Oyster Bay Estates

West of the Trail Homes for Sale

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 June 18, 2019
9
Listed
168
Avg. DOM
$519.48
Avg. $ / Sq.Ft.
$1,650,000
Med. List Price
9 Properties
$4,385,000
Subdivision: Oyster Bay Landings
4
Beds
4F11/2
Baths
5,428
Sq.Ft.
2007
Year Built
130
Days on Site
A4424301
MLS
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,...
$2,495,000
Subdivision: Oyster Bay Estates
3
Beds
2F11/2
Baths
3,160
Sq.Ft.
1962
Year Built
265
Days on Site
A4414590
MLS
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...
$2,100,000
Subdivision: Oyster Bay Landings
3
Beds
3
Baths
2,582
Sq.Ft.
1984
Year Built
72
Days on Site
A4432539
MLS
This BAYFRONT cottage, West of Trail, in-town location of distinction seems worlds away yet enjoys easy accessibility to the very best Sarasota has to offer. Hidden behind the gates of OYSTER BAY...
$1,995,000
Subdivision: Oyster Bay Estates
4
Beds
4F21/2
Baths
5,968
Sq.Ft.
2004
Year Built
261
Days on Site
A4414868
MLS
This property should be firmly on the radar of the savvy buyer seeking the utmost in quality construction with a classic Thorning Little architectural design. Delivering not only in value, scale and...
$1,650,000
Subdivision: Oyster Bay Estates
4
Beds
3F11/2
Baths
3,657
Sq.Ft.
1991
Year Built
135
Days on Site
A4425835
MLS
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...
Open 6/23
4487 Camino Real Sarasota, FL 34231
$1,150,000
Subdivision: Oyster Bay Estates
3
Beds
2F11/2
Baths
3,647
Sq.Ft.
1957
Year Built
148
Days on Site
A4424993
MLS
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...
$985,000
Subdivision: Oyster Bay Estates
3
Beds
3
Baths
2,389
Sq.Ft.
1954
Year Built
211
Days on Site
A4419648
MLS
Nearly ½ acre lake front lot in coveted Oyster Bay Estates! This is the perfect west of the trail location to build your dream home. Or, for those that love the mid-century style, work to revive this...
Open 6/23
1525 Kenilworth Street Sarasota, FL 34231
$775,000
Subdivision: Oyster Bay
3
Beds
2
Baths
2,183
Sq.Ft.
1987
Year Built
229
Days on Site
A4417849
MLS
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...
$749,000
Subdivision: Oyster Bay
4
Beds
2
Baths
1,889
Sq.Ft.
1969
Year Built
71
Days on Site
A4432827
MLS
Begin your dream home West of the Trail. This charming four-bedroom pool home is situated on a corner parcel spanning nearly a quarter-acre of lush, manicured property. Waiting for you to renovate or...

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