Oldsmar Homes with Guest Parking Features

Oldsmar Homes with Guest Parking Features

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County! Known for its picturesque landscapes and vibrant community spirit, Oldsmar offers the perfect blend of small-town charm and modern conveniences. With its prime location just a stone's throw from the stunning Gulf Coast, residents enjoy easy access to beautiful beaches, lush parks, and a plethora of recreational activities.

Oldsmar is not just about natural beauty; it’s also a hub of family-friendly attractions, top-rated schools, and community events that bring residents together. The city's commitment to preserving its rich history while fostering growth creates a unique atmosphere that appeals to all ages. Whether you're exploring the scenic trails of the nearby Upper Tampa Bay Trail or enjoying a leisurely afternoon at the Oldsmar Parks, there’s always something to do in this delightful city.

For those seeking homes in Oldsmar, you’ll find an array of properties that cater to various lifestyles, including homes with guest parking features. These residences are perfect for entertaining friends and family, providing ample space for visitors while ensuring convenience. Imagine hosting gatherings or welcoming guests without the hassle of parking concerns. With ample guest parking, you can focus on creating memorable moments in your beautiful Oldsmar home.

If you're looking to embrace a vibrant lifestyle in a welcoming community, Oldsmar is the ideal place to plant your roots. Come explore the charm of Oldsmar and discover your dream home today!

Newest Oldsmar Homes with Guest Parking Features

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code

Welcome to carefree Florida living in this beautifully updated second-floor, two-bedroom, two-bath condo nestled within the sought-after East Lake Woodlands community! The HOA fee includes an impressive array of amenities and services, including cable TV, internet, community pool access and maintenance, reserves, exterior and grounds maintenance, sewer, water, and trash. With so much included, your only utility expense is electricity—giving you more time to simply relax and enjoy your Florida lifestyle. Step inside and immediately appreciate the welcoming, light-filled interior and luxury vinyl wood-look flooring. The updated kitchen features granite countertops, tile backsplash, a pantry closet, updated hardware, and a double stainless-steel sink overlooking the breakfast bar. Open to the living and dining areas, the kitchen creates a comfortable flow for everyday living and entertaining, with room for a small dining table if desired. The spacious living and dining area is enhanced by a beautiful shiplap-style wood ceiling and warm wood-look flooring, creating an inviting atmosphere with plenty of character. All windows and sliding glass doors throughout the condo have been updated to hurricane-impact glass, providing added protection and peace of mind. The beautiful sliding glass doors open to your private, screened-in lanai—a wonderful extension of your living space and the perfect spot to enjoy your morning coffee, curl up with a good book, or dine al fresco. A charming nook on the lanai provides an ideal reading retreat, while a table and chairs would transform the space into your own private outdoor oasis. The lanai also offers private sliding-door access to the primary suite. Your primary suite is generously sized and offers exceptional storage, with three walk-in closets. The en-suite bathroom features a updated dual-sink vanity with additional storage and a convenient step-in shower with glass enclosure. The second bedroom is located toward the front of the condo and is bright, comfortable, and nicely sized, with two generous wall closets. A second full bathroom with a tub/shower combination is conveniently located off the hallway. The spacious laundry closet is located inside the unit - a rare feature in this community! Perhaps one of the most appealing features of this home is its peaceful setting. The condo backs to a private, tree-filled area with no immediate rear neighbors, creating a tranquil, park-like backdrop that you can enjoy from your screened lanai. Located just off Tampa Road, East Lake Woodlands offers a convenient central location with easy access to Tampa, Tampa International Airport, restaurants, shopping, golf, and Florida's beautiful beaches. You'll also enjoy convenient access to U.S. Highway 19 and St. Petersburg. With numerous updated done, this spacious, private, and wonderfully maintained condo offers the perfect combination of comfort, convenience, and carefree Florida living. Come see it for yourself and discover how easy Florida living can be!

128 Nancy Drive, Oldsmar

4 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code

Beautifully remolded villa in gated East Lake Woodlands is turnkey and move in ready. Recent updates include newly redesigned open concept kitchen with shaker style cabinets, soft close doors and drawers, under cabinet lighting, polished marble backsplash and beautiful Quartz countertops. All new stainless steel appliances including refrigerator, range, dishwasher, microwave and disposer. Master bath shower and floor features new elegant porcelain tile, new fixtures, lighting, mirrors and dual sink vanity with Quartz top. Second bath also updated with new tub, tile, fixtures, lighting, mirrors and vanity with Quartz top. All new doors, lighting, fixtures and beautiful Luxury Vinyl Plank flooring throughout with 5.5-inch baseboards. Home has all new recessed lighting fixtures as well as fresh interior paint in neutral colors. HVAV system and Electrical panel recently updated as well. All windows and sliders were updated in 2018 and are Impact rated. Shingle roof replaced in 2019. Water Heater 2018. Unit offers a private fenced patio off one of the bedrooms with a pleasant nature view. Two convenient storage/utility rooms - one next to the carport out front and another on the back screen porch that overlooks a pond. East Lake Woodlands offers a gated setting, mature landscaping, scenic golf course surroundings, and optional country club memberships with golf, tennis, pickleball, swimming, fitness, dining, and social amenities available. 24hr manned guard gate along with 2 championship 18-hole golf courses. Conveniently located near shopping, restaurants, parks, beaches, airports. Porch carpet to be replaced with commercial grade earth tone color.

110 Evelyn Court, Oldsmar

2 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

Virtually Staged. WELCOME TO WATERFRONT LIVING IN BAYSIDE TERRACE! Built in 2019, this spacious 2-bedroom, 2.5-bath townhome with an oversized loft offers 1,888 SF of beautifully designed living space in a gated community along Tampa Bay. The open-concept main level is designed for everyday living and entertaining, featuring real wood cabinetry, quartz countertops, included appliances and a large walk-in pantry. Storage is abundant throughout the home, with generous closets and thoughtfully designed storage space rarely found in townhome living. The dining and living areas flow effortlessly to a private screened porch, perfect for enjoying Florida living year-round. A ONE-YEAR-OLD A/C adds comfort and peace of mind! Upstairs, both oversized bedrooms feature private en-suite baths and excellent closet space, while the exceptionally spacious loft offers even more flexibility for a home office, media room, gym, playroom or second living area. The lifestyle continues outside your front door! Bayside Terrace offers resort-style amenities directly on Tampa Bay. Relax by the waterfront pool and enjoy spectacular west-facing sunsets from the cabanas, fish from the private community dock, or launch your kayak or paddleboard directly onto the bay. The community is gated with 24-hour virtual guard service, and pets are welcome! HOA fees include water, sewer, trash, basic cable, community amenities, maintenance, escrow reserves and 24-hour guard service. Leasing is permitted after two years of ownership. Centrally located in Oldsmar, with convenient access to Tampa, Clearwater, Westchase, Palm Harbor and Safety Harbor, plus nearby shopping, dining, parks, golf, recreation, Tampa International Airport and the Gulf beaches. Spacious. Storage-packed. Gated. Waterfront. Resort-style living. Come experience everything 2404 Arch Ave has to offer!

2404 Arch Ave, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv. ⋅ 34677 Zip Code

RARE FIRST-FLOOR, FULLY REMODELED 2 BED / 2 BATH CONDO IN OLDSMAR, PRICED TO STAND OUT. No stairs and no renovation project waiting for you. This move-in-ready 915 sq. ft. condo has been thoughtfully updated throughout with wood-look flooring, fresh neutral finishes and a bright, open living and dining area that opens directly to a private covered patio. The updated kitchen features shaker-style cabinetry with plenty of storage, quartz countertops, stainless steel appliances, modern hardware and a decorative tile backsplash. The spacious primary suite includes a large walk-in closet and updated ensuite bath with a tiled walk-in shower. The second bedroom is generously sized with excellent closet space, and the second full bath has also been updated with modern tile and a tub/shower combination. An interior laundry area with stacked washer and dryer adds another convenience rarely found at this price point. Gardens of Forest Lakes offers community amenities including a pool, tennis and basketball courts, playground, park and fishing dock, with convenient access to shopping, dining, parks, Tampa, Clearwater, Gulf beaches and Tampa International Airport. First floor, fully updated, two full baths, interior laundry and competitively priced within the community. This one is ready for its next owner.

133 Sabal Court Unit F, Oldsmar

4 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code

Welcome to 150 Poole Place, a spacious 4-bedroom, 2-bath villa offering approximately 1,550 square feet of flexible living space in the gated community of East Lake Woodlands. Ideally positioned along the 15th hole of the South Course, this immaculate home offers beautiful golf course views and a peaceful setting that can be enjoyed from multiple areas of the property. Inside, the split-bedroom floor plan provides privacy and versatility, with four bedrooms that can easily accommodate family, guests, a home office, or hobby space. The living room features a decorative electric fireplace that adds character and ambiance, while the kitchen offers generous cabinetry, ample counter space, and all appliances included. An enclosed Florida room expands the living area and creates a comfortable space to relax while overlooking the golf course. French doors, tile flooring throughout, plantation shutters, interior laundry, and ample storage add to the home’s functionality and appeal. Outdoor living continues with patio areas that offer the perfect place for morning coffee, entertaining, or simply enjoying the scenic surroundings. A new water softener system was installed in July 2026. The monthly HOA fee of $490.08 includes internet, cable, building maintenance, roof, and lawn care, providing a convenient low-maintenance lifestyle. East Lake Woodlands is known for its gated setting, mature landscaping, scenic golf course surroundings, and optional country club lifestyle. Golf, tennis, pickleball, swimming, fitness, dining, and social amenities are available through separate club membership. Conveniently located near shopping, restaurants, parks, beaches, airports, and all that the Tampa Bay area has to offer, 150 Poole Place combines space, flexibility, and a desirable golf course setting in one of Oldsmar’s most established communities.

150 Poole Place, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

Welcome to refined coastal living in this beautifully appointed 3-bedroom, 2.5-bath townhome located within a highly desirable waterfront community in Oldsmar. Offering a blend of contemporary design, quality construction, and low-maintenance living, this home is ideal for those seeking comfort, style, and convenience. This home, built in 2018, feels like brand new construction. Even though the home is only 8 years old, it shows like new construction, as it has only been lived in a short period of time over the past 8 yrs. Enter the home through the leaded glass front door and you’ll appreciate the bright, open-concept layout. Wood-look ceramic tile flooring extends throughout the entire home without transitions. The spacious living and dining areas are filled with natural light and flow seamlessly into the well-designed kitchen. The kitchen features contemporary cabinetry, premium quartz countertops, stainless steel appliances, and generous workspace for preparing meals and gathering with family and friends. Modern finishes, and carefully selected details create a polished and cohesive look throughout the home. Upstairs, the spacious primary suite offers a comfortable private retreat with a well-appointed en-suite bathroom and generous walk-in closet space. Two additional bedrooms provide flexibility for guests, family members, or a dedicated home office. A large loft creates valuable additional living space and is perfect for a media room, family room, play area, or home office. The 2nd floor also has a huge laundry room convenient to all bedrooms. Your garage is finished with an epoxy paint on the surface making for a very attractive and functional space. One of the home’s most appealing features is the private backyard setting with no direct rear neighbors. The covered rear porch provides a peaceful place to relax, entertain, or enjoy the outdoors while overlooking a more open and secluded backdrop. Home is being sold with washer & dryer, water softener and the water heater was replaced under a year ago. Energy-efficient windows and doors help enhance year-round comfort, while modern construction standards provide added peace of mind. Residents enjoy access to an impressive selection of community amenities, including a clubhouse, fitness center, resort-style pool, gated entry, sidewalks, and a community fishing pier. Conveniently located near parks, walking trails, shopping, dining, and entertainment, the community also offers easy access to Tampa, St. Petersburg, Clearwater, and the area’s beautiful Gulf beaches. Whether you’re searching for a primary residence or a low-maintenance Florida retreat, this exceptional home delivers stylish finishes, backyard privacy, generous living space, and an outstanding Tampa Bay location.

1103 Mango Court, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code

Virtually Staged. Virtually Staged. Welcome Home to this first floor 2 bedroom, 2 bath condo in Woodlake Run in East Lake Woodlands. Large open living/dining area with wood-like flooring and sliders to screened in Lanai. Tranquil wooded views with no rear neighbors. Nice open Kitchen off of dining area with stainless steel appliances, lots of cabinets and breakfast bar seating. Covered porch off of the kitchen with laundry closet & washer/dryer. Large Primary Bedroom with adjoining bath, step-in shower, 2 closets and a private slider to covered Lanai. 2nd Bedroom with private slider to covered porch and adjacent bath features step-in shower. New windows in 2021 along with new electrical panel box updated in 2021. Great Location, 2 community heated pools, golf course community, Shopping, Restaurants, Movie Theatre, County Parks, Beaches nearby. East Lake Woodlands offers Ardea Country Club with multiple memberships (with additional fees) which can include Clubhouse, golf, additional pools, tennis, fitness center, Clubhouse & restaurant. Listed for rent as well TB8526636.

135 Woodlake Wynde Unit 135, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv. ⋅ 34677 Zip Code

MOVE-IN READY FIRST-FLOOR, 2-BEDROOM, 2-BATH CONDO with BOTH BATHROOMS COMPLETELY REMODELED IN 2026, a BRAND-NEW WATER HEATER (AUGUST 2026), NEW AC (2021), NEW ELECTRICAL PANEL (2024) and an extensive list of recent improvements! Located in The Gardens of Forest Lakes, this light and bright ground-floor residence offers comfortable, low-maintenance living with no stairs and a peaceful setting surrounded by mature landscaping and expansive green space. Step inside to a freshly painted interior with tile flooring throughout, spacious living and dining areas, and sliding glass doors that open directly to the covered patio and lawn beyond. The kitchen offers abundant cabinetry, generous counter space, a breakfast/pass-through bar and a new microwave installed in May 2026. Both bathrooms have been completely renovated in 2026, including new insulation and drywall. The primary bath showcases a stylish new vanity and beautifully tiled walk-in shower, while the second bath features a new vanity and tub/shower combination. Both bedrooms are generously sized with ample closet space, and an interior laundry area adds everyday convenience. Additional 2026 improvements include new Sherwin-Williams paint throughout the entire condo including walls, ceilings, trim and doors, serviced windows and sliding doors with new locks, screens and sash caps, new closet doors, new window blinds and sliding-door verticals, new ceiling A/C vent covers, new hallway linen closet shelving, and new switch and outlet plate covers. Beyond the condo, enjoy an impressive array of community amenities in a scenic lakefront recreational setting. Forest Lakes offers a large community swimming pool and spa, tennis courts, basketball, racquetball/handball courts, playground, picnic and grilling areas, and a waterfront dock overlooking the lake. Mature trees, tropical landscaping and generous green spaces create an inviting setting throughout the community. With extensive recent improvements already completed, first-floor convenience and outstanding recreational amenities, this Oldsmar condo offers an exceptional opportunity for a primary residence, seasonal getaway, low-maintenance Florida home or great rental income opportunity. Great location close to Beaches, Parks, and Tampa International airport. Schedule your private showing today!

123 Loblolly Court Unit A, Oldsmar

4 Beds ⋅ 3 Baths ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code

Virtually Staged. Welcome to an exceptional 2,736-square-foot luxury home nestled within Cross Pointe, a gated community inside the prestigious guard gated golf community of East Lake Woodlands . Offering 4 bedrooms, 3 baths, a spacious 2-car garage,with workbench area. and bonus space. This beautifully appointed residence blends elegant finishes, thoughtful design, and exceptional outdoor living. Pool access & views from almost every room. Desirable split-bedroom floor plan features soaring ceilings and travertine flooring complemented by engineered hardwood & tile floors. The updated gourmet kitchen is designed for both everyday living and entertaining, featuring Bosch and Frigidaire appliances, (Range has induction cooktop & convection/air fry oven) quartz tops, crisp white cabinetry, and a striking navy island. Breakfast area overlooking pool. The family room offers a warm wood-burning fireplace (updated 2020) and a sophisticated navy wine bar, creating an inviting gathering space. Spacious primary suite includes a comfortable sitting area and sliders that open directly to the screened porch, offering beautiful views of the private pool and backyard . Walk-in closet with organizers. Primary bath has soaking tub, large marble shower, private water closet & dual sink vanities. 3 guest bedrooms, with one having an ensuite bath also providing convenient access to the pool area—perfect for effortless poolside living. Bonus/Flex room with its own A/C (2026) is perfect for an office, hobby room, studio, gym, etc. Outdoor living is truly exceptional. The screened rear porch features paver flooring and overlooks the Saltwater PebbleTec pool , complete with Caribbean blue tile, a charming, soothing waterfall and gazebo. Pool pump & new salt system (2025). An expanded paver patio (2025) extends into the private backyard, providing ample space for entertaining, relaxing, and enjoying the peaceful surroundings. Many updates include tile roof (2019), HVAC (2017), Water Heater (9/2026), Paver patio (2022), Kitchen updated (2020) with professional kitchen cabinet refinishing (2026), Bosch refrigerator (2025), Frigidaire appliances (2026). All ceiling fans updated (2024 & 2025). Newly textured ceilings (2022), modern lighting. With its luxurious finishes, spacious layout, updated kitchen, resort-style pool, and prime location within two prestigious gated communities, this home offers an exceptional Florida lifestyle with privacy, comfort, and elegance at every turn. Centrally located to Tampa International and St . Pete/Clearwater Airport, award winning beaches, boating and fishing, professional sporting events, historic Dunedin and Safety Harbor, Pinellas and Duke Energy Bike Trails, restaurants, shopping, and hospitals. East Lake Woodlands is a golf community with an optional membership available to the nationally renowned ELW Country Club, featuring outstanding amenities including two championship golf courses, sixteen tennis courts, pickleball, fully-equipped fitness center, lap & freeform pools, splash pad, dining, full social calendar/club, and is also part of ClubCorp/Invited with reciprocal rights to 300+ clubs. Low HOA and NO flood insurance required. A fantastic value! Call today for your private tour!

1723 Captiva Drive, Oldsmar

2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code

Welcome to this 2-bedroom, 2.5-bath townhome located in the desirable gated community of Countryside Key in the heart of Oldsmar. This spacious floor plan features two primary suites upstairs, each with its own private bathroom, while the convenient half bath downstairs is perfect for guests. Enjoy an open living and dining area with plenty of natural light and a private screened patio ideal for relaxing or entertaining. The seller is offering a concession toward new flooring and/or appliances, providing a great opportunity to personalize the home to your own style. Residents of Countryside Key enjoy access to a community pool, tennis courts, and beautifully maintained grounds, all just minutes from shopping, dining, parks, top-rated schools, Tampa International Airport, and the beaches.

366 Countryside Key Boulevard, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code

BACK ON THE MARKET SELLER FINANCING FELL THROUGH. Exceptional GROUND-FLOOR CORNER UNIT with Resort-Style living AT WOODLAKE RUN! Welcome home to this DESIRABLE 2-BEDROOM, 2-BATHROOM condo offering effortless ONE-LEVEL MAINTENANCE-FREE LIVING in the premier gated community of East Lake Woodlands! Boasting 924 SQ FT OF LIGHT-FILLED LIVING SPACE, this prime END-UNIT LOCATION features an OPEN FLOOR PLAN, modern WOOD LAMINATE AND TILE FLOORING throughout (NO CARPET!), and a bright LIVING/DINING ROOM COMBO ideal for entertaining. Enjoy total peace of mind with recent high-value updates including a New electrical panel (2026), 2023 A/C SYSTEM for ultimate energy efficiency, a BRAND-NEW DISHWASHER, and an in-unit washer/dryer set! Unwind on your PRIVATE COVERED PORCH overlooking tranquil green space and scenic pond views. Step right across the walkway to enjoy the REFRESHING COMMUNITY POOL DIRECTLY ACROSS THE BUILDING! Residents of East Lake Woodlands enjoy world-class amenities including 24/7 GUARDED GATE SECURITY, country club options, golf, tennis, and lush walking trails. The ALL-INCLUSIVE MONTHLY HOA conveniently covers water, sewer, trash, exterior building maintenance, cable TV, pest control, and pool upkeep. Ideally located near TOP-RATED SCHOOLS, DINING, SHOPPING, AND TAMPA INTERNATIONAL AIRPORT—this turn-key property is perfect as a PRIMARY RESIDENCE, WINTER RETREAT, OR INVESTMENT OPPORTUNITY! Schedule your private tour today!

10 Woodlake Place, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code

Price Improvement! Welcome home to this beautifully updated second-floor condo located in the highly sought-after, gated community of East Lake Woodlands with picturesque golf course views. Known for its peaceful surroundings and resort-style living, this community offers both comfort and convenience in an ideal setting. You are greeted by a new storm door before stepping inside to discover a bright and airy interior filled with natural light. This move-in-ready residence has been thoughtfully upgraded with an amazing eat-in kitchen featuring new quartz countertops, a closet pantry, newer appliances (only two - four years old), and Wi-Fi-compatible dishwasher and range—perfect for everyday living and entertaining alike with a convenient pass-through window to the dining area. Fresh interior paint and new LVP and tile flooring flow seamlessly throughout the home, complemented by energy-efficient LED lighting, ceiling fans, and updated bathrooms for a clean, modern, and cohesive design. The home also features upgraded, HOA-approved Stainmaster LVP underlayment for the LVP flooring, providing enhanced comfort and sound reduction. The air conditioning system is equipped with a UV light for improved air purification and indoor air quality. The spacious primary bedroom offers three closets, including two walk-in closets, a separate dressing area, and an updated en-suite bathroom with a walk-in tiled shower and glass door. The guest bedroom features generous wall closets. A brand-new washer and dryer are scheduled to be installed in mid-August and are conveniently located in the hall closet near the guest quarters. Generous storage and ample closet space add to the home's functionality and overall comfort. Enjoy the added privacy of a second-floor location while taking advantage of the exceptional lifestyle within East Lake Woodlands. The community pool and Condo 2 Clubhouse are just across the parking lot! Pets are welcome, and the monthly maintenance fee provides outstanding value and ease of living. If you're ready to explore, the location is fantastic. Nearby, Ardea Country Club offers optional private memberships with two heated swimming pools, two 18-hole championship golf courses, tennis and pickleball courts, a fitness center, clubhouse, restaurants, and a full calendar of social activities. The condo is also conveniently located near Westfield Countryside Mall, shopping, restaurants, entertainment, the beautiful beaches of Honeymoon Island, and numerous parks and walking trails for a relaxed Florida lifestyle. You'll also enjoy easy access to the charming downtown districts of Tarpon Springs, Dunedin, and Safety Harbor for even more dining, shopping, and entertainment.

222 Caryl Way, Oldsmar

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