South Sarasota Homes with Courtyard Exterior Features

South Sarasota Homes with Courtyard Exterior Features

Welcome to South Sarasota, Florida – a charming community that perfectly blends the tranquility of suburban living with the vibrant energy of coastal life. Nestled in Sarasota County, this delightful area is renowned for its lush landscapes, beautiful parks, and proximity to some of the most stunning beaches in the Sunshine State. With a rich cultural scene, South Sarasota offers a variety of dining, shopping, and entertainment options, making it an ideal place for families, retirees, and everyone in between.

One of the standout features of homes in South Sarasota is their exquisite courtyard exterior design. These homes often showcase beautifully landscaped courtyards that serve as private outdoor retreats, perfect for enjoying Florida's year-round sunshine. Picture yourself sipping coffee in the morning or hosting evening gatherings surrounded by lush greenery and blooming flowers. The courtyard not only enhances the aesthetic appeal of the property but also provides a serene space for relaxation and entertaining.

In South Sarasota, you’ll find a diverse range of housing options, from charming single-family homes to modern villas, all designed to embrace the Florida lifestyle. Many of these homes feature open floor plans, large windows, and seamless indoor-outdoor living spaces that invite the natural beauty of the area inside.

Whether you’re drawn by the allure of the beaches, the community spirit, or the architectural charm of courtyard homes, South Sarasota offers an inviting atmosphere that feels like home. Discover the perfect blend of comfort, style, and community in this picturesque corner of Florida!

Newest South Sarasota Homes with Courtyard Exterior Features

$329,900
2 Beds ⋅ 2 Baths ⋅ Villa Gardens SubDv. ⋅ 34231 Zip Code
Virtually Staged. Beautifully updated end-unit villa in Villa Gardens, ideally located just a few miles from world-famous Siesta Key Beach! This move-in-ready home has been extensively renovated and upgraded, combining stylish interiors with major improvements to the home’s systems. The updated eat-in kitchen features granite countertops, updated cabinetry and all newer appliances, while both the primary and guest bathrooms have been completely gutted and beautifully remodeled. The guest bath even features a jetted tub for a relaxing spa-like touch. Major improvements include a newer A/C system, newer water heater, new electrical panel, complete electrical rewiring and new outlets throughout the home. The windows have also been replaced with insulated windows, and hurricane-rated sliding doors enclose the lanai, creating wonderful additional flexible living space while allowing you to enjoy the peaceful surroundings year-round. One of the home's best features is its serene pond setting. Relax in the enclosed lanai and enjoy tranquil water views from this desirable end-unit location. Wood-look flooring, an insulated steel garage door and numerous thoughtful updates add even more appeal. Conveniently located near shopping, dining, everyday conveniences and the beautiful Gulf beaches, this extensively updated, maintenance-free villa offers the Florida lifestyle you've been looking for. Simply move in and enjoy!

5699 Westwind Ln, Sarasota
$759,000
5 Beds ⋅ 3 Baths ⋅ River Forest SubDv. ⋅ 34231 Zip Code
3 bedroom pool home with attached 2/1 with full kitchen. 2 miles to Siesta Key, easy commute to downtown Sarasota. Has a screened in pool, storage shed, fenced in yard and generator. Offered fully furnished! Excellent rental income opportunity. Rent both , live in one /rent the other or make it your large single family home.

2213 Wason Road, Sarasota
$143,500
2 Beds ⋅ 2 Baths ⋅ Pinewood Village SubDv. ⋅ 34231 Zip Code
DON'T MISS THIS ! 2 bed/2bath ground floor condo with private patio. has been rented for the past 13 years, vacant now, Close to restaurants shopping, grocery and schools. Extra storge closet, pool and fitness center. All measurements should be verified by buyer or buyers agent

2763 Woodgate Lane Unit 104, Sarasota
$1,200,000
5 Beds ⋅ 5 Baths ⋅ Ridgewood SubDv. ⋅ 34231 Zip Code
**Rare Sarasota 4-Plex – No Flooding, Prime Location & Exceptional Investment Opportunity!** Don't miss this rare opportunity to acquire a well-located **4-unit multifamily property** in one of Sarasota's most desirable rental markets. A standout feature of this property is that **it has experienced no flooding**, providing added confidence for investors focused on long-term ownership. Ideally located just minutes from Siesta Key Beach, Gulf Gate, Downtown Sarasota, shopping, dining, hospitals, and major employers, this asset offers immediate rental income with excellent potential for future appreciation and rental growth. Whether you're adding to your portfolio, completing a 1031 exchange, or seeking a high-demand multifamily asset, this property offers the location and stability investors are looking for. With limited multifamily inventory available in Sarasota, opportunities like this are becoming increasingly scarce. **Schedule your private showing today—properties with this combination of location, income potential, and no flooding don't stay on the market for long.**

2741 Parma Street, Sarasota
$325,000
2 Beds ⋅ 2 Baths ⋅ Ashton Lakes SubDv. ⋅ 34231 Zip Code
Welcome to Ashton Lakes, a maintenance-free community set on 33 acres of lush landscaping with four lakes — less than two miles from the beaches of Siesta Key. This beautifully maintained 2—bedroom, 2-bath residence has been thoughtfully updated throughout and delivers an easy blend of comfort, convenience, and coastal charm. Step inside to soaring vaulted ceilings and an abundance of natural light that gives the entire home an airy, light coastal feel. Sweeping lake views frame the living space, and a desirable one-car garage — a rarity at this price point — adds everyday practicality. The primary bath has been fully renovated, with additional updates in the guest bath, and a newly installed Murphy bed maximizes flexibility for guests, a home office, or both. Life at Ashton Lakes centers on its exceptional amenities: a recently updated clubhouse, two heated pools including a large pool with a dedicated lap lane, two tennis courts and four pickleball courts, shuffleboard, grilling stations, and more. A private footbridge connects residents directly to Merchants Mart shopping center, home to CVS, ACE Hardware, a Dollar store, restaurants, and Detwiler's Farm Market. You're also minutes from the Whole Foods anchored redevelopment at Sarasota Square and  Siesta Promenade, the new 24-acre mixed-use project at the northwest corner of U.S. 41 and Stickney Point Road. Downtown Sarasota and I-75 are both an easy reach. Recent updates include: HVAC in Jan 2026, deluxe fabric roller shade throughout in Feb 2026, murphey bed in Feb 2026, smart garage open in Feb 2026, refrigerator and washer in 2023, dry bar, primary bathroom, and guest bathroom.

5652 Ashton Lake Drive Unit 5652, Sarasota
$199,000
2 Beds ⋅ 2 Baths ⋅ Woodside Village West SubDv. ⋅ 34231 Zip Code
Beautiful location, in a quiet, well-kept 55+ community, excellent opportunity for rental investment or new home. Located less than 2 miles from Siesta Key beach, 15 minutes from Nokomis Beach, centrally located in Gulf Gate Sarasota, 20 minutes to downtown Sarasota or downtown Venice. New AC system in 2023 and New Roof in 2025. Short-term rentals are allowed with a minimum stay of 2 months, rentals are allowed after one year of ownership. One minute walk to community pool. One assigned parking spot with plenty of guest parking. Painted and ready to move in!

2105 Pueblo Circle Unit V2, Sarasota
$129,000
1 Beds ⋅ 1 Baths ⋅ Baywood Colony Gdn Apts SubDv. ⋅ 34231 Zip Code
Welcome to effortless Sarasota living at 5800 Hollywood Blvd—an inviting 1-bedroom, 1-bath condo ideally positioned for both comfort and convenience. This well-appointed residence offers a light and functional layout, perfect as a primary home, seasonal retreat, or investment opportunity—your chance to own a piece of paradise. Enjoy a relaxed coastal lifestyle just minutes from the world-renowned Siesta Key Beach, where powdery white sands and turquoise Gulf waters await. Everyday conveniences are at your doorstep, with an array of shopping, dining, and entertainment options nearby, creating the perfect balance of tranquility and accessibility. The interior offers a comfortable living space with a seamless flow, providing a welcoming environment to unwind or entertain. Whether you're enjoying a quiet morning or returning after a day at the beach, this residence delivers easy, low-maintenance living in a highly desirable location. An exceptional opportunity to own a piece of paradise in Sarasota at an attractive price point, close to everything that makes this area so sought after.

5800 Hollywood Boulevard Unit 112, Sarasota
$390,000
3 Beds ⋅ 3 Baths ⋅ Woodbridge SubDv. ⋅ 34231 Zip Code
Lender paid 1-0 Buydown Interest Rate by using our preferred lender! Welcome to Woodbridge Estates, where peaceful surroundings and natural beauty meet convenience and comfort. This VILLA feels like a single family home. Spacious 3-bedroom, 2 full and 1 half bath home has a large 2 car garage, offers an open floor plan with vaulted ceilings designed for easy Florida living and entertaining. The large living area flows seamlessly into the dining space and kitchen, creating an inviting atmosphere filled with natural light. The eat-in kitchen features stainless steel appliances, a pocket door for added privacy, an eat-at pass-through to the dining area, and a slider leading to a private courtyard—perfect for enjoying your morning coffee or evening relaxation. Sliders from both the living area and the primary suite open to a sunroom, extending your living space and bringing the outdoors in. The primary suite is a true retreat with a large walk-in closet and an en suite bath complete with dual sinks, a garden tub, separate shower, and private water closet. Bedrooms two and three each have sliders to a screened porch, providing private outdoor access and peaceful views. A convenient half bath is located off the foyer, while the laundry room includes a utility sink for added functionality. Surrounded by mature oak trees and lush landscaping, this pet-friendly community is ideal for walking and enjoying the outdoors. Residents of Woodbridge Estates enjoy access to a pond, pickleball and tennis courts, a HEATED community swimming pool, and an Association Manor House for social gatherings and events. Tucked away in a quiet setting yet just minutes from shopping, I-75, city conveniences, and some of the best beaches in the United States, this home offers the perfect balance of tranquility and accessibility. Gates are open 7am to 7pm daily

2644 Moss Oak Drive Unit 47, Sarasota
$359,000
3 Beds ⋅ 3 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Hey… have you heard about this little hidden gem called Crooked Creek? Tucked away alongside the natural beauty of Red Bug Slough, this community is one of Sarasota’s best-kept secrets—and this rarely available end-unit villa might just be the one you’ve been waiting for. Offering 3 bedrooms, 3 bathrooms, and a 2-car garage, this spacious residence just under 1,700 sq ft lives large with a flexible layout that’s hard to find. Two of the bedrooms are generous ensuites, perfect for guests or multi-generational living, while the third bedroom offers versatility as a home office or den with its own patio. Inside, you’ll love the no-carpet lifestyle with stylish vinyl plank and tile flooring throughout, complemented by two skylights that fill the home with natural light. Enjoy the large enclosed sunroom as well as an open outdoor private patio, ideal for morning coffee or unwinding in the peaceful, lush surroundings of mature Florida landscaping. This amazing community was Designed by renowned Sarasota School of Architecture architect Tim Seibert, and this villa blends timeless design with a serene, nature-inspired setting. The lifestyle? It’s just as impressive. Residents enjoy a heated pool, pergolas, large Gazebo, wooden footbridge, scenic walking paths, and the tranquility of nearby Red Bug Slough Preserve—all while being minutes from shopping, dining, and Siesta Key beaches. The HOA offers exceptional value, covering roof maintenance, exterior building care, ground maintenance, private roads, cable, and WIFI, Pest control, and trash, making for truly low-maintenance living. Plus, no age restrictions—this is NOT a 55+ community. Opportunities like this don’t come around often… especially in Crooked Creek. Come take a look—you may just fall in love.

3351 Thornwood Road Unit 3351, Sarasota
$1,025,000
2 Beds ⋅ 3 Baths ⋅ Bath And Racquet SubDv. ⋅ 34231 Zip Code
Under Construction. Experience refined luxury living at Bath & Racquet Residences, where modern elegance meets Sarasota’s storied legacy. This beautifully designed two bed 2.5-bath duplex residence features floor-to-ceiling windows, custom Italian cabinetry, quartz countertops, premium Bosch appliances, and a large outdoor patio overlooking the tennis courts. Beyond your doorstep, enjoy an unparalleled collection of resort-style amenities. The community and club feature a private pool, expansive two-acre park, dog park, playground, and a scenic 1-kilometer walking trail—perfect for an active outdoor lifestyle. Sports and wellness enthusiasts will appreciate 13 tennis courts, 2 pickleball courts, 4 padel courts, a resort-style club pool, on-site restaurant, state-of-the-art fitness center, and a full-service wellness spa. Located just 4 miles from the world-famous Siesta Key beaches and 3 miles from vibrant Downtown Sarasota, this address offers the perfect blend of luxury, convenience, and coastal sophistication. Bath & Racquet Residences presents a unique opportunity for both full-time residents and investors, with short-term rentals permitted (7-night minimum), offering flexibility and income potential. Under the guidance of Tommy Haas, former World No. 2 and official club ambassador, this iconic redevelopment reimagines the historic Bath & Racquet Club, originally founded in 1969. Once the home court of tennis legends such as Chris Evert and Martina Navratilova, the property now enters a new era—honoring its rich heritage while embracing modern elegance, wellness, and active living. Designed by Halflants + Pichette Architects, Bath & Racquet Residences and Club presents 256 luxury condominiums with low HOA fees.

2170 Robinhood Street Unit C2-102, 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
$269,900
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Nestled on the second floor of Sarasota's boutique Crooked Creek community, this thoughtfully updated two-bedroom, two-bath condominium offers a rare combination of refined interiors, natural surroundings, and low-maintenance living. Since 2022, the owners have invested significantly in the home. The kitchen was fully renovated in 2023 with sleek European-style cabinetry, black granite countertops, and all-new appliances , a clean, contemporary space that anchors the open living area. Underfoot, premium engineered hardwood flooring with a 4mm wear layer (refinishable) runs through the main living and dining rooms, installed in 2022. Overhead, a designer Hubbardton Forge light fixture in the dining area and a new ceiling fan with wall switch in the living room add considered detail throughout (2024). The second bathroom received a complete refresh in 2025 with a new toilet, vanity, and flooring. Fresh paint throughout ,the living and dining rooms, kitchen, master and second baths, hallway, and master bedroom ceiling ties everything together with a crisp, move-in ready finish. The functional floor plan is further enhanced by a glass-enclosed porch, offering additional living space and a seamless connection to the outdoors. The unit enjoys a private, tranquil setting with views of mature tropical landscaping and the adjacent Red Bug Slough Preserve a natural buffer that creates a true sense of retreat while keeping you centrally located. Crooked Creek is a 78-unit community with a heated pool, tennis and pickleball courts, a clubhouse, and outdoor gathering areas. Covered assigned parking and dedicated storage are included. Shopping, dining, and area beaches are all just minutes away.

4957 Cross Creek Road Unit 4957, Sarasota
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