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3329 Overcup Oak Terrace, Sarasota
$165,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Enjoy the Sarasota lifestyle in this completely updated, fully furnished home in Oakwood Manor, a gated 55+ community with a low HOA fee of just $210 per month! Move-in ready, this inviting home features an open floor plan, newer windows and sliding glass door, and plenty of storage. Whether you’re seeking a seasonal getaway or a full-time Florida residence, you’ll feel right at home. Oakwood Manor offers an impressive array of amenities, starting with a spacious clubhouse featuring a full commercial kitchen, event stage, audio/visual equipment, dance floor, fitness room, activities hall, and a library stocked with books, movies, and puzzles, plus a pool table. Outside, enjoy the extra-large heated pool with an accessible ramp, a spacious kidney-shaped hot tub, umbrella tables, lounge chairs, and updated shower rooms. Beautiful oak trees shade the park and picnic area, complete with tables and a community grill. Stay active with miniature golf, bocce ball, ping-pong, and cornhole—or take advantage of the adjacent Legacy Trail and 12 newer pickleball courts. Conveniently located just a short drive from Sarasota’s white-sand beaches, downtown, the marina, fishing pier, local golf courses, shopping, restaurants, museums, SRQ Airport, Sarasota Memorial Hospital, and Doctors Hospital. Unpack, settle in, and start enjoying your Florida lifestyle! Please note: Oakwood is a 55+ community. Pets and motorcycles are not permitted.

3329 Overcup Oak Terrace, Sarasota

7350 Palomino Trail, Sarasota
$1,699,000
5 Beds ⋅ 4 Baths ⋅ Saddle Creek SubDv. ⋅ 34241 Zip Code
Attention Investors, Builders, Equestrian Buyers, and Savvy Owner-Occupants: Incredibly rare 6+ acre private equestrian estate opportunity in the desirable Saddle Creek community of Sarasota. The owner’s surprise relocation gives you the unique chance to secure this massive 5 bed / 4 bath residence with over 5,200 sqft of living space, two separate garages with a total of 6 spaces, and endless long-term potential in one of Sarasota’s most sought-after acreage neighborhoods. So what makes this one so special? 1) Huge 6.09-acre private estate lot, offering exceptional space, privacy, and flexibility rarely found this close to Sarasota’s best amenities. 2) Massive 5,209 sqft residence featuring 5 bedrooms and 4 bathrooms, providing an incredible footprint for luxury renovation, multi-generational living, entertaining, or future customization. 3) Located in Saddle Creek, an established acreage community known for privacy, space, and access to approximately 25 miles of riding trails. 4) Exceptional equestrian location with horses permitted, and TerraNova Equestrian Center, one of the Sarasota area's premier competition venues, just 11 miles away. 5) Huge resort-style pool enclosure, offering the foundation for an incredible outdoor entertaining and relaxation space. 6) Two separate garages: one 4-car garage and one 2-car garage, providing incredibly ample room for vehicles, equipment, tools, toys, storage, and workshop use. 7) Spacious primary bath area featuring a jacuzzi tub, adding to the home’s luxury potential. 8) Property backs up to a canal, creating additional privacy and a peaceful natural backdrop. 9) Expansive lot with tons of room for further development, including equestrian improvements, outbuildings, gardens, outdoor entertainment areas, or a reimagined estate-style landscape. 10) Fantastic Sarasota location, under 25 minutes to University Town Center, Downtown Sarasota, and Sarasota’s renowned Gulf Coast beaches. Opportunities to acquire this level of land, square footage, privacy, and upside in Sarasota are exceptionally rare. Whether the goal is a luxury renovation, multi-generational residence, equestrian retreat, or simply owning a substantial piece of Sarasota acreage in a high-demand market, this one offers the scale and potential to make it happen. Easy to show. Feel free to soft pitch before writing anything up. MLS info sheet and disclosures available. No assignable contracts accepted.

7350 Palomino Trail, Sarasota

1930 29th Street, Sarasota
$220,000
2 Beds ⋅ 1 Baths ⋅ Newtown Heights SubDv. ⋅ 34234 Zip Code
Welcome to this CORNER LOT BLOCK home Located Just a few minutes from Downtown Sarasota and just 10mins from the Beach! Sitting in a HIGH & DRY part of SARASOTA in a NON-FLOOD Zone, So you don't have to worry about any Hurricanes or Flooding! And NO HOA or CDD Fees! This home has been Very Well maintained by the sellers and Tastefully UPDATED from Top to bottom!! This Home Features NEW FULL HOME SOLAR SYSTEM(2023) which saves you A lot of money on your Electric Bills (a $50,000 Value), New Fence (2026) Newer ROOF, Newer Windows, New Plumbing which includes a Whole Home RE-PIPE, a Newer Water Softener System, Newer Electrical, a Newer Kitchen with GRANITE Counter Tops and Newer Appliances. This home features an Open floor plan with Newer Wood like CERAMIC FLOORING Throughout! A Newer Bath with Custom Tiled bath/shower and Much more! Too Many Updates to even list! Offering an Oversized car Carport, as well as a separate room with a Newer Washer and Dryer and space for storage. A LARGE CORNER FULLY FENCED Yard with a Gate which allows for plenty of room to Enjoy our Beautiful Florida Outdoor Lifestyle AND has room to park your Boat or Rv. Almost impossible to find a Completely Remodeled home so Close to Downtown Sarasota, Beaches, Sarasota Memorial, Ringling Arts, and Sarasota Airport for Only $220k! Come Enjoy SARASOTA and the Florida Lifestyle with this Affordable and Easy Maintenance home!

1930 29th Street, Sarasota

777 John Ringling Boulevard Unit 2, Sarasota
$509,900
2 Beds ⋅ 2 Baths ⋅ Sarasota Harbor East SubDv. ⋅ 34236 Zip Code
NEWLY RENOVATED BAYFRONT CONDO in Sarasota Harbor East, a desirable 55+ waterfront community ideally positioned between downtown Sarasota, St. Armands Circle and Lido Beach. This ground-floor 2-bedroom, 2-bath residence offers expansive Sarasota Bay views and the convenience of first-floor living. The beautifully renovated interior flows into an enclosed four-season glass lanai, creating a comfortable place to enjoy the waterfront setting year-round. High-impact windows and sliding glass doors provide added protection and efficiency. Community amenities include a heated bayfront pool, updated clubhouse with kitchen and library, shuffleboard, kayak and bicycle storage, a waterfront walkway, covered assigned parking and additional guest parking. The association fee includes cable, internet, water, sewer, trash and extensive exterior and community maintenance. Enjoy a WALKABLE ISLAND LOCATION near St. Armands Circle with convenient access to Lido Beach, downtown Sarasota, dining, shopping and waterfront attractions. A rare opportunity to own a renovated ground-floor residence directly on Sarasota Bay. 2.3 miles to downtown Sarasota, less than 1 mile from St. Armands, 1.5 miles to Lido Beach and approximately 3 miles from the southern end of Longboat Key.

777 John Ringling Boulevard Unit 2, Sarasota

4956 Village Gardens Drive Unit 145, Sarasota
$249,900
2 Beds ⋅ 2 Baths ⋅ Village Gardens Apt SubDv. ⋅ 34234 Zip Code
Virtually Staged. Enjoy everyday living with the feel of a tropical getaway at Village Gardens, one of Sarasota’s hidden gems. Tucked beneath a canopy of towering palms, mature oaks, ferns and lush tropical landscaping, this charming community feels like a private oasis while keeping you close to everything Sarasota has to offer. Rarely available and beautifully remodeled, this villa-style condo offers an open, inviting floor plan filled with natural light. The great room flows into a completely redesigned kitchen where modern style meets functionality. Natural granite countertops, copper hardware, a farmhouse sink, soft-close cabinetry with a Lazy Susan, gas cooktop, built-in oven and microwave, and updated appliances create a kitchen that is as functional as it is beautiful. High windows and sliding glass doors bring an abundance of natural light into the main living space and lead to one of the home's most inviting features, the enclosed lanai. Complete with air conditioning and surrounded by wall-to-wall windows, this versatile space can be enjoyed year-round as an additional sitting room, home office or reading retreat. Inside, distinctive touches including solid wood barn doors add warmth and character to the bedroom suites, while the extensive renovation gives the home a fresh, updated feel throughout. Surrounded by the natural beauty that makes Village Gardens so special, this is far more than your typical condo. It's a unique Sarasota retreat offering character, thoughtful updates and a setting that truly feels like a little piece of paradise. Move right in, add your own personal touches and make it yours.

4956 Village Gardens Drive Unit 145, Sarasota

6580 Prairie Junction Trail, Sarasota
$1,050,000
3 Beds ⋅ 3 Baths ⋅ Myakka Valley Ranches SubDv. ⋅ 34241 Zip Code
Situated at the end of a quiet cul-de-sac, this beautifully rebuilt custom home (2015) sits on 5 stunning acres and was crafted on the original slab to meet current hurricane standards. Enjoy peace of mind with impact windows and doors, metal roofs on all buildings, a 16kW standby generator fueled by a 500-gallon inground propane tank, an electronic dog door, and an attached 2-car garage. Inside, enjoy a spacious great room featuring, a remote-controlled gas fireplace, 16 feet of fully retractable sliding doors, creating effortless indoor-outdoor living during Florida’s beautiful winter months. The seamless flow to the outdoor spaces makes this home ideal for entertaining or simply relaxing in the fresh air. The entire 5-acre property is fully fenced and cross-fenced with durable 2x4 no-climb horse wire, creating safe, secure pastures ideal for horses and livestock. Mature oak trees provide shade and beauty throughout the grounds. Enjoy your private outdoor oasis featuring a screened pool and pool cage with an outdoor kitchen perfect for relaxing or entertaining. Equestrians and hobby enthusiasts will appreciate the expansive outbuildings, including: Large workshop/garage with 3 horse stalls Covered wash rack Airconditioned tack room, storage, and bonus room Covered parking for trailers, equipment, or additional vehicles Separate pole barn with an oversized horse stall A rare blend of comfort, safety, and functionality perfect for those seeking space, privacy, and well-designed amenities.

6580 Prairie Junction Trail, Sarasota

72 N School Avenue, Sarasota
$1,250,000
3 Beds ⋅ 4 Baths ⋅ Premier On Main SubDv. ⋅ 34237 Zip Code
SPACIOUS 2,762 sq ft, LIGHT-FILLED END UNIT with significant recent upgrades, an attached 2-car garage plus additional carport. Premier on Main offers comfort, quality, and all the buzzing life of Downtown in the Uptown area of Sarasota without the bustle. Flexible floor plan allows for guests, roommates, and work-from-anywhere convenience with the ease of lock-and-leave living. FEATURES: Contemporary architecture & styling, Modern color palette and superior finishes, 3 ensuite bedrooms & baths, 3.5 baths, His and Her Master Custom California Closets, Private elevator, Lockout first floor suite, 4181 Sq ft total space, 620 sq ft deck spaces, 9ft ceilings, Japandi-style wet room in primary suite, KitchenAid appliances, large island, bar-height counter + custom pantry. Rooftop deck ready for your outdoor kitchen and entertainment amenities. Turnkey, pristine condition. PREMIER PERKS: LOW HOA $446/mth(landscape, water, sewer, trash), Flood Zone X, Weekly, monthly rentals, long-term leases allowed. Pet friendly, Energy efficient systems, Impact-rated windows & doors, Security system, Whole home water filtration, On-demand gas water heater. SARASOTA LIFE ELEVATED: Year-round sunshine, outdoor living, and a walkable culture bring the best of Florida to life. This urban-convenient location is bike-friendly with direct access to the Legacy Trail or hop on the nearby Bay Runner trolley for complimentary rides through downtown to Lido Beach and St Armands Circle. Take morning runs over the John Ringling Bridge, or kayak in the bay. Stroll through Main Street’s arts and cultural district, bike to the farmer’s market or Bayfront Park. Explore the lively restaurant and music scene to find your new favorite hang outs. End your days with drinks on the rooftop, enjoying the solitude or surrounded by family & friends, above the city lights and beneath the stars.

72 N School Avenue, 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

1764 24th Street, Sarasota
$249,999
4 Beds ⋅ 2 Baths ⋅ Newtown SubDv. ⋅ 34234 Zip Code
<BACK ON THE MARKET><LAST PRICE REDUCTION> INVESTOR SPECIAL in one of Sarasota's most desirable and rapidly growing neighborhoods! This unique abandoned duplex is packed with potential and ready for its next chapter. Situated on an oversized lot and currently vacant, this versatile property presents an outstanding opportunity for investors seeking a fix-and-flip, a long-term cash-flowing rental, or an owner-occupant looking to live in one unit while generating income from the other. With strong upside and endless possibilities, this is a rare chance to add value in an area experiencing continued growth. From the moment you arrive, the property offers excellent functionality and accessibility with a spacious covered carport providing protected parking and additional covered outdoor living space. A fully fenced front yard with gated entry enhances privacy while allowing convenient street access. Each unit features its own private entrance, making the layout ideal for tenants, multigenerational living, or house hacking. A covered walkway connects both units, while the expansive front and side yards provide ample space for additional parking, outdoor entertaining, or future improvements. The simple, low-maintenance exterior creates a solid foundation for renovation while maximizing long-term investment potential. Inside, one of the units features a functional layout with an open living and dining area that flows into the kitchen, creating an efficient use of space. Durable ceramic tile flooring extends throughout the home, while the kitchen offers generous cabinet and countertop space with excellent potential for modernization. The bedrooms are comfortably sized with built-in closets, and the full bathroom includes a tub/shower combination and practical layout. An attached utility and storage room provides additional flexibility for laundry, storage, or workshop space. This unit would benefit from cosmetic updates, making it an excellent value-add opportunity to increase equity and rental income. The second unit is currently secured, and keys are not presently available; however, the entire property is vacant, and the second unit is believed to offer a substantially similar floor plan and layout. Buyers are encouraged to verify all room dimensions, features, and condition during their own due diligence. Major improvements include a brand-new roof installed in 2023, providing significant value and peace of mind. Utilities are currently off. With no HOA and no rental restrictions, this property offers exceptional flexibility for both short- and long-term investment strategies. Whether you're looking to renovate and resell, build a long-term income-producing asset, or occupy one unit while renting the other, this Sarasota duplex offers incredible potential. Property is being sold as-is.

1764 24th Street, Sarasota

3615 Egerton Circle, Sarasota
$675,000
2 Beds ⋅ 2 Baths ⋅ Beneva Park SubDv. ⋅ 34233 Zip Code
Turnkey furnished and completely remodeled, this two-bedroom plus study/den being used as a 3rd bedroom, two-bath pool home rests along a quiet cul-de-sac in Sarasota's established Beneva Park, with a deep lawn running back to the pond behind the property. The interior has been reworked with intent. Luxury vinyl plank and tile flooring run throughout, recessed lighting has been added room to room, and a custom navy slat accent wall anchors the living room. The kitchen runs the length of the home with soft gray cabinetry, bright quartz countertops, black stainless steel appliances, a deep single-basin sink beneath a garden window, and a built-in coffee and wine bar with a beverage cooler at the far end. The dining room opens through a wall of sliders to the lanai, with a navy brick fireplace and wood mantel as its focal point. Privacy defines the split plan. The primary suite sits on its own wing with a private bath and walk-in closet, while a dedicated guest bedroom, a versatile study/den, and a full bath occupy the opposite side of the home. Enter through the glass doors and the property opens up. An expansive screened lanai and pool enclosure spans approximately 1,500 square feet, with a custom pool at its center. Beyond it, the yard keeps going, running past mature shade trees and a paver fire pit area all the way to the water's edge. A covered carport with custom wood screening handles day-to-day parking, while the enclosed former garage now serves as climate-controlled flex space well suited to a home gym, media room, or private studio, with laundry adjacent. Free from HOA restrictions, the property offers room to keep a boat, RV, or trailer on site, subject to Sarasota County code. Gulf Gate Village and the Legacy Trail are minutes away, Siesta Key Beach is a short drive, and downtown Sarasota's restaurants and galleries are close enough for a spontaneous evening out. New finishes throughout. Roof 2019, AC 2020. Offered turnkey furnished.

3615 Egerton Circle, Sarasota

5063 Village Gardens Drive Unit 9, Sarasota
$225,000
2 Beds ⋅ 2 Baths ⋅ Villa Gardens SubDv. ⋅ 34234 Zip Code
Welcome to this charming 2-bedroom, 2-bath end-unit villa nestled in the lush, tropical community of Village Gardens. Offering 966 square feet of comfortable living space, this light-filled home combines privacy, convenience, and the relaxed Florida lifestyle. Step inside to an inviting open living and dining area that flows seamlessly into a bright enclosed lanai overlooking peaceful green space—the perfect spot to unwind at the end of the day. The well-appointed kitchen and in-unit washer and dryer add everyday convenience, while the split-bedroom layout provides comfort and privacy for residents and guests alike. Outside, you'll appreciate the rare double covered carport and additional storage space. Village Gardens offers an exceptional array of amenities, including a heated community pool, clubhouse, tennis and pickleball courts, and beautifully maintained grounds. Close proximity to downtown Sarasota, Sarasota-Bradenton International Airport, UTC shopping and dining, world-renowned beaches, museums, and Gulf Coast attractions, this home offers easy access to everything the area has to offer. Whether you're looking for a year-round residence, seasonal retreat, or investment opportunity, this villa delivers outstanding value in one of Sarasota's most convenient locations.

5063 Village Gardens Drive Unit 9, Sarasota

3402 Shingle Oak Terrace, Sarasota
$143,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
You WILL LOVE Where You Live! PRICE ADJUSTMENT! Charming, cozy, and move-in ready in the highly desirable 55+ gated community of Oakwood Manor, the ONLY resident-owned park within Sarasota city limits—meaning NO LOT RENT! MAJOR IMPROVEMENTS provide peace of mind for years to come. Previous updates include vinyl siding, replacement windows, and the main sewer line (2018). Recent renovations include NEW LEVELING AND SUPPORT PIERS (10/2025), all NEW SUBFLOORING THROUGHOUT the home, including the Florida room (10/2025), fresh INTERIOR PAINT, LUXURY VINYL PLANK FLOORING THROUGHOUT the main living areas, and all NEW CARPET IN BOTH BEDROOMS (11/2025), a COMPLETE NEW TPO ROOFOVER (WITH A 20 YEAR TRANSFERABLE WARRANTY) AND NEW CARPORT with ADDITIONAL TIE-DOWNS RATED UP TO 150 MPH (2/2026), NEW HVAC system, ELECTRICAL PANEL NEW and METER BASE (3/2026), a NEW REAR CONCRETE PATIO (4/2026), and a NEWLY CONSTRUCTED FRAMED VINYL-SIDED SHED (6/2026).This delightful FULLY FURNISHED 2-bedroom, 2-bath bungalow-style home is proof that great things come in the perfect-sized package. Thoughtfully updated with quality improvements throughout, this home offers a desirable split-bedroom floor plan, abundant natural light, exceptional storage, and an inviting open-concept design. The added space of the living room push-out creates the perfect area for additional living or dining space, enhancing both comfort and functionality. The beautifully updated kitchen is designed for both functionality and style, featuring a built-in cooktop, built-in oven, overhead microwave, new refrigerator, garbage disposal, and ample cabinetry—making the most of every inch of space. The spacious front guest bedroom is highlighted by a large bay window that fills the room with natural light and is complimented by an en-suite bathroom and indoor laundry with stackable washer and dryer. A fully enclosed Florida room with newer windows and sliding glass doors provides approximately 120 square feet of additional living or entertaining space and features a convenient pass-through entrance to the front bedroom and guest bath, creating flexibility for guests, hobbies, or a relaxing sitting area. Oakwood Manor is a beautifully maintained, gated 90-acre community offering an exceptional Florida lifestyle with a low $210/month maintenance fee, which includes lawn care, cable TV, access to the heated pool and spa, clubhouse amenities, and more. Residents enjoy a spacious clubhouse with a fitness room, library, billiards, commercial kitchen, event hall, stage, dance floor, and an active social calendar filled with year-round activities, clubs, shuffleboard, putt-putt, and community events. Ideally located adjacent to the Legacy Trail and Sarasota's city-managed pickleball courts. Oakwood Manor is located nearby downtown Sarasota and the sandy shores of Lido Beach is an easy drive, with convenient access to shopping, dining, Tamiami Trail, and I-75. Please note that Oakwood Manor is an age-restricted community and does not permit pets or motorcycles.

3402 Shingle Oak Terrace, Sarasota

3324 Overcup Oak Terrace, Sarasota
$289,000
3 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN & FRIENDSHIP HAPPENS BIGGER, BETTER,AND READY TO ENJOY!!! Own your piece of paradise in Oakwood Manor, Sarasota's highly desirable resident-owned 55+ community located within the city limits. Spanning 90 beautifully landscaped acres, this vibrant community offers an exceptional resort-style lifestyle with remarkably low HOA fees of just $210 a month and no CDD or master association fees. Residents enjoy an impressive array of amenities including a welcoming clubhouse with commercial kitchen and event stage, fitness center, library, heated pool, oversized hot tub, bocce ball, shuffleboard, putt-putt golf, cornhole, and ping pong. Pickleball enthusiasts will appreciate the brand-new courts located just a short bike ride away along the Legacy Trail. With an active social calendar filled with events and activities, Oakwood Manor truly lives up to its reputation—where fun and friendship happen. A Rare Find — Impeccably Maintained & Truly Move-In Ready If you've been waiting for that special home, your search ends here. Built in 2005, this beautifully maintained 3-bedroom, 2-bath residence offers 1,545 square feet of thoughtfully designed living space and is being sold turnkey. Situated within easy walking distance of the community pool and amenities, this home is genuinely move-in ready—just bring your clothes and toothbrush. From the moment you step inside, you'll appreciate the spacious open floor plan, soaring ceilings, and abundant natural light streaming through numerous windows. The gourmet kitchen is designed to impress, featuring beautiful cabinetry, generous counter space, and an inviting layout that's perfect for everyday living and entertaining. The spacious primary suite includes a walk-in closet and an en-suite bath with a double vanity and walk-in shower. A standout feature rarely found in modular homes is the drywall construction throughout the walls and ceilings in most rooms, providing the look and feel of a traditional site-built home. Recent Updates Include: • New Roof (2025) • A/C replaced (2023) • All kitchen appliances replaced (2023) • Nice Large she for plenty of storage • Inside Laundry room with Utility laundry tub • Covered Carport with plenty of space for 2 cars • Tile flooring throughout all wet areas and the laundry room • Beautiful Bahama shutters on most windows Location, Location, Location Conveniently located just minutes from downtown Sarasota, Siesta Key Beach, St. Armand's Circle, SRQ Airport, shopping, dining, and two major hospitals, this home offers the perfect combination of comfort, convenience, and Florida lifestyle. Whether you're searching for a year-round residence or the perfect seasonal retreat, this exceptional home is an opportunity you won't want to miss.

3324 Overcup Oak Terrace, Sarasota

3226 Sweet Bay Terrace, Sarasota
$148,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
You WILL LOVE Where You Live! Welcome to 3226 Sweet Bay Terrace in the highly desirable 55+ gated community of Oakwood Manor, the ONLY resident-owned manufactured home park within Sarasota city limits—meaning NO LOT RENT! This well-maintained 2-bedroom, 2-bathroom home offers seamless laminate flooring throughout the main living areas, kitchen, and bedrooms, creating a clean, cohesive look that's both stylish and easy to maintain. Enjoy added peace of mind with a June 2026 FULL ROOF RESTORATION, featuring a silicone roofing system over the existing metal pan roof and backed by a 10-YEAR TRANSFERABLE WARRANTY. Additional updates include a newer carport with upgraded tie-downs rated up to 150 mph (2017), HVAC (2016), and water heater (2011). Best of all, the home experienced no damage from the 2024 storms. Furnishings include, but are not limited to, a full-size bed in the primary bedroom, two twin beds in the guest bedroom, dining table and chairs, living room sofa, side table, TV stand with TV, chair with ottoman, some FL room/Lanai furniture, and an equipped kitchen with items needed for everyday living. The additional 8x12 shed provides for ample storage and utility space. Oakwood Manor is a beautifully maintained, gated 90-acre community offering an exceptional Florida lifestyle with a low $210/month maintenance fee, which includes lawn care, cable TV, access to the heated pool and spa, clubhouse amenities, and more. Residents enjoy a spacious clubhouse with a fitness room, library, billiards, commercial kitchen, event hall, stage, dance floor, and an active social calendar filled with year-round activities, clubs, shuffleboard, putt-putt, and community events. Ideally located adjacent to the Legacy Trail and Sarasota's city-managed pickleball courts. Oakwood Manor is located nearby downtown Sarasota and the sandy shores of Lido Beach is an easy drive, with convenient access to shopping, dining, Tamiami Trail, and I-75. Please note that Oakwood Manor is an age-restricted community and does not permit pets or motorcycles. Don't miss this opportunity to own an affordable home in one of Sarasota's most unique and sought-after resident-owned communities!

3226 Sweet Bay Terrace, Sarasota

330 Crosby Court, Sarasota
$349,900
3 Beds ⋅ 1 Baths ⋅ Melody Heights SubDv. ⋅ 34237 Zip Code
Virtually Staged. One or more photos have been virtually staged. Positioned in one of 34237’s most desirable and high-upside pockets, this 3-bedroom home offers the ultimate central lifestyle. Located just minutes from the quartz sands of Siesta Key Beach, the vibrant Downtown Arts District, Selby Gardens, and the Sarasota Memorial corridor, this mid-century block home perfectly balances character, location, and opportunity. Beyond the peace of mind of a newer roof, the residence showcases timeless mid-century elements, anchored by beautiful, seamless terrazzo flooring and striking exposed beam ceilings. The floor plan flows effortlessly, beginning with a curated kitchen that embraces its mid-century roots with bold turquoise cabinetry, stainless steel appliances, and a French-door refrigerator. The kitchen opens directly to an inviting dining area, while the neutral, sunlit living room provides an ideal layout for effortless entertaining or relaxed everyday living. The primary suite is bathed in natural Florida light through dual windows, balanced by a classic accent tone that adds distinct character. The third bedroom offers complete flexibility as a dedicated executive office, creative studio, or fitness space. A classic, pristine bathroom features a generous vanity and a deep tub/shower combination. For quiet moments, a versatile bonus room serves as a sun-drenched reading nook or a seamless bridge to the outdoors. Practicality meets lifestyle with a dedicated interior laundry and utility room equipped with built-in storage. Outside, the property transforms into a private tropical retreat, complete with mature landscaping, curated garden beds, and a substantial storage shed perfectly sized for your beach gear, e-bikes, and tools. With local farmers markets, neighborhood cafés, and cultural venues just around the corner—plus swift access to US-41, I-75, and SRQ Airport—this property is a rare find. Whether envisioned as a stylish primary residence, a seasonal getaway, or a short-term rental asset, this home delivers the quintessential Sarasota lifestyle at an increasingly rare price point. This kind of opportunity in central Sarasota doesn't sit long. Let's get you in for a private showing.

330 Crosby Court, 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

4111 Sarasota Avenue, Sarasota
$419,900
2 Beds ⋅ 1 Baths ⋅ Indian Beach Map Of SubDv. ⋅ 34234 Zip Code
Now offered at a compelling new price of $419,900, this is your chance to move into the coveted Sapphire Shores neighborhood at an incredible value. This well-maintained home blends modern style with the laid-back charm of Sarasota living. Inside, the kitchen steals the show with sleek quartz countertops and premium GE Café appliances in a elegant matte finish—a setup that’s as functional as it is beautiful. Warm wood laminate flooring flows through the main living spaces, giving the home a fresh, contemporary feel that’s easy to maintain. The outdoor space is a true blank canvas. With a fully fenced yard already in place, there’s plenty of privacy for weekend hangouts, and more than enough room to put in a pool or design the tropical garden of your dreams. Just down the street, you can catch some of the best sunsets in the city at Sun Circle Park, or take a quick drive to the vibrant energy of Downtown Sarasota for world-class dining, shopping, and arts. Whether you’re looking for a stylish primary residence or a savvy investment in a prime location, this price improvement makes it a must-see. Roof 2018, A/C 2016, Water Heater 2020, Fence 2020.

4111 Sarasota Avenue, Sarasota

1610 22nd Street, Sarasota
$429,000
5 Beds ⋅ 2 Baths ⋅ Newtown SubDv. ⋅ 34234 Zip Code
This well-maintained duplex is ideally situated just minutes from the airport, downtown Sarasota, and the area’s world-renowned beaches. The property features two separately metered units, offering strong rental appeal and ease of management: Unit 1: 3 bedrooms, 1 bathroom Unit 2: 2 bedrooms, 1 bathroom Both units are tenant-occupied with long-term leases in place, generating a gross monthly rent of $3,350. Tenants pay their own water and electric, keeping operating expenses low for the owner. Situated on a desirable corner lot, the property also includes laundry hookups for added tenant convenience. Major updates have already been completed, providing peace of mind for investors: Newer roof Updated central A/C units Upgraded electrical and plumbing systems Unique Financing Opportunity: The seller is open to creative financing options and currently has a mortgage on the property, making this an excellent opportunity for buyers seeking flexible terms.

1610 22nd Street, Sarasota

209 Garfield Drive, Sarasota
$3,750,000
6 Beds ⋅ 7 Baths ⋅ Lido Beach SubDv. ⋅ 34236 Zip Code
There is only one – Shore Thing. Confident in name and effortless in design, Shore Thing captures the essence of coastal living with a refined, modern ease. Positioned a short stroll from the Lido Key’s beautiful beach with sweeping Gulf views, the residence blends natural textures, soft whites, and hues of blue to create a palette that feels both relaxed and elevated. Wicker accents, warm wood tones, and subtle gold finishes throughout the kitchen and baths introduce a layer of understated luxury that is both current and timeless. Designed for gathering across multiple levels, the home offers over 4,000 square feet of thoughtfully composed living space. The main living level features a fully equipped chef’s kitchen, expansive dining and living areas, and seamless access to a balcony for indoor-outdoor flow. Six bedrooms, including multiple en-suite retreats and custom bunk accommodations, provide flexibility for hosting family and guests with ease. A secondary club level introduces an additional living space complete with wet bar, gaming, and access to an upper terrace with panoramic views of the Gulf of Mexico, Lido Key, and downtown Sarasota. The rooftop deck offers a quiet vantage point for sunrise and sunset, reinforcing the home’s connection to its coastal surroundings. At ground level, the outdoor experience is equally considered — a resort-style pool and spa, covered patio with dining and lounge seating, outdoor grill, and recreational elements including ping pong create a private setting designed for both relaxation and entertainment. Ample parking, beach gear storage, and thoughtful utility spaces enhance everyday functionality. Playful in spirit yet composed in execution, Shore Thing is a residence that delivers exactly what its name suggests — a coastal experience that feels both certain and exceptional. This residence, teeming with innovative engineering and durable materials, is built to withstand coastal elements and the vibrancy of large gatherings and festive coastal vacations. More than a home, Shore Thing is part of an exclusive Vunique collection with a proven history of strong rental performance — each residence one-of-one, purpose-built to balance bold design and bespoke experience. Here, ownership transcends address; it becomes a mark of belonging to something beautifully uncommon. Furnishings available under a separate bill of sale.

209 Garfield Drive, Sarasota

3319 Overcup Oak Terrace, Sarasota
$199,500
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Big Price Adjustment made to allow for upgrades. This home combines convenience and style in a welcoming well-maintained and vibrant gated community. ABOUT THE HOME: This beautifully designed 2008 Manufactured home has 1,278 sf of living space and an ideal layout with the 2-bedroom 2 bath split floor plan offering both privacy and comfort, featuring a spacious living room with high ceilings and windows, perfect for relaxing or entertaining. The home includes a formal dining area with an oval dining set and a large kitchen with ample cabinets and a tile backsplash, pantry, refrigerator, stove, dishwasher and garbage disposal, complemented by a cozy breakfast dinette with a round table and seating for 4, a mounted flat screen TV and a sliding glass door leading to the carport—an ideal space for casual dining, games or working a puzzle. Just off the breakfast dinette are the full sized washer and dryer housed in a laundry closet. The large primary suite serves as a private retreat with a king bed, chest drawers, desk and walk in closet. This space is complete with an expansive en suite bathroom featuring dual sinks, a walk-in shower and WC nook. Sky lights in both bathrooms provide natural lighting. The large carport is roomy enough for 2 vehicles and/or an outdoor covered living area. The shed provides extra storage space. Home is partially furnished. Shingle roof replaced 1/2024 - Drywall in Living, Dining, and both Bedrooms ABOUT THE COMMUNITY: Oakwood Manor is located in the ONLY Resident Owned Park in the City limits of Sarasota!! The gated 90 acre community boasts a low maintenance fee of $210/month - affording a big "bang for your buck" with its vast amenities, starting 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 and 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 shuffle board courts, putt putt course, bocce ball, ping pong and corn hole. Please note that Oakwood is a 55+, no pet, no motorcycle Park. AREA INTEREST: 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 hospitals.

3319 Overcup Oak Terrace, 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

3332 Spanish Oak Terrace, Sarasota
$69,900
2 Beds ⋅ 1 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Looking for a space to INSTALL A NEW HOME in a RESORT STYLE COMMUNITY? Well look no further!! This lot is priced to sell and located in a beautiful centrally located gated community close to downtown Sarasota. LOT SIZE 50 x 80.5 / BUILDABLE SPACE 40 X 60.5 / no impeding trees. Home is being sold at lot value - home is a tear down - no interior access - showings are for lot and location only. Seller reserves the right to remove all appliances, furniture, fixtures, cabinets, personal items, etc prior to closing Buyer's developer to clear the lot and prep for Buyer's new home install. Located in the ONLY Resident Owned Park in the City limits of Sarasota!! The gated 90 acre community boasts a low maintenance fee with its vast amenities, starting 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 and 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 hospitals. Please note that Oakwood is a 55+, no pet, no motorcycle Park.

3332 Spanish Oak Terrace, Sarasota

703 Whitfield Avenue, Sarasota
$699,000
2 Beds ⋅ 4 Baths ⋅ Whitfield Country Club Estates SubDv. ⋅ 34243 Zip Code
Appraised at 750k this completely remodeled home over 375k spent up to an exceptional standard with expansive views of Sara Bay Golf Club. The home sits on a .38-acre lot and has a large completely enclosed swimming pool. Outdoor entertaining is a breeze with the indoor-outdoor patio accessed through expansive sliding doors. The kitchen designed for the chef of the family has stainless steel appliances along with Cambria quartz countertops with waterfall edges. Adjacent to the chef's kitchen is a separate wine and coffee area with built in wine fridge for your evening glass. The Primary bedroom features a huge his and hers closet along with a primary bathroom that has a soaking tub and dual outlet steam shower for your relaxation. The guest bedroom also has a contemporary feel along with walk in shower. All landscaping has been professionally installed and water for the exterior is fed from underground well water. There is also a new exterior shed for your belongings. The roof was replaced in 2023 and the attic completely insulated with closed cell foam insulation in the roof. Quick and easy access to Lido Beach, St. Armands Circle and downtown Sarasota, with UTC, Longboat Key and Anna Maria Island close by as well! Only one mile to Sarasota Bay but not in flood zone (Zone X). Gas is available with new meter. This house must be seen it will not disappoint. Bedroom Closet Type: Walk-in Closet. Owner financing available. Terms TBA

703 Whitfield Avenue, Sarasota

3410 Spanish Oak Terrace, Sarasota
$155,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Welcome to this beautifully maintained two bedroom, two bath sanctuary—perfect for your second home or retirement dreams. Begin your mornings on the spacious enclosed front lanai, savoring your coffee and the serene surroundings. This charming home features an open floor plan with a bright and airy living room, ideal for entertaining guests or unwinding after a day of activities. The modern kitchen boasts ample counter space and a cozy breakfast nook, making meal prep a delight. The master bedroom offers a peaceful retreat with an en-suite bathroom and a walk-in closet, while the second bedroom is perfect for guests or a home office. You’ll appreciate the convenience of plenty of parking under the carport and a full-size laundry in the shed at the back of the carport. Nestled in the vibrant, gated 90-acre Oakwood Manor community—the only land-owned manufactured home community in the City of Sarasota—this home is a treasure trove of amenities designed to enrich your lifestyle. For a reasonable monthly fee of $210, enjoy a large clubhouse with a commercial kitchen, event stage, fitness room, cozy library, and more. Unwind in the heated pool with a handicap ramp, relax in the spacious hot tub, or partake in outdoor activities like bocce ball, ping pong, and picnicking under beautiful oak trees. This age-restricted social haven is conveniently located next to the scenic Legacy Trail and city pickleball courts. Just a short trip from downtown Sarasota, stylish St. Armands Circle, and the world-renowned Siesta Key Beach, this community offers the ultimate in Florida living. Live where others vacation and make every day a delightful adventure! Please note, no pets or motorcycles are allowed. Come embrace the fun, active lifestyle you’ve always dreamed of!

3410 Spanish Oak Terrace, Sarasota

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