlands at The Meadows, where timeless design, privacy, and resort-style living come together beautifully. This impressive 3-bedroom, 2.5-bath pool home with a NEW ROOF offers approximately 2,046 square feet of thoughtfully designed living space on a generous .34-acre homesite with peaceful golf-course views. From the moment you enter, the home feels bright, spacious, and refined, with soaring vaulted ceilings, an open-concept layout, abundant natural light, and a desirable split-bedroom floor plan. The kitchen is designed for both everyday living and entertaining, featuring solid wood cabinetry, stone countertops, stainless-steel appliances, and ample prep and storage space. The living areas flow effortlessly to the private outdoor retreat, where a heated pool and spa, expansive covered lanai, outdoor shower, and tranquil golf-course backdrop create the perfect setting for entertaining, relaxing, and enjoying Florida’s year-round sunshine. The spacious primary suite provides a serene escape with a walk-in closet, beautifully appointed bath, soaking tub, and peaceful views, while the additional bedrooms perfect flexibility for guests, family, or a home office. Additional highlights include an attached 2-car garage, lush established landscaping, generous outdoor living space, and the peace of mind of a new roof. Ideally located within sought-after The Meadows, residents enjoy a beautifully maintained community surrounded by lakes, mature landscaping, walking and biking paths, recreational amenities, and an exceptional Sarasota location. Just minutes from UTC shopping and dining, downtown Sarasota, cultural destinations, and the Gulf Coast’s world-renowned beaches, this residence offers the perfect combination of luxury, convenience, and relaxed Florida living. A rare opportunity to own a beautifully maintained pool home with golf-course views and a new roof in one of Sarasota’s most established and desirable communities.Photos have been virtually Staged .

Highlights

Private pool

Property details

MLS #
MFRA4705361
Property type
Single Family Residence
Subdivision
THE HIGHLANDS
Status
Active
Days on market
23
On market date
September 14, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
N/A
Lot size
0.34 acres
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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 (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
GOCIO ELEMENTARY SCHOOL
1.17 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
2.48 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
2.25 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 23 days -- 151 fewer days than SARASOTA's current average of 174 days.
For reference, the median list price across 4,439 active listings in SARASOTA right now is $350,000.

Mortgage calculator

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Est. monthly payment
$5,046/mo
$162,600 down
$650,400 loan
Principal & interest$4,218
Property tax (est.)$678
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 2 days ago.

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.