Oldsmar Homes with Sidewalks Community Features

Oldsmar Homes with Sidewalks Community Features

Welcome to Oldsmar, Florida—a hidden gem nestled within the picturesque Pinellas County. This charming city, located just a stone's throw from the stunning Gulf Coast, offers residents a unique blend of suburban tranquility and vibrant community life. With its rich history dating back to the early 1900s, Oldsmar boasts a delightful small-town atmosphere, complemented by modern amenities and recreational opportunities.

One of the standout features of Oldsmar is its commitment to creating a walkable community. Homes with sidewalks are a hallmark of the area, inviting residents to take leisurely strolls through tree-lined streets, enjoy morning jogs, or engage in friendly conversations with neighbors. The sidewalks not only promote a healthy lifestyle but also foster a sense of community, making it easy for families and friends to connect.

Oldsmar is home to an array of parks, including the scenic Oldsmar Park and the expansive Mobbly Bayou Wilderness Preserve, where outdoor enthusiasts can explore nature trails, picnic areas, and serene waterfront views. The city's vibrant downtown area features charming shops, delightful eateries, and local events that bring residents together throughout the year.

Whether you're a first-time homebuyer or looking to settle into a peaceful community, Oldsmar offers a perfect blend of comfort, convenience, and charm. With its homes featuring sidewalks and a strong sense of community, you’ll find that Oldsmar is not just a place to live, but a place to thrive. Come and discover why so many are proud to call Oldsmar home!

Newest Oldsmar Homes with Sidewalks Community Features

1334 Fallsmeade Court, Oldsmar
$899,000
3 Beds ⋅ 3 Baths ⋅ Aberdeen Unit Two SubDv. ⋅ 34677 Zip Code
Luxury, privacy and breathtaking water views come together exceptionally in this home located in the desirable subdivision of Aberdeen in the gated golf community of East Lake Woodlands. Nestled on a cul de sac and perfectly positioned to be set back and angled from other homes, this residence affords real privacy. An approximately 200-foot-deep lot with neighbors on only one side along with an extended driveway gives the feeling of your own resort-style retreat - and it's Zone X which does not require flood insurance. From its striking architecture and stone-accented columns, this stunning three-bedroom-plus-office, two-and-a-half-bath, three-car garage home offers an impressive blend of elegance and thoughtful design. Step inside through the elegant double-glass entry doors and travertine foyer and immediately enjoy serene views extending through the home to the pool and water beyond. Soaring ceilings, crown molding and beautiful hardwood flooring create a memorable impression. Located at the front of the home, the office or den exudes an elegant, comfortable style and is highly versatile with ample room for a home office, den, exercise room or other possibilities. Inviting describes the dining room with warm natural light, exquisite chandelier and open flow to the living room so perfect for gatherings. French doors from the living room, breakfast area and primary suite provide an effortless connection to the covered lanai and private backyard retreat. The well-appointed kitchen features custom wood cabinetry including built-in glass display cabinets with serving space, a center island with bar seating and copper vegetable sink plus gleaming granite countertops accented with beautiful sparkle. Open to the kitchen, the family room offers a custom-designed stone fireplace that adds warmth and ambiance. A custom-designed entertainment center is nestled in the corner and can be removed since the owners kept original additional windows in place. Two generously sized secondary bedrooms provide comfortable accommodations and have access to the full bath updated with wood cabinetry and stunning tile accents. Measuring approximately 29 feet long, the primary suite provides luxury complete with sitting area to feel truly pampered. Classic touches continue in the updated primary bath with expansive dual vanities, gorgeous tile selections and large soaking tub. Outside, the covered living area is ideal for relaxing, dining and enjoying the beautiful water views in complete privacy. A special waterfall highlights the pool and spa with Mexican tumbled marble, creating a calming atmosphere in the lushly landscaped backyard. Additional highlights include a tile roof installed in 2012 and sleek, special-order Clopay high-impact garage doors and propane gas for the fireplace, outdoor grill and water heater. As a second residence, this home has been gently lived in and well maintained. From the secluded setting to the elegant finishes and serene water views, this is a true sanctuary that must be seen to be fully appreciated. For additional fees, optional memberships are available to Ardea Country Club, featuring two golf courses, a fitness center, tennis and pickle ball and pools as well as dining and special events and activities. And enjoy a premier location providing convenient access to Tampa International Airport, award-winning Gulf beaches, medical facilities, fine dining, professional sporting events and all Tampa Bay area has to offer.

1334 Fallsmeade Court, Oldsmar

238 Pelican Drive N, Oldsmar
$196,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Virtually Staged. Discover the perfect blend of comfort, convenience and coastal charm in this beautifully maintained, move-in ready, 2-bedroom, 2-bathroom, nestled in the heart of Oldsmar, Florida! Featuring a relaxed coastal vibe, this inviting home offers spacious living, dining and kitchen areas, newer stainless-steel appliances, updated bathroom vanities, beautiful laminate flooring, updated subflooring throughout, fresh paint throughout, a newer vapor barrier, and an open-concept layout. The generously sized primary suite features a spacious walk-in closet, an en-suite bathroom, with a separate garden-like tub, a separate water closet with walk-in shower creating a comfortable space to unwind. Located in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers an exceptional lifestyle with resort-style amenities including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. Enjoy the added advantage of owning the land with an affordable monthly HOA fee of just $70. One pet of any size is welcomed and two boat and RV storage areas are available for a low monthly rental fee. You’ll love the unbeatable location is less than a mile from Woodlands Square and just minutes to everyday conveniences. Honeymoon Island Beach is approximately 9 miles away, Mease Countryside Hospital among other health facilities are approximately 2 miles away, St.Pete/Clearwater Int'l Airport is a quick 11-miles away and Tampa Int'l Airport is only a 15-mile drive. For those of you who enjoy the outdoors, the adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, offering another wonderful way to embrace Florida’s outdoor lifestyle. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply soaking in the tranquil pond views, you’ll appreciate the welcoming atmosphere and vibrant lifestyle that make Gull-Aire Village such a special place to call home. Don’t miss this opportunity to enjoy affordable Florida living in a desirable, amenity-rich community. Schedule your private tour today! (Room dimensions are approximate and should be verified by the Buyer.)

238 Pelican Drive N, Oldsmar

105 Palmetto Court, Oldsmar
$165,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code
Just what you have been waiting for....! FIRST floor, pet friendly (up to 40 pounds), condo located in Cypress Estates III of the popular gated community of East Lake Woodlands Country Club, a community that has been designed to enhance your lifestyle. Direct entrance takes you to open views of the dining and living room area out thru the sliding doors to your screened lanai overlooking a park like setting view. This home has been carefully maintained and has a split bedroom plan and the primary bedroom offers two closets, ensuite bath with updated sink vanity and newer tiled shower in the primary bath. Spacious guest bedroom with wall closet. The laundry closet is located off your lanai with washer/dryer. There is a community pool just down from the condo, one covered parking space and other available guest spaces. Optionally, you could join the Ardea (formerly the East Lake Woodlands) Country Club for use of their facilities that will include Clubhouse, two Championship 18 hole golf courses, additional heated pools, tennis courts, fitness center and Clubhouse restaurants and social gatherings. Minutes away from Countryside Mall and the sandy beaches of Honeymoon Island along with parks, restaurants and entertainment. This is a gated, golf cart friendly community (must be street legal), which is handy to run over to the nearby shopping plaza for some of your everyday needs. Location is everything! It is approximately 15 miles from Tampa Airport and less than 10 miles to the beach. For more information about the community and the area go to the East Lake Woodlands website.

105 Palmetto Court, Oldsmar

5124 Pinnacle Drive, Oldsmar
$725,000
3 Beds ⋅ 2 Baths ⋅ Parcel B - The Pinnacle SubDv. ⋅ 34677 Zip Code
Highly sought after and well-maintained home in The Pinnacle Community located in Eastlake Woodlands! The Pinnacle Community is maintenance free and has their own community pool. This home sits on an oversized premium lot with views of the golf course, pond and preserve. This home has 3 bedrooms, 2 full baths and a 2-car garage. The light & bright kitchen is open, features KitchenAid Appliances, a snack bar with granite countertop, a large pantry, and plenty of cabinet space. The kitchen features eat-in space with seamless windows that overlook the golf course. Separate dining room which is open to the family room. The master bedroom is very large and has two walk-in closets and on-suite bathroom. Split bedroom floorplan. Other outstanding features include crown molding, luxury vinyl wood flooring, volume ceilings, neutral paint tones, and 4-in baseboards. The home overlooks the fairway of the 11th hole on the North Course. Enjoy the evenings lounging on the lanai! The home was recently painted (03/2024). Roof 2016. A/C Condensor 2021. Hot water heater 2022. Eastlake Woodlands is a gated community with plenty of sidewalks and trees. With a membership, you can join The Ardea Country Club which includes two renowned 18-hole golf courses, resort like pools, tennis courts, pickleball, a clubhouse/restaurant and fitness center. Eastlake Woodlands is centrally located to all Tampa Bay has to offer. Enjoy dining, shopping and highly rated schools. A short drive will take you to all area beaches, nature parks, sports, activities and the Tampa International Airport. This home is a must see and a pleasure to show!

5124 Pinnacle Drive, Oldsmar

1829 Foxboro Court, Oldsmar
$825,000
3 Beds ⋅ 2 Baths ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code
Welcome to your private retreat in the much sought-after gated, golf community of East Lake Woodlands. Beautifully renovated and move-in ready, this three-bedroom plus alcove, two-bath pool home is ideally positioned on a serene cul-de-sac with a beautifully landscaped lot, exceptional privacy and spacious yard. From the moment you arrive, the home’s high ceilings and abundant natural light create a bright and welcoming atmosphere. The open-concept seamlessly connects the living room and dining room making everyday living and entertaining effortless with a stunning view of the pool area and lush setting. The family room opens directly to the kitchen and features a wood-burning fireplace and plantation shutters. Designed for both style and function, the kitchen was updated in 2026 with signature finishes such as upgraded Latte Luxe quartz countertops, beautiful glass tile backsplash, an island with breakfast bar seating and Samsung Bespoke stainless steel appliances, including convection oven. Enjoy a spa-like escape with the luxurious primary bathroom renovated in 2026 with elegant creamy quartz countertops, dual vanities, backlit mirrors, a stunning walk-in shower and a sitting area all with bright natural light and exquisite chandelier – plus feel totally pampered with a custom closet featuring built-ins complete with well-designed accessory and jewelry drawers. With views of the sparkling pool and abundant greenery, the two secondary bedrooms offer comfortable accommodations, glass sliders and access to a well-appointed bath with calming tones, large vanity and walk-in shower and access to the pool area. The second bedroom even includes additional flexible space that can be used as a small office, study area or hobby space. Step outside to a serene view from the gorgeous covered and screened patio. The inviting pool and spa, highlighted with cream, beige, charcoal pavers, creates a relaxing setting for morning coffee, gatherings or quiet evenings while enjoying privacy. This outdoor space truly feels like a peaceful retreat and is ideal for enjoying the Florida lifestyle. Recent improvements provide added peace of mind and modern convenience. New landscaping and all new interior and exterior painting completed in 2025. Additional notable updates include the tile roof replaced in 2020, new gutters with leaf guards installed in 2024, water heater replaced in 2022 and new pool heater installed in 2025. Updates extend to the laundry room as well for added convenience and functionality complete with 2026 LG washer and dryer included in the sale. Also in 2026, the home was enhanced with a new security and lighting system, a new front-door security entry lock and a smart garage-door opener and new irrigation control panel in 2025. East Lake Woodlands offers a desirable location convenient to Tampa International Airport, top-rated schools, medical facilities, beautiful beaches and parks, professional sporting events and the area’s many dining, shopping, and entertainment destinations. Optional memberships to Ardea Country Club are available and provide access to two golf courses, fitness center, heated lap pool, a freeform pool with poolside café, tennis and pickleball, casual and fine dining and a wide array of events. With thoughtful renovations, a cul-de-sac location, premier landscaping and easy-maintenance finishes, this home allows you to truly relax in a tranquil setting and enjoy the many updates that have been completed!

1829 Foxboro Court, Oldsmar

10 Windrush Court, Oldsmar
$765,000
3 Beds ⋅ 3 Baths ⋅ Greenhaven Unit One SubDv. ⋅ 34677 Zip Code
Tucked away on a quiet cul-de-sac, with a BRAND NEW ROOF, this exceptional single-family residence sits on an oversized lot with tranquil pond views, offering a rare blend of privacy, elegance, and resort-style outdoor living. Designed for both relaxation and entertaining, the backyard retreat features an oversized heated swimming pool, expansive screened lanai, and a generous covered outdoor dining area just off the family room—perfect for hosting gatherings or enjoying Florida evenings. A fully equipped outdoor kitchen adds convenience, while automated wind-resistant screens protect the lanai space when needed. Off the primary suite, an additional private covered patio creates the perfect shaded escape. Inside, the recently remodeled kitchen and family room serve as the heart of the home, showcasing granite countertops, rich wood cabinetry, a striking metal tile backsplash, upgraded lighting and fan fixtures, dual microwave/oven, and a cooktop with breakfast bar overlooking the family room. A charming breakfast nook provides additional seating with picturesque views of the pool and outdoor living area. The family room impresses with soaring vaulted ceilings, skylights that flood the space with natural light, a stylish wet bar, and an electric fireplace insert that provides both warmth and ambiance. Both rear guest bedrooms feature engineered “Tiger Eye” wood flooring, fresh paint, and updated ceiling fans. The second bathroom has been tastefully updated with wood cabinetry, stone countertops, and tile flooring. Throughout the home, popcorn ceilings have been removed, giving every room a clean, modern finish. The primary suite offers a luxurious retreat, featuring engineered wood flooring in the bedroom and closet and a beautifully renovated ensuite bath with dual quartz vanities and an elegant open walk-in tile shower. The roof has been enhanced with a Roof Max protective treatment and transferable 5-year warranty, along with a 2015 A/C system. Combining thoughtful upgrades, refined interior spaces, and exceptional outdoor living, this home offers a private cul-de-sac setting with the perfect balance of comfort, style, and Florida lifestyle living. Additional upgrades and features include: • New Decorative carpet inset in the living room • Dining room with engineered wood flooring with newer Bay Window • Convenient guest half-bath • New double front entry doors with a custom tiled walkway and entry accents • Updated landscaping with new garden rock and curbing (2024) • New golf cart garage door ' New Interior and Exterior Painting and MORE! Combining thoughtful upgrades, refined interior spaces, and exceptional outdoor living, this home offers a private cul-de-sac setting with the perfect balance of comfort, style, and Florida lifestyle living. PLUS transferrable Home Warranty for Major components of the home.

10 Windrush Court, Oldsmar

392 Cobia Way, Oldsmar
$178,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Welcome home to your Florida Retreat in Oldsmar! Discover the perfect blend of comfort, convenience and coastal charm in this beautifully maintained, move-in ready, furnished 2-bedroom, 2-bathroom, nestled in the heart of Oldsmar, Florida! Featuring a relaxed coastal vibe, this inviting home offers updated kitchen cabinets, bathroom vanities and showers, laminate flooring throughout, built-in cabinetry in the kitchen and dining areas, and an open-concept layout. The spacious living room and dining areas, complemented by plantation shutters, provide a welcoming setting for entertaining guests or simply relaxing in comfort. The generously sized primary suite features an updated en-suite bathroom, a spacious walk-in closet and a walk-in shower. Additional improvements include double-pane windows throughout, a newer central air conditioning system, water heater and a leaf guard system, backed by a lifetime warranty. Located in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers an exceptional lifestyle with resort-style amenities including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. Enjoy the added advantage of owning the land with an affordable monthly HOA fee of just $70. One pet of any size is welcomed and two boat and RV storage areas are available for a low monthly rental fee. You’ll love the unbeatable location is less than a mile from Woodlands Square and just minutes to everyday conveniences. Honeymoon Island Beach is approximately 9 miles away, Mease Countryside Hospital among other health facilities are approximately 2 miles away, St.Pete/Clearwater Int'l Airport is a quick 11-miles away and Tampa Int'l Airport is only a 15-mile drive. For those of you who enjoy the outdoors, the adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, offering another wonderful way to embrace Florida’s outdoor lifestyle. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply soaking in the tranquil pond views, you’ll appreciate the welcoming atmosphere and vibrant lifestyle that make Gull-Aire Village such a special place to call home. Don’t miss this opportunity to enjoy affordable Florida living in a desirable, amenity-rich community. Schedule your private tour today!(Room dimensions are approximate and should be verified by the Buyer.)

392 Cobia Way, Oldsmar

145 Poole Place, Oldsmar
$229,995
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code
Discover the ease of Florida living in this inviting 2-bedroom, 2-bath villa nestled within the gated golf community of East Lake Woodlands in Oldsmar. Offering a comfortable layout, a peaceful setting, and a low-maintenance lifestyle, this home is an excellent opportunity for a full-time residence, seasonal retreat, or anyone looking to enjoy all that the Tampa Bay area has to offer. Inside, the functional floor plan offers comfortable living and dining spaces, with a well-appointed layout designed for both everyday living and entertaining. The two-bedroom, two-bath configuration provides flexibility for guests, a home office, or a dedicated hobby space. Step outside to enjoy your own outdoor space, perfect for a quiet morning coffee or relaxing at the end of the day. Covered parking, additional storage, and convenient guest parking add to the home's everyday appeal. One of the standout advantages of living in Cluster Homes is the maintenance-free lifestyle, with exterior maintenance, grounds care, trash service, and basic cable included. The beautifully landscaped, gated East Lake Woodlands community is known for its natural surroundings and bird sanctuary setting, with sidewalks and walking and biking paths that invite you to slow down and enjoy the scenery. Residents also have the option to join Ardea Country Club, offering two golf courses, swimming pools, tennis courts, an exercise room, and on-site dining through available social and golf memberships. The location makes enjoying Florida's outdoor lifestyle easy, with John Chestnut Park, Oldsmar Park, and Philippe Park in nearby Safety Harbor. When you're ready for a beach day, Caladesi Island State Park and Clearwater Beach are just a drive away. Shopping, restaurants, entertainment, and everyday conveniences are close at hand, while Tampa International Airport and St. Pete-Clearwater International Airport offer convenient options for travel. Enjoy the combination of gated-community living, recreational opportunities, and convenient access to the best of Tampa Bay. Schedule your private showing and discover the lifestyle East Lake Woodlands has to offer!

145 Poole Place, Oldsmar

131 Woodlake Wynde, Oldsmar
$154,500
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code
Whether you're seasonal or a full time resident, this East Lake Woodlands condo has it all! Enjoy being in a NON-Flood Zone with your monthly bills of Cable, Internet, Trash & Water already included in the HOA fee! This accessible first-floor condo is located just steps away from the heated community pool and bursts with potential. It is one of the most desired condo communities of East Lake Woodlands and is centrally located near the main Ardea clubhouse with quick gate access from both Tampa Rd and East Lake road entrances. Enjoy both of your front and back screened-in patios, providing two comfortable outdoor spaces to relax and enjoy nature without the bugs! Inside, you’ll find tile flooring throughout, a spacious living room and dining room combo with a wet bar, and an open kitchen with plenty of extra counter seating. The washer and dryer are conveniently located right outside the kitchen in the front patio laundry closet, and being on the first floor means easy access with no stairs to navigate. This guard-gated community offers a peaceful setting surrounded by mature landscaping and wildlife, and if you decide to join the Ardea club, the main clubhouse, golf course, and tennis courts are right across the street. The HOA fee includes: Cable TV, Internet, Water, Community Pool, Escrow reserves, Maintenance Exterior, Roof, Grounds Maintenance, Security and Trash. East Lake Woodlands is home to the Adrea Country Club offering a variety of optional memberships for homeowners to join. These exclusive amenities include Two Championship 18-hole Golf Courses, Tennis and Pickleball Courts, Clubhouse Bar, Casual and Fine Dining, Fitness Center, Splash Pad, Swimming Pools, Clubhouse Events and more. Centrally located near top-rated schools, trending restaurants, shopping, movies, parks, Tarpon Lake, Gulf Coast beaches, local hospitals, Tampa Airport and more, you’ll never run out of activities in town!

131 Woodlake Wynde, Oldsmar

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