Refine Search
Map
Sort by
1777 Alta Vista Street, Sarasota
$975,000
3 Beds ⋅ 2 Baths ⋅ Hudson Bayou SubDv. ⋅ 34236 Zip Code
Virtually Staged. Welcome to Cleary Cottage, a charming 1935 bungalow nestled in the highly sought-after Hudson Bayou neighborhood, West of Trail in the heart of Sarasota. Blending timeless character with thoughtful modern updates, this beautifully maintained 3-bedroom, 2-bath residence offers an inviting retreat just minutes from downtown Sarasota, Southside Village, Sarasota Memorial Hospital, Selby Gardens, the bayfront, and the area's renowned beaches. From the moment you arrive, the lush tropical landscaping, circular driveway, and welcoming screened front porch set the tone for this distinctive home. Inside, original hardwood floors, plaster walls, crown molding, and a classic brick fireplace celebrate the home's historic charm, while an updated kitchen featuring white cabinetry, stone-look countertops, stainless steel appliances, and tasteful finishes provides modern convenience. The comfortable floor plan offers inviting living and dining spaces, three bedrooms, and two updated bathrooms, including a primary bath with a beautifully tiled walk-in shower. A metal roof installed in 2018, an updated HVAC system, and hurricane protection improvements add to the home's appeal. Step outside to discover a private tropical oasis with mature landscaping, a backyard deck, and inviting outdoor spaces ideal for relaxing, entertaining, or enjoying Sarasota's year-round sunshine. The spacious screened front porch, complete with a charming porch swing, offers yet another place to unwind and enjoy the neighborhood. Located in FEMA Flood Zone X, this property offers the added advantage of being outside the designated high-risk flood area. Its location and zoning also create an attractive short-term rental opportunity, offering flexibility for buyers considering seasonal use, part-time occupancy, or income-producing potential. Whether you're searching for a full-time residence, seasonal escape, or a Sarasota property with flexible rental potential, Cleary Cottage delivers a special combination of character, comfort, and location. Experience the charm of Old Florida living with the conveniences of Sarasota's vibrant downtown, shopping, dining, cultural attractions, and world-famous Gulf Coast beaches close by. Schedule your private showing and discover what makes Cleary Cottage so special!

1777 Alta Vista Street, Sarasota
3308 Over Cup Oak Terrace, Sarasota
$174,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
WELCOME TO YOUR FLORIDA LIFESTYLE AT OAKWOOD MANOR! AFFORDABLE SARASOTA PARADISE IN A RESIDENT-OWNED 55+ COMMUNITY Live where every day feels like a vacation! Welcome to Oakwood Manor, one of Sarasota’s sought-after resident-owned 55+ communities. Set across 90 beautifully landscaped acres within Sarasota city limits, Oakwood Manor offers an appealing blend of affordability, comfort, and resort-style living for just $210/month HOA, with no CDD or master association fees. This well-maintained 2-bedroom, 2-bath home offers 1,152 square feet of inviting living space and is being sold turnkey, excluding personal items. Just bring your suitcase and start enjoying the Florida sunshine! Pride of ownership shines throughout this inviting home. The bright, enclosed sunroom, surrounded by windows and filled with natural light, is the perfect spot for morning coffee, afternoon relaxation, or entertaining friends. The spacious kitchen offers abundant cabinetry, a pantry, and a convenient center island, along with a ceramic cooktop range, microwave, dishwasher, and refrigerator. The kitchen flows easily into the dining area, creating a comfortable setting for everyday living and entertaining. The secondary bedroom features direct access to the guest bathroom, offering added privacy and a layout that functions almost like a second primary suite. HOME FEATURES & IMPROVEMENTS 2 bedrooms, 2 bathrooms, and 1,152 square feet of living space Bright, enclosed sunroom filled with natural light Spacious kitchen with center island, pantry, and abundant cabinetry Ceramic cooktop range, microwave, dishwasher, and refrigerator A/C replaced in 2022 Carport roof replaced in 2025 to meet the latest building code, as reported PVC plumbing from the home to the street replaced in 2021 Roof replacement history includes 2017 and 2019 Large storage shed Washer and dryer included RESORT-STYLE AMENITIES & AN ACTIVE LIFESTYLE Enjoy a wonderful selection of community amenities, activities, and opportunities to connect with neighbors: Heated swimming pool and oversized hot tub Clubhouse with commercial kitchen and event stage Fitness center and library Bocce ball and shuffleboard courts Putt-putt golf Active social calendar and welcoming neighbors Love pickleball? The Legacy Trail and its pickleball courts are just a short bike ride away! AN IDEAL SARASOTA LOCATION Conveniently located just minutes from downtown Sarasota, beautiful Siesta Key Beach, the shopping and dining of St. Armands Circle, Sarasota-Bradenton International Airport, and nearby hospitals and medical facilities. Even better, this home is just steps from the clubhouse, putting community activities and amenities within easy reach. Whether you're searching for a seasonal Florida retreat or a year-round residence, this inviting home offers an opportunity to enjoy the Sarasota lifestyle without the price tag of a traditional resort community. COME DISCOVER THE VALUE, THE LIFESTYLE, AND THE FRIENDLY COMMUNITY THAT MAKE OAKWOOD MANOR A SARASOTA HIDDEN GEM!

3308 Over Cup Oak Terrace, Sarasota
3309 Oakwood Boulevard S, Sarasota
$169,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Welcome to Your Florida Lifestyle at Oakwood Manor! Affordable Sarasota Living in a Resident-Owned 55+ Community Your slice of Sarasota paradise is waiting! Discover the perfect blend of affordability, comfort, and resort-style living at Oakwood Manor, one of Sarasota’s cherished resident-owned 55+ communities. Set across 90 beautifully landscaped acres within Sarasota city limits, this welcoming community offers an active lifestyle and a wonderful place to call home. Enjoy all this for just $210 a month in HOA fees, with no CDD or master association fees! Move-In Ready and Full of Charm This well-maintained 1977 home features 2 bedrooms, 2 bathrooms, and 1,056 square feet of inviting living space. Offered turnkey, excluding personal items, this home is ready for you to move in, unpack, and start enjoying the Florida sunshine! From the moment you arrive, you’ll appreciate the care and pride of ownership throughout. The bright, enclosed sunroom, surrounded by windows and filled with natural light, is the perfect place to sip your morning coffee, curl up with a good book, or entertain friends. Inside, the spacious kitchen offers abundant cabinetry and flows seamlessly into the dining area, creating a comfortable setting for everyday living and entertaining. Generous closet space throughout the home provides valuable storage, while the convenient indoor laundry area adds to the home’s functionality. Home Features & Recent Upgrades 2-bedroom, 2-bathroom floor plan Bright, window-filled enclosed sunroom Spacious kitchen with abundant cabinetry Cooktop, wall oven, dishwasher, and refrigerator included Roof replaced in 2023 A/C replaced in 2022 Laminate flooring throughout Updated outdoor electrical service in 2025 PVC plumbing from the home to the street replaced in 2023 Indoor laundry area with washer and dryer Carport roof reinforced to meet the latest code requirements Resort-Style Amenities and an Active Lifestyle At Oakwood Manor, there’s always something to enjoy! Whether you love staying active, socializing with neighbors, or simply relaxing in the Florida sunshine, this community offers something for everyone. Heated swimming pool and oversized hot tub Clubhouse with commercial kitchen and event stage Fitness center Community library Bocce ball and shuffleboard courts Putt-putt golf Active social calendar and welcoming neighbors Love pickleball? You’re just a short bike ride from the Legacy Trail and its new pickleball courts, making it easy to enjoy outdoor recreation and stay active. An Incredible Sarasota Location Enjoy the best of Sarasota living with beaches, shopping, dining, entertainment, and everyday conveniences just minutes away. Downtown Sarasota World-famous Siesta Key Beach St. Armands Circle’s shopping and dining Sarasota-Bradenton International Airport Nearby hospitals and medical facilities Even better, this home is ideally located just steps from the clubhouse, putting community activities, social events, and amenities conveniently close to home. Your Florida Dream Starts Here! Whether you’re searching for a seasonal retreat, a sunny retirement getaway, or a comfortable year-round residence, this home offers an inviting opportunity to enjoy the Sarasota lifestyle without the price tag of many resort-style communities. Please note: Community restrictions prohibit pets, motorcycles, and RVs.

3309 Oakwood Boulevard S, Sarasota
3867 Almond Avenue, Sarasota
$279,900
2 Beds ⋅ 2 Baths ⋅ Beverly Terrace SubDv. ⋅ 34234 Zip Code
Built in 2018 and beautifully maintained, this charming Sarasota home offers an appealing opportunity at $279,900. Its 735 square feet are well suited to someone seeking a manageable primary residence, a winter retreat, or an investment property. The smaller lot means less yard to maintain, and there is no HOA. Spend the winter in your own Sarasota getaway, then explore the possibility of renting it while you’re away. Its newer construction, excellent condition, and manageable size also make it an attractive option for a buyer looking to add a rental property to their portfolio. Whether you plan to live here year-round, visit seasonally, or invest, 3867 Almond Avenue offers flexibility at an approachable price. Based on six years of historical Airbnb short-term rental like-kind pro forma data, estimated gross revenue will likely range between $31,700 and $41,210. Your nightly rate will average about $146. Expect an occupancy rate of about 63%. Rental projections are based on a 2-bedroom, 2-bathroom property.

3867 Almond Avenue, Sarasota
3523 Longmeadow Unit 12, Sarasota
$159,000
1 Beds ⋅ 1 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code
THE MEADOWS BUNGALOW — SMALL IN SIZE, BIG ON CHARM! Welcome to your own little slice of The Meadows! This beautifully renovated furnished one-bedroom, one-bath end-unit villa in Bunker Oaks has the feel of a private Sarasota bungalow — cozy, stylish, carefree, and ready to enjoy. Every inch of this petite villa has been thoughtfully refreshed, featuring NEW flooring, NEW ceiling coverings, NEW kitchen cabinets, NEW shower door, fresh paint, and NEW furniture — including a new bed and dresser. The inviting bedroom is anything but ordinary, offering a custom closet, built-in vanity/desk, and charming farmhouse-style barn doors. The updated bathroom features a walk-in shower, new vanity and lighting, and beautifully refreshed shower tile. The open living space feels bright and clean, with the popcorn ceilings removed for a more modern finish. Step through the living area and onto your private patio overlooking the golf course and sparkling community pool. Just beyond your patio is a picnic area and grills — creating an easy place to relax, entertain, or soak up the Florida sunshine. A community bike rack is conveniently nearby, and the main Meadows clubhouse, fitness center and Jr. Olympic-size pool are just steps away. And then there’s The Meadows — one of Sarasota’s most established and amenity-rich communities. Wander or bike along approximately 14 miles of scenic trails beneath mature oaks, watch for abundant wildlife, or enjoy the community’s golf, tennis, pickleball, fitness, fishing, parks, butterfly garden and multiple recreation areas. The nearby Village shops offer dining, entertainment and a spa, medical offices, a preschool, hair salon and so much more. You'll never be bored with community events and activities throughout the year. Whether you're looking for a Sarasota getaway, easy winter retreat, first home, investment property, or a furnished place to call your own, this charming bungalow delivers an incredible lifestyle without the upkeep of a larger home. Best of all, monthly rentals are permitted, adding flexibility and investment appeal. For a peaceful, well-maintained community environment, Bunker Oaks in The Meadows has specific vehicle and pet restrictions. This residence does not allow pets, trucks or commercial vehicles, or motorcycles. Conveniently located just minutes from UTC, Whole Foods, Fresh Market, shopping, dining, downtown Sarasota and the Gulf beaches. Furnished, renovated and priced to sell — this little Meadows bungalow is ready for its next chapter!

3523 Longmeadow Unit 12, Sarasota
1841 Laurel Street, Sarasota
$1,000,000
2 Beds ⋅ 2 Baths ⋅ Laurel Park SubDv. ⋅ 34236 Zip Code
Discover the charm of downtown Sarasota from this expertly renovated residence in the heart of the coveted Laurel Park Arts District. Combining the character of a 1922 home with the comfort and style of modern living, this private, gated property is just moments from Main Street, Sarasota Bay, St. Armands Circle, Lido Beach, award-winning dining, boutiques, galleries and the city's vibrant arts and entertainment scene. Inside, the open-concept design features a stunning quartz island, beautifully updated kitchen and baths, custom closets and designer finishes throughout. The two-bedroom, two-bath main residence is complemented by a separate flex building with additional living space and a private laundry room, ideal for guests, a home office or creative studio. Outside, enjoy a fully fenced backyard with paver walkways, a lounging deck, covered carport, storage shed and outdoor shower. Major updates include a 2024 metal roof, 2023 HVAC, updated plumbing and a 2022 electrical panel. Offered fully furnished, this exceptional property is ready to enjoy.

1841 Laurel Street, Sarasota
10168 Silent Night Lane, Sarasota
$1,125,000
3 Beds ⋅ 3 Baths ⋅ Skye Ranch Neighborhood Four North SubDv. ⋅ 34241 Zip Code
THE DESIGNER RESIDENCE | 10168 SILENT NIGHT LANE A DESIGNER RESIDENCE WITH A VIEW THAT CANNOT BE REPLICATED. Welcome to an exceptional Sarasota residence where award-winning design, an extraordinary homesite, and resort-style living come together in remarkable fashion. Located within the highly sought-after Skye Ranch community, 10168 Silent Night Lane is a sophisticated 3-bedroom, 3-bathroom residence with a dedicated office, professionally curated by an award-winning designer whose vision is evident throughout every beautifully considered space. This is not simply a home with upgrades—it is a fully realized design experience. From the moment you enter, a refined and cohesive aesthetic unfolds through thoughtfully selected finishes, lighting, fixtures, architectural details, and designer touches. The result is a residence that feels polished, contemporary, and distinctly elevated while remaining warm and exceptionally livable. The true showstopper, however, may be found beyond the glass. Set on an expansive homesite with an extraordinary backdrop of two tranquil ponds and sweeping green space, the property enjoys a sense of openness and privacy that is increasingly difficult to find. Rather than looking directly into neighboring homes, the view extends across water and natural open space, creating a peaceful backdrop that changes beautifully throughout the day and becomes particularly captivating as the sun begins to set. Inside, the thoughtfully designed floor plan offers exceptional flexibility. The three bedrooms provide comfortable accommodations for family and guests, while the dedicated office creates an elegant private environment for working from home, reading, or simply escaping the pace of everyday life. The beautifully appointed living spaces are equally suited to quiet mornings and sophisticated entertaining. Then comes the lifestyle. As a resident of Skye Ranch, you are surrounded by an impressive collection of resort-style amenities designed to make every day feel like a getaway. The community's lifestyle offerings include resort-style pools, fitness facilities, tennis, pickleball, bocce, indoor basketball, rock climbing, sports fields, parks, dog parks, gathering spaces and an extensive network of scenic trails through the community's natural landscape. And beyond the gates, Sarasota delivers the lifestyle that has made this destination one of Florida's most coveted places to call home—world-class beaches, exceptional dining, cultural attractions, golf, boating and an extraordinary year-round outdoor lifestyle. Some homes are upgraded. Others are designed. Some homes have a view. Others have a setting. 10168 Silent Night Lane offers both. A professionally designed residence. An exceptional homesite. Two ponds and expansive green space. And the extraordinary lifestyle of Skye Ranch. This is not simply a place to live—it is a home designed to be experienced.

10168 Silent Night Lane, Sarasota
2048 5th Street, Sarasota
$349,900
2 Beds ⋅ 1 Baths ⋅ Park East Mhp Tpp SubDv. ⋅ 34237 Zip Code
Sweet Downtown Sarasota Cottage with Timeless Southern Charm - Charming, inviting, and full of character, this delightful 2-bedroom, 1-bath cottage captures the essence of old-Florida living in the heart of Downtown Sarasota. Framed by a classic picket fence and welcoming front porch, this is the kind of home that immediately feels special. Picture yourself relaxing with a glass of sweet tea on the porch, enjoying the easy pace of cottage living, then strolling to some of Sarasota’s wonderful restaurants, shops, galleries, and cultural destinations just beyond your doorstep. Inside, timeless details and thoughtful improvements create a warm and comfortable atmosphere. Beautiful hardwood floors grace the main living spaces, while built-in kitchen features add the character and charm that are increasingly hard to find in today’s homes. With 8-foot ceilings and an inviting layout, the home offers an appealing blend of vintage personality and everyday functionality. Numerous updates provide peace of mind, including new windows (2021), new refrigerator (2019), new washer and dryer (2019), new ceiling fans (2019), added insulation (2019), and new vinyl fencing (2019), roof is few years old and electric totally updated. Whether you’re searching for a charming primary residence, a Sarasota getaway, or an income-producing property, this cottage offers exceptional versatility. Located within Sarasota’s Downtown Neighborhood (DTN) district, the property is surrounded by the energy and convenience of downtown while retaining the intimate feel of a true neighborhood. There is no HOA and no CDD fee, and the property is located in the X flood zone, meaning flood insurance is not required by the lender based on the information provided. Enjoy downtown dining, shopping, art, entertainment, and cultural attractions virtually at your doorstep, with convenient access to bus routes and the beautiful Gulf beaches.

2048 5th Street, Sarasota
3415 Spanish Oak Terrace, Sarasota
$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
2947 Gillespie Avenue, Sarasota
$194,900
3 Beds ⋅ 1 Baths ⋅ Newtown Heights SubDv. ⋅ 34234 Zip Code
Welcome to this charming three-bedroom, one-bath home offering 864 square feet of comfortable living space in the historic Newtown Heights area, just minutes from the heart of downtown Sarasota. This home offers several important updates for added peace of mind, including a 2023 roof, 2025 AC system, an updated electrical panel installed in 2016, and newer windows. Inside, you’ll find newly installed luxury vinyl plank flooring throughout the main living areas and bathroom, while the kitchen features granite countertops and plenty of potential to make the space your own. Outside, the property includes a raised storage shed in the backyard, providing additional space for tools, equipment, and storage, along with a separate exterior laundry area. Conveniently located approximately two miles from downtown Sarasota, this home offers easy access to shopping, dining, entertainment, area beaches, and I-75 for convenient travel throughout the region. Whether you’re looking for an affordable place to call home or a property with plenty of potential, this Sarasota home is ready for its next owner. Buyer to verify public records for square footage, permitting, and home details.

2947 Gillespie Avenue, Sarasota
3329 Oakwood Boulevard S, Sarasota
$174,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIPS BEGIN! VALUE, LOCATION AND PRICED TO PERSONALIZE AND MAKE IT YOUR OWN!! 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 Built in 1976 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
3227 Bayberry Terrace, Sarasota
$270,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Oakwood Manor — Where Fun and Friendship Happen BEST VALUE**UPDATED**LOW HOA Experience resort-style living in the heart of Sarasota at Oakwood Manor, a beautifully maintained resident-owned 55+ community spanning 90 scenic acres. Enjoy an exceptional and affordable lifestyle with low HOA fees of just $210/ month and no CDD or master association fees. Pride of ownership shines throughout this meticulously maintained 1977-built home offering 2 bedrooms, 2 bathrooms, and 1,324 square feet of comfortable living space. Truly move-in ready, the owners have carefully updated and maintained the home so you can simply unpack and enjoy. Step inside to a spacious, light-filled sunroom surrounded by windows and accented with Plantation shutters — the perfect place to enjoy your morning coffee or unwind with a good book. The large kitchen features ample storage, granite countertops, designer cabinetry, and flows seamlessly into the dining area, creating an ideal layout for everyday living and entertaining. Kitchen Features: Granite countertops Updated kitchen cabinets Refrigerator only 3 months old Dishwasher Stove and microwave Tile backsplash Recent Updates Include: Newer windows A/C replaced in 2017 (3-ton, 14 SEER) Plumbing connected to city tap in 2017 Water heater replaced in 2025 Newer gutters Screened lanai added 2 years ago Whole-house water filtration system Upgraded tie-downs Carport screws replaced Community Amenities: Residents enjoy access to an impressive array of amenities, including: Clubhouse with commercial kitchen and event stage Fitness center Library Heated pool and spacious hot tub Bocce ball and shuffleboard courts Putt-putt golf Pickleball enthusiasts will appreciate being just a short bike ride from the Legacy Trail and its brand-new pickleball courts. This spotless home is ideally situated just steps from the clubhouse, providing convenient access to community activities and social events. Conveniently located near downtown Sarasota, Siesta Key Beach, St. Armand's Circle, shopping, Sarasota-Bradenton International Airport, and nearby hospitals, Oakwood Manor offers the perfect blend of comfort, convenience, and active Florida living. Please note: no pets, motorcycles, or RVs permitted. Whether you are searching for a seasonal retreat or a full-time residence, this exceptional home is a must-see.

3227 Bayberry Terrace, Sarasota
3221 Sumac Terrace, Sarasota
$179,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Welcome to Your Florida Lifestyle at Oakwood Manor AFFORDABLE SARASOTA PARADISE IN RESIDENT-OWNED COMMUNITY Live where every day feels like a vacation at Oakwood Manor — one of Sarasota’s most cherished resident-owned 55+ communities. Nestled within 90 beautifully landscaped acres inside the Sarasota city limits, Oakwood Manor offers the perfect blend of affordability, comfort, and active resort-style living — all for just $210/month HOA with no CDD or master association fees. This beautifully maintained 1976 home offers 2 bedrooms, 2 bathrooms, and 1,386 square feet of inviting living space. Being sold turnkey (excluding personal items), this home is truly move-in ready — just bring your suitcase and start enjoying the Florida sunshine. From the moment you arrive, you’ll appreciate the pride of ownership and meticulous care throughout. The bright and airy enclosed sunroom, wrapped in windows and filled with natural light, creates the perfect setting for morning coffee, afternoon reading, or gathering with friends. Inside, the spacious kitchen with abundant cabinetry flows effortlessly into the dining area, making entertaining easy and enjoyable. Both the kitchen and bathrooms have been tastefully updated, adding modern comfort while maintaining the home’s welcoming charm. Home Features & Recent Upgrades • Spacious 2-bedroom, 2-bath floor plan • Bright enclosed sunroom filled with natural light • Large kitchen with abundant cabinetry • Cooktop, wall oven, dishwasher, and refrigerator included • Updated kitchen and bathrooms • Newer windows throughout • A/C replaced in 2023 • Updated outdoor electrical service (2018) • PVC plumbing from home to street (2016) • Water heater less than 1 year old • Expanded shed featuring TWO air-conditioned rooms • Dedicated storage area • Laundry room with washer and dryer included • Decorative finished carport flooring Resort-Style Community Amenities Life at Oakwood Manor means there is always something to enjoy: • Heated swimming pool & oversized hot tub • Clubhouse with commercial kitchen & event stage • Fitness center • Library • Bocce ball & shuffleboard courts • Putt-putt golf • Active social calendar and friendly neighbors Love pickleball? You’re just a short bike ride from the Legacy Trail and its brand-new pickleball courts. Incredible Sarasota Location Enjoy being just minutes from everything that makes Sarasota special: • Downtown Sarasota • World-famous Siesta Key Beach • St. Armand's Circle shopping & dining • Sarasota-Bradenton International Airport • Nearby hospitals and medical facilities This spotless home is ideally located just steps from the clubhouse, making it easy to enjoy the community’s activities, events, and amenities. Please note: no pets, motorcycles, or RVs permitted. Whether you’re looking for a seasonal escape or a full-time Florida residence, this home offers the lifestyle you’ve been waiting for. Come discover why Oakwood Manor is one of Sarasota’s hidden gems.

3221 Sumac Terrace, Sarasota
3226 Sweet Gum Terrace, Sarasota
$142,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIP HAPPEN TURNKEY, UPDATED AND STEP FROM THE CLUBHOUSE Welcome to Oakwood Manor, a sought-after 55+ resident-owned community in the heart of Sarasota. Spanning 90 beautifully maintained acres, this vibrant neighborhood offers true resort-style living at an incredibly affordable $210/month. Enjoy a full lineup of amenities including a welcoming clubhouse with commercial kitchen and stage, fitness center, library, heated pool, hot tub, bocce ball, shuffleboard, and putt-putt golf. Love pickleball? You’re just a short bike ride to the Legacy Trail with brand-new courts. (Please note: no pets, motorcycles, or RVs permitted.) This meticulously maintained 2-bedroom, 2-bath home is being sold turnkey—just bring your suitcase and start enjoying the Florida lifestyle. Step inside to a bright, sun-filled living room surrounded by windows—perfect for morning coffee or relaxing afternoons. The spacious kitchen offers abundant cabinetry and flows seamlessly into the dining area, ideal for entertaining. It comes fully equipped with stove, microwave, refrigerator, plus a washer and dryer conveniently located just steps away. **Recent updates and features include: *New Vinyl Wood flooring throughout 2023 *Updated subflooring *Roof repairs (2024) *Hurricane straps on home and carport *AC with annual service contract *Tastefully updated guest bath **Located just steps from the clubhouse, you’ll have easy access to all community activities and social events. Prime Sarasota Location: Minutes to downtown, Siesta Key Beach, St. Armand's Circle, shopping, Sarasota-Bradenton International Airport, and top medical facilities. **Move-in ready, spotless, and truly maintenance-free—this home is a must-see!

3226 Sweet Gum Terrace, Sarasota
708 42nd Street, Sarasota
$619,000
3 Beds ⋅ 2 Baths ⋅ Indian Beach SubDv. ⋅ 34234 Zip Code
Come see this charming and peaceful Old Florida gem with detached cottage ideally situated in the desirable Indian Beach/Sapphire Shores neighborhood located west of the trail. Here is a rare opportunity to own two meticulously maintained homes within the city limits in Indian Beach/Sapphire Shores, a community rich with art, culture, and history. Picture tree-lined streets, character-filled homes, and being just moments from the shimmering Sarasota Bay. You are in for a treat as you enter the main home through a central air-conditioned enclosed front porch into a home with all of its original, timeless character including glass doorknobs, lovely baseboards and trim, vintage light fixtures, painted heart of pine floors, and functional double-hung windows. This original 1930s home (732 sf) features two bedrooms (freestanding wardrobes), one bath, and a spacious combination dining/living area. An additional wonderful highlight is the central air conditioned detached guest cottage (478 sf) with kitchen, living area, one bathroom and bedroom alcove along with a screened porch and patio, and attached one-car garage. This cottage is ideal for multi-generational living or Airbnb or full-time lease opportunities. All furnishings and fixtures convey: the front unit is partially furnished; the back unit is turn-key furnished. The property includes a very nice new 12x16 Tuff Shed ideal for an artist’s studio, workshop, or just additional storage. Set on a lush 12,000+ square foot lot, the property is spacious with plenty of room for parking, entertainment and other possibilities. You are sure to enjoy the established vegetable and flower gardens. Adding to the charm, you may catch sight of the neighborhood's colorful wild peacocks who love to display their feathers. Excellent location just minutes from the Ringling Museum, SRQ Airport, and downtown Sarasota as well as close proximity to Lido Key Beach, St. Armands Circle, and Siesta Key. Two high-end homes are currently under construction on the block. This sweet property is waiting to fit your needs whether as live-in residences, a rental investment, multi-generational living, or any combination thereof. This peaceful neighborhood in "Turks Cap" (sometimes referred to as the Museum District) has a rural feel with narrow, tree-lined streets and roaming peacocks. This is a no through street with no traffic. If you want quiet and relaxed, you have found the neighborhood.

708 42nd Street, Sarasota
3312 Overcup Oak Terrace, Sarasota
$154,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN, FRIENDSHIP, AND FLORIDA LIVING COME TOGETHER 2 BR*2 BA*TURNKEY*PRIME LOCATION WAKE UP TO SUNSHINE, STAY FOR THE LIFESTYLE!! Enjoy easy Florida living in one of Sarasota's most welcoming community where neighbors become friends and every day feels like a vacation. Located within the Sarasota city limits, Oakwood Manor is a beautifully maintained resident-owned 55+ community set on 90 lush acres. This highly sought-after neighborhood offers an exceptional and affordable lifestyle with an incredibly low $210 monthly fee, making it one of Sarasota’s best-kept secrets. Life here is all about enjoying the moment. Residents gather at the spacious clubhouse featuring a commercial kitchen, event stage, fitness center, and library. Spend your days relaxing in the heated pool or oversized hot tub, or stay active with bocce ball, shuffleboard, putt-putt, ping-pong, and the brand-new pickleball courts. The nearby Legacy Trail offers beautiful biking and walking just minutes from your door. Step inside this pristine, beautifully updated and fully furnished 2-bedroom, 2-bath home offering 1,120 sq. ft. of bright, open living space A BRAND NEW ROOF (2024) NEW 15 SEER AC WITH UPDATED DUCTWORK and updated bathrooms. Other Recent updates include: Beautifully updated bathrooms (2024) Full-size washer and dryer Refrigerator, range, and dishwasher included Freshly painted walls and ceilings in soft designer colors New Florida room flooring (2025) Perfectly located just steps from the amenity center, where you can enjoy the best of Oakwood Manor without even needing to get in the car. When you do venture out, you are only minutes from downtown Sarasota, Siesta Key Beach, St. Armand's Circle, SRQ Airport, shopping, dining, and two major hospitals. Please note: Oakwood Manor does not allow pets, motorcycles, or RVs. This isn’t just a home — it’s a lifestyle filled with sunshine, friendships, and the relaxed Florida living you’ve been dreaming of.

3312 Overcup Oak Terrace, Sarasota
1569 7th Street, Sarasota
$2,516,000
2 Beds ⋅ 1 Baths ⋅ Halls Sub James S SubDv. ⋅ 34236 Zip Code
SARASOTA ~ CITY OF SARASOTA ~ ROSEMARY DISTRICT ~ DOWNTOWN LIVING AND / OR INVESTMENT, WITH UPSIDE DEVELOPMENT OPPORTUNITIES! - WE ARE SELLING 4 CONTIGUOUS PROPERTIES WITH FOUR RENTAL HOMES ON AN ESTIMATED 23K SF +/- LAND!!!! Come and explore this unique opportunity to own and operate four contiguous properties with homes within the much sought after City of Sarasota "Rosemary District". The current rent roll is estimated at $100K +/-, all the current homes (4) are rented on an annual basis. The zoning does allow for short term weekly rentals, come and set up your own short term rental compound with estimated average daily rates @ $50.00 - $100.00 +/. Want another reason to look, owner will consider "owner financing" and/or selling off less then all four homes. There are just not many opportunities in the City of Sarasota to secure rezoned lands with the ability to use the current as-is property to secure carry income while waiting for the right timing to develop. The upside development in the Rosemary Zoning District: up to 7-stories with up to 30+ units. Property is very easy to show, sign is on site! NOTE: another contiguous parcel - rental home available for discussion.

1569 7th Street, Sarasota

How much is your home worth?

Get instant property value now!