Southside Homes

/19
$6,500,000
- Land
- 1.27 Acres
- $5,118,110 per Acre
3350 Old Oak Dr, Sarasota, FL 34239

Rarely does an opportunity like this come to market—a chance to own a piece of Old Florida on over an acre of lush, private grounds. Nestled in total seclusion, this extraordinary compound offers panoramic views of Sarasota Bay, Siesta Key, Bird Key, the Ringling Bridge, and downtown Sarasota. The property features a Mid-Century modern home alongside a vacant lot, creating endless possibilities

Nora Johnson MICHAEL SAUNDERS & COMPANY

3350 Old Oak Dr, Sarasota, FL 34239
/65
$1,900,000 Sold Mar 14, 2025
- 3,272 Sq Ft
- $581/SF
- 345 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2006
1964 Datura St, Sarasota, FL 34239

Experience unparalleled luxury in this exquisite 4 bedroom, 3.5 bath West of Trail executive home, located in the prestigious Southside School district, one block from Southside Village, and a few more blocks to the award-winning Sarasota Memorial Hospital. This freshly painted two-story masterpiece boasts a clean and contemporary Spanish Mediterranean style, with impressive street presence and

Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

1964 Datura St, Sarasota, FL 34239

/72
Est $2,799,810 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,446 Sq Ft
1706 Spring Creek Dr, Sarasota, FL 34239

1706 Spring Creek Dr, Sarasota, FL 34239

/35
$3,300,000
- Land
- 0.52 Acre
- $6,346,154 per Acre
3348 Old Oak Dr, Sarasota, FL 34239

Stunning Mid Century Masterpiece, close to beach and walk to Southside Village. Featuring cypress inside and out. High ceilings and open spaces offer comfort and airiness, while the walls of glass sliders and windows fill the interior with natural lighting while showcasing gorgeous views of the lush landscaping. The expansive great room features floor-to-ceiling sliders and a wood-burning

Nora Johnson MICHAEL SAUNDERS & COMPANY

3348 Old Oak Dr, Sarasota, FL 34239
/2
$460,000 Sold Feb 28, 2025
- 1,341 Sq Ft
- $343/SF
- 20 Days On Market
- 3 Beds
- 2 Baths
- Built 1954
3219 S East Ave, Sarasota, FL 34239

WOW- A GREAT NEW Price! This incredible home is now an even better deal - Don't miss your chance to make it yours! Charming Sarasota Home with PRIME Location, NO HOA and Endless Features! Step inside to appreciate the true beauty of this COMPLETELY RENOVATED gem at 3219 S East Avenue, where charm, comfort, and convenience come together in one incredible property. Located equidistant from Siesta

Joe Cleary RE/MAX ALLIANCE GROUP

3219 S East Ave, Sarasota, FL 34239

/65
Est $1,443,769 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,072 Sq Ft
1842 Grove St, Sarasota, FL 34239

1842 Grove St, Sarasota, FL 34239

/19
$9,800,000
- 7 Beds
- 8 Baths
- 7,181 Sq Ft
3350 Old Oak Dr, Sarasota, FL 34239

Rarely does an opportunity like this come to market, offering a piece of Old Florida on 2.1 lush acres and boasting breathtaking views of Sarasota Bay, Siesta Key, Bird Key, Ringling Bridge, and downtown Sarasota, this magnificent family compound features two custom-built Mid Century homes and a vacant lot, offering limitless possibilities. Designed to take advantage of the amazing views, the

Nora Johnson MICHAEL SAUNDERS & COMPANY

3350 Old Oak Dr, Sarasota, FL 34239
/2
$2,300,000 Sold Feb 26, 2025
- 3,151 Sq Ft
- $730/SF
- 960 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2024
1625 Hansen St, Sarasota, FL 34231

*Ready For Move-In*The Bahama by Heritage Builders is truly a masterpiece of Florida luxury living, expertly combining everything to be desired in a custom home. This spacious 4 Bedroom, 4-1/2 Bathroom dream home also delivers both a Bonus Room and a Private Study. The home’s elevation blends a tropical island aesthetic with classic architectural features including planation window coverings

Nancy Gretz PARADISE PROPERTIES FL LLC

1625 Hansen St, Sarasota, FL 34231

/38
Est $3,055,551 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,844 Sq Ft
1955 Datura St, Sarasota, FL 34239

1955 Datura St, Sarasota, FL 34239

/45
$629,000
- 2 Beds
- 2 Baths
- 980 Sq Ft
3511 Camino Real, Sarasota, FL 34239

MOTIVATED SELLER | Prime West-of-Trail Location | Move-In Ready |Nestled in one of Sarasota’s most coveted West-of-Trail neighborhoods, this 2BD/2BA home is just minutes from Siesta Key’s world-class beaches and surrounded by multimillion-dollar properties. With plenty of room for upgrades, this home presents an incredible opportunity to boost property value and maximize rental income —

Dean Hinterstoisser KELLER WILLIAMS ON THE WATER S

3511 Camino Real, Sarasota, FL 34239
/2
$1,025,000 Sold Feb 25, 2025
- 2,156 Sq Ft
- $475/SF
- 203 Days On Market
- 4 Beds
- 3 Baths
- Built 1954
3521 Flores Ave, Sarasota, FL 34239

Price Improvement! This stunning home, situated in a peaceful West of Trail neighborhood, sustained no water or wind damage from the 2024 hurricane season. Just a short walk from restaurants, shops, CineBistro, Publix, the post office, and more, this property offers both convenience and charm. Ideal for investors, it's located within city limits, allowing for weekly rentals. This spacious home

Jennifer Thompson WILLIAM RAVEIS REAL ESTATE

3521 Flores Ave, Sarasota, FL 34239

/65
Est $846,986 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,783 Sq Ft
3603 Almeria Ave, Sarasota, FL 34239

3603 Almeria Ave, Sarasota, FL 34239

/25
$6,900,000
- 5 Beds
- 7 Baths
- 6,710 Sq Ft
3544 San Remo Terrace, Sarasota, FL 34239

Located in the coveted West-of-Trail San Remo Estates, this rare double-lot, one-acre waterfront estate offers 200 feet of deep-water frontage with panoramic bay and Intracoastal views. Perfectly positioned near downtown Sarasota and Siesta Key, the property includes a protected boat basin for unmatched privacy and access.The gated 7,960 sq ft residence showcases modern Mediterranean

Charles & Gabe Buky COLDWELL BANKER REALTY

3544 San Remo Terrace, Sarasota, FL 34239
/2
$1,525,000 Sold Feb 14, 2025
- 2,304 Sq Ft
- $662/SF
- 59 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2015
1756 Stapleton St, Sarasota, FL 34239

Experience the pinnacle of modern living in this Platinum LEED-certified, fortress-built former model home. Situated in the gated and maintenance-free Granada Park community, which features a pool and cabana, this residence combines elegance, energy efficiency, and thoughtful design. This home offers 3 spacious bedrooms and 3 and a half bathrooms, constructed with solid concrete on both floors

Kim Ogilvie MICHAEL SAUNDERS & COMPANY

1756 Stapleton St, Sarasota, FL 34239

/38
Est $1,027,559 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,748 Sq Ft
1647 Catalonia Ln, Sarasota, FL 34239

1647 Catalonia Ln, Sarasota, FL 34239

/55
$489,500
- 3 Beds
- 1 Bath
- 1,382 Sq Ft
2065 Goldenrod St, Sarasota, FL 34239

Nestled in the heart of Sarasota within the top A-rated school district, this charming 3-bedroom, 1-bath home offers a prime position near various amenities. Located close to Siesta and Lido Key Beaches, the inviting shops and restaurants of Southside Village, the cultural richness of Downtown Sarasota, the upscale allure of St. Armands Circle, and the convenient Sarasota Memorial Hospital, this

Patrick Brogley KELLER WILLIAMS ON THE WATER S

2065 Goldenrod St, Sarasota, FL 34239
/2
$1,872,000 Sold Feb 10, 2025
- 2,956 Sq Ft
- $633/SF
- 123 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2024
3523 Jacinto Ct, Sarasota, FL 34239

Brand new and just completed luxury block home. This 2,958 SQFT home features 4 ample sized bedrooms, 3 with walk-in closets, each bedroom has a full bath. Large 18x15 loft/bonus room with a slider and covered back porch (loft can accommodate a king size bed, bunk beds, or multiple twin beds), PGT impact windows, wood floors throughout, metal roof, first floor master bedroom, master bath - all

Paul Defelice HOUSEMAX REALTY LLC

3523 Jacinto Ct, Sarasota, FL 34239

/59
Est $2,563,529 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,851 Sq Ft
1925 Oleander St, Sarasota, FL 34239

1925 Oleander St, Sarasota, FL 34239

/15
$269,000
- 2 Beds
- 2 Baths
- 1,122 Sq Ft
3360 S Osprey Ave Unit 102B, Sarasota, FL 34239

BERMUDA ON OSPREY - OASIS ON OSPREY. 1st. Floor end unit 2BR/ 2 full Baths Condo. West of Trail. Home in very private location in bldg. Tastefully newly renovated in light and cheery decor. Eat-In Kitchen with built-in features, granite countertops, wood cabinets, glass top range, microwave, refrigerator, dishwasher. (Eat-in area could be used as office, etc.) Living Room/Dining Room with

Larry Haymore RE/MAX ALLIANCE GROUP

3360 S Osprey Ave Unit 102B, Sarasota, FL 34239
/2
$1,600,000 Sold Feb 07, 2025
- 2,426 Sq Ft
- $660/SF
- 98 Days On Market
- 4 Beds
- 3 Baths
- Built 1943
3616 Flores Ave, Sarasota, FL 34239

True Vintage home from 1943. Charms abound throughout this wonderful, only second owner home. Original oak floors are only one of many features that await you when you enter the front door through the welcoming totally private courtyard. Present owners have done many upgrades through the years while maintaining the ambiance throughout. Legal, totally Furnished, self-contained, 5 room

Sheryl Morris REALTY SERVICES INC

3616 Flores Ave, Sarasota, FL 34239

/34
Est $1,082,723 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,360 Sq Ft
1750 S Oval Dr, Sarasota, FL 34239

1750 S Oval Dr, Sarasota, FL 34239

/2
$1,480,000
- Land
- 0.33 Acre
- $4,484,848 per Acre
2155 Oriole Dr, Sarasota, FL 34239

This is a vacant lot

Stephen Hachey FLAT FEE MLS REALTY

2155 Oriole Dr, Sarasota, FL 34239
/2
$2,950,000 Sold Jan 31, 2025
- 2,670 Sq Ft
- $1,105/SF
- 14 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2014
2004 S Osprey Ave, Sarasota, FL 34239

Experience the pinnacle of modern design and impeccable craftsmanship in this stunning architectural masterpiece West of the Trail. Perfectly situated in the heart of Southside Village, this extraordinary residence showcases a harmonious blend of streamlined concrete and warm mahogany, delivering a striking visual appeal that resonates with today’s discerning buyer. Designed with precision

Nora Johnson MICHAEL SAUNDERS & COMPANY

2004 S Osprey Ave, Sarasota, FL 34239

/52
Est $1,792,251 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,159 Sq Ft
1642 Shoreland Dr, Sarasota, FL 34239

1642 Shoreland Dr, Sarasota, FL 34239

/60
$2,700,000 New Construction
- 6 Beds
- 8 Baths
- 3,677 Sq Ft
2065 Goldenrod St, Sarasota, FL 34239

Experience refined coastal living in this newly constructed luxury residence located in the heart of Sarasota. This thoughtfully designed home offers over 3,600 square feet of living space, creating the perfect blend of comfort, privacy, and functionality for family and guests alike. From the moment you enter through the grand courtyard entryway, you are greeted with soaring ceilings and elegant

Domanic Calamese KW COASTAL LIVING III

2065 Goldenrod St, Sarasota, FL 34239
/2
$2,825,000 Sold Jan 24, 2025
- 2,844 Sq Ft
- $993/SF
- 14 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2024
1521 Bay Rd, Sarasota, FL 34239

Move-in ready and easy to see! Welcome to 1521 Bay Road, a brand-new single-story masterpiece by Majestik Homes, known for their high-quality craftsmanship. Nestled West of the Trail, this home seamlessly combines modern design with thoughtful functionality to create a luxurious and inviting living experience.As you enter through the impressive double front doors, you’re greeted by a

Charles Simons, III MAJESTIK REALTY

1521 Bay Rd, Sarasota, FL 34239

/53
Est $587,050 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,070 Sq Ft
2107 Orchid St, Sarasota, FL 34239

2107 Orchid St, Sarasota, FL 34239

/23
$3,200,000 New Construction
- 5 Beds
- 4.5 Baths
- 3,960 Sq Ft
1658 Bonita Ln, Sarasota, FL 34239

One or more photo(s) has been virtually staged. Drive under the serene canopy of oaks, and you will arrive at 1658 Bonita Lane, a brand-new custom construction, classic Spanish design inspired by the refined and timeless architecture of Palm Beach, Florida. Connected to nature with a quiet elegance, this residence features just under 4,000 square feet of 5 bedrooms, 4.5 baths and lots of

Sasha Rosin HORIZON REALTY INTERNATIONAL

1658 Bonita Ln, Sarasota, FL 34239
/2
$1,875,000 Sold Jan 24, 2025
- 2,439 Sq Ft
- $769/SF
- 0 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1928
1862 Prospect St, Sarasota, FL 34239

ACCEPTING BACK-UP OFFERS. Welcome to 1862 Prospect Street, "Big Banya.” This rare find in Southside Village features three bedrooms and three bathrooms, combining old Florida allure with modern amenities. Built in 1928, (affective build date 2013) it offers 2,439 square feet of living space on a half-acre lot adorned with beautiful gardens and majestic trees. As you enter, you are greeted by a

Georgia Salaverri COMPASS FLORIDA LLC

1862 Prospect St, Sarasota, FL 34239

/67
Est $1,387,184 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,430 Sq Ft
1614 Wisconsin Ln, Sarasota, FL 34239

1614 Wisconsin Ln, Sarasota, FL 34239

/7
$6,000,000 New Construction
- 5 Beds
- 9 Baths
- 4,765 Sq Ft
2100 Mcclellan Pkwy, Sarasota, FL 34239

Pre-Construction. To be built. Construction in progress. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sarasota. Developed by M&J Pham Development, this residence is a masterpiece of innovative, forward-thinking design and flawless craftsmanship. This home is 4,765 square feet, with 5 bedrooms, 7 baths and 2 half baths. Inside, you'll discover an

Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

2100 Mcclellan Pkwy, Sarasota, FL 34239
/2
$2,200,000 Sold Jan 15, 2025
- 2,617 Sq Ft
- $841/SF
- 8 Days On Market
- 4 Beds
- 5 Baths
- Built 2013
1815 Grove St, Sarasota, FL 34239

Experience unparalleled luxury and comfort in this stunning home, located in the highly sought-after West of the Trail neighborhood. Built in 2013, this residence effortlessly blends sophisticated design with functional living. Featuring a spacious open floor plan, a first-floor primary suite, a chef-inspired kitchen, and a private backyard oasis with a sparkling pool and outdoor kitchen, this

Mairead Smialek COLDWELL BANKER REALTY

1815 Grove St, Sarasota, FL 34239

/88
Est $3,529,424 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,224 Sq Ft
1410 Siesta Dr, Sarasota, FL 34239

1410 Siesta Dr, Sarasota, FL 34239

/96
$4,875,000 Open Fri 1PM - 4PM
- 4 Beds
- 4.5 Baths
- 3,970 Sq Ft
1827 Morris St, Sarasota, FL 34239

The “St. Michael” is award-winning Allegra Homes’ 2025 fully furnished model home supremely located just south of downtown Sarasota’s cultural epicenter in the coveted West of Trail area where residents know first-hand what a wonderful community they live in. Prepare to be captivated by the seamless fusion of modern design, artful nuances, and stylish sophistication. Every detail has been curated

Karen Greco GRECO REAL ESTATE

1827 Morris St, Sarasota, FL 34239
/2
$2,350,000 Sold Jan 08, 2025
- 2,762 Sq Ft
- $851/SF
- 0 Days On Market
- 4 Beds
- 3 Baths
- Built 1941
1750 Seminole Dr, Sarasota, FL 34239

Welcome to this timeless gem in the highly sought after McClellan Park neighborhood, West of Trail. Originally built in 1941 and thoughtfully remodeled in 2012, this lovely home seamlessly blends historic charm with modern luxury. As you step inside, you'll be greeted by the stunning original pecky cypress, high ceilings, and an abundance of natural light. The floor plan offers a perfect balance

Alison Elizalde MICHAEL SAUNDERS & COMPANY

1750 Seminole Dr, Sarasota, FL 34239

/60
Est $2,076,503 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,270 Sq Ft
1826 Boyce St, Sarasota, FL 34239

1826 Boyce St, Sarasota, FL 34239

/31
$2,899,990 New Construction
- 4 Beds
- 4 Baths
- 3,292 Sq Ft
1876 Magnolia St, Sarasota, FL 34239

Under Construction. This stunning 2-story “Palonia IV Coastal” floor plan is one of the newest additions to the Allegra Homes collection of exquisite luxury residences and is located in the prestigious West of Trail area near Siesta Drive, your direct pathway to Siesta Key. The cornerstone of the Allegra Homes’ vision is a dedication to excellence in custom home building and providing the very

Karen Greco GRECO REAL ESTATE

1876 Magnolia St, Sarasota, FL 34239
/2
$4,450,000 Sold Jan 02, 2025
- 4,215 Sq Ft
- $1,056/SF
- 5 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2020
1623 North Dr, Sarasota, FL 34239

We can’t remember the last time a home made us feel this way. Walking through this property, you instantly sense something extraordinary. Bringing a home like this to market is a rare privilege. Located in Cherokee Park, one of Sarasota’s most sought-after neighborhoods, this 4-bedroom, 4.5-bath home is a sanctuary of thoughtful design and unmatched craftsmanship. The oversized lot

Ryan Skrzypkowski COLDWELL BANKER REALTY

1623 North Dr, Sarasota, FL 34239

/80
Est $2,996,771 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,674 Sq Ft
1960 Boyce St, Sarasota, FL 34239

1960 Boyce St, Sarasota, FL 34239

/52
$3,000,000 Open Fri 1PM - 4PM
- 5 Beds
- 5 Baths
- 3,595 Sq Ft
1805 Goldenrod St, Sarasota, FL 34239

One or more photo(s) has been virtually staged. Welcome to this stunning 2-story luxury home built by M&J Pham Development, featuring 5 bedrooms, 5 bathrooms, and 3,595 square feet of living space. From the moment you step inside, you'll be captivated by the open floor plan, high-end finishes, and fantastic design. The home features a modern and elegant kitchen with top-of-the-line Viking

Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

1805 Goldenrod St, Sarasota, FL 34239

Showing Results 121 - 160, Page 4 of 18

Florida Sarasota County Sarasota Southside

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage