3460 WINDING OAKS DR #38
3460 WINDING OAKS DR #38 photo 2
3460 WINDING OAKS DR #38 photo 3
3460 WINDING OAKS DR #38 photo 4
3460 WINDING OAKS DR #38 photo 5
3460 WINDING OAKS DR #38 photo 6
3460 WINDING OAKS DR #38 photo 7
3460 WINDING OAKS DR #38 photo 8
3460 WINDING OAKS DR #38 photo 9
3460 WINDING OAKS DR #38 photo 10
3460 WINDING OAKS DR #38 photo 11
3460 WINDING OAKS DR #38 photo 12
3460 WINDING OAKS DR #38 photo 13
3460 WINDING OAKS DR #38 photo 14
3460 WINDING OAKS DR #38 photo 15
3460 WINDING OAKS DR #38 photo 16
3460 WINDING OAKS DR #38 photo 17
3460 WINDING OAKS DR #38 photo 18
3460 WINDING OAKS DR #38 photo 19
3460 WINDING OAKS DR #38 photo 20
3460 WINDING OAKS DR #38 photo 21
3460 WINDING OAKS DR #38 photo 22
3460 WINDING OAKS DR #38 photo 23
3460 WINDING OAKS DR #38 photo 24
3460 WINDING OAKS DR #38 photo 25
3460 WINDING OAKS DR #38 photo 26
3460 WINDING OAKS DR #38 photo 27
3460 WINDING OAKS DR #38 photo 28
3460 WINDING OAKS DR #38 photo 29
3460 WINDING OAKS DR #38 photo 30
3460 WINDING OAKS DR #38 photo 31
3460 WINDING OAKS DR #38 photo 32
3460 WINDING OAKS DR #38 photo 33
3460 WINDING OAKS DR #38 photo 34
3460 WINDING OAKS DR #38 photo 35
3460 WINDING OAKS DR #38 photo 36
3460 WINDING OAKS DR #38 photo 37
3460 WINDING OAKS DR #38 photo 38
3460 WINDING OAKS DR #38 photo 39
3460 WINDING OAKS DR #38 photo 40
3460 WINDING OAKS DR #38 photo 41
3460 WINDING OAKS DR #38 photo 42
3460 WINDING OAKS DR #38 photo 43
3460 WINDING OAKS DR #38 photo 44
3460 WINDING OAKS DR #38 photo 45
3460 WINDING OAKS DR #38 photo 46
3460 WINDING OAKS DR #38 photo 47
3460 WINDING OAKS DR #38 photo 48
3460 WINDING OAKS DR #38 photo 49
3460 WINDING OAKS DR #38 photo 50
3460 WINDING OAKS DR #38 photo 51
3460 WINDING OAKS DR #38 photo 52
3460 WINDING OAKS DR #38 photo 53
53 photos

$1,150,000

3460 WINDING OAKS DR #38
LONGBOAT KEY, FL 34228
Listed by Bruce Myer · COLDWELL BANKER REALTY
Bedrooms
3
Bathrooms
3.1
Living area
2,608 sqft
Year built
1988

About this home

Tucked within Winding Oaks, one of Longboat Key’s most sought-after villa communities, this 3BR/3BA residence offers the scale and comfort of a single-family home paired with the simplicity of maintenance-free living. From the paver drive and walkway to the stepped front entry, the residence creates an inviting first impression before opening into a home defined by volume, light and connection to the outdoors. Step inside and soaring ceilings immediately create a sense of openness, while high-set windows invite natural light to move throughout the living spaces. Tile flooring and soft neutral tones create a clean backdrop that complements the peaceful setting just beyond the glass. Renovated in November 2025, the kitchen has been thoughtfully opened and redesigned into a true centerpiece for gathering and everyday living. A substantial island with seating anchors the space, along with stone countertops, white cabinetry, stainless steel appliances, a range hood, wine refrigerator and tile backsplash. An abundance of windows and an adjoining sitting area create a bright, welcoming space whether hosting guests or enjoying a quiet morning. The dining area transitions naturally into the living room, where cathedral ceilings, a corner fireplace and sliding glass doors connect the interior to the outdoors. Beyond, an expansive screened deck overlooks the community lake and fountain, creating a peaceful setting with multiple areas for dining, relaxing or entertaining. Privacy walls on either side enhance the feeling of seclusion while keeping the water views front and center. The primary suite is spacious and calming, featuring vaulted ceilings, engineered wood floors, a wall of sliding glass doors opening to the deck and a large walk-in closet with extensive built-ins. Also renovated in November 2025, the primary bath offers dual vanities, a walk-in shower, dressing area and separate water closet. Guest accommodations are equally well planned. One bedroom includes an en suite bath and walk-in closet, while another is currently configured as an office space with sliding glass doors opening to a private patio. Updated baths throughout, an in-residence laundry room and a 2-car garage add convenience. Set within the Harbourside golf course community, Winding Oaks offers a serene environment with a gated entrance, community pool and spa, and access to the full range of Bay Isles amenities, including deeded beach access through the private Bay Isles Beach Club.

Highlights

WaterfrontFireplace

Property details

MLS #
MFRA4695005
Property type
Condominium
Subdivision
WINDING OAKS
Status
Active
Days on market
N/A
On market date
June 2, 2026
Stories
N/A
Garage spaces
2
Lot size
N/A
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
BAYSHORE ELEMENTARY SCHOOL
4.23 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
677
Student:teacher ratio
14.7:1
District
MANATEE
Middle
ELECTA LEE MAGNET MIDDLE SCHOOL
4.91 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
780
Student:teacher ratio
16.6:1
District
MANATEE
HighCharter
STATE COLLEGE OF FLORIDA COLLEGIATE SCHOOL
4.63 mi away · Grades 6-12
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
504
Student:teacher ratio
25.2:1
District
MANATEE

Mortgage calculator

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

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$7,075/mo
$230,000 down
$920,000 loan
Principal & interest$5,967
Property tax (est.)$958
Home insurance (est.)$150

Similar homes you might like

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