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 December 13, 2019
11
Listed
186
Avg. DOM
$439.81
Avg. $ / Sq.Ft.
$1,374,900
Med. List Price
11 Properties
$3,100,000
Subdivision: Oyster Bay Estates
4
Beds
4F11/2
Baths
4,783
Sq.Ft.
2006
Year Built
136
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...
$2,449,000
Subdivision: Oyster Bay Estates
4
Beds
4F21/2
Baths
5,968
Sq.Ft.
2004
Year Built
51
Days on Site
A4449050
MLS
This impeccably built custom home in one of the premier neighborhoods in Sarasota has everything you could want! With almost 6,000 square feet of refined living space, coupled with almost 2,000 feet...
$1,995,000
Subdivision: Oyster Bay Landings
3
Beds
3
Baths
2,582
Sq.Ft.
1984
Year Built
250
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
3F11/2
Baths
4,407
Sq.Ft.
2006
Year Built
117
Days on Site
A4443962
MLS
Spectacular Tuscan Masterpiece in Oyster Bay Estates, Sarasota's most coveted West-of-the-Trail neighborhood. This Spanish-Italian design home was built in 2006 by custom-builder Bruce Saba with...
$1,460,000
Subdivision: Oyster Bay Estates
4
Beds
3F11/2
Baths
3,657
Sq.Ft.
1991
Year Built
313
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...
$1,374,900
Subdivision: Oyster Bay Estates
4
Beds
3F11/2
Baths
3,613
Sq.Ft.
1997
Year Built
283
Days on Site
N6104544
MLS
Located in the coveted Oyster Bay neighborhood this Key West style exterior and contemporary interior home sits on a half acre lot. The newly remodeled open floor plan boasts 12 to 29 ft. ceilings...
$1,100,000
Subdivision: Oyster Bay Estates
3
Beds
3F21/2
Baths
3,292
Sq.Ft.
1957
Year Built
56
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...
$1,085,000
Subdivision: Oyster Bay Estates
3
Beds
2F11/2
Baths
2,765
Sq.Ft.
1957
Year Built
326
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...
$965,000
Subdivision: Oyster Bay Estates
3
Beds
3
Baths
2,389
Sq.Ft.
1954
Year Built
389
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...
$859,950
Subdivision: Oyster Bay Estates
4
Beds
3
Baths
2,821
Sq.Ft.
1959
Year Built
102
Days on Site
A4444434
MLS
Seldom available and a hidden gem "West of the Trail" and on the lake in Oyster Bay, one of the most sought out areas in Sarasota. The value of this property is in the land. The buyers wishing to...
$525,000
Subdivision: Oyster Bay Estates
3
Beds
2
Baths
1,549
Sq.Ft.
1958
Year Built
29
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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