South Sarasota | Southwest Florida Real Estate

SOUTH SARASOTA | Southwest FL Real Estate

Homes in south Sarasota have the best of both worlds, just south of beautiful Downtown Sarasota and just inland from Siesta Key - all of the location at a fraction of the price! Bee Ridge Road and Clark Road are the two major roads leading to Siesta Key and encompass the communities of Phillippi Landings, Oyster Bay Estates, Ridge Wood Heights, Pelican Cove, South Gate Ridge and Gulf Gate Estates.

Esplanade by Siesta Key

Esplanade by Siesta Key is not on the island of Siesta Key and it's beaches but it is just inland, east of the Tamiami Trail and near Stickney Point Road which leads over to Siesta Key. This newer community started construction of paired villas and single family homes in 2013 and now is complete with 247 residences. The villas and homes run from 2-3 bedrooms and 2-3 baths from 1,856 to 2,842 square feet, built by Taylor Morrison. It is a gated community on over 75 acres. Like other Esplanade communities such as the one in Lakewood Ranch, it has upscale resort-style amenities such as the heated lagoon pool and spa, clubhouse with a fitness center & catering kitchen, outdoor grill and fire pit area. There are also sports courts for beach volley ball, tennis and bocce ball. It also has a dog park. The quarterly fees also include lawn maintenance for all homes and roof maintenance is included for the villas.

Gulf Gate in South Sarasota

Homes in the Gulf Gate communities are just minutes from the beaches of Siesta Key but are priced at a fraction of the price that you will find for homes on the island. There are 3 communities of Gulf Gate, Gulf Gate Woods and Gulf Gate East. All have low HOA fees that maintain the lakes and landscaping at the entrances and are patrolled by a voluntary security patrol 24 hours a day. At this time, Gulf Gate East is the only community with deed restrictions. All are near shopping, movie theaters, the South County YMCA and the Gulf Gate Library. There are bike lanes along Gulf Gate Drive and the communities are also near the Legacy Trail which has over 10 miles of paved trails spanning from South Sarasota to Venice.

Homes in these communities were built from the 1960's to the 1980's with Gulf Gate East being the newest, built in the mid-1980's with home sizes from 1,100 - 3,600 square feet. The larger homes were built on the cul-de-sacs in the rear of the Gulf Gate East neighborhood with some lots as large as an acre. Many homes have been updated over the years and current prices range from the low $200,000's to the mid-to-high $500,000's.

Oyster Bay Estates

Find your waterfront estate home in this community west of the Trail with homes overlooking Oyster Bay, Roberts Bay and the Gulf of Mexico. The community also hosts the Field Club, tennis, yachting and social activities. Homes feature 3 - 6 bedrooms, 3 - 5 baths from the high $700,000's to over $5 million dollars, most with private pools. Ideally situated near the beaches of Siesta Key and minutes from downtown Sarasota with it's gourmet restaurants, museums and nightlife.

Phillippi Landings

Looking for a luxury waterfront condominium community in Sarasota? You'll find it at Phillippi Landings. This gated community was built in 2006 and is situated on 10 acres of tropical landscape with a community boat ramp, boat docks, fishing pier, pool and spa and fitness club. Near the downtown Sarasota Opera House, Oslo Theatre, Van Wezel Performing Arts Hall and the Bayfront water and dog parks.

Pelican Cove

Looking for an active condominium community nestled in a lush tropical neighborhood just inland from Siesta Key? You'll find it at Pelican Cove. There are 731 units from 1 to 4 bedrooms priced from the low $100 to mid $500 thousands built between 1975 and 1981. The complex has 6 heated pools, 4 tennis courts, basketball and shuffleboard courts, 5 miles of walking trails, fishing areas and 86 boat slips that can be rented on an annual basis. There is also kayak and canoe storage and a launch area along with 3 community centers that host card and cooking clubs, yoga & dance and art studios. The Pavilion has an auditorium and stage for music and art exhibitions. Condo fees cover the 24-hour guard service at the front entrance, private roads, flood insurance, water, sewer, garbage removal and all of the amenities. Owners may have 2 dogs or cats and the units may be leased twice a year for a minimum of 2 months.

Just Listed | Latest Homes for Sale in South Sarasota

4431 Camino Real, Sarasota $5,000,000

Pre-Construction. To be built. Welcome to 4431 Camino Real, an architectural masterpiece to be built in the upscale Oyster Bay Estates, Sarasota, Florida. This luxurious,...

5 Beds
5 Baths
Oyster Bay Estates SubDv.
34231 Zip Code

3636 Mineola Drive, Sarasota $1,457,363

" short stories" Once you cross the bridge, lies a mid century modern gem. What you see is real""...NOTHING IS VIRTUALLY STAGED... Centrally located in Southgate on a q...

2 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

2301 Haley Lane, Sarasota $6,500,000

Family owned for over 50 years. Truly one of a kind 3 1/2 +/- Acre ESTATE with 20 ...YES 20 income producing 8 HOMES & 6 DUPLEXS. Homes build in the early 90's Duplex's b...

Ridgewood SubDv.
34231 Zip Code

2849 Webber Street, Sarasota $500,000

This home offers a combination of convenience, comfort, and outdoor enjoyment, making it a desirable place to live, especially for those who appreciate the Florida lifest...

3 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

5591 Cannes Circle Unit 204, Sarasota image

5591 Cannes Circle Unit 204, Sarasota — E $619,900

Experience luxurious Florida living at Phillippi Landings, a waterfront community nestled along the tranquil shores of Phillippi Creek. Here, nature's beauty, serenity, a...

2 Beds
2 Baths
Phillippi Landings SubDv.
34231 Zip Code

4752 Lark Ridge Circle, Sarasota $359,900 ▼

Don't miss this incredible opportunity! Step into this charming 2-bedroom, 2-bath home with an added bonus room, and discover a world of possibilities. Recent upgrades, i...

2 Beds
2 Baths
South Gate Ridge SubDv.
34233 Zip Code

3442 Fairview Drive, Sarasota $549,300

Welcome to your ideal Sarasota sanctuary! Nestled on a peaceful, idyllic street, this charming property is ready to make your dreams come true. Let's dive into the hi...

3 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

1519 Clower Creek Drive Unit 149, Sarasota image

1519 Clower Creek Drive Unit 149, Sarasota — Bldg 19 $525,000

This delightful 3-Bedroom ground floor Condo will enchant you with its wonderful, serene and peaceful view to Clower Creek. Nestled in lush native vegetation, Southern or...

3 Beds
2 Baths
Pelican Cove SubDv.
34231 Zip Code

1514 S Lake Shore Drive, Sarasota $1,999,000

Nestled on one-third of an acre in the picturesque West of Trail community of Oyster Bay Estates, this captivating one-of-a-kind home combines striking artisan and archit...

3 Beds
3 Baths
Oyster Bay Estates SubDv.
34231 Zip Code

3037 Goldenrod Street, Sarasota $510,000

One or more photo(s) has been virtually staged. “One or more photo(s) was virtually staged.” Welcome to this spacious Pool home located in the sought-after SOUTH GATE ne...

3 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

2723 Sheridan Drive, Sarasota $589,000

Welcome to the historic community of Southgate in the heart of Sarasota! This gorgeous 3 bedroom, 2 bath home is in a great location, has a 2 car garage, an amazing lana...

3 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

2415 S Tuttle Avenue, Sarasota $494,997 ▼

Location, location, location! This updated home is in a desirable location of South Gate just minutes from Downtown, the beach, and ONLY 3 minutes to ARLINGTON PARK! As y...

2 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

5545 Rollingwood Drive, Sarasota $515,000 ▼

BACK ON THE MARKET, Buyer's financing fell through. Beautiful 4br 3ba Pristinely landscaped, Huge Screened Lanai featuring a large 14 x 28 in Ground Pool and Privacy Fenc...

4 Beds
3 Baths
Ridgewood Estates SubDv.
34232 Zip Code

3200 Pinecrest Street, Sarasota $675,000 ▼

One or more photo(s) has been virtually staged. Completely renovated and tastefully updated home in the heart of South Gate. This 3-bedroom, 2-bathroom home sits on an o...

3 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

3750 Mundy Ridge Drive, Sarasota $465,000

STUNNING HOME, REMODELED, SPACIOUS, SPLIT FLOOR PLAN: 3/2 BED/BATH! QUIET, WELL ESTABLISHED NEIGHBORHOOD IN THE MIDDLE OF SARASOTA, FLORIDA! 4.8 MILES FROM SIESTA KEY, FL...

3 Beds
2 Baths
South Gate Ridge SubDv.
34233 Zip Code

1815 N Lake Shore Drive, Sarasota $2,795,000

Located “West of Trail” in one of the most sought-after areas in Sarasota this stunning home is perfectly positioned on a corner lot amidst the lush Florida landscape to ...

3 Beds
3 Baths
Oyster Bay Estates SubDv.
34231 Zip Code

4755 Lark Ridge Circle, Sarasota $499,000 ▼

Brand new AC just installed August 2023!!! 3 miles to the #1 Siesta Key Beach! Welcome to South Gate Ridge! This 5-star VRBO money-making machine is up for grabs. With an...

3 Beds
2 Baths
South Gate Ridge SubDv.
34233 Zip Code

3246 Elmore Place, Sarasota $549,000 ▼

Don't miss this opportunity for a beautifully renovated and move-in ready home in the heart of Southgate! The updates to this lovely property include a complete re-roof w...

2 Beds
2 Baths
South Gate SubDv.
34239 Zip Code

3575 Webber Street, Sarasota $525,000 ▼

Introducing a Lucrative Investment Opportunity in South Gate! This exquisite 10-office property offers almost 2000 square feet of prime commercial space, nestled within a...

South Gate SubDv.
34239 Zip Code

3200 Gulf Watch Court, Sarasota $375,999 ▼

One or more photo(s) has been virtually staged. Seller Financing Available!!! Experience the allure of living in the perfect blend of comfort and convenience. Your searc...

2 Beds
2 Baths
Gulf Gate Glen SubDv.
34231 Zip Code

2585 Clematis Street, Sarasota $3,500,000

Pre-Construction. To be built. Don't miss this Brand New - Pre-Construction Home! Courtyard Modern's newest design features a resort-style heated pool and spa! The pr...

6 Beds
6.5 Baths
Southgate SubDv.
34239 Zip Code

2317 & 2321 Bee Ridge Road, Sarasota image

2317 & 2321 Bee Ridge Road, Sarasota $2,225,000 ▼

Are you looking for a new location on a busy road for your dealership or automotive business? This one is perfect for that!! 5,777/sq.ft. of working space. 7 - 10x10 o...

South Gate SubDv.
34239 Zip Code

2124 Clematis Place, Sarasota $1,910,000 ▲

Pre-Construction. To be built. "EAST IS THE NEW WEST" Pre-Construction. To be built. Pre-Construction. To be built. PRE-Construction "PRICING" Buyer may modify plans to ...

4 Beds
3.5 Baths
South Gate SubDv.
34239 Zip Code

2301 Haley Lane, Sarasota $6,500,000

Family owned for over 50 years. Truly one of a kind 3 1/2 +/- Acre ESTATE with 20 ...YES 20 income producing 8 HOMES & 6 DUPLEXS. Homes build in the early 90's Duplex's...

3 Beds
40 Baths
Ridgewood SubDv.
34231 Zip Code

2434 Hamlin Lane, Sarasota $2,090,000

Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction. To be built. PRE-Construction "PRICING" 10 month build time. Still time to make it your ow...

3 Beds
3.5 Baths
South Gate SubDv.
34239 Zip Code

2524 Fruit Tree, Sarasota $2,025,000

Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction. To be built. "EAST IS THE NEW WEST" Pre-Construction. To be built. Pre-Construction. To be...

4 Beds
4.5 Baths
South Gate SubDv.
34239 Zip Code

2534 Fruit Tree, Sarasota $3,200,000

Pre-Construction. To be built. Pre-Construction. To be built. "EAST IS THE NEW WEST" Pre-Construction. To be built. Pre-Construction. To be built. PRE-Construction "PRICI...

6 Beds
6.5 Baths
South Gate SubDv.
34239 Zip Code

2512 Jefferson Circle, Sarasota $3,130,000 ▼

Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction. To be built. "EAST IS THE NEW WEST" Pre-Construction. To be built. Pre-Construction. To be...

6 Beds
6 Baths
South Gate SubDv.
34239 Zip Code

5591 Cannes Circle Unit 205, Sarasota image

5591 Cannes Circle Unit 205, Sarasota — E $650,000 ▼

Ready for your slice of paradise? Welcome to sought-after Phillippi Landings in Sarasota, situated on 10 acres of lush tropical landscape along Phillippi Creek. This go...

2 Beds
2 Baths
Phillippi Landings SubDv.
34231 Zip Code

3314 Jaffa Dr, Sarasota $548,000 ▼

This Exceptional home boasts an OPEN SPACIOUS INTERIOR sure to impress even the most discerning buyers. Located on a quiet shaded street just off Siesta Drive in the high...

2 Beds
2 Baths
Southgate SubDv.
34239 Zip Code

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Testimonials

Lisa Salvato - 5 stars! John is fabulous! He listened to what we wanted and emailed us only properties that applied. We live in New York and were interested in purchasing a Florida property. Having never met him prior to our visit to view the key properties of interest, from his e-mails, we didn't know what to expect . We feel like we hit the jackpot, John was professional, courteous and went out of his way to show us condos in a spread-out area. We have now closed on that purchase. Thank-you John for being a great negotiator and knowledgeable in your field. Your follow-through beyond the closing is appreciated and impressive. Thank-you Leslie for your work in the background to follow-up with all of the condo documents. We have sold and purchased homes before and John is at the top! February 2018

Robert Theofel — Above and beyond! Every aspect of the home buying process from initial search to closing went without a hitch due to Leslie and John’s expertise. When searching for a home, we received recommendations that were within our search criteria and the team was always available to show the homes that we selected. The recommendations we received during the negotiating, buying and closing process were excellent and we were able to close within a month of the initial viewing of the property. I would highly recommend them to anyone looking to buy a home!

Curt Johnson — My wife and I needed to sell our house, however there was much to do to get it ready. John and Leslie let us know how to fix-up the house to get the best possible response at the showings. We got it done and sold our house within 2 days of listing it with them. I think one of the best things I walked away with from the experience is how I felt trusting them with my home knowing that they had my best interest at hand. I would recommend John and Leslie to anyone who wants to be successful in selling or buying a home.

Jennifer Pearson — Leslie and John went above and beyond to help us sell our home! We had relocated 1900 miles away as we were trying to sell our house. They were in constant contact with us regarding the house and showings. They helped us find maintenance people when needed and even completed some things themselves. We would highly recommend them and should we return to the area, we will definitely use them to purchase a home!

Valerie Bologna — 5 stars! John helped my husband and I find a condo in Sarasota while we are living in another state. If there was something that we were interested in, he would go out right away and take pictures of the place and e-mail them to us. He never made us feel like we were wasting his time even though our purchase was not a million dollar listing! In a few years we will be calling on John again to find us a permanent place to live instead of seasonally. My husband and I appreciate all that he and his wife Leslie have done for us to make this purchase go as smooth as possible and we feel like we have gained new friends as well!

Victoria Harlow — 5 stars! Leslie went above and beyond with advice on staging, open houses, and cleaning and caring for my property while I was absent. Her teammate and husband John make a stellar team. I was so happy to get a great offer so close to my asking price. Awesome work! Thank-you for being vigilant and for the awesome care you took with selling my house. Your are the best that I've encountered after selling three houses over the years!

Edy Campos — 5 stars! - Can't get any better than John! He helped me all the way until the end, gives great advice, works fast, follows up and doesn't waste time. If you are serious about finding a place to call "home", I really recommend John Gregory!

Nancy Gallagher — If you're looking for a new home in Florida, John is a tireless agent to have on your side! If he doesn't know the answer to a question (which is rare) he will find it and in a timely manner! I highly recommend his services.