Oldsmar Homes with Sidewalks Community Features

Oldsmar Homes with Sidewalks Community Features

Oldsmar, a charming city located in Pinellas County, Florida, is a place that offers a perfect blend of small-town charm and modern amenities. Situated in the heart of the Tampa Bay area, Oldsmar is known for its picturesque landscapes, friendly community, and a wide range of recreational activities.

With its true sense of community, Oldsmar is a haven for those seeking a neighborhood with Homes with Sidewalks Community Features. These communities are designed to provide a safe and pedestrian-friendly environment, encouraging residents to explore their surroundings on foot or by bike. Sidewalks not only enhance the aesthetic appeal of the neighborhoods but also promote a healthy and active lifestyle.

Living in a Homes with Sidewalks Community in Oldsmar offers numerous benefits. Families with children can enjoy strolling or biking around the neighborhood, knowing that their little ones can play safely. Sidewalks also provide a space for neighbors to interact, fostering a strong sense of community and creating opportunities for friendships to flourish.

In addition to the Homes with Sidewalks Community Features, Oldsmar offers a variety of amenities and attractions. From beautiful parks and nature trails to vibrant shopping and dining options, there is something for everyone. The city is also known for its excellent schools, making it an appealing choice for families.

Whether you're looking for a peaceful place to retire or a vibrant community to raise a family, Oldsmar, Florida, with its Homes with Sidewalks Community Features, is a city that offers both comfort and convenience.

Newest Oldsmar Homes with Sidewalks Community Features

166 Manta Circle, Oldsmar
$234,900
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Spacious 1992 Jacobsen home with 1,444 square feet of living area, now available in the desirable 55+ Gull-Aire Village community. Ideally located on Manta Circle, this home features an open floor plan that is perfect for entertaining, a bonus room suitable for a home office or den, a large indoor laundry room, and new baseboards throughout. Recent updates include a TPO roof and windows installed in 2020, a new water heater installed in 2025, and a new air-conditioning system installed in 2019 with a warranty contract through 2028. The exterior was freshly painted in October 2026. Additional features include two storage sheds for bikes, tools, or workshop space and a welcoming screened porch at the front of the home. Gull-Aire Village offers an active, well-maintained, pet-friendly community with a vibrant clubhouse, heated pool and spa, pool table, shuffleboard, bocce ball court, bingo, card games, line dancing, and other regular activities. Golf-cart-friendly streets make getting around the neighborhood easy and enjoyable. The HOA fee is just $70 per month, and ownership includes the land—there is no lot rent. Conveniently located across from AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store, with numerous dining options nearby, including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Super Walmart, Publix, and Countryside Hospital are approximately 10 minutes away. Enjoy easy access to a scenic canal-side biking and walking trail within the community, as well as the beautiful beaches of Honeymoon Island and Caladesi State Park, approximately ten miles away. Room sizes are approximate.

166 Manta Circle, Oldsmar
109 Lakeside Drive, Oldsmar
$199,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Welcome to this stunning, ground floor 2 bedroom to 2 bath condo in a guarded and gated community of East Lake Woodlands, where you can enjoy a maintenance-free Florida living at its best. Step inside and discover the seamless combination of quality updates with comfort. The spacious living and dining areas flow seamlessly together, creating an inviting, open atmosphere perfect for entertaining or simply relaxing at home. The well-appointed kitchen features a breakfast nook, convenient breakfast bar with a pass-through to the dining area, making both casual meals and gatherings a breeze. The desirable split-bedroom floor plan provides privacy, while the generously sized primary suite is a true retreat, featuring THREE walk-in closets! Additional highlights include plantation shutters throughout, living room fireplace, and an enclosed, all-weather Florida room overlooking a pond. Imagine starting your mornings with coffee while enjoying the serene water views or unwinding in the evening surrounded by nature. Enjoy the convenience of a lock-and-leave Florida lifestyle, with monthly condo fees covering basic cable, internet, water, sewer, and trash removal. Less time worrying about maintenance means more time enjoying everything Florida has to offer! Nestled within the well-established East Lake Woodlands community, residents enjoy the comfort of guarded entry. For those seeking an active, resort-inspired lifestyle, optional membership to Ardea Country Club offers access to golf, tennis, pickleball, fitness facilities, clubhouse amenities, and more. Location is another standout feature! Conveniently situated near shopping, restaurants, parks, entertainment, and everyday essentials, with easy access to Tampa International Airport and St. Pete-Clearwater International Airport. Whether you're looking for a full-time residence or a seasonal Florida getaway, this exceptional ground-floor condo checks all the boxes! Beautiful updates, spacious living, pond views, and a sought-after gated community make this an opportunity you won't want to miss. Come experience the charm, comfort, and convenience of East Lake Woodlands living!

109 Lakeside Drive, Oldsmar
1609 Vineyard Lane, Oldsmar
$349,900
3 Beds ⋅ 2 Baths ⋅ Tuscany Woods Preserve SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome to this inviting two-story townhome featuring 3 bedrooms, 2 full bathrooms, 1 half bathroom, and 1,525 square feet of living space! Built in 2017, this home offers a functional floor plan with comfortable living areas perfect for everyday living and entertaining. The spacious layout provides plenty of flexibility, while the attached 1-car garage offers convenient parking and additional storage space. Enjoy the benefits of townhome living with a low-maintenance lot and plenty of potential to make this space your own. Whether you're looking for your next home or an investment opportunity, this property has plenty to offer. Schedule your showing today! One or more photos have been virtually staged.

1609 Vineyard Lane, Oldsmar
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
1633 Shady Oaks Drive, Oldsmar
$545,000
3 Beds ⋅ 3 Baths ⋅ Eastlake Oaks Ph 3 SubDv. ⋅ 34677 Zip Code
Pool, heated spa, and a 3-car garage in East Lake Oaks. This 3-bedroom, 2.5-bath Oldsmar home pairs a screened outdoor setup with solid updates: roof 2017, AC 2021, and vinyl fence 2021. The two-story layout opens with vaulted ceilings over a combined living and dining room. The kitchen features wood cabinetry, stainless steel appliances, and an eat-in area, and it opens to the family room for easy everyday flow. The remodeled primary bath includes dual sinks, a standalone tub, and a separate shower. Out back, the screened lanai offers covered seating, the heated spa, and the pool, all within a vinyl-fenced yard for added privacy. Community amenities include a pool, playground, and ponds. Harbor Palms Nature Park, Estuary Preserve, and Sheffield Park are nearby for bike trails, disc golf, and tennis. Centrally located near shopping, restaurants, and theaters, with easy drives to downtown Safety Harbor, downtown Dunedin, Tampa, the airports, and Clearwater Beach.

1633 Shady Oaks Drive, Oldsmar
129 Caryl Way Unit 129, Oldsmar
$129,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Short Sale. UNAPPROVED SHORT SALE – Renovation Opportunity in Highly Desirable East Lake Woodlands! Bring your vision and transform this 2-bedroom, 2-bathroom condo into your ideal Florida retreat! Located within the highly sought-after, guard-gated community of East Lake Woodlands in Oldsmar, this property presents an excellent opportunity for buyers looking to renovate and make it their own. Whether you're searching for a primary residence, seasonal getaway, or investment opportunity, this condo offers plenty of potential. Enjoy the beautiful surroundings of this established community, conveniently located near shopping, dining, entertainment, beaches, and everything the Tampa Bay area has to offer. The HOA fee includes cable TV, high-speed internet, water, sewer, trash collection, exterior maintenance, grounds maintenance, community pool, and reserves, providing added convenience and value. Property is being sold as an unapproved short sale, subject to lender approval. Bring your creativity and take advantage of this opportunity to own in one of Oldsmar's most desirable communities!

129 Caryl Way Unit 129, 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
4798 Augusta Avenue, Oldsmar
$560,000
4 Beds ⋅ 3 Baths ⋅ Worthington SubDv. ⋅ 34677 Zip Code
Welcome to 4798 Augusta Ave, located within the desirable East Lake Woodlands community! Enjoy the peace and tranquility of a quiet, serene street where local wildlife sightings add to the charm of the neighborhood. Convenient resident entry provides quick access in and out of the community, making everyday travel a breeze. Inside, luxury vinyl plank flooring installed in 2023 offers a fresh, cohesive look throughout the home. The functioning fireplace adds warmth and character, while the whole-house water softener provides an added layer of everyday comfort. Major updates include a 2015 roof, 2019 A/C, impact-rated sliding glass doors installed in 2021, a rescreened lanai in 2021, and exterior paint completed in 2019 and interior painted in 2024. The home has never flooded. The community also features Ardea Country Club, where members can enjoy access to two 18-hole championship golf courses, a swimming pool, hard and soft tennis courts, pickleball courts, a playground, a gym, and Heron’s Bar and Grille With thoughtful updates, desirable community amenities, and a peaceful setting, this home is ready for its next owner to make it their own!

4798 Augusta Avenue, Oldsmar
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