Oldsmar Homes with Sidewalks Community Features

Oldsmar Homes with Sidewalks Community Features

Welcome to Oldsmar, Florida—a charming city nestled in the heart of Pinellas County, where the sun-drenched landscapes and vibrant community spirit come together in perfect harmony. Just a stone's throw from the stunning Gulf Coast, Oldsmar offers residents a delightful blend of suburban tranquility and urban convenience. With its picturesque parks, scenic waterfront, and an array of recreational activities, this city is a hidden gem for families, retirees, and everyone in between.

One of the standout features of Oldsmar is its inviting neighborhoods, particularly those homes with sidewalks that encourage a sense of community and connection. Imagine taking leisurely strolls along tree-lined streets, where neighbors greet each other with friendly waves and children play safely outside. These sidewalks not only promote an active lifestyle but also create a welcoming atmosphere that fosters friendships and camaraderie.

Oldsmar boasts a rich array of amenities, from local shops and restaurants to beautiful parks and nature trails, making it easy to enjoy the great outdoors. The nearby Oldsmar Parks and Recreation department offers a plethora of activities, including sports leagues, fitness classes, and seasonal events that bring the community together.

In Oldsmar, you’ll find homes that reflect the warmth and charm of the city itself. Whether you’re seeking a cozy single-family home or a spacious townhome, the properties here are designed to enhance your lifestyle. With sidewalks winding through the neighborhoods, you’ll have the perfect backdrop for your new adventures in this vibrant, welcoming community. Come explore Oldsmar—where every street feels like home!

Newest Oldsmar Homes with Sidewalks Community Features

2063 Warwick Drive, Oldsmar
$895,000
4 Beds ⋅ 3 Baths ⋅ Warwick Hills SubDv. ⋅ 34677 Zip Code
SPECTACULAR PRESERVE VIEW! Enjoy the privacy and solitude of this beautiful home backing to the 8500 acre Brooker Creek Preserve with frequent sightings of dear and wildlife. Great curb appeal with custom glass front doors, landscaping and lighting. The interior of the home features a split floor plan with 4 bedrooms, an office and 3 full baths. The back bedrooms would also make a great in-law suite or media room. Entertain formally in the living and dining room with preserve view or casually poolside with heated pool and spa. The gourmet kitchen is the heart of the home with granite counters, abundant cabinets and counter space, stainless appliances and a breakfast nook. The kitchen opens to the family room and the outdoor pool and preserve view. The owner’s suite is a retreat with pool and patio access, walk in closet with custom shelving, crown molding and plantation shutters. The en-suite bath is complete with granite counters, double sinks, garden tub and walk in shower. Additional features include a security system, crown molding, in home vacuum, motorized window coverings, gas fireplace, outdoor lighting and plantation shutters. Live the Florida lifestyle! Take a dip in the heated salt pool, soak in the spa or unwind on the expansive deck overlooking the preserve. The outdoor kitchen has a gas grill and sink. An additional patio in the backyard is great for entertaining. The expansive backyard is private and perfect for sports, children and pets. LOCATION! Live on a quiet street in the Warwick Hills subdivision of Eastlake Woodlands. Eastlake Woodlands is a golf and tennis community with two renowned golf courses and clubhouse. Membership in the newly remodeled premiere Ardea Country Club is required to enjoy golf, tennis, pickle ball, swimming pools, child activity center and newly refurbished gym. Eastlake Woodlands is central to all dining, shopping and highly rated schools. A short drive will take you to all area beaches, activities and the Tampa International Airport. Be sure to watch the video and look at the 360 interior views!

2063 Warwick Drive, Oldsmar
260 Balsam Drive, Oldsmar
$205,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome home to this beautiful 2-bedroom, 2-bathroom villa nestled within the highly desirable gated community of East Lake Woodlands! Offering an exceptional blend of comfort, style, and functionality, this inviting residence features a desirable split-bedroom floor plan designed to provide privacy for both owners and guests. Step inside to discover a spacious, light-filled living room, perfect for everyday living and entertaining. A dedicated dining area and charming wet bar create the ideal setting for hosting family and friends. The well-appointed kitchen features a full appliance package, abundant cabinetry, and generous counter space, providing both convenience and functionality. The spacious primary suite offers a peaceful retreat, complete with a walk-in closet and private en-suite bathroom featuring a large walk-in shower. The secondary bedroom is conveniently located near a full guest bathroom, providing comfort and privacy for visitors. An expansive additional family room offers versatile living space, ideal for a media room, home office, or relaxing entertainment area. Enjoy the best of Florida's indoor-outdoor lifestyle with two inviting outdoor spaces! Sliding glass doors lead to a private, fenced front courtyard, perfect for enjoying your morning coffee, outdoor dining, or simply unwinding in a tranquil setting. At the rear of the home, a generously sized enclosed porch provides additional space for relaxing or entertaining year-round. Located within the beautiful, gated East Lake Woodlands community, residents have the opportunity to enjoy an array of exceptional amenities through optional club membership, including championship golf, tennis, fitness facilities, dining, and a variety of social activities. Surrounded by lush landscaping and a peaceful atmosphere, this sought-after community offers a wonderful Florida lifestyle. Conveniently situated near shopping, restaurants, entertainment, medical facilities, and major roadways, this villa combines the tranquility of gated community living with easy access to everyday conveniences. Don't miss this wonderful opportunity to own a beautiful villa in one of the area's most desirable communities. Schedule your private showing today and experience all that East Lake Woodlands has to offer!

260 Balsam Drive, Oldsmar
209 Dolphin Drive, Oldsmar
$194,900
2 Beds ⋅ 2 Baths ⋅ Gull Aire Vlg SubDv. ⋅ 34677 Zip Code
In Gull Aire Village, Oldsmar’s 55+ community, you own the land under your home and pay just $70 a month in HOA fees. This 2-bedroom, 2-bath home is move-in ready. Fresh paint, wood-look floors, and ceiling fans run throughout. A tiled Florida room welcomes you inside, and the open living room centers on a cozy fireplace for the cooler evenings. The spacious kitchen has plenty of cabinet space, a breakfast bar for morning coffee, and stainless appliances, including the range, dishwasher, and microwave. Storm season is less stressful here, with hurricane shutters and a hurricane-rated sliding glass door that opens to ramp access. The AC has been regularly maintained, and the laundry area has new flooring. An enclosed workshop gives you room for projects and hobbies. Outside your door you’ll find an active clubhouse, library, billiards, shuffleboard, and a heated pool and spa. One pet of any size is welcome, and leasing is allowed. Restaurants, shopping, and entertainment are a stones throw from here and Gulf beaches and Tampa-area airports are a short drive away. Homes at this price with land ownership don’t last, so schedule your private showing today. Room sizes are approximate and should be verified.

209 Dolphin Drive, Oldsmar
90 Evelyn Court, Oldsmar
$269,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code
Virtually Staged. OPPORTUNITY KNOCKS! This 2-bedroom, 2-bath East Lake Woodlands villa offers a stunning water view & is competitively priced for a prompt sale! The elevated, expanded living space has tile &/or laminate flooring throughout, & a small deck overlooks the water, a peaceful & serene spot for your outdoor chairs. The walls have been freshly painted in a neutral color, & the home has also been professionally cleaned so it sparkles. The updated kitchen features an island, granite countertops, a newer window, & ample wood cabinetry. Major system updates include the HVAC (2024), water heater (2023), electrical panel (2022), & roof (2020). The home does need a few cosmetic updates, but at this price you have room to make it your own. There is also a warranty paid for the buyer to cover you for the first year of ownership from Americas Preferred Home Warranty which allows you to use your own contractors for any covered repairs. PLUS, you are within East Lake Woodlands, a premier country club community with major amenities available to members of Ardea Country Club (private). If you like golf, tennis, pickleball, putting greens, a clubhouse with a fitness center, two pools, restaurant and snack bar plus more....this is the place for you! (club membership requires an additional fee, please contact Ardea for more information). No other villa on the market matches this location & view, so don't wait. Schedule your showing today!

90 Evelyn Court, Oldsmar
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
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
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