Winding Oaks Condos For Sale | Longboat Key, FL
Winding Oaks Community Guide
Winding Oaks, built 1988-1991, sits in Longboat Key with homes 2,039 – 2,678 sq ft with a gated entrance and a community pool.
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Winding Oaks Condominiums in Longboat Key, FL.
Winding Oaks condos for sale sit inside Bay Isles on Longboat Key, 56 villas in 28 duplex buildings on 14.5 acres. Mix of 32 three-bedroom and 24 two-bedroom units, one level, with two-car garages and private walled courtyards. Many have private pools.
The community recently completed nearly $3 million in capital improvements: infinity pool, tile roofs, paver drives, exterior painting. Fully funded reserves, so no surprise assessments looming. Pets welcome, one of the few pet-friendly communities on Longboat Key. You get access to the private Bay Isles Beach Club on Gulf of Mexico Drive, plus optional membership at the Longboat Key Club for golf and tennis. Town Shoppes of Bay Isles, with the only supermarket and pharmacy on the island, is about a mile away.
Photos of Winding Oaks
Winding Oaks Condo Facts
| Price Range: | $895kโ$1.2M |
| Year Built: | 1988 – 1991 |
| Size (Sq. Ft.): | 2,039 – 2,678 |
| Min. Lease: | 3 Months |
| Leases/ Year: | 3 |
| Gated: | ✔ Yes |
| Pool: | ✔ Yes |
| Pets Allowed: | ✔ Yes |
| Golf Course: | ✖ No |
| CDD Fee: | ✖ No |
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.
Amenities:
Gated Community, Golf, Pool, Hot Tub, Spa, Recreation Building, Security, Waterfront Complex.
Fees Include:
Building Exterior, Cable, Community Pool, Escrow Reserves Fund, Fidelity Bond, Flood Insurance, Ground Maintenance, Pest Control.
Condos For Sale in Winding Oaks | Longboat Key, FL.
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Map of Winding Oaks
Additional Winding Oaks Condo Information
The neighborhood is managed by a hands-on Homeowners Assoc. & Board of Directors. Residents enjoy the beauty, security & benefits of Bay Isles, including access to Bay Isles Beach Club on the Gulf of Mexico. The community is pet-friendly, and residents enjoy numerous neighborhood social activities.
Winding Oaks Condominiums
Winding Oaks has about 56 condos, built between 1988-1991.
Yes, Winding Oaks has a heated pool.
Yes, Winding Oaks is a gated community within Bay Isles Lonbboat Key.
Winding Oaks is located in a golf course community. Residents may join the Longboat Key Club which offers the Islandside 18 Hole Golf Course and Harbourside 27 Hole Golf Course. Additionally, there are two clubhouses, 6 restaurants, an award winning tennis center with 22 Har-Tru courts, fitness center, full-service spa, and a 29 slip marina within Longboat Key Club.
Winding Oaks is located about 8.3 miles from downtown Sarasota.
Winding Oaks is located about 1.7 miles from Bay Isles Beach Club. Residents of Winding Oaks have a membership to Bay Isles Beach Club.
Winding Oaks is located about 11.6 miles from the Sarasota International Airport.
Yes, however we recommend that you consult with a Realtor to get specific pet policy info for this community. We are happy to help you.
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.
Insight For Winding Oaks
Learn our thoughts as professional Sarasota Realtors for the pros, cons, lifestyle, and proximity to beaches, shopping, and downtown.
Our Personal Winding Oaks Insights
Pros
- Maintenance-free villas that live like single homes
- Pet-friendly community
- Membership to Bay Isles Beach Club.
Considerations
- No boat docks available in community
Shopping
- Publix grocery store is 1.1 miles
- UTC Mall is about 17.9 miles
- Saint Armands Circle is about 5.7 miles
Beach
- Longboat Key is private beach
- Lido Key Beach is 6.1 miles
- Siesta Key Beach is 15.1 miles
Lifestyle
- Peaceful private beach living
- First class amenities optionally available at Longboat Key Club
- Fine and casual restaurants located on Longboat Key
Downtown Sarasota
- 9.7 miles
- 22 minute drive
Explore Longboat Key FL. Condominiums
Compare Longboat Key condo communities by location, amenities, price, and lifestyle.
Filter by community features:
-
Aquarius Club
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
57
1,551
1974 - 1975
3 Months
1
$1.5Mโ$1.6M
Amenities:
Fitness, Laundry Facility, Recreation Building, Tennis Courts, Water Access, Waterfront Complex.
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Banyan Bay Club
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
44
1,1128 - 1,460
1973 - 1974
3 Months
3
$595kโ$794k
Amenities:
Dock, Fishing Pier, Fitness, Irrigation, Maintenance Free, Recreation Building, Tennis Courts, Water Access, Waterfront Complex.
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Bay Harbour
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
39
1,194 - 1,474
1969 - 1970
1 Month
2
$650kโ$700k
Amenities:
Boat Slips, Dock, Elevators, Fitness, Maintenance Free, Storage, Water Access, Waterfront Complex.
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Bayport
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
136
1,456 - 2,186
1980 - 1985
1 Month
12
$450kโ$1.4M
Amenities:
Building Exterior, Cable, Community Pool, Escrow Reserves Fund, Flood Insurance, Ground Maintenance, Insurance Building, Manager, Pest Control, Recreational Facilities, Roof, Tennis Courts, Trash Removal, Water/Sewer.
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Beach Castle
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
21
711 - 2,330
1972 - 1976
1-7 Days
365
$450k-$845k
Amenities:
Community Hot Tub/Spa, Fishing Pier, Laundry Facility, Maintenance Free, Water Access, Waterfront Complex.
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Beach Harbor Club
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
133
698 - 2,544
1969 - 1970
3 Months
2
$290kโ$550k
Amenities:
Boat Slip, Buyer Approval Required, Dock, Elevators, Fishing Pier, Fitness, Recreation Building, Storage, Shuffleboard, Water Access, Waterfront Complex.
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Beaches
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
73
1,510 - 2,122
1983 - 1984
3 Months
2
$1.0Mโ$2.5M
Amenities:
On-Site manager, Gated Community, 24 hr Concierge, Beach Front Views, Elevators, Fitness Facility, Gated, Media Room, Pool, Spa, Tennis.
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Beachplace
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
336
1,172 - 1,819
1979 - 1981
1 Month
12
$600kโ$2.2M
Amenities:
Recreation Building, Elevators, Fitness Facility, Pool, Tennis Courts, Gated Community.
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Buttonwood Cove
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
56
1,284 - 2,568
1979 - 1980
1 Month
3
$440kโ$1.0M
Amenities:
Dock, Elevators, Fishing Pier, Maintenance Free, Recreation Building, Storage, Tennis Courts, Water Access, Waterfront Complex.
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Cabana Beach Club
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
11
612 - 990
1970 - 1971
1-7 Days
52
$400k-$500k
Amenities:
BBQ picnic area, Beach Access, Private Boat Docks, Laundry Facility, Water Access, Waterfront Complex.
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Casa Del Mar
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
89
900 - 1,000
1972 - 1973
1-7 Days
52
$600kโ$800k
Amenities:
Pool, Tennis Courts, Pickleball, Basketball, Shuffleboard, Kayak Racks, Fitness Room, Clubhouse, Library, Storage.
-
Castillian
Total Homes:
Size (SqFt.):
Year Built:
Min. Lease:
Leases/ Yr:
Pricing:
60
1,340 - 1,870
1978 - 1979
1 Month
2
$900k-$1.25M
Amenities:
Heated oversized pool, Spa, Tennis Court, Secured Entry, Under-Building Parking, Storage locker.
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Broker Associate & Realtors
Buying or Selling in Winding Oaks?
Your local Winding Oaks real estate experts.
Bill & Cheryl McCue and the Sarasota Homes Group know Winding Oaks inside and out. 23 years of experience helping buyers and sellers in this market.
- Local Winding Oaks Realtor with deep market knowledge.
- Top 2% selling Realtors in Sarasota & Manatee County.
- 23 years full-time experience.
- Current listings, sold data, and market trends for this area.
- Specializing in buying, listing, and selling homes in this market.
- Free market valuation for owners in this area.
- 100โs of 5-star reviews on Google, Realtor.com, Zillow, Homes.com and more.
- Sold over 500+ homes.
Bill & Cheryl McCue
Sarasota Homes Group
