Homes For Sale Near Brookside Middle School, Siesta Key FL

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

Virtually Staged. PRICED BELOW APPRAISED VALUE! This spacious 4-bedroom, 3.5-bath Sarasota home offers over 3,000 square feet of living space, an impressive 3-car garage, exceptional flexibility, and beautiful indoor-outdoor living. A BRAND-NEW ROOF WILL BE INSTALLED PRIOR TO CLOSING, offering added value and peace of mind for the next owner. Step inside to soaring ceilings, abundant natural light, and a dramatic staircase that immediately gives the home a bright and open feel. The formal living and dining areas provide plenty of space for entertaining, while the separate family room with fireplace creates a comfortable setting for everyday living. Just off the foyer is a private office with extensive built-in shelving, ideal for working from home, a library, or additional flex space. The spacious kitchen features abundant cabinetry and counter space, along with a movable island that allows you to customize the layout to suit your needs. Just beyond the kitchen is an air-conditioned Florida room, creating another comfortable year-round space to relax and enjoy views of the surrounding greenery. The first floor also offers an oversized bedroom with a walk-in closet, perfect for guests, extended family, or use as a downstairs primary bedroom. A full bathroom is conveniently located just steps away. Upstairs, you’ll find three additional bedrooms, including the spacious primary suite and two versatile guest or secondary bedrooms. The primary suite features a large walk-in closet and a spacious bathroom with a soaking tub, separate shower, and double-sink vanity. One of the most special features of the home is the direct access from the primary bedroom to the expansive private deck, offering plenty of space for outdoor seating, relaxing, and entertaining. The two additional bedrooms share another full bathroom, and the upstairs flex area can easily serve as a second living room, media room, playroom, or sitting area. Outside, mature tropical landscaping creates a private and peaceful setting with lush greenery, a charming fountain, and multiple areas for outdoor enjoyment. The hot tub conveys with the sale, adding another inviting feature to the outdoor space. A spacious laundry room and the 3-car garage provide excellent storage and everyday functionality. Conveniently located near Siesta Key beaches, Downtown Sarasota, Sarasota Memorial Hospital, shopping, dining, schools, and entertainment, this home offers the perfect combination of space, privacy, versatility, and location. Offering an exceptional combination of space, privacy, flexibility, and a convenient Sarasota location, this home is ready for its next owner to make it their own.

2429 Whippoorwill Circle, Sarasota

$695,000

Tamiami Park A Resub Of SubDv. ⋅ 34231 Zip Code

Looking to develop in one of Sarasota's hottest areas? Look no further. This rare 100' x 100' lot offers an exciting redevelopment opportunity in South Sarasota. The oversized parcel may provide the potential to divide into two separate lots, with the possibility of a home and ADU on each — creating a potential four-unit residential rental opportunity, subject to zoning and county approval. The property could also be an excellent opportunity for a duplex development, offering another potential path for an investor or builder looking to maximize the value of the site. The existing property features a 1,084-square-foot, 2-bedroom, 2-bath Florida home, along with a 1.5-car garage, with laundry room that includes full size washer and dryer. The home also includes a beautiful swimming pool. The fully fenced lot offers privacy and plenty of space while providing a unique opportunity to live in or rent the existing home as you plan for future redevelopment. With its desirable South Sarasota location, this property is close to Siesta Key Beach, Gulf Gate, the Legacy Trail, shopping, dining, and everything Sarasota has to offer. Bring your vision and take advantage of the possibilities this oversized lot presents. Opportunities to develop a property of this size and location are becoming increasingly difficult to find.

3928 S East Avenue, Sarasota

$599,000

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

LOCATION, LOCATION, LOCATION! Welcome to this charming South Gate pool home, ideally situated on a quiet street just minutes from Sarasota Memorial Hospital, Downtown Sarasota, shopping, dining, schools and world-famous Siesta Key Beach. Set on a generous quarter-acre lot, this property offers a wonderful combination of location, privacy, character and Florida outdoor living with plenty of opportunity to make it your own. The true showstopper is the private backyard tropical oasis, surrounded by lush mature landscaping and mango trees. At the heart of the outdoor space is a stunning free-form saltwater pool, renovated in 2015, surrounded by an expansive travertine pool deck perfect for relaxing, entertaining and enjoying the Florida sunshine year-round. The fully fenced backyard provides exceptional privacy and plenty of room for gatherings, gardening or simply unwinding in your own tropical retreat. Inside the home is filled with character and distinctive architectural details. A dramatic floor-to-ceiling Coral Keystone wood-burning fireplace anchors the living room, while beautifully restored terrazzo flooring flows through the living room, dining room, kitchen and hallways. All three bedrooms feature warm wood flooring. The kitchen offers solid-surface countertops, stainless steel appliances, a skylight and a charming garden window overlooking the courtyard entry and established herb garden. Additional features include thermal-pane windows, two tankless water heaters and a convenient interior laundry room. The second bathroom, added in 2017, features an interior sink and toilet and also functions as a convenient pool bath with an outdoor shower. The third bedroom currently does not have a closet but can easily be converted back, offering flexibility for use as a bedroom, home office or den. An oversized two-car garage provides excellent storage and includes a dedicated 7' x 7' workshop area. Additional improvements include a full reroof in 2017, AC replacement in 2024, new 4-inch PVC sewer piping from the home to the Air Vac tap and fresh interior paint in the living room, dining room and kitchen. With its generous lot, established tropical setting, private saltwater pool and highly desirable South Gate location, this home offers something increasingly difficult to find, a property that can be enjoyed today while still providing the opportunity to update and make it uniquely your own. Whether you're relaxing poolside beneath the mature landscaping, entertaining friends in the expansive backyard or enjoying convenient access to Sarasota's beaches, downtown and everyday amenities, 3536 Jaffa Drive is ready for its next chapter. Schedule your private showing today!

3536 Jaffa Drive, Sarasota

$1,075,000

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!From Bee Ridge Rd, Turn South on School, North on Hansen or Roselawn St. Go to address. From US41 Turn East on Roselawn and go to address.

2047 Roselawn Street, Sarasota

2753 Orchid Oaks Drive Unit 104, Sarasota

$258,000

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

$154,500

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

$849,000

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

$669,000

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

$334,900

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

Back on the Market with needed repairs completed and several new updates! Now, 4003 Booth Pl has a Clean 4 point inspection Report! 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

Homes For Sale Near Brookside Middle School, Siesta Key FL

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