West of the Trail

Sarasota Homes for Sale

Waterfront Homes, Luxury Homes and Condos

West of the Trail are defined as the neighborhoods "west" of US Hwy 41 or the Tamiami Trail. The most popular West of the Trail neighborhood is the community located centrally around the Plaza anchored by Morton's Gourmet Market. Within walking distances to the market, Sarasota Memorial Hospital and neighborhood restaurants such as Libby's, Hillview Grill and Knick's Tavern, these single-family homes are of mixed architectural styles. Many are old Florida homes and the properties are exquisite. Older homes are being removed or updated in this area and builders are adding all the designer touches in kitchens, bathrooms and fabulous new landscaping to make way for new mini-mansions. Also, close to downtown Sarasota and the beaches of Siesta Key, this beautiful community a is a "must see" for convenience and location, location, location.  Read More...

Included below are West of the Trail homes and condos for sale in the Sarasota, FL area, updated daily from the Sarasota MLS. If you would like more information on any of these Sarasota properties for sale, just click the "Request More Information" button when viewing the details of that property. We can provide you with disclosures, past sales history, dates and prices of homes recently sold nearby, and more.

And, if you haven't already, be sure to register for a free account so that you can receive email alerts whenever West of the Trail homes come on the market in Sarasota.
West of the Trail March 29, 2023
151
Listed
89
Avg. DOM
$796.66
Avg. $ / Sq.Ft.
$1,699,000
Med. List Price
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151 Properties
Page 1 of 13
4645 Ainsley PLACE Sarasota, FL 34234
$14,000,000
Neighborhood: Indian Beach Map Of
4645 Ainsley PLACE
Sarasota, FL 34234
7
Beds
6
Baths
4,272
Sq.Ft.
1935
Year Built
36
Days on Site
A4561241
MLS
Introducing a landmark waterfront estate on the idyllic Sarasota Bay, this extraordinary 4.15 acre parcel offers unmatched beauty, location, historical charm, and potential. The estate is perfectly...
Michael Saunders & Company
1610 N Lodge Dr Sarasota, FL 34239
$11,700,000
Neighborhood: Cherokee Lodge
1610 N Lodge Dr
Sarasota, FL 34239
6
Beds
6F21/2
Baths
6,800
Sq.Ft.
2024
Year Built
62
Days on Site
A4558525
MLS
Under Construction. Waterfront. Under construction. Encapsulating a perfect combination of comfort and luxury this spectacular two story coastal modern single family home is situated in Cherokee Park....
Coldwell Banker Realty
900 Alameda Ln Sarasota, FL 34234
$10,900,000
Neighborhood: Whitakers W H Prop
900 Alameda Ln
Sarasota, FL 34234
5
Beds
5F21/2
Baths
4,799
Sq.Ft.
1973
Year Built
66
Days on Site
U8188295
MLS
Fall under the spell of Ventana, named after the owner's idyllic visit to the Ventana Inn on Big Sur, in California. Located in the oldest settlement in Sarasota, on 210 feet of Indian Beach. This is...
Coldwell Banker Realty
555 Quay COMMON #1801 Sarasota, FL 34236
$9,999,000
Neighborhood: Ritz-Carlton Residences Sarasota Bay
555 Quay COMMON #1801
Sarasota, FL 34236
4
Beds
4F11/2
Baths
4,942
Sq.Ft.
2024
Year Built
76
Days on Site
A4557210
MLS
One or more photo(s) has been virtually staged. Pre-Construction. To be built. Now taking reservations! Brought to you by Kolter Urban and designed by award-winning SB Architects this iconic new,...
Premier Sothebys Intl Realty
555 Quay COMMON #2003 Sarasota, FL 34236
$9,599,000
Neighborhood: Ritz-Carlton Residences Sarasota Bay
555 Quay COMMON #2003
Sarasota, FL 34236
3
Beds
3F11/2
Baths
4,357
Sq.Ft.
2024
Year Built
69
Days on Site
A4558024
MLS
One or more photo(s) has been virtually staged. Pre-Construction. To be built. Now taking reservations! Brought to you by Kolter Urban and designed by award-winning SB Architects this iconic new,...
Premier Sothebys Intl Realty
1465 Hillview Dr Sarasota, FL 34239
$9,575,000
Neighborhood: Harbor Acres
1465 Hillview Dr
Sarasota, FL 34239
5
Beds
6F11/2
Baths
6,654
Sq.Ft.
2023
Year Built
406
Days on Site
A4515981
MLS
One or more photo(s) has been virtually staged. Under Construction. Crafted by the award-winning Custom Home Builder, Dynan Construction, this captivating West Indies-inspired waterfront residence is...
Keller Williams Classic Group
1515 Hillview Dr Sarasota, FL 34239
$8,400,000
Neighborhood: Harbor Acres
1515 Hillview Dr
Sarasota, FL 34239
4
Beds
4F21/2
Baths
5,424
Sq.Ft.
2023
Year Built
174
Days on Site
A4522100
MLS
Under Construction. Imagine living on one of Sarasota's most desirable streets in a gorgeous, new, waterfront home...Your dreams can come true! Presenting another stunning design by Coastal Luxury...
Coldwell Banker Realty
1479 Bay Point Dr Sarasota, FL 34236
$6,850,000
Neighborhood: Bay Point Park 2
1479 Bay Point Dr
Sarasota, FL 34236
4
Beds
3
Baths
3,783
Sq.Ft.
1949
Year Built
41
Days on Site
A4561284
MLS
Rare opportunity to build your "dream home" in one of the most exclusive waterfront areas West of Trail neighborhoods. The property offers breathtaking views of Sarasota Bay and Golden Gate Point....
Premier Sothebys Intl Realty
1100 Blvd of The Arts #1710 Sarasota, FL 34236
$6,800,000
Neighborhood: One Park
1100 Blvd of The Arts #1710
Sarasota, FL 34236
3
Beds
5
Baths
3,848
Sq.Ft.
2023
Year Built
44
Days on Site
A4560825
MLS
Pre-Construction. To be built. With world-class architecture and interiors, the 18-story One Park is bringing a quintessential lifestyle to one of Downtown Sarasota's most sought after locations,...
Coldwell Banker Realty
1370 Tangier WAY Sarasota, FL 34239
$6,699,000
Neighborhood: San Remo Estates Unit 3
1370 Tangier WAY
Sarasota, FL 34239
4
Beds
4
Baths
3,506
Sq.Ft.
1979
Year Built
72
Days on Site
A4557324
MLS
This custom remodeled home is located on more than a hundred feet of beautiful Sarasota Bay with wide open Bay views. Deep sailboat water with new dock and boatlift. This 4 bedroom, 4 bath home is in...
Bright Realty
2168 Sparrow Ct Sarasota, FL 34239
$6,300,000
Neighborhood: Paradise Shores
2168 Sparrow Ct
Sarasota, FL 34239
4
Beds
4
Baths
4,643
Sq.Ft.
2001
Year Built
87
Days on Site
A4555954
MLS
Unrivaled location, breathtaking views, and ideal water access combine with an impeccably constructed and maintained home to offer one of the finest bayfront opportunities in Sarasota today. This...
Coldwell Banker Realty
1400 Tangier WAY Sarasota, FL 34239
$6,250,000
Neighborhood: San Remo Estates
1400 Tangier WAY
Sarasota, FL 34239
3
Beds
2
Baths
3,068
Sq.Ft.
2023
Year Built
2
Days on Site
A4565547
MLS
One or more photo(s) has been virtually staged. Under Construction. Welcome to this 3,068 sqft, one of a kind coastal contemporary home nestled in the highly sought after San Remo Estates. An M&J...
Bright Realty

There is quite a variety of home styles in this area. Old Florida, Spanish Mediterranean, ranch homes and a sprinkling of contemporary designs are mixed through the water front, canals and mainland in the West of the Trail stretch from Manatee County to Sarasota County. The neighborhoods are lush with tropical plantings and colorful with blooms year round.

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