Oyster Bay Estates

West of the Trail Homes for Sale, Sarasota

A wonderful community West of the Trail, Oyster Bay Estates offers affordable family homes or magnificent mansions on the water. Some of the homes were built in the 1950s and architectural home styles are mostly mixed from old Florida to newly built custom waterfront mansions. Older homes can be updated by adding all the designer touches in kitchens, bathrooms and fabulous new landscaping. This beautiful community is a great family neighborhood or retirement community for the luxury real estate buyer.

This waterfront community is a short drive to beaches, downtown Sarasota's cultural amenities, hospitals, restaurants and professional services.

Browse all home listings currently available West of the Trail in Oyster Bay. Check out your options and call or email us if you would like details on any of these properties. You can also click the "Request More Info" button for a quick reply on any property.

We can also provide you with available disclosures, sales history, dates and sale prices of comparable properties. We are here to help!

Oyster Bay Estates January 16, 2019
7
Listed
163
Avg. DOM
$556.21
Avg. $ / Sq.Ft.
$2,250,000
Med. List Price
7 Properties Found.
Sort By:
1409 S Lake Shore Drive
Sarasota, FL 34231
1409 S Lake Shore Drive Sarasota, FL 34231
1 of 23
$4,950,000
Subdivision: Oyster Bay Estates
BEDS
4
BATHS
4
SQ.FT.
5,193
BUILT
2018
ON SITE
217Days
MLS
A4405978
Pre-construction: TO BE BUILT. This incredibly beautiful home will be built on prestigious South Lake Shore Drive- a long-established, highly-regarded Oyster Bay Estates neighborhood. Tucked away on...
1329 N Lake Shore Drive
Sarasota, FL 34231
1329 N Lake Shore Drive Sarasota, FL 34231
1 of 27
$2,495,000 ( $355,000 )
Subdivision: Oyster Bay Estates
BEDS
3
BATHS
3
SQ.FT.
3,160
BUILT
1962
ON SITE
112Days
MLS
A4414590
Introducing this private 1-acre Old Florida style waterfront estate property with open views of Sarasota Bay in one of Sarasota's most beloved neighborhoods, Oyster Bay. This property enjoys 100 feet...
1235 N Lake Shore Drive
Sarasota, FL 34231
1235 N Lake Shore Drive Sarasota, FL 34231
1 of 25
$2,395,000 ( $330,000 )
Subdivision: Oyster Bay Estates
BEDS
4
BATHS
3
SQ.FT.
3,535
BUILT
1970
ON SITE
303Days
MLS
A4213972
Water views in the front and back of this 4BR plus family and bonus rooms Oyster Bay home create an idyllic backdrop for an easygoing family lifestyle. This private residence is surrounded by lush...
1818 N Lake Shore Drive
Sarasota, FL 34231
1818 N Lake Shore Drive Sarasota, FL 34231
1 of 41
$2,250,000 ( $245,000 )
Subdivision: Oyster Bay Estates
BEDS
3
BATHS
6
SQ.FT.
5,968
BUILT
2004
ON SITE
108Days
MLS
A4414868
This Oyster Bay Estates residence designed by accomplished architect, Thorning Little, embodies classic Italianate design with Moorish influences. Framed by mature palms and lush hedges, this West of...
1616 N Lake Shore Drive
Sarasota, FL 34231
1616 N Lake Shore Drive Sarasota, FL 34231
1 of 39
$1,125,000
Subdivision: Oyster Bay Estates
BEDS
3
BATHS
3
SQ.FT.
2,389
BUILT
1954
ON SITE
58Days
MLS
A4419648
Perfect west of the trail location to build your dream home. A true tropical haven, and one of the most sought after neighborhoods in Sarasota - Oyster Bay Estates abuts Sarasota Bay and is located...
4557 Camino Real
Sarasota, FL 34231
4557 Camino Real Sarasota, FL 34231
1 of 25
$995,000 ( $100,000 )
Subdivision: Oyster Bay
BEDS
4
BATHS
5
SQ.FT.
3,771
BUILT
1983
ON SITE
276Days
MLS
A4215896
This charming four-bedroom Oyster Bay home is spacious and built with custom details. Located "West of the Trail" in a wonderfully central spot, only minutes from downtown Sarasota's bustling city...
1525 Kenilworth Street
Sarasota, FL 34231
1525 Kenilworth Street Sarasota, FL 34231
1 of 49
$789,000 ( $10,000 )
Subdivision: Oyster Bay
BEDS
3
BATHS
2
SQ.FT.
2,183
BUILT
1987
ON SITE
76Days
MLS
A4417849
Stunning renovation west of the Trail! This light and bright California Contemporary has walls of windows and cathedral ceilings making it feel as one with the outdoors. The expansive floor plan...

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