USAFLLongboat KeyWinding Oaks35-3466 Winding Oaks Dr

Virtual Tour

$795,000

For Sale

22 days ago

35 - 3466 Winding Oaks Dr, Longboat Key, FL

Condo

MLS® A4686581

2 Bed

2 Bath

2039 sqft

2 Parking

Key Facts
Description
Rooms
Map

Key Facts

Type Condominium

Levels Residential

Size 2039 sqft

Garage Yes

HOA Fees

Taxes $4,919

Days Active 21

Approx. Age 1988

Avg. Price Per Sqft $389

MLS® Number A4686581

Property Address: 35-3466 Winding Oaks Dr, LONGBOAT KEY, FL, 34228-4140

Average square foot calculated using Size range provided by listing agent.

Description

Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities.

MLS® NumberA4686581

Locker

Ensuite LaundryNo

Balcony

Furnished

Laundry LevelLaundry Room

Exposure

Exterior

GarageYes

Approx. Age1988

Stories1

Pets

Included in Maintenance Fee

Heat

Hydro

Water

Building Insurance

Condo Taxes

Cable TV

Central Air

Parking Maintenance

Utilities

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Apr 7, 2026List Date

$795,000List Price

Commute

Commute

Starting Address

Destination Address

Like what you see?

Complete the form and we'll be in touch. No login necessary.

Add a Comment

I want to view this property

By pressing "Take a Tour", I confirm that I have read and agree to the eXp Privacy Policy, and Terms of Use.

By pressing "Take a Tour", I am electronically signing and consenting to receive marketing comms about real estate brokerage and mortgage lending services, delivered via email, phone and/or text (using "automated technology" such as an automatic telephone dialing system, and/or an artificial or prerecorded voice), from eXp Realty® and its independent contractor real estate professionals and their affiliate SUCCESS® Lending using the contact information I provided. Your consent is not a condition of purchase and you may revoke it at any time by replying "STOP" to any texts. Text HELP for more info. Message and data rates may apply. You may also contact us directly at 1-844-683-4664.

Similar Listings

Comparable Properties

Explore eXp Find an Agent Join eXp Investor Relations Company Careers Home Guides

eXp Life Zoocasa SUCCESS®SUCCESS® Lending eXp Revenos eXp Commercial eXp Luxury eXp Land and Ranch Accessibility

Terms and Conditions Privacy Rights Request Privacy Policy Cookie Policy Brand Guidelines Help Sitemap

2219 Rimland Drive, Suite 301, Bellingham, Washington, 98226

1 833-303-0610

[email protected]

eXp REALTY

DMCA Notice

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply

Fair Housing and Reasonable Accommodations

MLS Compliance Statements

Karen Richards - Designated Managing Broker, Broker Operations - TX

Texas Real Estate Commission information about brokerage services

Texas Real Estate Commission Consumer Protection Notice

eXp Realty® is committed to adhering to the guidelines of The New York State Fair Housing Regulations.The Fair Housing Notice →

*Standardized Operating Procedure for Purchasers of Real Estate Pursuant to Real Property Law 442-H.Learn More →

eXp Realty of California, Inc. | CA DRE# 01878277 | Deborah Penny - Designated Broker

eXp Realty of Southern California, Inc. | CA DRE#01325837 | Jason Crawford – Designated Broker

eXp Realty of Greater Los Angeles, Inc. | CA DRE# 01240990 | Mike Mendibles - Designated Broker

eXp Realty of Northern California, Inc. | CA DRE# 01951343 | Ryan Rosas - Designated Broker