Homes For Sale Near Brookside Middle School, Siesta Key FL

6 Beds ⋅ 4 Baths ⋅ Roselawn SubDv. ⋅ 34231 Zip Code

Discover this turnkey duplex — a fully updated 6-bed, 4-bath property (3 bedrooms and 2 baths per unit) offering exceptional income potential in a prime location. Each spacious unit features modern finishes and thoughtful layouts for comfortable living. Enjoy private oasis backyards with dedicated heated pools and fully fenced privacy on both sides — perfect for tenants seeking resort-style relaxation without sharing space. Separate entrances from Roselawn Street and Hansen Street. Recent upgrades include a new metal roof (2025) and comprehensive updates throughout, ensuring low maintenance and strong rental appeal. This duplex is an excellent investment, currently positioned to generate reliable income in a high-demand Sarasota rental market. Central Sarasota location provides easy access to world-famous Siesta Key Beach (minutes away via North Siesta Key Bridge), shopping, restaurants, parks, and everyday conveniences. Quick drives to downtown Sarasota, I-75 make it ideal for residents and investors alike. Whether you're expanding your portfolio or seeking a smart income-producing property, this updated duplex delivers value, privacy, and location in one package. Don't miss out — schedule a showing today!

2047 Roselawn Street, Sarasota

$269,000

2 Beds ⋅ 2 Baths ⋅ Orchid Oaks SubDv. ⋅ 34239 Zip Code

Welcome to this beautifully updated 2-bedroom, 2-bathroom condo in the highly sought-after Orchid Oaks community. This spacious, wheelchair-accessible ground-floor residence combines comfort, convenience, and peace of mind, making it the perfect place to call home. Designed for long-term peace of mind, this home includes hurricane-impact windows, upgraded plumbing and electrical systems, a newer AC system and water heater, and the added benefit of being elevated above flood level. One of the standout features of this unit is its exceptional accessibility. The assigned carport is the very first parking space directly in front of the condo, making unloading groceries, luggage, or everyday essentials incredibly easy. With no stairs to navigate, this home offers effortless living for all. Inside, you'll find 1,365 square feet of thoughtfully updated living space featuring luxury vinyl plank flooring throughout and an open-concept floor plan filled with natural light. The remodeled kitchen boasts modern appliances, generous counter space, and abundant cabinetry, while both bathrooms have been tastefully renovated with contemporary finishes and fixtures. Enjoy your morning coffee or unwind in the evening on the screened lanai overlooking peaceful Phillippi Creek—a tranquil setting just minutes from Sarasota's renowned shopping, dining, and Gulf Coast beaches. Additional features include: Spacious primary suite with updated, spacious en-suite bathroom, Luxury vinyl plank flooring throughout, Pet friendly community with nearby dog park and Community walking paths. Condo fees include clubhouse, pool, insurance, exterior maintenance, pest control, water, sewer and trash! Located in the desirable Orchid Oaks community, this move-in-ready condo offers low-maintenance living in an ideal Sarasota location. Whether you're looking for a full-time residence or a seasonal retreat, this beautifully updated home is ready for you to move in and enjoy.

2753 Orchid Oaks Drive Unit 104, Sarasota

$168,900

2 Beds ⋅ 1 Baths ⋅ Sunland Apts SubDv. ⋅ 34239 Zip Code

Virtually Staged. GREAT LOCATION for Seasonal or Full time 55+ Residents. Just minutes from downtown Sarasota & a straight drive to Siesta Keys world-famous beaches. Interior completely remodeled, designed the Kitchen with an open layout with Quartz Countertops, custom white cabinets, & SS Appliances. Bathroom got a complete makeover. New Luxury Vinyl flooring throughout, new modern interior Doors, Fans & Lighting. Community Pool, Laundry facilities & storage space for each unit. Walk to Dining, Shopping & CMX Cinemas/Bistro. Low HOA Monthly Fee.

3755 S School Avenue Unit 54, Sarasota

$869,000

3 Beds ⋅ 3 Baths ⋅ South Gate SubDv. ⋅ 34239 Zip Code

A beautifully reimagined South Gate residence, this 3 bedroom, 3 bathroom home blends modern sophistication with timeless Sarasota charm. Set on an elevated 14,005 sq ft corner lot, the property offers exceptional privacy, mature landscaping, and an abundance of fruit-bearing trees, all supported by an irrigation system. Inside, the split floor plan provides effortless livability, complemented by a dedicated private office and an additional bonus room ideal for flexible lifestyle needs. Two of the bedrooms are ensuite, creating comfortable retreats for family or guests. The heart of the home is the gourmet kitchen, featuring 42" cabinetry, quartz countertops, stainless steel appliances, and a large picture window that fills the space with natural light. The adjoining dining area offers generous room for gatherings, while the family room with its sleek electric fireplace creates a warm, inviting atmosphere. Thoughtful upgrades continue throughout: a totally renovated interior, and an oversized two-car garage with epoxy flooring. Outside, a paver circular drive and a charming covered front porch with new Trex decking elevate curb appeal. With its expansive lot, there is ample room to add a pool and create a true Sarasota oasis. Located in the coveted South Gate community, this home offers unmatched convenience just minutes to fine dining, boutique shopping, world renowned beaches, and vibrant downtown Sarasota.

2465 Foster Lane, Sarasota

$215,000

2 Beds ⋅ 2 Baths ⋅ Orchid Oaks SubDv. ⋅ 34239 Zip Code

Top-floor corner unit at Orchid Oaks that comes fully furnished, turnkey, and move-in ready. This beautifully updated 2BD/2BA, 1,376 sq ft condominium is tucked beneath a canopy of mature oaks just off Phillippi Creek, offering the rare combination of natural serenity and central Sarasota convenience. The updated kitchen has been opened up and features a hood, wine fridge, and ample cabinetry. Open living and dining areas flow seamlessly to a screened lanai with electric fireplace and TV overlooking the community pool with a true treetop escape. Primary suite has a king bed, walk-in closet, and en suite bath. Guest bedroom with two twins. No carpet, only tile and LVP throughout the unit. The in-unit laundry is right off the entry with cabinetry. One covered assigned parking space. Community has additional parking available and amenities include a pool, clubhouse, gazebo, walking trails, a dog run, plus a creekside dock. The association maintains and provides private access to the shopping center next door and the HOA dues include elevator, water, sewer, cable, pest control, roof, painting, lawn service, exterior maintenance and building insurance. 30-day minimum lease allowed up to three times per year which makes it an excellent for option for seasonal use or income production. Minutes to Siesta Key, Downtown Sarasota, SRQ Airport, golf, dining, and shopping. Relaxed Florida living at its finest.

2746 Orchid Oaks Drive Unit 301, Sarasota

$925,000

4 Beds ⋅ 2 Baths ⋅ South Gate SubDv. ⋅ 34239 Zip Code

From the moment you arrive, you’ll fall in love with the charm, warmth, and unbeatable location of this tropical Mediterranean retreat in Sarasota’s highly desirable South Gate neighborhood, located within the coveted Southside School District. Perfectly situated in the heart of it all, this home places you just minutes from the world-renowned Siesta Key Beach while also being steps away from your favorite restaurants, boutique shopping, grocery stores, gyms, movie theater, and everyday conveniences. This is the rare opportunity to enjoy a true walkable lifestyle while still having the privacy and comfort of a spacious family home. Light-filled and inviting, this beautifully maintained single-story residence offers an open and airy floor plan designed for both relaxing and entertaining. With four spacious bedrooms, two remodeled bathrooms, multiple living and dining areas, a breakfast nook, sunroom, and dedicated home theater room, there is space for everyone to gather while still enjoying privacy and comfort. Large sliding glass doors, solar tubes, and gorgeous porcelain marble-look flooring fill the home with natural light and create a bright, welcoming atmosphere throughout. Step outside and discover your own private backyard paradise. The newly added heated pool with paver deck, lush tropical landscaping, fenced yard, and multiple entertaining spaces create the perfect setting for enjoying Florida living year-round. Whether you’re unwinding by the electric fireplace, soaking in the jetted tub, hosting friends and family, or biking to Siesta Key for sunset, this home offers the lifestyle buyers dream about. Thoughtful updates include a 2022 roof, newer flooring throughout, updated bathrooms, and a new water heater. The oversized two-car garage with space for a workshop, spacious laundry room, circular paver driveway, and sprinkler system on well water add both convenience and value. Currently operating as a successful vacation rental with weekly rentals allowed within city limits, the property also presents exceptional income-producing potential or flexibility for a future in-law suite. Offering one of the lowest costs per square foot in South Gate, this exceptional property combines location, lifestyle, and versatility in one unforgettable home buyers will instantly fall in love with.

3524 S School Avenue, Sarasota

$679,000

3 Beds ⋅ 2 Baths ⋅ Southgate SubDv. ⋅ 34239 Zip Code

PRICE IMPROVEMENT!!! Private Oasis Awaits! This home is perfect for year round living, a Florida get away or an income generating property. It offers 3 bedrooms and 2 bathrooms and just under 2,000 square feet of comfortable living. The layout is thoughtfully designed, with 3 separate sitting areas with an abundant natural light through the large windows. The tiled flooring provides a clean, modern aesthetic, complemented by the neutral color palette. The updated kitchen is spacious, with ample wood cabinetry and a quartz countertop, providing plenty of storage and preparation space. The primary bedroom is generously sized with a bathroom, offering a comfortable retreat and a door to walk out onto covered lanai. Additional features include an inside laundry room, newer appliances, energy-efficient double-pane windows, tile roof only 10 years old and plantation shutters throughout for added charm. The outdoor space is perfect private oasis for relaxation while enjoying the sparkling resurfaced pool with a screened enclosure. The oversized lot features lush landscaping and spacious paved driveway, creating a welcoming outdoor atmosphere. In addition, the backyard is fenced in for pets with plenty of room to store watercraft. If desired, the property is Airbnb-ready and is within city limits so weekly rentals are approved. The city location makes for an ideal choice to call home to escape and relax on Siesta Key beaches or explore downtown Sarasota and all it has to offer.

3537 S School Avenue, Sarasota

$355,900

3 Beds ⋅ 2 Baths ⋅ Brookside SubDv. ⋅ 34231 Zip Code

Welcome to this FRESH and Bright centrally located home in Sarasota! It offers 3 bedrooms, 2 bathrooms, and valuable updates that provide both comfort and peace of mind. A BRAND NEW ROOF was just installed in June 2026, while the freshly painted interior (May 2026), finished in a soft/neutral white, creates a light-filled and inviting atmosphere throughout the home. The beautifully updated kitchen features newer appliances, cabinetry, white quartz countertops, and fixtures, blending style and functionality for everyday living and entertaining. The spacious primary suite is complemented by a stunning bathroom renovation completed in March 2026, showcasing modern finishes and thoughtful design. The water softener is also new. Step outside and enjoy the spacious screened lanai, an ideal setting for morning coffee, evening relaxation, or gathering with family and friends. The large private backyard is shaded by mature trees, offering both beauty and privacy. A one-car carport under the main roofline adds convenience and enhances the property's overall value. Located within the highly sought-after Riverview School District, this home is just minutes from Siesta Key's world-famous beaches, vibrant downtown Sarasota, premier shopping and dining, parks, and major medical facilities. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional location offers enduring appeal. With many of the major improvements already completed—including the new roof, fresh interior paint, updated kitchen, renovated primary bathroom, and new water softener—this property presents an outstanding opportunity to enjoy the Sarasota lifestyle from day one. Combining desirable updates, a prime location, and room to make it your own, this home is ready to welcome its next owner.

4003 Booth Place, Sarasota

$1,050,000

6 Beds ⋅ 5 Baths ⋅ Sarasota Springs SubDv. ⋅ 34231 Zip Code

Being sold with the adjacent single-family home (MLS#A4682693) 3 UNITS TOTAL for $1,550,000 Welcome to Gone Coastal Villas, a rare three-unit coastal retreat just minutes from world-famous Siesta Key Beach in Sarasota. This exceptional property offers the perfect blend of personal enjoyment and income potential, ideal as a family compound, investment property, or both. Comfortably accommodating up to 12 guests, it’s perfectly suited for large gatherings or three separate vacation groups. The duplex features two mirrored two-bedroom, two-bath residences, each with private driveways, one-car garages, laundry, and storage. The beautifully updated Flamingo and Coastal cottages showcase open floor plans, vaulted ceilings, screened patios with grilling areas, and private above-ground spas. Adjacent is the Seashell Cottage, a charming single-family two-bedroom, one-bath home with a refined coastal contemporary design. All three turnkey furnished residences have been thoughtfully updated with cohesive coastal contemporary finishes. The shared courtyard offers an inviting outdoor experience with astro turf, a heated saltwater pool with sun shelf, gated vinyl fencing, lighted pathways, epoxy walkways, and paver driveways. Major improvements include new roofs (2017), on-demand hot water systems in all units, and newer HVAC systems. Located within one mile of shopping, dining, and entertainment, Gone Coastal Villas is truly move-in ready and positioned for immediate income with no upfront improvements required. Being sold with the adjacent single-family home (MLS#A4682693).

2051 Roselawn Street, Sarasota

$740,000

4 Beds ⋅ 4 Baths ⋅ Weslo Willows SubDv. ⋅ 34231 Zip Code

This MULTI-GENERATIONAL home has a total of four bedrooms with Two Primary Suites located on both the 1st and 2nd floors. Two additional upstairs bedrooms share a full bath with a tub. The ample Foyer with Cathedral Ceilings leads to the Open Living & Dining area; and the 15’ x 21’ Family Room with fireplace. A Den with murphy bed and a half bath are adjacent to Foyer. The enclosed porch opens to a covered patio and a spiral staircase leading to the roof deck above the first-floor Primary. Seller offering credit of up to $10,000 towards repairs & improvements. The hot tub is ready, and the laundry room plus 3-car garage offer ample storage. Repairs to roof deck surface to be scheduled for July. This home is conveniently located to the beaches, schools, shopping, and downtown Sarasota.

2429 Whippoorwill Circle, Sarasota

Homes For Sale Near Brookside Middle School, Siesta Key FL

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Homes for sale Near Brookside Middle School, Siesta Key FL

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