Sarasota Real Estate - West of the Trail
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Featured West of the Trail Homes for Sale
Welcome to Mandarin Park, one of Sarasota’s most desirable gated communities, where beautiful homes, privacy, and an unbeatable location come together in the heart of the...
- 2 Beds
- 2 Baths
- Mandarin Park SubDv.
- 34239 Zip Code
Built in 1910, this original Lexington model Sears, Roebuck and Co. kit house offers a rare opportunity to own a remarkable piece of Sarasota history. Once ordered by mai...
- 3 Beds
- 3 Baths
- Corwood SubDv.
- 34234 Zip Code
Experience the best of Sarasota living in this exceptional West of Trail residence by Heritage Builders. Ideally positioned in the coveted Oyster Bay area near the histor...
- 4 Beds
- 5 Baths
- Johnson Estates SubDv.
- 34231 Zip Code
This is the one * LOCATED IN THE HIGHLY DESIRABLE AQUALANE ESTATES, JUST A MILE FROM WORLD FAMOUS SIESTA KEY BEACH, THIS CUSTOM HOME OFFERS AN INCREDIBLE OPPORTUNITY TO O...
- 4 Beds
- 2 Baths
- Aqualane Estates SubDv.
- 34231 Zip Code
Wonderful home! Was used as an AirBNB/VRBO for years and now it's available for you! Furniture negotiable. Walk to Southside Elementary school! Superior location in S...
- 2 Beds
- 1 Baths
- Granada Park SubDv.
- 34239 Zip Code
Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and ...
- 3 Beds
- 4 Baths
- Cherokee Park SubDv.
- 34239 Zip Code
Welcome to this stunning BRAND-NEW CONSTRUCTION home in Sarasota, offering 2,678 square feet of beautifully designed living space with 4 bedrooms, 4.5 bathrooms, a privat...
- 4 Beds
- 5 Baths
- Indian Beach SubDv.
- 34234 Zip Code
Nestled within the desirable West of Trail Southpointe Shores Community, this home benefits from top-rated school zones and a serene, upscale waterfront atmosphere. This ...
- 3 Beds
- 2 Baths
- Southpointe Shores SubDv.
- 34231 Zip Code
Wake up to the salt air. This gorgeous updated Indian Beach home is perfectly situated close to downtown, west of Trail/west of Bayshore. Take a 4-minute walk to see the ...
- 4 Beds
- 2 Baths
- Indian Beach Map Of SubDv.
- 34234 Zip Code
Behind a private gate and beneath a canopy of tropical foliage, 1621 Bay Point Court offers a secluded waterfront retreat just moments from downtown Sarasota and the open...
- 4 Beds
- 5 Baths
- Mooring At Bay Pointe The SubDv.
- 34236 Zip Code
Rarely available in Cherokee Park, widely regarded as one of Sarasota’s most desirable West of Trail neighborhoods, 1722 North Drive presents an extraordinary opportunity...
- 3 Beds
- 2 Baths
- Cherokee Park SubDv.
- 34239 Zip Code
Virtually Staged. Welcome to 5166 Kestrel Park Terrace, an exceptional opportunity in the highly sought-after gated community of The Landings. Privately positioned on an ...
- 4 Beds
- 4 Baths
- The Landings SubDv.
- 34231 Zip Code
Build something extraordinary in Sapphire Shores, one of Sarasota's most coveted bayfront neighborhoods, where canopied streets, custom architecture and the open water of...
- Sapphire Shores SubDv.
- 34234 Zip Code
Pre-Construction. To be built. UNDER CONSTRUCTION — HEMINGWAY LUXURY MODEL BY COURTYARD MODERN HOMES- OR BUILD TO SUIT STARTING AT $4,500,000.00 -- A striking new express...
- 5 Beds
- 6 Baths
- Harbor Acres SubDv.
- 34239 Zip Code
Classic Sarasota charm takes on a fresh, sophisticated spirit in this beautifully updated residence, where relaxed interiors, thoughtful details and lush outdoor spaces c...
- 3 Beds
- 3 Baths
- Poinsettia Park SubDv.
- 34239 Zip Code
Completely rebuilt from the ground up, this is a rare opportunity to own essentially new construction on one of the largest usable lots in Granada, one of Sarasota's most...
- 3 Beds
- 3 Baths
- Granada SubDv.
- 34239 Zip Code
Welcome to this beautifully refreshed, single-story residence in Bay View Heights, one of Sarasota’s most coveted West of Trail neighborhoods. Set on a generous 15,625-sq...
- 4 Beds
- 4 Baths
- Bay View Heights SubDv.
- 34239 Zip Code
West of Trail living at its finest! Nestled on a quiet street in one of Sarasota's most coveted neighborhoods, 1750 Alta Vista offers the perfect blend of timeless charm,...
- 3 Beds
- 2 Baths
- West Of Trail SubDv.
- 34236 Zip Code
Some properties offer a view. This extraordinary 1.41 acre Oyster Bay estate offers an entire waterfront world of its own and is one of the best waterfront locations that...
- 4 Beds
- 8 Baths
- Oyster Bay Estates SubDv.
- 34231 Zip Code
Experience Sarasota living at its finest in this beautifully crafted new-construction home West of Trail. Offering five bedrooms and five-and-a-half baths, the residence ...
- 5 Beds
- 6 Baths
- Lewis Combs Sub SubDv.
- 34239 Zip Code
Excellent opportunity to own an 8,158 sq. ft. vacant lot in a prime Sarasota location, less than 2 miles from Siesta Key and Downtown Sarasota. This south-facing lot offe...
- Hartland Park SubDv.
- 34239 Zip Code
Welcome to this exceptional waterfront home in the highly sought-after Harbor Acres neighborhood. With more than 5,000 square feet of living space, this five-bedroom, fiv...
- 5 Beds
- 7 Baths
- Harbor Acres SubDv.
- 34239 Zip Code
Welcome to an understated masterclass in coastal sophistication. Custom-built by renowned builder Jonas Yoder, this new construction residence offers over 3,000 square fe...
- 4 Beds
- 4 Baths
- Matheneys Sub SubDv.
- 34239 Zip Code
A private garden retreat in one of Sarasota’s most coveted West of Trail locations.** Nestled among lush tropical gardens and mature landscaping, 3424 Old Oak Drive is a ...
- 3 Beds
- 2 Baths
- Shoreland Woods SubDv.
- 34239 Zip Code
Built in 2022 by SRQ Builders, this Sarasota waterfront home in Sapphire Shores offers 117 feet of waterfront along a protected yacht basin with views of Sarasota Bay. Se...
- 3 Beds
- 4 Baths
- Sapphire Shores SubDv.
- 34234 Zip Code
Motivative seller bring all offers Sapphire Shores neighborhood directly overlooking Ca d' Zan open bay and just minutes from Ringling Museum area and Asolo Theater incre...
- Sapphire Shores SubDv.
- 34234 Zip Code
Motivated Seller bring all offers Sapphire Shores neighborhood directly overlooking the open bay has 187 feet of waterfront and Ca d' Zan and minutes from Ringling Museum...
- Sapphire Shores SubDv.
- 34234 Zip Code
Prime Multifamily Development Opportunity in Sarasota's Historic District Exceptional corner lot in the heart of Sarasota's sought-after Historic District, offering an...
- Petroutsa Brothers Sub SubDv.
- 34236 Zip Code
LIVE THE WATERFRONT & BOATING LIFESTYLE in highly desirable SOUTHPOINTE SHORES! Perfectly positioned DIRECTLY ACROSS THE STREET FROM THE COMMUNITY BOAT RAMP AND DOCK—appr...
- 3 Beds
- 2 Baths
- Southpointe Shores SubDv.
- 34231 Zip Code
Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms w...
- 5 Beds
- 3 Baths
- Bayview SubDv.
- 34239 Zip Code
West of the Trail lot overlooking scenic 60-acre Phillippi Estate Park which is a County Park located on the banks of Phillippi Creek. 50’x 167’ lot with central water an...
- Florence SubDv.
- 34231 Zip Code
West of the Trail lot overlooking scenic 60-acre Phillippi Estate Park which is a County Park located on the banks of Phillippi Creek. 50’x 167’ lot with central water an...
- Florence SubDv.
- 34231 Zip Code
Rare opportunity to create a custom waterfront residence on approximately 0.95 acres in Sarasota. Located on Tidewood Avenue, this spacious corner lot homesite overlooks ...
- Baywood Colony Westport SubDv.
- 34231 Zip Code
Rare opportunity to create a custom waterfront residence on approximately 0.70 acres in Sarasota. Located on Tidewood Avenue, this spacious homesite overlooks the Intraco...
- Baywood Colony Westport SubDv.
- 34231 Zip Code
Some homes are built. Others are envisioned. 1516 Ridgewood is the result of an uncompromising pursuit of excellence—a California Pacific Palisades-inspired waterfront es...
- 4 Beds
- 5 Baths
- Aqualane Estates SubDv.
- 34231 Zip Code
Welcome to this exceptional new construction, upgraded residence located West of Trail, featuring 5 bedrooms, 5 full bathrooms, and 3,640 square feet of thoughtfully cura...
- 5 Beds
- 5 Baths
- Poinsettia Park SubDv.
- 34239 Zip Code
Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 b...
- 4 Beds
- 6 Baths
- Poinsettia Park SubDv.
- 34239 Zip Code
Where the World's Most Exclusive Resorts Inspire Everyday Living. Imagine waking each morning in a residence that rivals the refined elegance of an Aman Private Estate...
- 5 Beds
- 6 Baths
- Lewis Combs Sub SubDv.
- 34239 Zip Code
Discover exceptional West of Trail living in Lincoln Park, an intimate waterfront enclave located along Hudson Bayou in Sarasota, Florida. This beautifully appointed resi...
- 3 Beds
- 3 Baths
- Lincoln Park On Hudson Bayou SubDv.
- 34236 Zip Code
On an elevated lot in the quiet, refined community of Kentwood Estates near Oyster Bay, this modern residence exudes Zen-like sophistication. From its contemporary archit...
- 3 Beds
- 3 Baths
- Kentwood Estates SubDv.
- 34231 Zip Code
Located on approximately 200 feet of open Bay frontage in one of Sarasota's most prestigious neighborhoods, this remarkable property enjoys a postcard-worthy setting on m...
- 4 Beds
- 4 Baths
- 34231 Zip Code
Pre-Construction. To be built. Situated in San Remo Estates, one of Sarasota's most exclusive waterfront communities, this upcoming new construction home, designed and bu...
- 4 Beds
- 6 Baths
- San Remo Estates SubDv.
- 34239 Zip Code
ATTENTION BOATERS!! Waterfront dream home – move-in ready! Just a quick (429 yard) boat ride to the ICW - no bridges - a straight shot to the water. Head out to the newly...
- 3 Beds
- 2 Baths
- Bay View Acres SubDv.
- 34231 Zip Code
Poised on one of the prettiest tree-lined West of Trail streets, this modern coastal residence offers the ideal blend of casual elegance, thoughtful design, and everyday ...
- 4 Beds
- 3 Baths
- Poinsettia Park SubDv.
- 34239 Zip Code
Fully renovated waterfront estate in Coral Cove, one of Sarasota’s most desirable West of Trail communities. Set on an elevated 0.59-acre corner lot directly across from ...
- 4 Beds
- 4 Baths
- Coral Cove SubDv.
- 34231 Zip Code
**This is the One!** Welcome to a beautifully renovated 3-bedroom, 2.5-bath pool home blending modern luxury with Sarasota charm in one of the area's most desirable locat...
- 3 Beds
- 3 Baths
- Hartland Park SubDv.
- 34239 Zip Code
Build Your Dream Home on Sarasota Bay in Sapphire Shores! Set on an expansive 0.34-acre (14,665-sq.-ft.) waterfront lot, this property presents a rare opportunity to c...
- Sapphire Shores SubDv.
- 34234 Zip Code
Pre-Construction. To be built. Welcome to effortless coastal luxury in the coveted Harbor Acres neighborhood, where timeless glamour meets breezy, tropical elegance. The ...
- 4 Beds
- 5 Baths
- Harbor Acres SubDv.
- 34239 Zip Code
Virtually Staged. In the heart of Southside Village, this exceptional home offers one of Sarasota’s sought-after lifestyles. Just west of Tamiami Trail in Poinsettia Park...
- 4 Beds
- 4 Baths
- Poinsettia Park SubDv.
- 34239 Zip Code
Exceptional Sarasota bayfront homesite in Indian Beach/Sapphire Shores. A rare opportunity to build your custom waterfront home on one of Sarasota's most desirable bayfro...
- Sapphire Shores SubDv.
- 34234 Zip Code
West of the Trail
View our featured West of the Trail Listings above or create a search with your own criteria.
One of the hottest Sarasota Real Estate areas is this area known as West of the Trail. Located between Route 41 and the shoreline, this area features homes varying in architectural style and price with many located directly on the water overlooking Sarasota Bay. New construction homes also continue to come on the market as do the occasional land or lot for sale.
Living in this area affords the homeowner the true meaning of the Sarasota lifestyle. With its close proximity to downtown, the beaches of Siesta Key and Lido Key and all the cultural attractions of this beautiful city, the area West of the Trail is truly one of Sarasota's premier locations.
The homes located West of the Trail in Sarasota range in styles from tastefully appointed estates to mid-century modern to historical mission style bungalows, but all have one thing in common: they enjoy an unmatched location.
Our website provides property information on listings in real time. That means as soon as they are entered into the the official Realtor®’s database, any search you've created on our website will be updated with notification. All information is updated every 15 minutes so you can be sure to have the most recent information available.
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Below are all current Sarasota West of the Trail home listings on the MLS. These are sorted from lowest price to highest and are updated every 15 minutes by the official Realtor®’s database.
For new construction opportunities, contact us. I can provide you with floorplans, upgrade lists, site plans, unadvertised leaseback and spec home opportunities as well.
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