Mid Town Sarasota Homes with Gated Amenities

Mid Town Sarasota Homes with Gated Amenities

Welcome to Midtown Sarasota, a vibrant gem nestled in the heart of Sarasota County, Florida. Known for its eclectic blend of urban charm and natural beauty, Midtown Sarasota offers residents a unique lifestyle that balances modern conveniences with a relaxed, coastal atmosphere. This dynamic neighborhood is characterized by its lush landscapes, friendly community, and a variety of amenities that cater to all lifestyles.

Midtown Sarasota is not just a place to live; it’s a community that thrives on connection and convenience. Here, you'll find a diverse array of shops, restaurants, and cultural attractions, all just a stone's throw away. From local boutiques to trendy cafes, the area is brimming with options for dining and entertainment. Additionally, the stunning beaches of Sarasota are merely minutes away, providing endless opportunities for sun-soaked relaxation and outdoor adventures.

For those seeking a touch of exclusivity and security, Midtown Sarasota boasts an impressive selection of homes with gated amenities. These properties offer not only the peace of mind that comes with gated living but also a sense of community among neighbors. Many of these homes are designed with luxurious features, spacious layouts, and beautiful outdoor spaces, perfect for entertaining or enjoying quiet evenings at home.

Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Midtown Sarasota has something for everyone. Embrace the lifestyle you’ve always dreamed of in this enchanting neighborhood where every day feels like a vacation. Discover the charm of Midtown Sarasota and find your dream home today!

Newest Mid Town Sarasota Homes with Gated Amenities

$145,000
2 Beds ⋅ 3 Baths ⋅ Ramblewood Acres SubDv. ⋅ 34237 Zip Code
Virtually Staged. Step into affordable Florida living in Ramblewood Acres! This condo is situated in a well estbablished gated community known for its convenience to all the best places in Sarasota. This well maintained, move-in-ready townhome offers a smart, functional layout. Granite counters, stainless steel appliances, and a passthrough to the dining area - perfect for easy entertaining. The large living area offers a main-level half bath for extra convenience. Upstairs, two large bedrooms each feature private en-suite baths and oversized wall to wall closets. One bedroom offers a serene balcony and the other a generous sundeck, your choice of personal retreat. Ramblewood Acres offers three pools, including one heated pool, a dog park, clubhouse, basketball and tennis courts, playground, and shuffleboard. New Roof, Fresh Interior Paint, New Tile Flooring in the front patio! Fees include basic cable, pest control, on-site management, and more for low-maintenance living. The location puts you nearby everything. Charming downtown Sarasota, Baltimore Orioles Baseball, St. Armands Circle for shopping and dining, escape to any one of our beautiful beaches including nearby world famous Siesta Key or Lido beach. Stunning sunsets, Powder Sand, and Crytal Blue waters! UTC’s shopping and dining are within a short drive, and SRQ Airport is conveniently nearby. Golfers will love the convenience of having the newly renovated Bobby Jones Golf Course just around the corner or the Meadows Golf Club now open to the Public. Well-funded association reserves help support the community’s long-term maintenance and capital improvement needs. Don’t miss this opportunity, schedule your showing and discover your Florida lifestyle right here on the Suncoast!

3365 Ramblewood Drive N Unit 35C8, Sarasota
$149,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIPS BEGIN! LOW-MAINTENANCE LIVING IN A HIGH-VALUE LOCATION ** Welcome to Oakwood Manor, Sarasota’s only resident-owned 55+ community within the Sarasota city limits—where affordability meets an active, social lifestyle. This 2-bedroom, 1.5-bath home offers 749 sq. ft. of living space and sits on a desirable oversized lot (50 x 80.5), giving you extra room and exciting potential. A spacious covered and screened Florida room welcomes you at the front of the home—perfect for morning coffee, entertaining guests, or simply enjoying the Florida lifestyle year-round. Major Updates Already Done: ** A/C replaced in 2020 ** Roof replaced in 2023, new flooring through out 2026, new Kitchen, new baths and half bath and newly painted interior. Oakwood Manor spans 90 beautifully maintained acres and is known for its low maintenance fees and friendly, welcoming atmosphere. Community Amenities Include: ** Clubhouse with fitness room, dance floor & library ** Heated pool & hot tub ** Putt-putt golf, bocce ball, shuffleboard & cornhole ** Ping-pong & pool table ** Shaded seating areas & picnic park with grill ** Full calendar of social events and activities Love pickleball? Courts are just a short bike ride away along the Legacy Trail, located right next to the community. You’re also just minutes from downtown Sarasota, Gulf beaches, shopping, dining, and major hospitals—everything you need, right at your fingertips. Note: no pets, motorcycles or trucks community

3415 Spanish Oak Terrace, Sarasota
$260,000
3 Beds ⋅ 2 Baths ⋅ Villagio SubDv. ⋅ 34237 Zip Code
Welcome to maintenance-free, resort-style living in the heart of Sarasota! Move-In Ready completely furnished 3 bedroom/2BA Condo located on the first floor in the beautiful Villagio community. From the moment you step inside, you’ll appreciate the bright, open-concept living and dining area, with stylish tile flooring throughout the home. This home features an outdoor covered lanai with sliding doors from both the primary bedroom and dining area that brings in lots of natural light where you will capture the fresh Florida breeze with your morning coffee or evening cocktail. The open living, dining and kitchen areas are perfect for everyday comfort or entertaining. The well designed kitchen offers wood cabinetry, every appliance you will need and a tall pantry next to the refrigerator. Retreat to the spacious primary suite, your own private haven featuring an ensuite bathroom with shower and tub combo, a generous walk-in closet, and a versatile office or additional storage nook. Two additional bedrooms provide ample closet space, and the guest bathroom has a bathtub and shower combo. An in-unit laundry room with washer and dryer adds everyday convenience. This unit has a covered parking included. The community is gated, and all the buildings painted in 2024 and all the roofs replaced in 2021. Residents enjoy outstanding amenities, including a clubhouse with fitness center, heated resort-style pool, tennis and pickleball court, putting green, picnic area and a fenced dog park. Ideally situated near downtown Sarasota, marinas, and the Baltimore Orioles’ spring training facility at Ed Smith Stadium. You’ll also be just a short drive away from the stunning beaches of Lido Key and Siesta Key. Travel is effortless with close proximity to Sarasota/Bradenton International Airport and I75 and US301 close by. Whether you’re seeking a full-time residence, a winter retreat, or an investment opportunity this exceptional condo offers it all.

1025 Villagio Circle Unit 101, Sarasota
$155,000
1 Beds ⋅ 1 Baths ⋅ Park View SubDv. ⋅ 34237 Zip Code
The best-priced unit in gated ParkView — with income in place through March 2027! Beautifully updated and in move-in-ready condition, this 1 BR/1 BA second-floor corner unit occupies the desirable northwest corner of the building, offering added privacy, extra natural light, and serene park views from an elevated vantage point. The west-facing front welcomes gorgeous afternoon light and sunset skies, while the interior shows like new. Inside you'll find stainless steel appliances, granite countertops, a new dishwasher ('24), an in-unit washer/dryer, and ceramic tile throughout the main living area and bath. Freshly painted with brand-new, high-quality carpet installed in March 2026 (bedroom, hallway, and walk-in closet), the unit is clean, bright, and truly turnkey. Priced to be the most affordable home in all of ParkView, this is a rare chance to own in one of Sarasota's most convenient gated communities at a price point you won't find anywhere else in the complex. A responsible annual tenant is in place through March 31, 2027, providing income while you plan your move. ParkView is a gated community centrally located less than 5 minutes from downtown Sarasota. Residents enjoy two swimming pools, outdoor grilling and entertainment areas, a fitness room, and a recently renovated clubhouse. You're just minutes from St. Armands Circle, Lido Beach, Longboat Key, Siesta Key, the Ringling, the Van Wezel, downtown theatres, dining, shopping, and Sarasota's celebrated arts and cultural scene — with quick access to US-41, I-75, and the airport. Whether you're looking for a primary residence, a seasonal getaway, or a first step into ParkView at the community's best price, this condo delivers unmatched value in a prime location. Schedule your showing today! Seller pays for Owner's Title Policy and selects Cloud Title

972 La Costa Circle Unit 8, Sarasota
$155,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Charming, cozy, and move-in ready in the highly desirable 55+ gated community of Oakwood Manor, the ONLY resident-owned park within Sarasota city limits—meaning NO LOT RENT! This delightful FULLY FURNISHED 2-bedroom, 2-bath bungalow-style home is proof that great things come in the perfect-sized package. Thoughtfully updated with quality improvements throughout, this home offers a desirable split-bedroom floor plan, abundant natural light, exceptional storage, and an inviting open-concept design. The added space of the living room push-out creates the perfect area for additional living or dining space, enhancing both comfort and functionality. The beautifully updated kitchen is designed for both functionality and style, featuring a built-in cooktop, built-in oven, overhead microwave, new refrigerator, garbage disposal, and ample cabinetry—making the most of every inch of space. The spacious front guest bedroom is highlighted by a large bay window that fills the room with natural light and is complimented by an en-suite bathroom and indoor laundry with stackable washer and dryer. A fully enclosed Florida room with newer windows and sliding glass doors provides approximately 120 square feet of additional living or entertaining space and features a convenient pass-through entrance to the front bedroom and guest bath, creating flexibility for guests, hobbies, or a relaxing sitting area. Major improvements provide peace of mind for years to come. Previous updates include vinyl siding, replacement windows, and the main sewer line (2018). Recent renovations include new leveling and support piers (10/2025), all new subflooring throughout the home, including the Florida room (10/2025), fresh interior paint, luxury vinyl plank flooring throughout the main living areas, and all new carpet in both bedrooms (11/2025), a complete new TPO roofover and new carport with additional tie-downs rated up to 150 mph (2/2026), new HVAC system, electrical panel, and meter base (3/2026), a new rear concrete patio (4/2026), and a newly constructed framed, vinyl-sided storage shed (6/2026). Oakwood Manor is a beautifully maintained, gated 90-acre community offering an exceptional Florida lifestyle with a low $210/month maintenance fee, which includes lawn care, cable TV, access to the heated pool and spa, clubhouse amenities, and more. Residents enjoy a spacious clubhouse with a fitness room, library, billiards, commercial kitchen, event hall, stage, dance floor, and an active social calendar filled with year-round activities, clubs, shuffleboard, putt-putt, and community events. Ideally located adjacent to the Legacy Trail and Sarasota's city-managed pickleball courts. Oakwood Manor is located nearby downtown Sarasota and the sandy shores of Lido Beach is an easy drive, with convenient access to shopping, dining, Tamiami Trail, and I-75. Please note that Oakwood Manor is an age-restricted community and does not permit pets or motorcycles.

3402 Shingle Oak Terrace, Sarasota
$145,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIP HAPPEN TURNKEY SARASOTA RETREAT IN ONE OF THE AREA’S BEST-VALUE 55+ COMMUNITIES Don’t miss this beautifully maintained 2-bedroom, 2-bath turnkey home offering 1,056 sq. ft. of comfortable living space in Oakwood Manor, a highly desirable resident-owned 55+ community located in the heart of Sarasota. Whether you’re searching for the perfect winter getaway or a full-time Florida residence, this move-in-ready home offers comfort, convenience, and exceptional value—all with an affordable $210/month HOA fee. Set within 90 beautifully maintained acres, Oakwood Manor is known for its friendly atmosphere, active lifestyle, and resort-style amenities. Residents enjoy a welcoming clubhouse with commercial kitchen and stage, fitness center, library, heated pool, hot tub, bocce ball, shuffleboard, and putt-putt golf. Pickleball lovers will appreciate being just a short bike ride from the Legacy Trail and its brand-new pickleball courts. (Please note: no pets, motorcycles, or RVs permitted.) Inside the home, pride of ownership is evident throughout. The bright and cheerful living room is filled with natural light from surrounding windows, creating a warm and inviting space to relax and unwind. The spacious kitchen offers abundant cabinetry and opens nicely to the dining area, making it ideal for both everyday living and entertaining. The home is being sold turnkey, so you can simply bring your suitcase and start enjoying the Florida lifestyle from day one. Both bathrooms have been tastefully updated, and the interior color palette perfectly complements the relaxed coastal feel of the home. This property has been lovingly maintained and truly needs nothing—just move right in and enjoy. Recent updates include: New flooring (2016) Fresh interior paint Roof coating (2025) New carport (2025) New blinds throughout New front awnings One of the standout features of this home is the private backyard with no neighbors behind, offering a peaceful setting to enjoy the outdoors. You’ll also love being just steps from the clubhouse, making it easy to take advantage of all the social events and community activities Oakwood Manor offers. Location is everything, and Oakwood Manor delivers. Conveniently located close to downtown Sarasota, Siesta Key Beach, St. Armand's Circle, shopping, dining, Sarasota-Bradenton International Airport, and local hospitals, this community combines an unbeatable Sarasota location with low-maintenance living and outstanding value. Homes in Oakwood Manor that are this clean, turnkey, and well-located don’t come along often—schedule your showing today and come see why so many love calling this community home.

3383 Oakwood Boulevard N, Sarasota
$289,000
3 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN & FRIENDSHIP HAPPENS JUST BRING YOUR CLOSTHES AND TOOTHBRUSH!!! Own your piece of paradise in Oakwood Manor, Sarasota's highly desirable resident-owned 55+ community located within the city limits. Spanning 90 beautifully landscaped acres, this vibrant community offers an exceptional resort-style lifestyle with remarkably low HOA fees of just $210 a month and no CDD or master association fees. Residents enjoy an impressive array of amenities including a welcoming clubhouse with commercial kitchen and event stage, fitness center, library, heated pool, oversized hot tub, bocce ball, shuffleboard, putt-putt golf, cornhole, and ping pong. Pickleball enthusiasts will appreciate the brand-new courts located just a short bike ride away along the Legacy Trail. With an active social calendar filled with events and activities, Oakwood Manor truly lives up to its reputation—where fun and friendship happen. A Rare Find — Impeccably Maintained & Truly Move-In Ready If you've been waiting for that special home, your search ends here. Built in 2005, this beautifully maintained 3-bedroom, 2-bath residence offers 1,545 square feet of thoughtfully designed living space and is being sold turnkey. Situated within easy walking distance of the community pool and amenities, this home is genuinely move-in ready—just bring your clothes and toothbrush. From the moment you step inside, you'll appreciate the spacious open floor plan, soaring ceilings, and abundant natural light streaming through numerous windows. The gourmet kitchen is designed to impress, featuring beautiful cabinetry, generous counter space, and an inviting layout that's perfect for everyday living and entertaining. The spacious primary suite includes a walk-in closet and an en-suite bath with a double vanity and walk-in shower. A standout feature rarely found in modular homes is the drywall construction throughout the walls and ceilings in most rooms, providing the look and feel of a traditional site-built home. Recent Updates Include: • New Roof (2025) • A/C replaced (2023) • All kitchen appliances replaced (2023) • Nice Large she for plenty of storage • Inside Laundry room with Utility laundry tub • Covered Carport with plenty of space for 2 cars • Tile flooring throughout all wet areas and the laundry room • Beautiful Bahama shutters on most windows Location, Location, Location Conveniently located just minutes from downtown Sarasota, Siesta Key Beach, St. Armand's Circle, SRQ Airport, shopping, dining, and two major hospitals, this home offers the perfect combination of comfort, convenience, and Florida lifestyle. Whether you're searching for a year-round residence or the perfect seasonal retreat, this exceptional home is an opportunity you won't want to miss.

3324 Overcup Oak Terrace, Sarasota
$84,900
2 Beds ⋅ 3 Baths ⋅ Ramblewood Acres SubDv. ⋅ 34237 Zip Code
Short Sale. Located in a desirable Sarasota location, this 2-bedroom, 2.5-bath townhome offers a functional two-story floor plan with covered parking and comfortable living spaces designed for everyday convenience. The layout provides well-separated bedrooms, each with access to bathroom facilities, making it an excellent option for a variety of living arrangements. The first floor features newly installed flooring, creating a refreshed living space ready for the next owner's personal touches. Based on available information, the property appears to be in generally good condition; however, buyers are encouraged to conduct their own inspections to verify the condition and functionality of all systems, components, and improvements. Conveniently located near shopping, dining, parks, medical facilities, downtown Sarasota, and the area's renowned Gulf Coast beaches, this property offers an excellent opportunity to enjoy everything Sarasota has to offer. Buyers and agents should review all MLS supplements and private remarks for important information regarding the purchase process. Buyers should verify all information. Agents: Please review all private remarks and MLS supplements prior to scheduling a showing.

3312 Ramblewood Place, Sarasota
$152,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
*Additional photos coming soon* Welcome to 3226 Sweet Bay Terrace in the highly desirable 55+ gated community of Oakwood Manor, the ONLY resident-owned manufactured home park within Sarasota city limits—meaning NO LOT RENT! This well-maintained 2-bedroom, 2-bathroom home offers seamless laminate flooring throughout the main living areas, kitchen, and bedrooms, creating a clean, cohesive look that's both stylish and easy to maintain. Enjoy added peace of mind with a June 2026 FULL ROOF RESTORATION, featuring a silicone roofing system over the existing metal pan roof and backed by a 10-YEAR TRANSFERABLE WARRANTY. Additional updates include a newer carport with upgraded tie-downs rated up to 150 mph (2017), HVAC (2016), and water heater (2011). Best of all, the home experienced no damage from the 2024 storms. Being offered FURNISHED, this home is truly move-in ready. Furnishings include, but are not limited to, a full-size bed in the primary bedroom, two twin beds in the guest bedroom, dining table and chairs, living room sofa, side table, TV stand with TV, chair with ottoman, some FL room/Lanai furniture, and an equipped kitchen with items needed for everyday living. The additional 8x12 shed provides for ample storage and utility space. Oakwood Manor is a beautifully maintained, gated 90-acre community offering an exceptional Florida lifestyle with a low $210/month maintenance fee, which includes lawn care, cable TV, access to the heated pool and spa, clubhouse amenities, and more. Residents enjoy a spacious clubhouse with a fitness room, library, billiards, commercial kitchen, event hall, stage, dance floor, and an active social calendar filled with year-round activities, clubs, shuffleboard, putt-putt, and community events. Ideally located adjacent to the Legacy Trail and Sarasota's city-managed pickleball courts. Oakwood Manor is located nearby downtown Sarasota and the sandy shores of Lido Beach is an easy drive, with convenient access to shopping, dining, Tamiami Trail, and I-75. Please note that Oakwood Manor is an age-restricted community and does not permit pets or motorcycles. Don't miss this opportunity to own an affordable home in one of Sarasota's most unique and sought-after resident-owned communities!

3226 Sweet Bay Terrace, Sarasota
$270,000
3 Beds ⋅ 2 Baths ⋅ Villagio SubDv. ⋅ 34237 Zip Code
You can move in immediately or rent right away for everything you could need is included - furniture, decor, window treatments, kitchen service items, sheets, towels, porch furniture and pillows, all appliances. This is truly turnkey! Three bedroom units are coveted and particularly when they include a deeded carport for parking. The has been beautifully remodeled with granite countertops, luxury linoleum throughout, and all furniture and decor to match the Florida coastal lifestyle. The buildings are only two stories high and this condo is on the second floor eliminating any issues of pedestrian or car traffic directly in front of your windows or any potential rising water. Villagio has remained a community in high demand due to its proximity to downtown Sarasota, the spring training stadium for the Baltimore Orioles, sporting parks, independent restaurants and stores, grocery, schools, and public transportation. Villagio is a gated community with a pool, fitness room, clubhouse, pool, tennis and pickleball courts, a small putting green, designated dog area, and green space with picnic tables. It remains a wonderful place to live full-time, seasonally, or as a rental investment (one month minimum, maximum 3 times per year). Pet and all age-friendly.

1010 Villagio Circle Unit 201, Sarasota
$152,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Welcome to 115 White Oak Way, where thoughtful updates, low-maintenance living, and an unbeatable Sarasota location come together in one exceptional home. Nestled within Oakwood Manor, Sarasota's only gated, resident-owned manufactured home community inside the city limits, this beautifully renovated 2-bedroom, 2-bath residence offers approximately 1,280 square feet of comfortable living space, including a spacious enclosed lanai perfect for relaxing or entertaining. The heart of the home is the stunning 2025 kitchen featuring new cabinetry, quartz countertops, stainless steel appliances, and a fresh, modern design. Luxury vinyl plank flooring flows throughout, while updated bathrooms, new lighting, ceiling fans, refreshed outlets, and a new front door complete the move-in-ready appeal. A roof resealed in 2024 and a 3-ton Rheem HVAC provide added peace of mind. Ideally situated near both community entrances and just a short stroll to the clubhouse, this home offers easy access to everything Oakwood Manor has to offer. Enjoy land ownership with an affordable $210 monthly fee that includes beautifully maintained common areas and outstanding amenities, including a heated pool and spa, fitness room, library, clubhouse, bocce, shuffleboard, putt-putt golf, cornhole, horseshoes, and a full calendar of social activities. Outdoor enthusiasts will love being adjacent to the Legacy Trail and only steps from public pickleball courts. Plus, you're just minutes from downtown Sarasota, Siesta Key and Lido Key beaches, SRQ Airport, Sarasota Memorial Hospital, Doctors Hospital, golf courses, shopping, dining, and the arts. Whether you're looking for a full-time residence or the perfect Florida retreat, this beautifully updated, land-owned home offers comfort, convenience, and an active 55+ lifestyle in one of Sarasota's most desirable manufactured home communities. Community rules prohibit motorcycles and dogs; qualified service or therapy animals are permitted. Schedule your private showing today and discover why so many love calling Oakwood Manor home.

115 White Oak Way, Sarasota
$174,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIPS BEGIN! PRICED TO PERSONALIZE IN SARASOTAS BEST KEPT SECRET PERFECT FLORIDA RETREAT!! Welcome to Oakwood Manor, Sarasota's only resident-owned 55+ community within the city limits—where affordability, convenience, and an active social lifestyle come together. This spacious 2-bedroom, 2-bath home offers 1,344 square feet of living space and is situated on a desirable lot within the community. A large covered and screened Florida room welcomes you home and provides the perfect space for morning coffee, entertaining friends, or simply enjoying Florida's beautiful weather year-round. The attached oversized shed houses the washer and dryer and offers plenty of additional storage or room for hobbies and projects. This home is priced to give you options: • Move in and enjoy as-is • Update and personalize to your own style • Create the Florida retreat you've always wanted Major Updates Already Completed: • A/C replaced in 2021 • Electrical panel replaced in 2026 Oakwood Manor spans 90 beautifully maintained acres and is known for its low maintenance fees, strong sense of community, and welcoming atmosphere. You'll be hard-pressed to find a better value anywhere within the City of Sarasota. Community Amenities Include: • Clubhouse with fitness center, dance floor, and library • Heated swimming pool and hot tub • Mini golf, bocce ball, shuffleboard, and cornhole • Ping-pong and pool table • Shaded gathering areas and picnic park with grill • Full calendar of social activities, events, and clubs Love pickleball? Public courts are just a short bike ride away via the Legacy Trail, located adjacent to the community. Conveniently located just minutes from downtown Sarasota, world-famous Gulf beaches, shopping, dining, cultural attractions, and major medical facilities, you'll have everything you need right at your fingertips. Community Restrictions: No pets, motorcycles, or trucks permitted

3329 Oakwood Boulevard S, Sarasota
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