Twin Oak Pond Homes For Sale | Siesta Key, FL

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Twin Oak Pond Community Guide

Twin Oak Pond: 37 homes in Siesta Key, built 1956-2005.

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Twin Oak Pond Real Estate in Siesta Key, FL

Twin Oak Pond homes for sale sit on Canopy Road in northeast Siesta Key, roughly 37 single family homes dating back to the 1950s, vintage cottages sitting alongside contemporary custom builds. Sizes run 1,400 to over 3,000 square feet, two to four bedrooms, with tall trees and tropical landscaping giving the streets a quiet, rustic feel popular with retirees and middle-aged buyers. Some vintage homes are ready for updating or a full teardown for new construction, and the annual HOA fee stays low.

Glebe Park sits right at the neighborhood’s edge, a 10-acre space with a playground, picnic areas, and sports fields, home to the Suncoast Sports Club’s youth programs. It’s pet-friendly here, and Siesta Key Public Beach is about a mile away. Siesta Village and downtown Sarasota both sit a short drive out, and public and private schools serve the area.

Twin Oak Pond Neighborhood Facts

5221 Winding Way, Siesta Key, FL 34242, USA

Residences: 37

Categories:

Price Range:$450k-$1.2M
Year Built:1956 – 2005
Size (Sq. Ft.):944 – 2,100
Min. Lease:1 Month
Leases/ Year:12
Gated:✖ No
Pool:✖ No
Fences:✖ No
Golf Course: ✖ No
CDD Fee:✖ No

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*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.

Amenities:

Less than 1 mile to the beach.

Fees Include:

Deed Restrictions

Homes For Sale in Twin Oak Pond

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Map of Twin Oak Pond

Map showing location of Twin Oak Pond Homes For Sale | Siesta
  Key, FL
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Additional Twin Oak Pond Neighborhood Information

The annual HOA fee for Twin Pak Pond homes is reasonable, but we always recommend buyers verify the lease policy and deed restrictions.  Siesta Key Public Beach is just one a mile away.  There you can spend an easy day of sunbathing, walking on the silky quartz-like sands and be entertained by the dolphins and tropical birds as they dive through the glittering water of the Gulf of Mexico. Siesta Village has that beach vibe with a variety of shops, dining and beach bars with live music.  Downtown Sarasota has more art and theatrical venues along with trendy shops and international restaurants.

Twin Oak Pond Frequently Asked Questions

Twin Oak Pond Real Estate


How large is the Twin Oak Pond neighborhood in Siesta Key?

Twin Oak Pond is about 37 homes, built between 1950’s – present.

Is there a community pool in Twin Oak Pond?

No, Twin Oak Pond does not have a community pool.

Is Twin Oak Pond in Siesta Key a gated community?

No, Twin Oak Pond is not a gated community.

Is Twin Oak Pond in Siesta Key a maintenance-free neighborhood?

The homeowners are responsible for their own yard care.

Does Twin Oak Pond allow fences?

Yes, some homes in Twin Oak Pond have fencing, however there may be HOA restrictions regarding which lot locations may have a fence, or the size or type of fence allowed. It is important to check HOA rules for specific fencing requirements prior to making a purchase decision.

What public beach access point is closest to Twin Oak Pond?

Twin Oak Pond is located about 1 mile from the main entrance to Siesta Key Beach.

How far is Twin Oak Pond from downtown Sarasota?

Twin Oak Pond is located about 6 miles from downtown Sarasota.

How far is the Sarasota International Airport from Twin Oak Pond?

Twin Oak Pond is located about 10 miles from the Sarasota International Airport.

*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.

Insight For Twin Oak Pond

Learn our thoughts as professional Sarasota Realtors for the pros, cons, lifestyle, and proximity to beaches, shopping, and downtown.

Twin Oak Pond Homes For Sale in Siesta Key, FL.
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Our Personal Twin Oak Pond Insights

Sarasota FL. Homes For Sale
"Pros" icon - Happy Face

Pros

  • Canopy tree neighborhood
  • Walk to Glebe Park
  • Walk to the beach
traffic jam
"Cons" icon - Indifferent Face

Considerations

  • No waterfront homes
shopping district near UTC Mall
"Shopping" icon - Shopping Bag

Shopping

  • Grocery store is 3.7 miles
  • Siesta Village is 2.2 miles
  • Nearest mall is 3.9 miles
Siesta Key Beach Residences Condos in Siesta Key, FL. - Beach
"Beach" icon - Beach and umbrella

Beach

Couple Outdoor Dining
"Lifestyle" icon - Fork & Knife

Lifestyle

  • Great neighborhood for beach lovers
  • Beach vacation vibe
  • Both fine dining and casual beach bars within minutes
One Park Condos in Downtown Sarasota, FL - Exterior of Building at Sunset
"Downtown" icon - Downtown buildings

Downtown Sarasota

  • 6.0 miles
  • 18 minute drive

Explore Siesta Key FL. Neighborhoods

Compare Siesta Key communities by location, amenities, price, and lifestyle.

More Details

Filter by community features:

1-12 of 41 Filtered Results
  • Banyan Club Homes For Sale in Siesta Key, FL.

    Banyan Club

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    13

    N/A

    1979 - 1982

    8-12 Months

    1

    Amenities:

    Pool, Tennis Court, Maintenance-Free Landscaping.

    View Banyan Club Homes
  • Bay Island Homes For Sale in Siesta Key, FL.

    Bay Island

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    166

    1,500 - 8,138

    1925 - 2024

    1 Week

    52

    $1.0M-$18.0M

    Amenities:

    Waterfront.

    View Bay Island Homes
  • Bay Island Shores Homes For Sale in Siesta Key, FL.

    Bay Island Shores

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    60

    2,943 - 6,827

    1952 - 2015

    1 Week

    52

    $2.4M-$7.0M

    Amenities:

    Waterfront.

    View Bay Island Shores Homes
  • Bayou Louise Homes For Sale in Siesta Key, FL.

    Bayou Louise

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    25

    N/A

    1940 - 1988

    1 Week

    52

    Amenities:

    Waterfront

    View Bayou Louise Homes
  • Blind Pass Homes For Sale in Siesta Key, FL.

    Blind Pass

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    12

    2,256 - 15,000

    1954 - 2010

    1 Week

    52

    $1.3M-$8.5M

    Amenities:

    Waterfront

    View Blind Pass Homes
  • Cocoanut Bayou Homes For Sale in Siesta Key, FL.

    Cocoanut Bayou

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    50

    3,147 - 6,838

    1950 - 2012

    No Minimum

    52

    $3.0M-$10.0M

    Amenities:

    Waterfront

    View Cocoanut Bayou Homes
  • Fiddler Bayou Homes For Sale in Siesta Key, FL.

    Fiddler Bayou

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    11

    1,700 - 8,600

    1950 - 2008

    No Minimum

    No Minimum

    $400k-$15.0M

    Amenities:

    No HOA

    View Fiddler Bayou Homes
  • Gulf Water View Homes For Sale in Siesta Key, FL.

    Gulf Water View

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    250

    1,869 - 7,052

    1950 - 2024

    Varies

    Varies

    $500k-$3.0M

    Amenities:

    No HOA in most neighborhoods

    View Gulf Water View Homes
  • Harmony Homes For Sale in Siesta Key, FL.

    Harmony

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    96

    1,930 - 5,078

    1955 - 2024

    1 Month

    12

    $995k-$4.5M

    Amenities:

    No HOA

    View Harmony Homes
  • Hidden Harbor Homes For Sale in Siesta Key, FL.

    Hidden Harbor

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    45

    1,358 - 8,165

    1954 - 2024

    1 Month

    12

    $1.6M-$15.0M

    Amenities:

    Waterfront, Deed Restrictions, Homes with Boat Docks.

    View Hidden Harbor Homes
  • Mangroves Homes For Sale in Siesta Key, FL.

    Mangroves

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    27

    2,567 - 3,917

    1975 - 1989

    8-12 Months

    1

    $1.1M-$3.5M

    Amenities:

    Waterfront

    View Mangroves Homes
  • Midnight Harbor Homes For Sale in Siesta Key, FL.

    Midnight Harbor

    Total Homes:

    Size (SqFt.):

    Year Built:

    Min. Lease:

    Leases/ Yr:

    Pricing:

    13

    2,522 - 5,142

    1951 - 2006

    No Minimum

    No Minimum

    $1.9M-$4.5M

    Amenities:

    Waterfront

    View Midnight Harbor Homes
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Bill & Cheryl McCue - Sarasota Realtors
Bill & Cheryl McCue
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Buying or Selling in Twin Oak Pond?

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Bill & Cheryl McCue and the Sarasota Homes Group know Twin Oak Pond inside and out. 23 years of experience helping buyers and sellers in this market.

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