Sarasota FL Homes for Sale Under $300,000

Homes for Sale Under $300,000 In Sarasota FL

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Homes for Sale Under $300,000 in Sarasota FL

$149,900
2 Beds 2 Baths Oakwood Manor SubDv. 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIPS BEGIN! FRESH, UPDATED, AND READY TO ENJOY! NEW KITCHEN**NEW BATHS** NEW FLOORING** NEW LOOK! ** 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

$149,900
2 Beds 2 Baths Glen Oaks Gdn Apts SubDv. 34232 Zip Code
Virtually Staged. Welcome to Glen Oaks where location, lifestyle, and value come together in one beautifully updated 55+ community home. This spacious 2-bedroom, 2-bath residence features a recently painted and very well maintained space, with newer appliances and new water heater in 2022. The oversized primary suite includes two spacious closets, and the smart layout makes the home feel significantly larger than its approximately 950 sq ft. One of the standout features is the back patio overlooking peaceful open green space, and the front door overlooking beautifully maintained courtyard. The location is exceptional. Residents are just steps from a public golf course and lawn bowling. UTC mall and downtown Sarasota are both just 5 miles away, I-75 is only 4 miles, and SRQ airport is only 6 miles. Enjoy easy access to world-famous Gulf Coast beaches including Lido Key at 7 miles away and Siesta Key Beach just 10 miles away. Anna Maria is also an easy drive for dining, shopping, and beach days. Residents here enjoy access to community amenities including a pool, fitness center, shuffleboard, and pet-friendly policies. All within a welcoming 55+ community. Whether you're searching for a full-time Sarasota residence, seasonal getaway, winter retreat, low-maintenance snowbird lifestyle near golf, shopping, dining, and beaches, this home checks all of the boxes.

1310 Glen Oaks Drive E Unit 383E, Sarasota

$149,900
3 Beds 2 Baths Tregate East SubDv. 34233 Zip Code
Bright, spacious, and ideally located in the heart of Sarasota! This well-maintained 3-bedroom, 2-bath condo in a desirable 55+ community offers a flexible floor plan filled with natural light throughout the day. One of the standout features is the exceptionally large 20’ x 12’ third bedroom, perfect as a den, hobby room, media room, or additional living space. The kitchen features granite countertops, abundant cabinetry, and a pantry, providing excellent storage and functionality. Pocket doors to the guest bedroom and bath create privacy for visiting family and friends. Enjoy sunny mornings or relaxing afternoons on the south-facing screened lanai, bringing wonderful light into the home throughout the day. This condo is offered fully furnished and includes a covered carport parking space. The air conditioning system was replaced just two years ago, offering added peace of mind. The $615 monthly fee includes water, sewer, trash, cable TV, and internet, making it easy to enjoy a low maintenance Florida lifestyle. Residents enjoy a community pool and clubhouse with kitchen, and one of the most unique features of this location is the rare walkability — you can easily stroll to Publix, Walmart, HomeGoods, banks, restaurants, and more. Located mid-Sarasota just minutes to downtown, UTC, and the Gulf beaches, this is a great opportunity to own an affordable 3-bedroom home in a highly convenient location, perfect for year-round living or a seasonal Florida retreat. Opportunities like this — a 3-bedroom condo in Sarasota at this price point — are rarely available. 55+ community. No pets and no rentals permitted. Laundry room conveniently located just down the hall, with potential for in-unit washer and dryer installation

3983 Maceachen Boulevard Unit 424, Sarasota

$149,900
2 Beds 1 Baths Oakwood Manor SubDv. 34237 Zip Code
A Great Deal!! Discover the ease and comfort of Florida living in this thoughtfully maintained TURNKEY furnished home located in the ONLY gated 55+ Resident Owned Park in the City limits of Sarasota!! This 2 bedroom home has beautiful curb appeal with the landscaped pavers and palm trees. This home has been tastefully decorated and offers a peaceful, move-in-ready retreat— ideal for seasonal or full time residents seeking simplicity, and comfort. Guest will appreciate the split plan feature with the 3rd bedroom which can also be used as a Den/Office. Enter through the quaint French doors to a cottage style queen set, separate AC system, flat screen TV, and private wardrobe. There is plenty of space for up to 9 with a king bed, queen bed, double bed and both the sofa and loveseat convert into a queen-size sleeper with a new mattress and a single sleeper loveseat, making this ideal for visiting guests. The dining table stores extra leaves and there is seating for 6. The coffee table rises to accommodate additional table space. The kitchen has great natural lighting and includes stainless steel appliances installed in 2020. The dishwasher, rolling island, CD radio player and water filter system were installed after 2021. The pantry provides plenty of room for storage needs. Embrace a relaxed Florida lifestyle with a good book or visit with friends in the screened lanai. Whether you are arriving for the season or enjoying full-time living, immediately begin soaking in Florida’s warm weather, friendly community, and relaxed pace of life. Upgrades include: Vinyl siding, extra large storage room that can be used as a Florida room as well, separate shed room, washer/dryer and utility sink in the storage area, screen lanai added 2024, HVAC system installed 2020 maintained and enhanced by a whole-house duct enlargement for improved airflow throughout the home. Water heater 2025, vapor barrier replaced 2023, Interior upgrades include the stainless steel appliances, some drywall, updated entry door, and all flooring has been updated. Additionally, there is a hurricane shutter and rain gutters. The utility room adds exceptional value, featuring an additional refrigerator, a washer and dryer, offering convenience and extra storage, perfect for seasonal living or hosting guests. Note: a few pictured items do not convey with sale. About Oakwood....This 55+ gated 90 acre community boasts a low maintenance fee of $210/month. Its vast amenities start with the spacious Clubhouse outfitted with a full commercial cook kitchen, event stage, audio/visual, dance floor, state of the art fitness room, activities hall, library with books/movies/puzzles and a pool table. Outside recreation includes an extra large heated pool with a handicap ramp, a spacious kidney shaped hot tub, ample umbrella tables, lounge chairs and updated shower rooms. Oak trees shade the beautiful park area, picnic tables and a community grill. Additional amenities to enjoy are the community putt putt course, bocce ball, ping pong and corn hole. Oakwood Manor is a vibrant community with numerous social events and activities. It is conveniently located adjacent to Legacy Trail and 12 newer pickle ball courts. Just a short drive to our crystal sand beaches, downtown area, the marina, fishing pier, local golf courses, shopping, variety of restaurants, the museum, SRQ airport, SMH and Doctors hospital. Please note that Oakwood is a no pet, no motorcycle Park.

3317 Overcup Oak Terrace, Sarasota

$149,000
2 Beds 1 Baths Lenray Heights SubDv. 34234 Zip Code
Discover an exciting opportunity in Sarasota with this 2-bedroom, 1-bath home situated on a residential lot in an established neighborhood. Offering a convenient location and plenty of potential, this property is ideal for an investor, renovator, or buyer looking to create a home tailored to their vision. The property features a private yard and presents an opportunity to renovate, update, or explore its possibilities based on your needs and plans. Located just minutes from US-301, the property provides convenient access to major roads and everything Sarasota has to offer. Enjoy nearby shopping, restaurants, grocery stores, schools, parks, and local services, making everyday living easy and convenient. Downtown Sarasota is also close by, offering an exciting mix of dining, entertainment, arts, cultural attractions, and waterfront experiences. For those who enjoy Florida's coastal lifestyle, Sarasota's beautiful beaches and Gulf Coast destinations are within an easy drive. Spend the day enjoying the sun and water, then return home to the convenience of being close to the city's amenities. With its central location, established surroundings, and potential for transformation, this property offers an excellent opportunity to invest in the Sarasota market and bring your own ideas to life. Whether you're looking for your next renovation project, an investment opportunity, or a property in a convenient Sarasota location, this home is ready for its next chapter.

2619 19th Street, Sarasota

$149,000
2 Beds 2 Baths Glen Oaks Estates SubDv. 34232 Zip Code
Welcome to Glen Oaks Garden, a vibrant community! This beautifully updated corner 2 bedroom, 2 bath condo with elevator access, modern style, comfort, and an unbeatable location. Step inside to find an updated kitchen featuring beautiful cabinetry, newer stainless-steel appliances, granite countertops and travertine backsplash. This second floor unit features tile and bamboo flooring throughout. Freshly painted with crown molding in the living room and master bedroom. Master has ensuite bathroom and walk-in closet. Enjoy your morning coffee or evening wind-down on the screened balcony with peaceful nature and partial golf course view making for the perfect retreat. The Glen Oaks Garden community has a fantastic array of amenities, including an Olympic size heated pool, clubhouse, exercise room, sauna, shuffleboard, private storage 5 x 6 locked storage unit and more. For golf enthusiasts, the newly renovated Bobby Jones Golf Club and nature trails are just around the corner! With its prime central location, you'll love the proximity to Downtown Sarasota, the shops and restaurants of UTC mall, SRQ Airport, and 15 minutes to Siesta Key and Lido beach two of the world-famous Gulf beaches. With exquisite modern upgrades and an active lifestyle waiting for you, this condo is ready for you to move right in and start enjoying the Florida life. Pet friendly, covered parking.

1520 Glen Oaks Drive E Unit 248, Sarasota

$145,900
2 Beds 2 Baths Oakwood Manor SubDv. 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIP HAPPEN TURNKEY, WELL MAINTAINED AND READY TO ENJOY-SARASOTA LIVING MADE EASY!!! 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

$145,000
3 Beds 3 Baths Shadybrook Village Condo SubDv. 34243 Zip Code
Welcome to 1125 Longfellow Way, where peaceful preserve views, thoughtful updates, and an incredibly convenient Sarasota location come together in this spacious 3-bedroom, 2.5-bath end-unit condo. With approximately 1,365 square feet of living space spread across two levels, this home offers the comfort and feel of a single-family residence while maintaining the ease of low-maintenance Florida living. Being an end unit makes all the difference, bringing in additional natural light, while offering a greater sense of privacy. Inside, the home feels fresh and inviting with an open living and dining area complemented by quartz countertops, updated cabinetry, modern lighting and plumbing fixtures, fresh interior paint, and new carpet throughout. The layout provides plenty of room for both everyday living and entertaining, while three bedrooms upstairs create separation between your living and private spaces. Just beyond the main living area, step outside to your private patio overlooking the preserve. With no immediate rear neighbor and a backdrop of natural Florida greenery, it’s a peaceful place to start your morning with coffee, unwind in the evening, or enjoy Sarasota’s beautiful year-round weather. The community offers even more to enjoy with a swimming pool, clubhouse, tennis courts, and basketball court, and the recently completed community roofs provide an added benefit for the next owner. Perhaps one of the best features of this home is its location. Tucked away from the busier parts of town while still just minutes from University Parkway, UTC, SRQ International Airport, shopping, restaurants, golf, and everyday conveniences; you’ll also have easy access to Downtown Sarasota and the Gulf beaches when it’s time to enjoy everything the area is known for. Whether you're searching for a full-time residence, seasonal Florida escape, or an annual rental property, 1125 Longfellow Way offers an appealing combination of space, privacy, amenities, and location. Come see just how easy Sarasota living can be.

1125 Longfellow Way Unit 125-B, Sarasota

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