Osprey/Nokomis Homes under $500,000

Osprey/Nokomis Homes under $500,000

Welcome to the serene and picturesque communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. These charming towns boast a perfect blend of coastal beauty, rich history, and vibrant local culture, making them an ideal destination for those seeking a laid-back lifestyle by the Gulf of Mexico.

Osprey is known for its lush landscapes and stunning waterfront views, providing residents with a tranquil escape from the hustle and bustle of city life. Here, you can explore the scenic trails of the Oscar Scherer State Park or indulge in a day of sun and sand at nearby Nokomis Beach. The area is also home to a variety of boutique shops, delightful dining options, and cultural attractions, such as the historic Spanish Point, which offers a glimpse into the region's rich heritage.

Nokomis, just a stone's throw away, is equally enchanting. With its friendly atmosphere and beautiful parks, it’s a great place for families and retirees alike. The community hosts various events throughout the year, fostering a strong sense of camaraderie among residents.

For those seeking to make Osprey or Nokomis their home, there are fantastic opportunities available with homes priced under $500,000. Whether you’re looking for a cozy bungalow, a charming single-family home, or a maintenance-free villa, you’ll find a variety of options that suit your lifestyle and budget. Embrace the Florida dream and discover the perfect home in these delightful communities, where every day feels like a vacation. Let Osprey and Nokomis welcome you with open arms!

Newest Osprey/Nokomis Homes under $500,000

120 Villa Drive Unit 120, Osprey
$465,000
2 Beds ⋅ 2 Baths ⋅ Sorrento Villas SubDv. ⋅ 34229 Zip Code
FULLY FURNISHED WATERFRONT VILLA • PRIVATE DOCK WITH 10,000-LB BOAT LIFT • NO FIXED BRIDGES • DIRECT ACCESS TO THE INTRACOASTAL WATERWAY & GULF OF AMERICA! BRING YOUR BOAT AND START LIVING THE FLORIDA WATERFRONT LIFESTYLE! Welcome to this fully furnished, 2-bedroom, 2-bath waterfront villa in Sorrento Villas, offering an exceptional boating opportunity with NO FIXED BRIDGES between your private dock and the Intracoastal Waterway! Featuring a private dock, 10,000-lb boat lift and unobstructed bridge clearance to the ICW, this property is especially appealing to boating enthusiasts seeking convenient access for larger vessels. Cruise the Intracoastal Waterway, head into the Gulf of America, explore Siesta Key and Midnight Pass, or spend the afternoon discovering waterfront restaurants and nearby coastal destinations. With your boat just steps from your back door, the Florida boating lifestyle is yours to enjoy! Inside, discover 1,404 square feet of inviting living space, offered FULLY FURNISHED for a convenient, turnkey transition to waterfront living. The open floor plan features tile flooring, a spacious living area and an updated kitchen with wood cabinetry, granite countertops, stainless steel appliances, a large island and an extended breakfast bar. A natural stone accent wall adds character, while expansive windows and glass doors fill the living areas with natural light and showcase the waterfront setting. Outdoor living is where this property truly shines! Step onto your screened lanai and enjoy peaceful canal views, tropical landscaping and the coastal breeze. Just beyond the lanai, a limestone walkway leads to your waterfront patio and private dock, creating an inviting setting for morning coffee, afternoon relaxation or evening conversations overlooking the water. Boating enthusiasts will appreciate the updated dock, 10,000-lb boat lift, dedicated fish-cleaning station and updated water and electrical connections. The dock approach has also been raised with additional cement. Numerous improvements include a new electrical panel and breakers, new lanai screening, rain gutters, updated landscaping, a new garage door motor, track and keypad, luxury vinyl plank flooring in the primary bedroom and an updated kitchen faucet. Additional features include hurricane shutters, a tile roof installed in 2009, an A/C system installed in 2015 and an attached garage. Ideally located in Osprey between Sarasota and Venice, this waterfront retreat offers convenient access to Siesta Key, Nokomis Beach, Oscar Scherer State Park, shopping, dining and outdoor recreation. FULLY FURNISHED AND READY FOR YOUR NEXT CHAPTER! With no fixed bridges to the Intracoastal Waterway, direct boating access to the Gulf of America, a private dock and a 10,000-lb boat lift, this property offers the freedom to explore Southwest Florida's waterways right from your backyard. YOUR BOAT. YOUR DOCK. YOUR GATEWAY TO THE GULF!

120 Villa Drive Unit 120, Osprey
2104 Tocobaga Lane, Nokomis
$494,000
3 Beds ⋅ 2 Baths ⋅ Calusa Lakes SubDv. ⋅ 34275 Zip Code
Pack your bags and start living the Florida lifestyle! This beautifully UPDATED and TURNKEY FURNISHED 3-bedroom, 2-bath home in the exclusive gated community of Calusa Lakes is ready for you to simply move in and enjoy. Nestled in the sought-after Woodland Trails neighborhood, Calusa Lakes boasts 460 acres of lush landscaping and 28 picturesque lakes. This light and inviting home features an open-concept living area, versatile den currently used as a dining room, dedicated laundry room, and spacious screened lanai designed for effortless indoor-outdoor living. Disappearing sliders from the living area, breakfast nook and primary suite open to the lanai, creating the perfect setting for morning coffee or relaxed Florida evenings. Recent updates include a 2017 tile roof, fresh interior paint, updated tile flooring, new baseboards, modern lighting, new kitchen sink and faucet, and updated exterior lighting. A side-entry garage, extended driveway, lawn maintenance included, and location just steps from the community pool add to the easy-living appeal. Calusa Lakes offers a guard house, tennis and pickleball courts, an 18-hole regulation-length semiprivate golf course, countless activities, and the Calusa Clubhouse restaurant available to all residents. Optional Golf Club membership is available. Ideally located near Nokomis Beach, Oscar Scherer State Park, Legacy Trail, shopping, dining, and Sarasota Memorial Hospital, this is Florida living made easy—beautifully furnished, thoughtfully updated, and ready when you are!

2104 Tocobaga Lane, Nokomis
145 Edgewood Drive, Osprey
$175,000
2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code
Discover comfortable Florida living in this charming 2-bedroom, 2-bath manufactured home ideally located in Osprey’s popular Arbors community. Positioned on a spacious corner lot, this inviting residence features a bright, open layout with the living room flowing naturally into the dining area and kitchen. A standout feature is the beautifully renovated enclosed front porch, complete with hurricane-impact windows—an ideal spot for morning coffee, relaxing, or enjoying the Florida sunshine year-round. The updated light and bright kitchen adds a fresh, clean feel, while a covered one-car carport and convenient storage shed provide practical storage and parking. Residents of The Arbors enjoy an active community lifestyle with a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area, and a variety of social activities. Conveniently located between Sarasota and Venice, you’re close to shopping, dining, entertainment, performing arts, and the Gulf beaches. A great opportunity to enjoy an easygoing Florida lifestyle in a welcoming Osprey community!

145 Edgewood Drive, Osprey
717 Pine Run Dr. Unit 717, Osprey
$159,900
1 Beds ⋅ 1 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Ready for your own slice of Florida paradise? This fully furnished, turnkey one-bedroom condo in Osprey’s Pine Run community is ready to welcome you home. Its second-floor setting offers a charming treehouse feel, surrounded by the community’s lush, natural landscape. Well cared for and thoughtfully updated, this condo features BRAND-NEW A/C (SEPTEMBER 2026), A NEW TANKLESS WATER HEATER (2025), AND A NEW HURRICANE-RATED SLIDING GLASS ENTRY DOOR (2022). Soaring ceilings and three sliding glass doors fill the open living and updated kitchen area with natural light, creating a bright, airy atmosphere. The screened balcony is an inviting spot for morning coffee or relaxing at the end of the day. A carport space directly below the condo provides convenient covered parking, along with an oversized storage closet. Whether you’re purchasing your first Florida home, downsizing, or looking for a winter retreat, this condo offers comfortable, easy living. Shopping and restaurants are within easy walking distance, with the local favorite Casey Key Fish House and Tiki Bar just down the street, along with the Intracoastal Waterway. Nearby Blackburn Point Park and its boat launch offer even more ways to enjoy the outdoors. Pine Runs’ amenities include pickleball and tennis courts, two pools, a community clubhouse, and a fitness area - all nestled within a lush, natural setting. Come take a look and picture yourself enjoying the Florida Lifestyle!

717 Pine Run Dr. Unit 717, Osprey
206 Brigantine Way Unit 206, Nokomis
$254,900
2 Beds ⋅ 2 Baths ⋅ Fairwinds Village SubDv. ⋅ 34275 Zip Code
Welcome Home to your beautifully updated 2 bedroom villa in the highly coveted Fairwinds Village. With a waterfront Clubhouse within an active and welcoming 55+ community boasting with first class amenities. Imagine... living in a maintenance free, pet friendly home close to Nokomis and Venice Beaches, restaurants, shopping, entertainment and so much more. This villa is located within a quiet cul de sac just steps from the Clubhouse, a waterfront park and all the amenities Fairwinds have to offer. Check out the new kitchen boasting new stainless steel appliances, white shaker style cabinets, quartz counters, and pantry. New light plank style luxury vinyl flooring and newly painted walls throughout the home creates a continuous open and coastal feel including a bright and airy 4-season glass room for entertaining or simply relaxing. A spacious Owners Suite with “3” closets and a nicely appointed spa inspired bath with large quartz topped vanity and a marble inspired tile surrounding the tub-shower combination. The guest room is peaceful and welcoming to your guests with a bright and comfortable bath nearby hosting a glass enclosed shower with marble inspired tile. The private laundry just steps outside the kitchen makes handling this task with ease. Covered parking with a separate entry into the kitchen brings ease to shopping days. FairWinds Village is a community situated directly on a canal that leads to Lyons Bay and the Intercoastal. A first class Active Community Clubhouse includes a full service kitchen for community events, private rentals and is next to the shuffleboard and bocce ball courts. Best of all, you are near the local marina that offers boat rentals and waterfront dining. The docks can be sub-leased or may be available from the Association directly on a first come - first served basis. The community also offers kayak/canoe racks and a launching area, next to the waterfront park and picnic areas. There is plenty of guest parking and many organized activities and community events. Don’t let this opportunity pass you by. This community is highly sought after and rarely available. Today is the day…

206 Brigantine Way Unit 206, Nokomis
7303 Jessie Harbor Drive Unit 7303, Osprey
$449,000
3 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.

7303 Jessie Harbor Drive Unit 7303, Osprey
1112 Sunset Avenue, Nokomis
$279,000
2 Beds ⋅ 2 Baths ⋅ From A Pt 25 Ft E Of Nw Cor Of Sw 1/4 Of Se 1/4 Of SubDv. ⋅ 34275 Zip Code
Discover the charm of coastal living in this beautifully updated 2-bedroom, 2-bath home, located just 3 miles from historic Downtown Venice & 2.1m to Nokomis' beautiful sandy beaches! Thoughtfully remodeled and move-in ready, the home features a desirable split-bedroom floor plan, offering comfort and privacy for residents and guests alike. Both rooms feature walk in closets for plenty of storage. Step outside to your own private retreat, where a fully fenced yard wraps around a serene outdoor space that includes a covered patio and outdoor kitchen perfect for entertaining. The property experienced no flooding during recent hurricanes, peace of mind for Florida homeowners! Outdoor enthusiasts will appreciate being just one block from the well known Legacy Bike Trail, while the Gulf beaches, local restaurants, boutique shopping, and everyday conveniences are all within easy reach. Perfectly positioned between the beach and I-75, this home combines the relaxed Venice lifestyle with an incredibly convenient location.

1112 Sunset Avenue, Nokomis
203 Rubens Drive Unit F, Nokomis
$135,000
2 Beds ⋅ 2 Baths ⋅ Sorrento Park SubDv. ⋅ 34275 Zip Code
Welcome to relaxed Gulf Coast living in this spacious, move-in-ready second-floor condo, beautifully positioned beside the natural landscape of Oscar Scherer State Park. A private screened front porch creates a welcoming entrance and includes a convenient laundry and storage closet with shelving. Inside, the light-filled layout offers two bedrooms and two full bathrooms, including a primary suite with an en-suite bath and walk-in closet. The main living area opens to an impressive 26-by-8-foot screened lanai with peaceful preserve views—an inviting place to enjoy morning coffee, watch Florida wildlife, entertain friends, or simply unwind. Sliding enclosure panels add flexibility for seasonal enjoyment. Thoughtful updates and practical features include a Comfortmaker HVAC system installed in June 2023 with a warranty reported by the owner through June 2033, along with a washer and dryer from 2024. The building received a new roof in 2025, according to Sarasota County permit records. Generous storage includes a large closet on the rear lanai, additional shelving in the front-porch laundry closet, and a spacious padlocked storage closet attached to the assigned carport. Residents also enjoy access to the community pool. The entrance to Oscar Scherer State Park is just a short bicycle ride away, with the Legacy Trail only a little farther. Nokomis Beach and Casey Key are approximately 8–10 minutes away, along with popular waterfront dining at Pop’s Sunset Grill and Deep Lagoon Seafood & Oyster House. Historic Downtown Venice is approximately 12 minutes away, and Sarasota Memorial Hospital–Venice is approximately 10 minutes away. Convenient access to U.S. 41 and I-75 makes Sarasota, Siesta Key, and Sarasota Bradenton International Airport—approximately 30–35 minutes away—easy to reach. Come experience the peaceful preserve setting, generous living space, exceptional storage, and convenient Nokomis lifestyle. Schedule your private showing today.

203 Rubens Drive Unit F, Nokomis
5695 Archipelago Street, Nokomis
$324,900
3 Beds ⋅ 3 Baths ⋅ Palmero SubDv. ⋅ 34275 Zip Code
Don't miss this exceptional opportunity to own an immaculate 3 bedroom, 2.5 bath townhome on a sought-after waterfront lot with a southern exposure that ensures abundant natural light throughout the day. This newly built townhome has been freshly painted and features new carpet, making it truly move-in ready. The kitchen stands out with its light gray shaker-style cabinets, stainless steel appliances, quartz countertops, a large center island, and a spacious walk-in pantry. It flows seamlessly into the living and dining area, making it perfect for entertaining. Additional storage is conveniently located under the stairs. All bedrooms are thoughtfully positioned upstairs, including a primary suite that provides stunning views of the serene pond. With a walk-in closet and an en-suite bath, this space is designed for comfort and convenience. An attached one-car garage adds extra storage and accessibility. Step outside onto the rear patio to enjoy sunshine and peaceful water views, or take full advantage of Palmero's outstanding resort-style amenities just a short walk away. Palmero is a gated community with low HOA fees and no CDD fees. Residents enjoy a community pool and spa, splash pad, fire pit, volleyball and basketball courts, playground, and dog park. The community location provides easy access to the pristine Suncoast beaches, Sarasota, downtown Venice Island, and I-75. Palmero is the ideal choice for those seeking a vibrant, amenity-rich Florida lifestyle while remaining close to all that the area has to offer. Whether you're searching for a full-time residence or a seasonal Florida retreat, this move-in-ready townhome represents the perfect fusion of location, convenience, and coastal living. Call us today for your private showing.

5695 Archipelago Street, Nokomis
313 Palestro Street, Nokomis
$380,000
3 Beds ⋅ 2 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code
Mrs. Clean lives here. Immaculately maintained...like new... just two years old, this home shows the care of an owner who takes pride in every detail. Quartz countertops, upgraded lighting, ceiling fans, and wood-look slate blinds add style throughout. Luxury vinyl flooring finishes two bedrooms, while tile runs through the remaining living areas and den. The primary bedroom also features insulated cellular shades.~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Outside, mature landscaping and fresh St. Augustine sod give the home a welcoming look. The backyard is fully fenced for dogs, but can be removed. Under-soffit lighting adds an evening glow, and the lanai has its own ceiling fan. The home also includes A Full House Water Softener, Water Purification System, an additional 3rd outdoor spigot, and conveniently placed exterior outlets for holiday and landscape lighting.~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Even the garage has been thoughtfully finished, with a utility sink, upper cabinet, Polyurethane-Coated Floor, overhead storage, and added shelving. Additional shelving in the closets and pantry, plus an outlet in the air-handler room for charging a vacuum, make everyday organization easier. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Toscana Isles adds a resort-style setting to all those thoughtful upgrades. This gated neighborhood offers a clubhouse, an infinity-edge pool, fitness center, tennis and pickleball courts, bocce, a dog park, and a kayak launch. Whether you’d rather spend an afternoon on the water or relax by the pool, there’s plenty to enjoy close to home.

313 Palestro Street, Nokomis
142 2nd Avenue, Nokomis
$429,000
3 Beds ⋅ 2 Baths ⋅ Springhill Park SubDv. ⋅ 34275 Zip Code
This 3 bedroom, 2 bath Florida cottage gives you the kind of space, character and freedom that is getting harder to find, with a large private pool, NO HOA, a spacious fully fenced yard and a 472 square foot workshop, all conveniently located between Sarasota and Venice. It is comfortable, flexible and full of personality, with room to relax, entertain, work on projects and make the home completely your own. Inside, the split floor plan gives the primary suite separation from the second and third bedrooms while keeping the home easy and connected. The kitchen work completed in 2023 included tile flooring, backsplash, custom countertops and a dry bar, giving the space warmth and character that fits the Florida cottage feel. The primary bedroom features luxury vinyl plank flooring, trim molding, a smart fan/light and a walk-in closet. The ensuite includes tile flooring, a tiled shower and wall surround, vanity, fixtures and hardware. The second and third bedrooms and guest bath also received improvements, and the bonus room gives you another place to show your own style, whether that means a home office, guest space, reading room, craft room or something entirely your own. Then there is the 472 square foot workshop. This is not just extra storage. It is real space for hobbies, tools, equipment and projects, and for buyers who have ever wished for room to actually do the things they enjoy, this may be one of the features they love most about the property. Once you walk into the backyard, you may not want to leave. The large private pool was resurfaced in 2022 and retiled in 2025, with plenty of surrounding space for lounging, entertaining or simply enjoying a quiet Florida afternoon. The 6 foot fence creates privacy, while tropical landscaping and fruit producing trees make the space feel lush and lived in, including a lime tree now producing fresh limes. The outdoor shower is perfect after a swim or a day at the beach, and a repaired well pump supplies a dedicated hose near the pool with well water for landscaping and plants. This home also has plenty of substance behind the charm. A 24-gauge metal roof with hurricane straps was installed in 2022, and the 5 ton HVAC system with UV light and replacement ductwork dates to 2020. Septic components, including the tank, leach field and lift station, were replaced in 2019, and the system was most recently serviced in July 2026. A 50 amp whole house generator outlet was added in 2024, and the backyard fence was re-stained in 2025. From here, everyday can feel like a getaway. Nokomis Beach and the Legacy Trail are each approximately 3 miles away, Oscar Scherer State Park is about 5 miles away, and Downtown Venice is approximately 5.6 miles from home. Sarasota and Siesta Key are also within easy reach, along with golf, boating, dining, shopping and multiple Gulf Coast beaches. Updates & Features This is the kind of home that lets you bring your own style to it. Enjoy the pool, fill the workshop with the projects you have been waiting to start, turn the bonus room into the space you actually need, plant more, entertain more, spend more time outside and enjoy having the freedom to use your home your way.

142 2nd Avenue, Nokomis
100 Circuit Road Unit S-7, Nokomis
$37,000
Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code
This premium marina dock slip offers the ultimate combination of convenience, top-tier service, and immediate deep-water access. Slip S-7 is 40L x 10W X 8.5H, and can suit a vessel that is 39L X 9W X 7.5H and is located on the top middle rack in the South building. Gulf Harbor Marina is situated in a prime location just 10 minutes from the Venice Jetty and the I-75 corridor, this full-service marina boasts No Fixed Bridges to the Gulf pathway, making it a boater's dream. Environmental excellence and peace of mind come standard, as the facility proudly holds both Clean Marina and Clean Boatyard Designations. Property management is highly cost-effective with low monthly administrative charges, while the facility stays open 7 days a week to serve you. Your boating lifestyle is fully supported by an impressive suite of on-site amenities and professional care. Unmatched Convenience: Enjoy unlimited splashes a month powered by large capacity fork trucks, alongside dedicated boat wash racks, a fish station, and a flush service. Fuel & Supplies: Access discounted fuel sales for owners and tenants, with ice, live shrimp, and frozen bait available right at the fuel dock. There are several covered self service bays to work on your vessel with water and electric provided. Attached to the marina is a service shop if you choose to hire a technician to work on your boat as well as a parts supply shop to prick up any boat or motor parts you might need. Gulf Harbor Marina is located adjacent to two waterfront restaurants and just moments from a county park, public beach, and a public boat ramp. Experience stress-free boating backed by award-winning service in a location that puts the open ocean minutes from your slip.

100 Circuit Road Unit S-7, Nokomis
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