Oldsmar Homes with Sidewalks Community Features

Oldsmar Homes with Sidewalks Community Features

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County. This charming city, known for its friendly atmosphere and vibrant community, offers a unique blend of suburban tranquility and urban convenience. With its prime location just a stone's throw away from the stunning Gulf Coast beaches, Oldsmar is perfect for those who appreciate both relaxation and adventure.

Oldsmar is renowned for its picturesque parks, scenic waterfront views, and a plethora of recreational activities. Residents can enjoy the lush landscapes of the Oldsmar Park or take a stroll along the serene trails of the nearby Upper Tampa Bay Trail. The city also hosts a variety of community events throughout the year, fostering a strong sense of belonging among its residents.

One of the standout features of Oldsmar is its family-friendly neighborhoods, particularly those with homes that boast sidewalk community features. These neighborhoods are designed to promote an active lifestyle, encouraging residents to take leisurely walks, bike rides, or simply enjoy the fresh Florida air. Sidewalks not only enhance the aesthetic appeal of the community but also provide safe and convenient access to local parks, schools, and shops.

Whether you’re a first-time homebuyer or looking to settle down in a welcoming community, Oldsmar offers a diverse range of homes with sidewalks that cater to every lifestyle. Experience the charm of Oldsmar, where community spirit thrives, and every day feels like a vacation. Come discover your dream home in this delightful city, where the sun shines bright, and neighbors become friends.

Newest Oldsmar Homes with Sidewalks Community Features

10 Windrush Court, Oldsmar
$765,000
3 Beds ⋅ 3 Baths ⋅ TB8558083 MLS
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.

10 Windrush Court, Oldsmar
392 Cobia Way, Oldsmar
$178,000
2 Beds ⋅ 2 Baths ⋅ TB8557814 MLS
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
$235,000
2 Beds ⋅ 2 Baths ⋅ TB8557674 MLS
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
600 Shore Drive E, Oldsmar
$899,000
3 Beds ⋅ 4 Baths ⋅ TB8557359 MLS
Half an acre of direct waterfront on Old Tampa Bay with 108 feet of frontage and a 203-foot-deep lot on Shore Drive E, Oldsmar's most sought-after waterfront street. Open bay views west across the water, a second-floor balcony that showcases spectacular sunset views of Tampa Bay, and a screened pool and spa on a paver deck facing the bay. The existing 1962 two-story block and stucco home, 2,454 sf with 4 full baths, tile roof, and fireplace, flooded in 2024 and has been professionally remediated, with lower-level drywall removed to the flood line. Two paths forward: build new on one of the larger waterfront parcels on the street, or keep and lift. Unique to this property: the seller has been approved for Elevate Florida, the state's FEMA-funded residential elevation program, with an estimated $402,000 in federal funding toward raising the existing home above the floodplain (Structure Elevation), along with adding an additional 800 sqft of under-roof living space. Subject to an owner cost share per the FDEM financial packet. Per the Florida Division of Emergency Management, a new owner may elect to continue the approved project after closing, subject to completing program documentation and assuming program obligations, including a deed restriction requiring NFIP flood insurance for the life of the elevated structure. All figures are estimates from the FDEM financial packet and are subject to change. Buyer to verify all program terms directly with FDEM. No HOA, no CDD. Walkable to Mobbly Bayou Beach Park, RE Olds Park and Veterans Park, and the Oldsmar boat ramp. Minutes to Tampa International Airport and the Gulf beaches. Cash or construction financing. Seller's flood disclosure, remediation documentation, FDEM correspondence, and survey available in attachments.

600 Shore Drive E, Oldsmar
4798 Augusta Avenue, Oldsmar
$575,000
4 Beds ⋅ 3 Baths ⋅ TB8555008 MLS
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
366 Rainforest Court, Oldsmar
$524,900
4 Beds ⋅ 2 Baths ⋅ TB8555675 MLS
Welcome to this beautifully maintained 4 bedroom, 2 bathroom home in The Fountains at Cypress Lakes where comfortable living meets timeless style. An inviting open-concept floor plan, soaring vaulted ceilings and abundant natural light create a bright and airy atmosphere throughout. Ceramic tile flooring extends throughout the home offering a cohesive look and easy-care convenience. The stunning remodeled kitchen serves as the heart of the home featuring gorgeous granite countertops, a stylish tile backsplash, a stainless steel undermount sink, refaced cabinetry and a convenient pantry closet. The spacious living area showcases a fireplace converted to electric adding a cozy touch to the home's welcoming ambiance. Both bathrooms were remodeled in 2015 and thoughtful improvements include HVAC replacement in 2022, stainless steel appliances installed in 2019, hurricane-impact windows installed in 2019 and fresh exterior paint in 2026. A new roof is scheduled for installation in October 2026. Additional highlights include new ceiling fans, abundant storage, linen closets, an irrigation system utilizing reclaimed water and an inviting screened-in back patio with attractive paver flooring. The screened lanai is an ideal setting for morning coffee, outdoor dining or relaxing evenings. The driveway and patio pavers were installed in 2008, adding to the home's established outdoor appeal. Located in Flood Zone X, this property offers added peace of mind and flood insurance is generally not required by lenders for financed purchases in this zone. Perfectly positioned in the heart of Tampa Bay, The Fountains at Cypress Lakes offers convenient access to Tampa, St. Petersburg, the beautiful Gulf beaches and Tampa International Airport while providing a peaceful, nature-inspired community setting. Forest Lakes elementary school is conveniently located directly across the street from the neighborhood which is a highly rated elementary school that boasts an A rating and ranks among the top public elementary schools in Pinellas County. Enjoy nearby shopping, exceptional dining and outdoor recreation at Bicentennial Park, R.E. Olds Park and Veterans Memorial Park all within just a few miles. Combining a desirable location, inviting indoor and outdoor living spaces and numerous valuable updates, this home is a wonderful opportunity to enjoy the best of the Tampa Bay lifestyle!

366 Rainforest Court, Oldsmar
131 Woodlake Wynde, Oldsmar
$159,500
2 Beds ⋅ 2 Baths ⋅ TB8546978 MLS ⋅ 131 BLDG.
AMAZING POTENTIAL in East Lake Woodlands, NON-Flood Zone and your Cable, Internet & Water is included in the HOA! This accessible first-floor condo is a fantastic opportunity to create your forever dream space. Located directly across from the heated community pool, this condo bursts with potential and is located in a highly desirable central location within the East Lake Woodlands community. Enjoy both your screened-in front and back 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
127 Nancy Drive Unit 127, Oldsmar
$205,000
2 Beds ⋅ 2 Baths ⋅ TB8552761 MLS ⋅ 4 BLDG.
Move-In Ready, Renovated First-Floor Condo in East Lake Woodlands! Relax & enjoy effortless Florida living w/ the much-coveted combination of a FIRST-FLOOR, MOVE-IN READY, MAINTENANCE-FREE 2-bedroom, 2-bath condo in the desirable gated golf community of East Lake Woodlands! This beautifully updated home has all the bells & whistles, including granite countertops, shaker-style cabinetry, tiled backsplash, LED lighting, tile & luxury laminate flooring throughout, Maytag washer & dryer, & an inlaid travertine-tiled patio floor. You'll like the peace of mind of a newer HVAC System & water heater (both '21). Be "wowed" w/ the peaceful & tranquil conservation & wooded views from the rear of the home! The excellent floorplan provides an open feel w/ abundant natural light & rear sliders leading to your private covered patio w/ additional storage—a perfect spot to relax & enjoy the natural surroundings. The desirable two-way split-bedroom plan offers both privacy & functionality. The spacious primary suite features an impressive three walk-in closets—one large & two additional closets—along w/ a private bath suite. Both bedrooms feature luxury laminate flooring w/ NO CARPET. Ground-floor living makes everyday access easy, & covered parking adds another level of convenience. Even better, the community swimming pool & clubhouse are located directly across the street, making it easy to enjoy the Florida lifestyle just steps from home. This Condo is NOT in a flood zone (Zone X). For those seeking additional resort & country club amenities, Ardea Country Club offers optional private memberships for addl. fees, incl. access to two 18-hole championship golf courses, tennis & pickleball, fitness center & classes, heated lap & free-form pools, dining, & social events. Membership is separate from the community. East Lake Woodlands offers a premier Oldsmar location convenient to shopping, restaurants, parks, medical facilities, A-rated schools, Tampa International Airport, award-winning Gulf beaches, & the many professional sporting events, concerts & entertainment destinations throughout the Tampa Bay area. Whether you're looking for a full-time residence, seasonal Florida retreat, or investment opportunity, this renovated first-floor condo combines comfort, convenience, peaceful, wooded views & the gated-community lifestyle that makes East Lake Woodlands such a desirable place to call home!

127 Nancy Drive Unit 127, Oldsmar
110 Lakeside Court Unit 110, Oldsmar
$149,900
2 Beds ⋅ 2 Baths ⋅ TB8554398 MLS ⋅ Bldg 5 BLDG.
Virtually Staged. Welcome to effortless Florida living in this beautifully updated 2-bedroom, 2-bathroom second-floor condo, ideally situated within the gated community of East Lake Woodlands. Offering a spacious great-room floor plan and a recently remodeled interior, this charming residence combines comfort, convenience, and a relaxed resort-style lifestyle. The inviting kitchen has been upgraded with tile countertops and a contemporary backsplash, creating a stylish and functional space for everyday living and entertaining. The main living areas and bedrooms feature comfortable carpeting, while both bathrooms offer neutral finishes and appointments, providing a versatile backdrop for your personal decorating style. The generously sized primary bedroom offers an abundance of space and features two walk-in closets for exceptional storage. Sliding glass doors provide easy access to the private screened-in porch, where you can unwind with your morning coffee or enjoy a peaceful evening while taking in relaxing views of the expansive green space. The porch also provides convenient access to the laundry closet. Recent improvements include a new hot water heater installed in 2026, offering added peace of mind for the new owner. The condo also includes covered carport parking conveniently located next to the mailbox, making everyday living even more convenient. Residents of this quiet, well-maintained gated community have access to a beautiful community pool, providing the perfect setting for cooling off, relaxing, or entertaining guests. For those seeking an even more elevated country-club lifestyle, residents have the option to join Ardea Country Club for an additional fee. Membership opportunities include access to an impressive array of amenities, including: Two championship 18-hole golf courses, Pickleball and tennis courts, Olympic-style lap pool, Fitness center, On-site restaurant A variety of social activities and events Beyond the community, the location offers exceptional convenience. Enjoy easy access to airports, medical facilities, shopping, restaurants, beautiful Gulf beaches, and a wide variety of entertainment and recreation, all just a short drive away. Whether you're looking for a full-time residence, a seasonal retreat, or a low-maintenance Florida getaway, this lovely East Lake Woodlands condo offers comfort, convenience, and carefree living in a peaceful country-club setting.

110 Lakeside Court Unit 110, Oldsmar
151 Lakeview Way Unit 151, Oldsmar
$189,000
2 Beds ⋅ 2 Baths ⋅ TB8553074 MLS ⋅ 5 BLDG.
Virtually Staged. WATERFRONT, GROUND FLOOR, UPDATED and MOVE-IN READY! Enjoy one of the most peaceful, nature-filled views in the highly sought-after East Lake Woodlands community from this beautifully updated 2-bedroom, 2-bath condo with assigned COVERED PARKING. Step inside to a spacious, open layout with NO CARPET and plenty of natural light. The updated kitchen features NEW GRANITE COUNTERTOPS, NEW CABINETS, a pantry closet, generous storage, and a large breakfast bar overlooking the dining and living areas. The inviting living room features a cozy WOOD-BURNING FIREPLACE, perfect for those occasional cool Florida evenings. Sliding glass doors from BOTH the living room and primary suite open to the tiled lanai, creating a wonderful extension of the living space and the perfect place to enjoy your morning coffee while taking in the tranquil WATERFRONT VIEW and surrounding wildlife. The spacious primary suite features QUARTZ COUNTERTOPS, WALK-IN SHOWER, and a stylish NEW BARN DOOR. The guest bathroom includes a newer vanity, and both bathrooms feature NEW ELONGATED CHAIR-HEIGHT TOILETS installed in 2023. You'll also appreciate the abundance of closet and storage space throughout the home. Additional updates include a NEW A/C IN 2023, NEW BLINDS IN 2023, NEW CEILING FANS, laminate flooring in both bedrooms, and ceramic tile throughout the remainder of the condo, including the lanai. Assigned covered parking is included, along with plenty of additional guest parking. The community HEATED POOL is just a short walk away for year-round enjoyment. East Lake Woodlands offers a beautiful, gated country club setting surrounded by mature landscaping, lakes, and natural Florida scenery. Optional club memberships provide access to additional amenities that may include golf, tennis, fitness, dining, pools, and clubhouse facilities. Conveniently located near shopping, restaurants, parks, beaches, and Tampa International Airport. GROUND FLOOR + WATERFRONT VIEW + UPDATED INTERIOR + COVERED PARKING + NO CARPET = Florida living made easy!

151 Lakeview Way Unit 151, Oldsmar
210 Woodlake Wynde, Oldsmar
$177,000
2 Beds ⋅ 2 Baths ⋅ TB8554024 MLS ⋅ 210 BLDG.
Welcome to this inviting 2-bedroom, 2-bathroom condo in the gated Woodlake Run community, in the coveted East Lake area, offering a comfortable layout and a peaceful pond view. This 2nd floor unit provides a spacious living room area, ample storage, vaulted ceilings, tile flooring, and transom windows on both sides that bring in an abundance of natural light. A convenient dry bar with recessed lighting adds a great touch for entertaining. Sliding glass doors lead to the screened-in patio, creating a relaxing outdoor space overlooking the pond. The patio also features a dedicated washer and dryer closet for added convenience. The primary suite offers a tranquil retreat with his-and-hers closets, a sliding glass door providing direct access to the screened patio and pond view, plus an extended vanity and tub/shower combination. The second bedroom is generously sized and is complemented by a full bathroom. Tile flooring runs throughout the main living areas, while the bedrooms feature newer Luxury vinyl plank flooring. Recent major updates include a 2024 HVAC system and 2021 water heater. The HOA includes gate access with guard, access to the community pool, cable TV, internet, exterior maintenance, grounds maintenance, sewer, water, trash, and designated parking & guest parking. Conveniently located in Oldsmar, this condo offers a great combination of comfort, low-maintenance living, and desirable community amenities. Enjoy easy access to many of the area's popular attractions, including Oldsmar's waterfront, parks, recreation areas, and nearby shopping and dining. The area's location also provides convenient access to Tampa, making it easy to enjoy the city's restaurants, entertainment, sporting events, and cultural attractions. Tampa International Airport is also within convenient driving distance, adding to the appeal for travelers and those looking for an accessible Tampa Bay location.

210 Woodlake Wynde, Oldsmar
1750 Split Fork Drive, Oldsmar
$625,000
4 Beds ⋅ 3 Baths ⋅ TB8553412 MLS
Virtually Staged. Welcome to this spacious and well-maintained **4-bedroom, 3-bath Oldsmar home offering 2,460 square feet of living space**, a great layout, and plenty of room to spread out. As soon as you enter, the **high vaulted ceilings** create an open, airy feel and showcase the generous living areas throughout the home. Situated on a **larger lot in a quiet neighborhood**, the home also features an approximately **14' x 17' rear addition**, providing valuable extra space and flexibility. This area can function as a **bonus room or 4th bedroom and has its own mini-split system**, making it comfortable and versatile for guests, a home office, playroom, gym, or additional living space. Step outside to the screened pool and enjoy a **gorgeous water view**, creating a peaceful Florida setting that’s perfect for relaxing or entertaining. The home has been **very well kept and maintained**, with additional highlights including a **2018 roof** and a functional floor plan that makes great use of the space. This is a great opportunity to own a spacious home with a pool, water view, larger lot, and flexible living space in a desirable Oldsmar location.

1750 Split Fork Drive, Oldsmar
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