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 March 22, 2019
9
Listed
123
Avg. DOM
$464.68
Avg. $ / Sq.Ft.
$1,195,000
Med. List Price
9 Properties Found.
Sort By:
1404 Kenilworth Street
Sarasota, FL 34231
1404 Kenilworth Street Sarasota, FL 34231
1 of 43
$4,595,000
Subdivision: Oyster Bay Landings
BEDS
4
BATHS
5
SQ.FT.
5,428
BUILT
2007
ON SITE
42Days
MLS
A4424301
Art you can live in! World renowned and acclaimed architect, Guy Peterson, designed another modern masterpiece of remarkable craftsmanship and pure minimalist aesthetic. It all began with a vision,...
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
177Days
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...
1818 N Lake Shore Drive
Sarasota, FL 34231
1818 N Lake Shore Drive Sarasota, FL 34231
1 of 41
$1,995,000 ( $500,000 )
Subdivision: Oyster Bay Estates
BEDS
4
BATHS
6
SQ.FT.
5,968
BUILT
2004
ON SITE
173Days
MLS
A4414868
Incredible value, as Seller has reduced by $500,000! This Oyster Bay Estates residence designed by architect, Thorning Little, embodies classic Italianate design right down to the exterior appearance...
4439 Westwood Lane
Sarasota, FL 34231
4439 Westwood Lane Sarasota, FL 34231
1 of 23
$1,650,000
Subdivision: Oyster Bay Estates
BEDS
4
BATHS
4
SQ.FT.
3,657
BUILT
1991
ON SITE
47Days
MLS
A4425835
Warm, Inviting and in a Stellar Location! Enter through the stunning, arched wood doorway, you will be met with a true sense of serenity. Every detail has been carefully thought of in this...
4487 Camino Real
Sarasota, FL 34231
4487 Camino Real Sarasota, FL 34231
1 of 46
$1,195,000
Subdivision: Oyster Bay Estates
BEDS
3
BATHS
3
SQ.FT.
2,765
BUILT
1957
ON SITE
60Days
MLS
A4424993
Beautiful West of the Trail contemporary home in the sought-after Oyster Bay area and walking distance to The Field Club. It's situated on ½ acre with beautiful gardens surrounding the home...
1616 N Lake Shore Drive
Sarasota, FL 34231
1616 N Lake Shore Drive Sarasota, FL 34231
1 of 27
$1,000,000 ( $125,000 )
Subdivision: Oyster Bay Estates
BEDS
3
BATHS
3
SQ.FT.
2,389
BUILT
1954
ON SITE
123Days
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
$949,000 ( $146,000 )
Subdivision: Oyster Bay
BEDS
4
BATHS
5
SQ.FT.
3,771
BUILT
1983
ON SITE
341Days
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
141Days
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...
1801 Field Road
Sarasota, FL 34231
1801 Field Road Sarasota, FL 34231
1 of 33
$499,000
Subdivision: Oyster Bay Estates
BEDS
2
BATHS
2
SQ.FT.
1,682
BUILT
1966
ON SITE
7Days
MLS
A4430615
** MUST SEE ** Oyster Bay Estates Presents a Botanical Paradise in this Fantastic 2 Bed, 2 Bath Pool Home. Sitting on a 15,500ft2 (.35 acres) lot, native plantings, blooming flowers, soaring palms,...

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