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.
Sold for $758,500
$758,500
3466 WINDING OAKS DRIVE #35, LONGBOAT KEY, FL 34228
2beds
2,039sqft
Condominium
Built in 1988
-- sqft lot
$750,500 Zestimate®
$372/sqft
$5,696 Estimated rent
Home value
$750,500
$713,000 - $788,000
$5,696/mo
Zestimate® history
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List your homeWhat's special
Gated entranceTwo-car garageHigh ceilingsCommunity poolLarge windowWell-done tile detailsJacuzzi tub
Zillow last checked:
Listing updated:
Listed by:
Bruce Myer 941-376-5311,
COLDWELL BANKER REALTY 941-383-6411
Bought with:
Patti Bosco, 3428631
MY FLORIDA BROKER
Source: Stellar MLS,MLS#: A4686581
Originating MLS: Sarasota - Manatee
Originating MLS: Sarasota - Manatee
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 240 Square Feet
- Dimensions: 15x16
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 210 Square Feet
- Dimensions: 15x14
Balcony porch lanai
- Level: First
- Area: 560 Square Feet
- Dimensions: 35x16
Dining room
- Level: First
- Area: 144 Square Feet
- Dimensions: 12x12
Family room
- Level: First
- Area: 208 Square Feet
- Dimensions: 16x13
Kitchen
- Level: First
- Area: 187 Square Feet
- Dimensions: 17x11
Living room
- Level: First
- Area: 285 Square Feet
- Dimensions: 15x19
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Laundry: Laundry Room
Features
- Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat
- Flooring: Tile, Hardwood
- Doors: Sliding Doors
- Windows: Window Treatments
- Has fireplace: No
Interior area
- Total structure area: 2,568
- Total interior livable area: 2,039 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage Door Opener
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: One
- Stories: 1
- Patio & porch: Covered, Deck, Rear Porch
- Exterior features: Irrigation System, Lighting, Sidewalk, Storage
- Pool features: Heated, In Ground
- Has view: Yes
- View description: Water
- Water view: Water
Lot
- Size: 13.84 Acres
- Residential vegetation: Mature Landscaping
Details
- Parcel number: 0004121035
- Zoning: MUC1
- Special conditions: None
Construction
Type & style
- Home type: Condo
- Architectural style: Other
- Property subtype: Condominium
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Other
Condition
- Completed
- New construction: No
- Year built: 1988
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Community & HOA
Community
- Features: Deed Restrictions, Pool
- Pet fee: $0 monthly
- Subdivision: WINDING OAKS
HOA
- Has HOA: No
- Amenities included: Pool
- Services included: Community Pool, Reserve Fund, Insurance, Maintenance Structure, Maintenance Grounds, Pest Control, Pool Maintenance, Private Road, Sewer, Trash, Water
- HOA fee: $2,294 monthly
- HOA name: Advanced Management / AMIA
- HOA phone: 941-383-3200
- Second HOA name: Bay Isles Homeowners Association
- Second HOA phone: 941-383-3200
Location
- Region: Longboat Key
Financial & listing details
- Price per square foot: $372/sqft
- Tax assessed value: $619,100
- Annual tax amount: $4,918
- Date on market: 4/7/2026
- Cumulative days on market: 43 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 6/12/2026 | Sold | $758,500-4.6%$372/sqft |
Source:  Stellar MLS #A4686581 Report a problem | ||
| 5/20/2026 | Pending sale | $795,000$390/sqft |
Source: Stellar MLS #A4686581 Report a problem | ||
| 4/7/2026 | Listed for sale | $795,000+89.3%$390/sqft |
Source: Stellar MLS #A4686581 Report a problem | ||
| 6/26/2013 | Sold | $420,000-2.1%$206/sqft |
Source: Public Record Report a problem | ||
| 5/22/2013 | Price change | $429,000-8.5%$210/sqft |
Source: Coldwell Banker Residential Real Estate - St Armands #A3964396 Report a problem | ||
| 11/29/2012 | Price change | $469,000-4.1%$230/sqft |
Source: Coldwell Banker Residential Real Estate - St Armands #A3964396 Report a problem | ||
| 9/1/2012 | Price change | $489,000-8.6%$240/sqft |
Source: Coldwell Banker Residential Real Estate - St Armands #A3964396 Report a problem | ||
| 8/13/2012 | Listed for sale | $535,000$262/sqft |
Source: COLDWELL BANKER RES R E #A3964396 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,919 +2.5% | $405,343 +2.9% |
| 2024 | $4,798 +2.2% | $393,919 +3% |
| 2023 | $4,695 +1.9% | $382,446 +3% |
| 2022 | $4,606 -1.4% | $371,307 +3% |
| 2021 | $4,673 +7.3% | $360,492 +8.9% |
| 2020 | $4,357 +3.4% | $330,959 +2.3% |
| 2019 | $4,215 | $323,518 +1.9% |
| 2018 | $4,215 +1.8% | $317,486 +2.1% |
| 2017 | $4,142 +4.1% | $310,956 -26.3% |
| 2016 | $3,978 | $422,000 +12.4% |
| 2015 | $3,978 +0.2% | $375,300 +6.7% |
| 2014 | $3,972 -24.7% | $351,600 |
| 2013 | $5,274 +28.6% | $351,600 +11% |
| 2012 | $4,102 +4.9% | $316,800 +2.9% |
| 2011 | $3,911 -9.5% | $308,000 -6.2% |
| 2010 | $4,321 +12.8% | $328,184 +2.7% |
| 2009 | $3,830 | $319,556 +0.1% |
| 2008 | $3,830 -1.1% | $319,237 +3% |
| 2007 | $3,872 | $309,939 +2.5% |
| 2006 | -- | $302,380 +3% |
| 2005 | -- | $293,573 +3% |
| 2004 | $4,092 -3% | $285,022 +1.9% |
| 2003 | $4,216 -1.4% | $279,708 +2.4% |
| 2002 | $4,275 +5.7% | $273,152 +1.6% |
| 2001 | $4,043 +1.5% | $268,850 +3% |
| 2000 | $3,984 | $261,019 |
Find assessor info on the county website
Neighborhood: 34228
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Nearby schools
GreatSchools rating
- 10/10Southside Elementary SchoolGrades: K-5Distance: 7.3 mi
- 5/10Booker Middle SchoolGrades: 6-8Distance: 6.1 mi
- 3/10Booker High SchoolGrades: 9-12Distance: 5.3 mi
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Estimated market value
$750,500
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Estimated market value
$750,500
- Florida
- Sarasota County
- Longboat Key
- 34228
- 3466 WINDING OAKS DRIVE Unit 35
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