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 April 1, 2020
11
Listed
155
Avg. DOM
$460.04
Avg. $ / Sq.Ft.
$1,700,000
Med. List Price
11 Properties
$4,650,000
Subdivision: Oyster Bay Landings
4
Beds
4F21/2
Baths
5,889
Sq.Ft.
2006
Year Built
78
Days on Site
A4455314
MLS
Inspired Coastal Design. Located in the private gated enclave of Oyster Bay Landings, this amazing waterfront residence combines unique architecture and incredible interior design to create a...
$2,995,000
Subdivision: Oyster Bay Estates
4
Beds
4F11/2
Baths
4,783
Sq.Ft.
2006
Year Built
246
Days on Site
A4442286
MLS
Tucked away on Lakeshore Drive in a storybook lakefront setting, this exquisite estate embodies tropical elegance and style. Luxurious appointments, state-of-the-art amenities, and a romantic water...
$2,300,000
Subdivision: Oyster Bay Estates
3
Beds
3F11/2
Baths
3,003
Sq.Ft.
1956
Year Built
37
Days on Site
A4460954
MLS
Mid-Century Modern, canal-front home on over 1/2 acre in desirable Oyster Bay Estates. Easy access to Roberts Bay/Intracoastal.
Partial westerly views provide for breathtaking sunsets from the...
$2,250,000
Subdivision: Oyster Bay Estates
4
Beds
4F21/2
Baths
5,968
Sq.Ft.
2004
Year Built
104
Days on Site
A4454495
MLS
Set in Oyster Bay Estates and remarkable in every way is Villa Lidia, a stunning example of architectural mastery and creatively imagined by acclaimed architect Thorning Little. Impressive in both...
$2,250,000
Subdivision: Oyster Bay Estates
5
Beds
4F11/2
Baths
5,043
Sq.Ft.
1972
Year Built
62
Days on Site
A4458536
MLS
The motivated owner has positioned this property to be one of the best waterfront opportunities in the marketplace today. Located on a boat basin in the beloved neighborhood of Oyster Bay, its...
$1,700,000
Subdivision: Oyster Bay Estates
5
Beds
5
Baths
4,460
Sq.Ft.
1980
Year Built
17
Days on Site
A4462797
MLS
Stunning Oyster Bay 4460 sq.ft. estate has been carefully designed to blend into the natural setting of this secluded ½ acre property. Beautifully imagined and masterfully constructed home features 5...
$1,460,000
Subdivision: Oyster Bay Estates
4
Beds
3F11/2
Baths
3,657
Sq.Ft.
1991
Year Built
423
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...
$1,085,000
Subdivision: Oyster Bay Estates
3
Beds
2F11/2
Baths
2,765
Sq.Ft.
1957
Year Built
436
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...
$999,000
Subdivision: Oyster Bay Estates
3
Beds
3F21/2
Baths
3,292
Sq.Ft.
1957
Year Built
166
Days on Site
A4449196
MLS
1613 Field Rd. West of the trail in the sought-after Oyster Bay neighborhood. Featuring 3BR/3BA/2HBA, two story pool home with fully private fenced backyard. Perfect for entertaining family and...
$599,000
Subdivision: Oyster Bay Estates
3
Beds
2
Baths
2,427
Sq.Ft.
1959
Year Built
6
Days on Site
A4464087
MLS
Prime West of Trail single family home (buildable lot) located in the Oyster Bay Estates subdivision. Lot dimensions are 100' x 150' (.34 acre) Major renovation required to update this 1959 3BR/2BA...
$515,000
Subdivision: Oyster Bay Estates
3
Beds
2
Baths
1,549
Sq.Ft.
1958
Year Built
139
Days on Site
A4451784
MLS
This mid-century home in Oyster Bay Estates defines Florida living as it used to be. Lushly landscaped with oak trees, bamboo and exotic plants, you'll be living in a tropical wonderland. As you are...

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