Homes East of Trail

$159,000
1 Beds ⋅ 1 Baths ⋅ Park Lane SubDv. ⋅ 34237 Zip Code ⋅ A4701212 MLS ⋅ Active Status ⋅ Park Lane BLDG.
Completely updated one-bedroom, one-bathroom condo in the much sought after community of Park Lane. This home offers stylish, move-in-ready living in one of Sarasota's most convenient locations. Every detail has been thoughtfully updated, creating a home that blends modern finishes with effortless, low-maintenance living. The beautifully remodeled kitchen features quartz countertops, a glass tile backsplash, stainless steel appliances, and recessed lighting, with tile flooring throughout. The updated bathroom showcases a custom frameless glass shower enclosure, and additional improvements include new doors, new windows, and updated appliances, providing peace of mind for years to come. Conveniently located just across from Publix and minutes from Downtown Sarasota, you'll enjoy easy access to award-winning dining, shopping, theaters, Payne Park, Marina Jack, St. Armands Circle, Lido Key Beach, and the world-famous beaches of Siesta Key. The community maintains a peaceful residential atmosphere with no pets and no smoking permitted. Leasing is allowed with a minimum three-month lease, limited to two leases per year. Subleasing and commercial use are prohibited. Whether you're searching for a full-time residence, seasonal retreat, or low-maintenance Sarasota getaway, this beautifully updated condominium offers exceptional value, outstanding convenience, and true move-in-ready condition. Schedule your private showing today.

2155 Wood Street Unit A22, Mid Town Sarasota
$524,995
4 Beds ⋅ 2 Baths ⋅ Southgate SubDv. ⋅ 34239 Zip Code ⋅ A4701097 MLS ⋅ Active Status
Investor Opportunity or Ideal Owner-Occupant Duplex in Desirable Southgate – Sarasota, FL Exceptional opportunity to own a solid block construction duplex in the highly sought-after Southgate area of Sarasota. Offered at $524,995, this versatile, well-maintained property is perfect for investors seeking reliable rental income or buyers looking to live in one unit while generating income from the other. With no HOA and separate electric and water meters for each unit, this property offers the flexibility and convenience today’s buyers and investors are looking for. Each spacious unit features 2 bedrooms, 1 full bathroom, an open-concept kitchen, dining area, and a comfortable great room, creating a bright, inviting living space that appeals to both homeowners and tenants. Ceramic tile flooring throughout provides durability, easy maintenance, and a clean, timeless look. Each unit also includes a pantry/laundry room with washer and dryer hookups, adding valuable storage and everyday convenience. A convenient two-car carport is located between the units, providing covered parking and additional convenience for both residences. This property has been meticulously maintained and offers numerous valuable updates that provide peace of mind for years to come. Highlights include a 75-year-rated metal roof installed approximately eight years ago, HVAC systems replaced within the last four and five years, respectively, and newer water heaters in both units. The beautifully landscaped grounds reflect pride of ownership and enhance the property’s curb appeal. Location is one of this property’s greatest assets. Nestled in the established Southgate neighborhood, you’ll enjoy the convenience of being just 10 minutes from vibrant downtown Sarasota, where exceptional dining, shopping, arts, entertainment, and cultural attractions await. Even better, you’re only 15 minutes from the world-renowned white sands of Siesta Key Beach and beautiful Lido Beach, making this an outstanding location for both residents and tenants alike. Whether you’re expanding your investment portfolio, searching for a multi-generational living opportunity, or looking to offset your mortgage with rental income, this duplex offers exceptional value in one of Sarasota’s most desirable and centrally located neighborhoods. Don’t miss this rare opportunity to own a move-in-ready, income-producing property in the heart of Sarasota.

2911 Bentley Street, Central Sarasota
$254,000
2 Beds ⋅ 2 Baths ⋅ Village Green SubDv. ⋅ 34232 Zip Code ⋅ A4701181 MLS ⋅ Active Status ⋅ 1537 BLDG.
Welcome to carefree Florida living in the highly desirable Village Green, a well-established 55+ maintenance-free community in the heart of Sarasota. This spacious and FURNISHED 2-bedroom, 2-bath end-unit villa with a versatile den offers over 1,650 square feet of comfortable living space designed for both relaxation and entertaining. The open floor plan with luxury vinyl plank flooring throughout the home seamlessly connects the living, dining, and kitchen areas, while the expansive Florida room showcases beautiful views of the lush, park-like grounds. Step outside to your private paver patio, the perfect place to enjoy your morning coffee or unwind in the evening. Just a short stroll away, you'll find the heated community pool surrounded by mature landscaping and majestic oak trees. The flexible den is ideal for a home office, hobby room, or potential third bedroom. Additional highlights include abundant storage, an attached one-car garage, updated major systems, and the convenience of maintenance-free living. Perfectly located just minutes from Siesta Key Beach, downtown Sarasota, shopping, dining, medical facilities, golf courses, and the Legacy Trail, this home offers the ideal blend of tranquility and accessibility. Whether you're searching for a full-time residence or a seasonal Florida retreat, this exceptional villa is ready to welcome you home. Schedule your private showing today!

3626 Medford Lane Unit 1537, Central Sarasota
$439,900
3 Beds ⋅ 2 Baths ⋅ Avon Heights SubDv. ⋅ 34237 Zip Code ⋅ A4701131 MLS ⋅ Active Status
Welcome to this 3-bedroom, 2-bathroom residence featuring a 2-car attached garage, an open floor plan and 9-foot ceilings that create a bright, spacious feel throughout. Step outside to enjoy the screened lanai overlooking the fully fenced backyard—perfect for relaxing or entertaining. Major updates provide peace of mind, including a new roof (2021), new A/C (2020), impact glass windows & sliding glass doors (2023), HVHZ impact front door (2021) new garage door (2022), fresh exterior paint 2025, a tankless natural gas water heater (2024), induction range (2024), dishwasher (2026) and washer & gas dryer (2024). Originally built in 1995 and ideally located within the City of Sarasota, this home offers exceptional convenience just minutes from downtown Sarasota, Sarasota Memorial Hospital, the YMCA, Arlington Park, and the Legacy Bike Trail. Best of all, there are no HOA or CDD fees, giving you added flexibility and lower ownership costs. This move-in-ready home combines quality updates, a prime location, and everyday comfort—don't miss this outstanding opportunity!

2354 Tami Sola Street, Mid Town Sarasota
$499,000
3 Beds ⋅ 2 Baths ⋅ South Haven SubDv. ⋅ 34231 Zip Code ⋅ A4700998 MLS ⋅ Coming Soon Status
COMING SOON!! WELCOME TO YOUR PRIVATE OASIS NESTLED IN THE HEART OF SARASOTA!! THIS IS A MUST SEE - TRULY ONE OF A KIND PROPERTY LOCATED ON AN OVERSIZED ALMOST 1/2 ACRE LOT WITH NO HOA RESTRICTIONS! You will be amazed when you pull up into your beautifully landscaped circular granite chip driveway. This area can be the new home for your RV, boat, work trucks and even another dwelling. This property is in a prime location and can be a family's OR an investors dream being minutes from everything that Sarasota has to offer-conveniently located less than 5 miles from famous Siesta Key Beach, premier shopping, coffee, and dining, including Trader Joes and Starbucks, US-41, I-75, top rated schools, and countless recreational opportunities. This property truly offers the best of both worlds - you can enjoy the tranquility of a secluded setting that offers the charm and serenity of country living, with super easy access to modern conveniences.-----------HOME DETAILS: •ON .45 ACRES-LESS THAN 5 MILES FROM THE WORLDS FAMOUS SIESTA KEY BEACH AND STEPS FROM US 41 •3 BEDROOM 2 BATH 1505 SQUARE FOOT UPDATED HOME •ROOF 9 YEARS OLD, AC, DUCT WORK, INSULATION AND WATER HEATER LESS THAN 5 YEARS OLD•PORCELAIN TILE AND LVP THROUGHOUT THE HOME•LARGE UTILITY ROOM THAT CAN ALSO BE USED AS A BONUS ROOM •STUNNING ENTERTAINMENT AREA THAT INCLUDES A 6-SEATER HOT TUB, FIRE PIT, EXTENSIVE SEATING AREA, AND NIGHTTIME LIGHTING •SPACIOUS FENCED IN BACKYARD THAT IS FULLY ARTIFICIALLY TURFED AND LANDSCAPED WITH AMPLE SPACE FOR OUTDOOR ACTIVITIES AND/OR FURRY FRIENDS TO PLAY SAFELY•NO HOA - ROOM FOR RV'S, BOAT, WORK TRUCKS, GARAGE, ADDITIONAL LIVING QUARTERS AND MORE•COUNTY WATER AND SEWER•EQUIPPED WITH NEW WHOLE HOME KOHLER GENERATOR•RESORT STYLE LANDSCAPING WITH FULL IRRIGATION SYSTEM AND NIGHTTIME LIGHTING SURROUNDING THE HOME•HOME IS NOT IN FLOOD ZONE•WELL REGARDED ZONED SCHOOLS INCLUDE PHILIPPI SHORES ELEMENTARY, SARASOTA MIDDLE AND RIVERVIEW HIGH•****This home will be available to view for the first time on SUNDAY -8/2/26 - 12:00pm-4pm****DO NOT MISS OUT ON THIS SPECTACULAR MUST SEE HOME! See YOU Sunday!!

2137 Worrington Street, South Sarasota
$580,000
3 Beds ⋅ 2 Baths ⋅ Village Green Club Estates SubDv. ⋅ 34239 Zip Code ⋅ A4700094 MLS ⋅ Active Status
Offering remarkable pool home with an outstanding Sarasota location, this low HOA fee community in Village Green Club Estates delivers the perfect combination of comfort, functionality, and Florida living. Situated on a spacious corner lot, this solid block home features a thoughtfully designed split-bedroom floor plan, multiple living areas, and a private backyard retreat—creating an ideal setting for everyday living and entertaining. Inside, the bright and open layout provides exceptional flexibility with a spacious living room and separate family room, giving everyone room to gather or unwind. An electric fireplace adds warmth and ambiance, while the functional design allows for seamless flow throughout the home. The split-bedroom floor plan offers outstanding privacy for owners and guests alike. The spacious primary suite is tucked away on one side of the home and features a large walk-in closet and private en-suite bathroom. Two additional bedrooms are positioned on the opposite side of the home and share a full bath with direct access to the pool, making it ideal for guests and outdoor entertaining. Step outside to your private backyard oasis. The newly resurfaced pool is perfect for enjoying Florida’s year-round sunshine, while the covered lanai provides a comfortable space for outdoor dining or relaxing overlooking the fully fenced backyard. The home has been exceptionally maintained, with major improvements already completed for added peace of mind. A new roof was installed in 2020, the air conditioning system was replaced in 2022, and most of the kitchen appliances have been updated within the past few years, allowing the next owner to move in with confidence. Village Green Club Estates is one of Sarasota’s most established neighborhoods, known for its mature landscaping, beautifully maintained homes, and remarkably low HOA fees. Residents also enjoy the nearby Village Green Golf Club, where affordable annual and monthly membership options make it easy to enjoy golf, dining, and an active social atmosphere without the obligation of mandatory membership. Situated in the heart of Sarasota off Bee Ridge Road between US-41 and I-75, this home is just minutes from Downtown Sarasota, Siesta Key Beach, Lido Beach, the Legacy Trail, Payne Park, Sarasota High School, Brookside Middle School, and the Sarasota Art Museum. Enjoy convenient access to Sarasota’s renowned dining, shopping, cultural attractions, Big Olaf Ice Cream, Yoder’s Fresh Market, the YMCA, Locklear Park, and the area’s beautiful Gulf beaches. This is a rare opportunity to own a beautifully maintained pool home in one of Sarasota’s most desirable established communities. Combining major system updates, low HOA fees, optional golf membership, and an unbeatable central location, this home offers the perfect Florida lifestyle. Schedule your private showing today.

3304 Spring Mill Circle, Central Sarasota
$279,000
2 Beds ⋅ 1 Baths ⋅ Bahia Vista Highlands SubDv. ⋅ 34237 Zip Code ⋅ A4700688 MLS ⋅ Active Status
Two platted lots totaling nearly a quarter acre in Sarasota's Bahia Vista Highlands, one block from Pinecraft and minutes to downtown. The property includes a 1958 single-story home with attached carport, an in-ground pool with patio, and a deep, tree-shaded yard. Central to Sarasota Memorial, Bahia Vista and Tuttle shopping, and the bayfront.

1125 Pattison Avenue, Mid Town Sarasota
$620,000
2 Beds ⋅ 3 Baths ⋅ Payne Park Sub SubDv. ⋅ 34237 Zip Code ⋅ TB8532054 MLS ⋅ Active Status ⋅ Na BLDG.
This beautiful new paired home in Payne Park Village blends vibrant lifestyle spaces with top-quality craftsmanship. Achieve your interior design ambitions in the glamorous and spacious open-concept floor plan with beautiful laminate flooring and huge, energy-efficient windows that fill the home with cool natural light. The epicurean kitchen includes a breakfast island with quartz countertops and white 42"cabinets and a step-in pantry. Your elegant Owner's Retreat features luxury bathroom amenities and an enhanced walk-in closet. The downstairs bedroom provides a private bathroom and a brilliant place for growth and personalization. With Downtown Sarasota in your backyard, and direct access to legacy trail, you are sure to live your best life here in Payne Park Village.

2317 Lindstrom Street, Mid Town Sarasota
$1,500,000
3 Beds ⋅ 3 Baths ⋅ Joiners A L Sub SubDv. ⋅ 34239 Zip Code ⋅ A4700669 MLS ⋅ Active Status
Experience custom luxury living in the heart of Sarasota! This beautifully crafted home, nestled on a large corner lot, offers the perfect blend of timeless design and modern comfort, just minutes from Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, Arlington Park, and world-famous beaches. Inside, you'll find rich hardwood floors, soaring ceilings, an open-concept layout, and a striking double-sided natural gas fireplace. The chef's kitchen features granite countertops, premium stainless steel appliances, gas cooking, custom cabinetry, and a large center island. The spacious primary suite includes a spa-inspired bath with a freestanding soaking tub, oversized walk-in shower, custom walk-in closet, and dual vanities. Step outside to your private tropical retreat with a covered lanai, saltwater pool, lush landscaping, and a fully fenced yard. Additional highlights include impact windows and doors, natural gas, tankless water heater, and exceptional custom craftsmanship throughout. This is Sarasota living at its finest.

2395 Hyde Park Street, Central Sarasota
$135,000
2 Beds ⋅ 2 Baths ⋅ Park Lane SubDv. ⋅ 34237 Zip Code ⋅ A4700899 MLS ⋅ Active Status ⋅ Park Lane BLDG.
This is the one! Two bedroom, two bathroom, first floor, back corner unit, directly adjacent to Payne Park in highly desirable Downtown Sarasota at the Retro Chic Park Lane community! Split floor plan for privacy means a primary bedroom with ensuite bath & dedicated full bath for guests. Vintage details include custom built ins and original terrazzo floors! Open living area with glass sliders leads to an enclosed lanai overlooking the lushly landscaped courtyard with inground pool. Recent updates include a New Stove, Microwave, Refrigerator, Water Heater, Roof, Sewer Line & Parking Lot! Embrace the best of Sarasota living with the beautiful Payne Park at your doorstep featuring 29 acres of recreation & relaxation complete with walking trails, bike path, skate park, playground, frisbee golf, tennis courts & more! Dedicated parking space in front of unit, separate & secure storage space & two laundry facilities on site. Adjacent to Publix supermarket, & close proximity to Selby Botanical Gardens, amazing restaurants and urban amenities like the Bayfront Park, weekly farmers market & so much more including the boutiques of St. Armand's circle, white sands of Lido Beach & the world renowned Siesta Key! Perfect choice for a snowbird's winter retreat, in town escape, affordable primary residence or investment property!

2155 Wood Street Unit A26, Mid Town Sarasota
$325,000
2 Beds ⋅ 1 Baths ⋅ Rio Vista SubDv. ⋅ 34239 Zip Code ⋅ A4700500 MLS ⋅ Active Status
Perfectly positioned in a desirable Sarasota location, this charming two-bedroom, one-bath home offers easy access to everything the Gulf Coast has to offer, including the world-renowned Siesta Key Beach, Downtown Sarasota, Southside Village, Arlington Park, the Ringling Museum, and Marie Selby Botanical Gardens. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this property combines convenience with the best of the Florida lifestyle. Originally built in 1958, the home has been thoughtfully updated while maintaining its timeless character. The light-filled interior features a renovated kitchen complete with granite countertops and stainless steel appliances, along with an updated bathroom that provides a fresh, modern feel. Every space has been designed to offer both comfort and functionality. The home's major improvements provide added value and peace of mind, including a metal roof installed in December 2022, a 2016 electrical panel upgrade, a three-year-old air conditioning system backed by a 10-year warranty, and a water heater replaced approximately one year ago. Impact-rated doors and hurricane fabric window screens offer additional storm protection, while the regularly maintained well and septic system help keep utility costs efficient. Spend your days enjoying nearby beaches, kayaking through scenic mangrove tunnels, exploring local boutiques, or dining at Sarasota's popular restaurants. This move-in-ready home is an excellent opportunity to enjoy a well-maintained property in one of the area's most sought-after locations.

3035 Hillview Street, Central Sarasota
$2,700,000
4 Beds ⋅ 4 Baths ⋅ Sarasota Heights SubDv. ⋅ 34239 Zip Code ⋅ A4700863 MLS ⋅ Active Status
Under Construction. Stunning new construction 4-bedroom, 4-bathroom modern farmhouse luxury home developed by Rustic Appeal LLC and built by EJM Custom Homes, situated on a prime corner lot in Arlington Park, one of Sarasota's most sought-after neighborhoods. Spanning 4,288 sq ft across two stories with a 4-car garage, this thoughtfully designed residence masterfully blends warm farmhouse character with contemporary finishes: natural stone, PVC cladding, and a striking standing seam metal roof on the exterior give way to an equally impressive interior. The grand foyer welcomes you with soaring double-height ceilings, floor-to-ceiling glazing windows, and a hand-crafted custom floating staircase. The gourmet chef's kitchen features a Calacatta marble waterfall island, custom cabinetry with extensive storage, professional-grade ZLINE appliances, built-in wine fridge, and separate bar area perfect for family gatherings and entertaining. The primary suite is a true retreat with a freestanding soaking tub, extended dual vanity with makeup area, heated floors, Delta dual shower system, brushed gold fixtures, and private balcony access. Three additional bedrooms include spa-inspired baths with unique color and design. Enjoy Florida living with a salt-water pool, spa, and outdoor kitchen. The oversized 4-car garage completes this one-of-a-kind offering. Just 5 minutes from Downtown Sarasota, 8 minutes from Siesta Key Beach, 10 minutes from St. Armands Circle, and walkable to Southside Village. Estimated delivery early 2027.

2082 Datura Street, Central Sarasota
Start Your Search
board logo

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,

East of Trail (Tamiami), Sarasota, FL: Charming Neighborhood and Coastal Living

Discover the enchanting neighborhood of East of Trail, also known as Tamiami, where charming streetscapes and coastal living come together to create a unique Sarasota experience. Positioned east of the Tamiami Trail, this area offers residents a blend of historic charm, proximity to the bay, and easy access to cultural amenities. Join us as we explore the allure of East of Trail.

 

Key Features:

Historic Homes and Tree-Lined Streets:

East of Trail is known for its historic homes and tree-lined streets, creating an inviting and timeless atmosphere. Residents can explore neighborhoods adorned with character and charm.

Southside Village:

Southside Village, located within East of Trail, is a trendy area featuring boutique shops, cafes, and upscale dining options. Residents can enjoy a leisurely stroll through this vibrant district with its eclectic offerings.

Sarasota Memorial Hospital:

The presence of Sarasota Memorial Hospital adds a practical dimension to the neighborhood, providing residents with healthcare facilities and services within close proximity.

Proximity to Sarasota Bay:

East of Trail is situated in close proximity to Sarasota Bay, allowing residents to enjoy the coastal lifestyle. Scenic views, parks, and waterfront activities contribute to the overall appeal of living in this coastal neighborhood.

 

Real Estate Opportunities:

Explore the real estate offerings in East of Trail, featuring a mix of historic homes, charming residences, and modern developments. The neighborhood's real estate landscape caters to individuals seeking a blend of coastal living and historic charm.

 

Why Choose East of Trail (Tamiami):

Historic Charm and Character:

East of Trail exudes historic charm and character, with tree-lined streets and well-preserved homes that create a welcoming and timeless ambiance.

Southside Village Lifestyle:

Southside Village offers a trendy and vibrant lifestyle with boutique shops, cafes, and upscale dining options. Residents can embrace a social and leisurely atmosphere just steps away from their homes.

Healthcare Accessibility:

The presence of Sarasota Memorial Hospital ensures that residents have convenient access to healthcare services. This practical amenity enhances the neighborhood's overall livability.

Coastal Living Experience:

The proximity to Sarasota Bay allows residents to embrace the coastal living experience. Whether enjoying waterfront parks, engaging in water activities, or simply savoring scenic views, East of Trail provides a quintessential coastal lifestyle.

 

 

East of Trail invites you to experience the charm of historic streetscapes, coastal living, and the vibrancy of Southside Village. Connect with our real estate experts today to explore the diverse homes and lifestyle opportunities that await you in this captivating neighborhood. East of Trail is not just a location; it's a community where residents can enjoy the best of Sarasota's coastal charm, historic ambiance, and the convenience of a trendy village lifestyle.