Love Life
3427 Winding Oaks Drive 14, LONGBOAT KEY, FL 34228
Request More Information
  • All fields are required.
  • MLS#: A4686623 ( Residential )
  • Street Address: 3427 Winding Oaks Drive 14
  • Viewed: 41
  • Price: $1,150,000
  • Price sqft: $352
  • Waterfront: Yes
  • Wateraccess: Yes
  • Waterfront Type: Lake Front,Pond
  • Year Built: 1988
  • Bldg sqft: 3270
  • Bedrooms: 3
  • Total Baths: 3
  • Full Baths: 3
  • Garage / Parking Spaces: 2
  • Days On Market: 22
  • Additional Information
  • Geolocation: 27.3779 / -82.6228
  • County: MANATEE
  • City: LONGBOAT KEY
  • Zipcode: 34228
  • Subdivision: Winding Oaks
  • Building: Winding Oaks
  • Elementary School: Soutide
  • Provided by: COLDWELL BANKER REALTY
  • Contact: Carolyn Donnelly, PA
  • 941-383-6411
  • mfrmls
  • DMCA Notice
  • Description
    Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three bedroom villa offers an easy, elevated way to enjoy Sarasotas coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single family home with the simplicity of maintenance free ownershipideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide plank tile floors create a light, welcoming feel, while floor to ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white lacquer cabinetry, stone countertops, and premium appliancesperfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa like bath, and a generous walk in closet. Two additional en suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the areawhile always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-

  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Awning(s), Lighting, Sliding Doors
  • Flooring: Luxury Vinyl, Tile
  • Living Area: 2555.00
  • Roof: Tile
Property Information
  • Property Condition: Completed
School Information
  • School Elementary: Southside Elementary
Garage and Parking
  • Garage Spaces: 2.00
  • Open Parking Spaces: 0.00
  • Parking Features: Deeded, Driveway, Garage Door Opener
Eco-Communities
  • Pool Features: Gunite, Heated, In Ground
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air
  • Heating: Central, Electric, Natural Gas
  • Pets Allowed: Cats OK, Dogs OK, Number Limit, Yes
  • Sewer: Public Sewer
  • Utilities: Electricity Connected, Natural Gas Available, Sewer Connected, Underground Utilities, Water Connected
Amenities
  • Association Amenities: Maintenance, Pool, Spa/Hot Tub, Tennis Court(s)
Finance and Tax Information
  • Home Owners Association Fee Includes: Guard - 24 Hour, Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Management, Pest Control, Private Road, Security
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2025
Other Features
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Association Name: Winding Oaks/Neil Fleet
  • Association Phone: 941-383-3200
  • Country: US
  • Furnished: Turnkey
  • Interior Features: Built-in Features, Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
  • Legal Description: UNIT 14 WINDING OAKS
  • Levels: One
  • Area Major: 34228 - Longboat Key
  • Occupant Type: Vacant
  • Parcel Number: 0004121014
  • Style: Coastal
  • Unit Number: 14
  • View: Golf Course, Water
  • Views: 41
  • Zoning Code: MUC1
Similar Properties

Active
Details for 4311 Gulf Of Mexico Drive 501, LONGBOAT KEY, FL 34228
$1,200,000.00 ($968.52 / sqft )

4311 Gulf Of Mexico Drive 501 Virtual Tour More Like This

PARADISE BEACHFRONT CONDO! It does not get better than this. Panoramic Gulf and Bay Views and beach views from every room. Enjoy relaxing at the beach or at the pool. This 2 bedroom, 2 bathroom condo

  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1239 sqft
  4. Approx. 1.82 acres
  1. MLSID: A4601858
  2. Provided by SPECIALIZED REAL ESTATE LLC
  3. Contact Otto Hajek
  4. mfrmls
  5. DMCA Notice
Active
Details for 100 Sands Point Road 324, LONGBOAT KEY, FL 34228
$1,100,000.00 ($566.72 / sqft )

100 Sands Point Road 324 Virtual Tour More Like This

BACK on the market after beautiful renovations!! Unit is impeccably maintained. It has a new air conditioner, roof and upgraded insulation. It is being offered below appraised value! Sands Point i

  1. Bedrooms: 3
  2. Baths: 2
  3. Approx. 1941 sqft
  1. MLSID: A4609759
  2. Provided by LOKATION
  3. Contact Carolyn Clark, PA
  4. mfrmls
  5. DMCA Notice
Active
Details for 1000 Longboat Club Road  1105, LONGBOAT KEY, FL 34228
$1,050,000.00 ($755.40 / sqft )

1000 Longboat Club Road 1105 Virtual Tour More Like This

Seller wants offers! Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Res

  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1390 sqft
  1. MLSID: A4657701
  2. Provided by ROSEBAY INTERNATIONAL REALTY, INC
  3. Contact Tina Rudek Stark, PA
  4. mfrmls
  5. DMCA Notice
Active
Details for 1105 Gulf Of Mexico Drive 402, LONGBOAT KEY, FL 34228
$1,105,000.00 ($740.62 / sqft )

1105 Gulf Of Mexico Drive 402 Virtual Tour More Like This

Beachplace at Longboat Key: Gulf front luxury and rental friendly, turnkey furnished investment opportunity! An iconic condominium in the mid century modern style, Beachplace was constructed under the

  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1492 sqft
  4. Approx. 5.01 acres
  1. MLSID: A4661696
  2. Provided by DUNCAN REAL ESTATE, INC.
  3. Contact Tom Aposporos
  4. mfrmls
  5. DMCA Notice
Active
Details for 1055 Gulf Of Mexico Drive 504, LONGBOAT KEY, FL 34228
$1,299,000.00 ($810.36 / sqft )

1055 Gulf Of Mexico Drive 504 Virtual Tour More Like This

This direct Gulf front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Keys beachfront lifestyle. Perfectly positioned to capture unobstructed views of t

  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1603 sqft
  4. Approx. 7.98 acres
  1. MLSID: A4663883
  2. Provided by COLDWELL BANKER REALTY
  3. Contact Roger Pettingell
  4. mfrmls
  5. DMCA Notice
Active
Details for 210 Sands Point Road 2405, LONGBOAT KEY, FL 34228
$1,150,000.00 ($1,769.23 / sqft )

210 Sands Point Road 2405 Virtual Tour More Like This

Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suite at Inn on the Beach offers a unique opportunity to own within the prestigious Longboat Key Club Resort. Span

  1. Bedrooms: 1
  2. Baths: 1
  3. Approx. 650 sqft
  1. MLSID: A4664039
  2. Provided by COLDWELL BANKER REALTY
  3. Contact Bruce Myer
  4. mfrmls
  5. DMCA Notice
Active
Details for 5320 Gulf Of Mexico Drive 101, LONGBOAT KEY, FL 34228
$1,150,000.00 ($869.24 / sqft )

5320 Gulf Of Mexico Drive 101 Virtual Tour More Like This

Rarely Available at Longboat Landing! This 3 bedroom, 2 bath second floor condo offers the ultimate in coastal living with only 9 total units/owners in the entire communityproviding privacy, exclusivi

  1. Bedrooms: 3
  2. Baths: 2
  3. Approx. 1323 sqft
  4. Approx. 1.53 acres
  1. MLSID: A4666843
  2. Provided by KELLER WILLIAMS ON THE WATER S
  3. Contact Schuyler Burke
  4. mfrmls
  5. DMCA Notice
Active
Details for 240 Sands Point Road 4205, LONGBOAT KEY, FL 34228
$1,115,000.00 ($1,742.19 / sqft )

240 Sands Point Road 4205 Virtual Tour More Like This

This junior suite, located in Building 4, offers spectacular northwest facing views of the Gulf, providing owners with breathtaking sunsets and expansive water vistas. For those seeking accommodation

  1. Bedrooms: 1
  2. Baths: 1
  3. Approx. 640 sqft
  4. Approx. 4.13 acres
  1. MLSID: A4667038
  2. Provided by PREMIER SOTHEBY'S INTERNATIONAL REALTY
  3. Contact Jackie Kleppinger
  4. mfrmls
  5. DMCA Notice
Active
Details for 240 Sands Point Road 4206, LONGBOAT KEY, FL 34228
$1,115,000.00 ($1,742.19 / sqft )

240 Sands Point Road 4206 Virtual Tour More Like This

This junior suite, located in Building 4, offers spectacular northwest facing views of the Gulf, providing owners with breathtaking sunsets and expansive water vistas. For those seeking accommodation

  1. Bedrooms: 1
  2. Baths: 1
  3. Approx. 640 sqft
  4. Approx. 4.13 acres
  1. MLSID: A4667039
  2. Provided by PREMIER SOTHEBY'S INTERNATIONAL REALTY
  3. Contact Jackie Kleppinger
  4. mfrmls
  5. DMCA Notice
Active
Details for 1211 Gulf Of Mexico Dr  108, LONGBOAT KEY, FL 34228
$1,189,000.00 ($583.99 / sqft )

1211 Gulf Of Mexico Dr 108 Virtual Tour More Like This

Experience the ultimate in Gulf front living from this meticulously updated 1827 sq. ft. beach retreat located on the sunny southern side and offering peaceful Gulf and courtyard vistas. The open floo

  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 2036 sqft
  1. MLSID: A4667361
  2. Provided by ROSEBAY INTERNATIONAL REALTY, INC
  3. Contact Tina Rudek Stark, PA
  4. mfrmls
  5. DMCA Notice
Headshot for Associate Dennis Dial
  1. The Dial Team
  2. Tropic Shores Realty
  3. Love Life
  4. Mobile: 561.201.4476
  5. dennisdialsells@gmail.com