Oldsmar Homes with Trees/Woods View

Oldsmar Homes with Trees/Woods View

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County, where the charm of small-town living meets the vibrancy of Florida’s natural beauty. Known for its lush landscapes and a strong sense of community, Oldsmar offers a unique blend of suburban tranquility and outdoor adventure. With its proximity to Tampa Bay and the stunning Gulf Coast, residents enjoy the best of both worlds: serene living and exciting urban amenities just a short drive away.

One of the standout features of Oldsmar is its abundance of homes surrounded by breathtaking trees and wooded views. Imagine waking up each morning to the soothing sounds of nature and the sight of majestic oaks and pines swaying gently in the breeze. These homes provide not just a residence, but a lifestyle enriched by the beauty of the great outdoors. Whether you’re sipping your morning coffee on a spacious deck or hosting a family barbecue in your backyard, the serene ambiance created by the lush greenery is unparalleled.

Oldsmar is also home to several parks and recreational areas, including the popular Oldsmar City Park and the scenic Upper Tampa Bay Trail, perfect for hiking, biking, and enjoying leisurely strolls. With a variety of local shops, restaurants, and community events, Oldsmar fosters a vibrant spirit that welcomes new residents with open arms.

If you’re searching for a home that offers a picturesque view and a close-knit community, Oldsmar is the perfect place to plant your roots. Discover the tranquility and charm of living among the trees in this delightful Florida city!

Newest Oldsmar Homes with Trees/Woods View

$849,900
4 Beds ⋅ 3 Baths ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code
Nestled within a gated neighborhood inside an exclusive gated golf course community, this exceptional single-family home offers the perfect blend of privacy, space, and luxury. Situated on an expansive lot of about 1/3 of an acre, the property enjoys a serene preserve backdrop, creating a peaceful setting with a spacious backyard and plenty of room to relax, entertain, or create your dream outdoor retreat. Thoughtfully designed with flexibility and comfort in mind, this spacious residence features four bedrooms, three full bathrooms, and a dedicated office, providing abundant space for a growing family, multiple home offices, hobby rooms, or welcoming guests with ease. High and Tray ceilings enhance the home's open, airy feel, while engineered wood flooring throughout the main living areas adds warmth, style, and timeless appeal. The heart of the home is the expansive family room and kitchen combination, designed for both everyday living and effortless entertaining. A cozy dining nook complements the generous snack bar, offering ample seating for family and friends. The kitchen is enhanced by taller cabinetry featuring distinctive glass inserts and decorative accent lighting with multiple color options, adding both elegance and personality. Anchoring the family room is a striking wood-burning fireplace featuring a custom mantel with an updated stacked-stone surround, creating a warm and inviting focal point for gatherings or quiet evenings at home. Step outside to your own private resort-style oasis. The expansive screened lanai, rescreened in 2023, surrounds a beautifully renovated pool and entertaining area. A Pebble Tec pool finish, sun shelf, dramatic stacked-stone waterfall, elegant travertine pool deck, and updated wet bar—all completed in 2023—create an exceptional outdoor living experience. The oversized three-car garage is equally impressive, featuring a professionally finished Spartacote Sparta-Chip floor for a clean, upscale appearance. Additional upgrades include Wi-Fi-enabled garage door openers and a hurricane-rated garage door, both installed in 2018, providing modern convenience and peace of mind. This meticulously maintained home has been extensively updated, allowing the next owner to move in with confidence. Significant improvements include a new roof (2019), hurricane-rated windows and doors (2022), remodeled hall and pool bathrooms (2017), replacement chimney cap (2024), hot water heater (2024), water softener (2025), and numerous thoughtful enhancements throughout. These investments not only enhance the home's beauty but also provide exceptional value, efficiency, and long-term peace of mind. Located within one of the area's premier gated golf course communities, this home offers the opportunity to enjoy an exceptional lifestyle, with golf and social memberships available for purchase separately. Combining generous living spaces, extensive upgrades, luxurious indoor and outdoor amenities, and an outstanding homesite, this remarkable residence is a rare opportunity to experience the very best of Florida living.

4987 Cross Pointe Drive, Oldsmar
$495,000
3 Beds ⋅ 2 Baths ⋅ Fountains At Cypress Lakes Ii-A The SubDv. ⋅ 34677 Zip Code
Discover your own slice of Florida paradise with this charming three-bedroom, two-bathroom home, perfectly situated in the highly sought-after community of The Fountains at Cypress Lakes in Oldsmar. Boasting a private, sparkling in-ground pool, this beautiful home is conveniently in walking distance of the local elementary school, and easy access to local shops, restaurants, local airports and beautiful Florida beaches. This community has so much to do! Enjoy the many parks, nearby ice-skating arena. pickleball courts, childrens spray park, Oldsmar Sports Complex and local movie theater. The sports complex is home to Oldsmar BMX and Oldsmar Little League. Step inside to a thoughtfully designed floor plan that maximizes comfort and functionality. Enjoy beautiful newly installed Luxury Vinyl Plank through out the home with a transferable warranty! The spacious living areas provide ample room for both daily living and hosting guests. The well-appointed kitchen is perfect for preparing meals, while the inviting bedrooms offer a peaceful retreat at the end of the day. New cellular blinds just installed. The primary suite includes 2 walk-in closets and an en-suite bathroom for added convenience and privacy. The windows in the home have solar film which reduce heat and UV rays, increase privacy and improve energy efficiency. There is a newly installed hot water heater with a transferable warranty. The HVAC is equipped with a HEPA filter, UV light and Guardian device that kills bacteria, mold and viruses in the duct work. The attic has extra insulation which also helps improve the home's energy efficiency. The sparkling pool has a Stonescape surface for enhanced durability and a comfortable non-slip surface, and pavers for the pool deck complete the sophisticated look complementing the overall design of the backyard. The two-car garage is equipped with a back-up battery for the door opener for added peace of mind. The true highlight of this home is the private backyard oasis. Imagine spending sunny Florida afternoons lounging by your own pool or relaxing on the beautiful lanai with your morning coffee, enjoying the tranquility and greenery of your backyard. With the home backing up to conservation, you'll often be treated to the delightful sight of deer, egrets, ibis, sandhill cranes, hawks and songbirds in your backyard, adding a unique touch of wildlife to your everyday life. The Fountains at Cypress Lakes is a well-maintained community known for its pride of ownership and manicured landscapes. Residents enjoy a low annual HOA fee and no CDD fees, making it an attractive option for homeowners. Don't miss out! Schedule your showing today!

333 Tavernier Drive, Oldsmar
$259,900
2 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit Five SubDv. ⋅ 34677 Zip Code
Investor special with exceptional upside! This concrete block 2-bedroom, 2-bath, 2-car garage home is priced to sell and offers outstanding renovation potential. Situated on a nicely sized lot with beautiful lake views and no rear neighbors, the fully fenced backyard has plenty of room for a pool. The home has an updated electrical panel. The HVAC system was updated in 2019. The roof was last replaced in 2009. The office provides approximately 270 additional square feet beyond the heated living area, offering flexible space for a home office, hobby room, or future expansion. (The second bathroom is located in the garage.) Enjoy a great central location just a short walk to Sheffield Park and Harbor Palms Nature Park, featuring walking trails, a boardwalk, fishing pier, and kayak launch. No HOA and convenient access to Tampa, St. Petersburg, Gulf beaches, shopping, dining, and Tampa International Airport. Cash offers only. Property is being sold As Is with no repairs. Can be purchased individually or as part of a package with MLS #TB8366557 (613 Chestnut St.) and MLS #TB8366564 (204 Shore Dr. W.), all offered by the same seller.

704 Lemonwood Drive, Oldsmar
$149,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Maintenance free condo living within the prestigious gates of East Lake Woodlands! Pride of ownership abounds in this well maintained first floor unit offering just under 1,100 sq ft of fine Florida living with 2 bedrooms, 2 bathrooms and a convenient covered carport. Open concept floor plan with a great room that combines living and dining spaces ideal for family gatherings and entertaining. Living and entertaining space is extended outside with sliding glass doors leading to a lanai looking out on the community’s well-manicured green spaces. A serene setting for morning coffee or afternoon cocktails. The lanai also houses a convenient storage closet. The spacious kitchen includes an eat-in area and features tile flooring. The appliances include a ceran top range, built-in microwave, refrigerator (5 yrs old) and dishwasher. Privacy prevails with an ideal split bedroom layout. The primary bedroom is located just off the living room and offers generous storage boasting 2 walk-in closets and an additional wall closet and the room offers a sliding glass door to the lanai. The ensuite features a single vanity with dressing area and a walk-in shower. The secondary bedroom is located on the opposite side of the home and features laminate flooring, a wall closet & ceiling fan. The hall bathroom is designed with a single vanity and a tub/shower combination. The hallway laundry closet is perfectly situated for ideal convenience, and the seller is generously including the washer and dryer. Additional features include AC 2022, WH 2022. The HOA includes exterior and grounds maintenance, community pool, water, sewer, trash, cable, internet. This condo is just steps away from the community pool! The home is zoned for exceptional schools and near to all, restaurants, shopping, medical and of course the famed Gulf beaches are nearby. The recently renovated Ardea Country Club lies within the gates of East Lake Woodlands. The club offers several levels of membership and has an impressive array of amenities including 2 championship golf courses, 2 resort style heated pools, 12 pickleball courts, 14 clay tennis courts, state-of-the-art fitness center, restaurant and bar. Magnificent home in a convenient location… carefree Florida living!

129 Nancy Drive, Oldsmar
$665,000
3 Beds ⋅ 2 Baths ⋅ Parcel B - The Pinnacle SubDv. ⋅ 34677 Zip Code
RARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. "THIS IS A MAINTENANCE FREE COMMUNITY." WALK THRU DOUBLE GLASS ENTRY DOORS TO FOYER THAT OPENS TO LIVING ROOM. LIGHT AND BRIGHT EXPANDED FAMILY ROOM AND KITCHEN OFFERS QUIET VIEWS OF CONSERVATION AND GOLF COURSE AREA. NEWLY EXPANDED LANAI WITH PARORAMIC BIRDCAGE SCREENING. KITCHEN OVER LOOKS FAMILY ROOM HAS CENTER ISLAND AND WOOD CABINETRY, BUILT-IN PANTRY, GRANITE COUNTER TOPS AND ALL STAINLESS-STEEL APPLIANCES. SEPARATE DINING ROOM WITH EASY ACCESS FROM THE KITCHEN. MASTER BEDROOM WITH TWO WALK-IN CLOSETS AND MASTER BATH WITH FREE STAND TUB, SEPARATE STALL SHOWER, PRIVATE TOILET CLOSET, DOUBLE SINK VANTY WITH GRANITE COUNTER AND CUSTOM TILE. OFFICE WITH DOUBLE DOOR ENTRY CAN ALSO BE USED AS THIRD BEDROOM WITH CLOSET. SECLUDED SECOND BEDROOM IS PERFECT FOR GUESTS WITH ADJOINING BATH. INSIDE LAUNDRY ROOM WITH UTILITY SINK AND EXTRA STORAGE. GARAGE HAS EXTRA STORAGE AND SPACE FOR TWO CARS. THIS SEPTACULAR HOME LOCATED ON A PRIVATE CUL-DE-SAC. FOR SOCIAL ENJOYMENT YOU CAN RELAX IN THE COMMUNITY POOL. CLUBHOUSE MEMBERSHIP IS ALSO AVAILABLE FOR TENNIS AND GOLF. CLOSE TO BEACHES, SHOPPING, HOSPITALS, AND AIRPORTS. THIS IS WAITING FOR YOU!

5250 Pinehurst Court, Oldsmar
$399,000
3 Beds ⋅ 2 Baths ⋅ Heatherwood Unit One Condo SubDv. ⋅ 34677 Zip Code
Beautifully updated condo in East Lake Woodlands with 3 bedrooms, 2 full baths, 1 car garage and an added BONUS space/office! Right as you enter, notice the entire entryway is newly UPDATED with a custom door, paint, sconce lighting and Stanton carpet up the stairwell. Prepared to be wowed in the living room by the elegant, NEW custom built entertainment center with an electric fireplace. Set your color of choice and it can heat up the room for chilly nights. With the natural light, luxury vinyl plank flooring, vaulted ceilings, 2 huge fans on remotes.. this is quite the spot for entertaining. Kitchen features newer leathered granite countertops, wood cabinetry with soft close doors, stainless steel appliances, breakfast bar and new custom drapes. Step outside to the fully screened lanai with adjustable sunshades. Cool off with a new variable speed fan while enjoying all the wildlife East Lake Woodlands as to offer. The owner's suite also has a sliding door to the lanai, 2 closets with ample space, double bathroom vanities, countertops, garden tub and floor-to-ceiling tiled, glass-enclosed shower. Two other bedrooms with large windows share an updated bathroom. Enjoy an upstairs inside laundry with storage space and a bonus room with a convenient wet bar area. This space can be a TV room, office, playroom, sitting room for morning coffee..the ideas are endless. Additional updates include new epoxy garage floor, remote blinds, and light fixtures. HOA fee includes internet, cable, water, sewer, trash, community pool, exterior maintenance, grounds and insurance. Furniture is also available for purchase. East Lake Woodlands is central to Florida's most famous beaches, shopping, Tampa airport, A-rated schools and numerous dining options. There also is an option to join the Ardea Country Club and have access to 2 championship golf courses, tennis courts, fitness center, clubhouse, dining, swimming pools and social events. Don't miss this opportunity!

208 Clays Trail Unit 208, Oldsmar
$299,900
2 Beds ⋅ 2 Baths ⋅ St Andrews Condo SubDv. ⋅ 34677 Zip Code
Experience resort-style living in this beautifully renovated 2-bedroom + loft, 2-bath condominium offering approximately 1,600 square feet of bright, open living space. Perfectly positioned overlooking tranquil water and the golf course, this exceptional home combines modern updates with soaring architectural details in one of Oldsmar's most desirable communities. The impressive great room welcomes you with dramatic vaulted ceilings, abundant natural light, and a striking spiral staircase leading to a versatile loft—ideal for a home office, media room, or guest space. The remodeled kitchen features crisp white cabinetry, quartz countertops, stainless steel appliances, recessed lighting, and a breakfast bar that opens seamlessly to the living and dining areas. The spacious primary suite offers peaceful water views, private access to the screened lanai, a custom walk-in closet, and a beautifully renovated en-suite bath complete with a luxurious oversized walk-in shower and dual vanities. The generous second bedroom is located near the updated guest bath, providing privacy for family or visitors. Step outside to the expansive screened lanai and enjoy picturesque views of the pond and golf course—the perfect setting for your morning coffee or relaxing evenings. Features You'll Love 2 Bedrooms + Spacious Loft 2 Fully Updated Bathrooms Approximately 1,600 Sq. Ft. Soaring Vaulted Ceilings Dramatic Spiral Staircase Beautifully Renovated Kitchen with Quartz Counters Stainless Steel Appliances Luxury Vinyl Plank Flooring Throughout Custom Walk-In Closet Oversized Primary Shower with Designer Tile Full-Size Washer & Dryer Large Screened Lanai Water & Golf Course Views Assigned Covered Parking Located just minutes from shopping, restaurants, parks, Tampa International Airport, and some of the area's best beaches, this move-in-ready home offers the perfect blend of comfort, style, and convenience. Schedule your private showing today and discover everything this exceptional Oldsmar home has to offer! Newer AC 3/2022.

60 St Andrews Place Unit 60, Oldsmar
$279,900
2 Beds ⋅ 2 Baths ⋅ Heatherwood Unit One Condo SubDv. ⋅ 34677 Zip Code
Maintenance free condo living in the sought after community of “Heatherwood” within the gates of prestigious East Lake Woodlands! This lovely first floor, fully remodeled end unit offers you over 1,200 sq ft of fine Florida living. Boasting 2 bedrooms, 2 bathrooms and 1 car garage, this modern open concept floor plan is ideal for family gatherings and entertaining. Lavish comfort from floor to ceiling as you enter to luxury vinyl flooring and soaring ceilings in the spacious great room with an abundance of natural light in your living and dining areas. Gorgeous, updated kitchen overlooks the great room with a convenient breakfast bar, white soft close cabinetry including cabinet pantry, granite countertop, dual undermount stainless steel sink and SS appliances including a ceran top range (2025), built-in microwave, dishwasher (2025) and 3 door refrigerator (2025). Extend your living and entertaining outdoors through the sliding glass doors to the screened lanai area with generous outdoor seating space for family enjoyment. The luxury vinyl flooring continues throughout the ideal split bedroom layout. Privacy prevails! The primary bedroom is located off of the great room and offers an elegant double door entry. The ensuite features white, soft close cabinetry, dual vanities with granite countertops, undermount sinks, linen and wall closets, a full walk-in shower with designer tile accents, ledge seat and glass door. The secondary bedroom is located on the opposite side of the home and features a wall closet & ceiling fan. The updated hall bathroom is designed with a single vanity, granite counter with undermount sink, and a tub/shower combination. A perfectly situated hallway laundry closet leads to the garage. Additional features include AC 2020, WH 2024. The HOA includes exterior maintenance and grounds, community pool, water, sewer, trash, cable, internet and exterior insurance. This premium homesite is just steps away from the community pool! The home is zoned for exceptional schools and near to all, restaurants, shopping, medical and of course the famed Gulf beaches are nearby. The recently renovated Ardea Country Club lies within the gates of East Lake Woodlands. The club offers several levels of membership and has an impressive array of amenities including 2 championship golf courses, 2 resort style heated pools, 12 pickleball courts, 14 clay tennis courts, state-of-the-art fitness center, restaurant and bar. Magnificent home in a prime, convenient location… carefree Florida living!

215 Clays Trail, Oldsmar
$558,900
3 Beds ⋅ 2 Baths ⋅ Fountains At Cypress Lakes Ii-B SubDv. ⋅ 34677 Zip Code
Welcome Home to this highly sought-after and well established community of The Fountains At Cypress Lakes. MOVE IN READY! Offering Privacy, serenity, and modern upgrades, this residence is a rare find. Enjoy peaceful comfortable living on the expansive screened in lanai and pool overlooking lush landscaping and stone walk-ways, towering trees, Pond, and Conservation area. Secluded Park-like setting. Enjoy the views as you enjoy the wildlife sightings. Three bedroom split plan with a separate Study/Bonus room. The bonus room adjoins the main living areas with double entry doors, and back door to pool area. Dining room and Great room with direct access to the lanai. through the double glass door. Gourmet kitchen features plenty of space for eat-in area, solid counter tops, pantry closet, and Breakfast bar, and custom wood cabinetry. You will enjoy entertaining in this open concept home. Accent walls and insets to showcase your artwork and or special pieces. Beautiful flooring throughout. Inside Utility room with extra shelving. Double wide baseboards throughout. Large primary suite with 2 walk-in closets. Primary bath with sunken tub, and separate walk-in shower with designer tile and custom glass shower doors. Shutters on all windows. Oversized 3 car garage with workbench, and custom overhead storage rack. This neighborhood is tucked away and Minutes to all shopping, restaurants, and convenient to all medical facitlities, hospitals and Tampa Airport. Golfcourse's and beaches close by. Well maintained and pride of ownership.

392 Tavernier Circle, Oldsmar
$629,000
3 Beds ⋅ 2 Baths ⋅ Worthington SubDv. ⋅ 34677 Zip Code
Welcome to 859 Inverry Drive in the highly sought-after East Lake Woodlands community of Oldsmar! Beautifully renovated from top to bottom, this exceptional pool home combines modern updates, timeless style, and Florida living at its finest. From the moment you arrive, you'll be captivated by the home's exceptional curb appeal, mature landscaping, and inviting presence. Step inside to discover a completely updated interior featuring luxury flooring, a stunning remodeled kitchen, and beautifully renovated bathrooms. Every detail has been thoughtfully designed to create a move-in-ready home that feels both elegant and comfortable. The spacious floor plan provides an ideal setting for everyday living and entertaining, while large windows fill the home with natural light. The chef-inspired kitchen showcases stylish finishes, updated cabinetry, and modern appliances, making it the heart of the home. Step outside to your private backyard retreat where a sparkling pool awaits. Surrounded by lush landscaping, the outdoor living space offers the perfect setting for relaxing, hosting guests, or enjoying year-round Florida sunshine. Located in the desirable East Lake Woodlands community, this exceptional home provides convenient access to shopping, dining, parks, golf, and top-rated schools. With extensive renovations already completed, all that's left to do is move in and enjoy. Don't miss your opportunity to own this beautifully updated pool home in one of Oldsmar's most desirable neighborhoods!

859 Inverry Drive, Oldsmar
$129,000
2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv. ⋅ 34677 Zip Code
Welcome home to this conveniently located family friendly home in the Gardens of Forest Lakes. 2 bedrooms/2 baths ground floor, corner unit in a non-flood zone. Open floor plan with sliding door to the patio, with a storage room for those extras. This beautiful community boast a playground, swimming pool, basketball court, tennis courts, walking paths and a beautiful lake with a fishing dock. Conveniently located near shopping, dining, parks and easy access to Tampa, Clearwater and St. Pete. Oldsmar has a desirable small town feel with all the conveniences of the city.

140 Hunter Lake Drive Unit F, Oldsmar
$525,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
Are you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from everywhere you want to be? Experience effortless coastal living in this exceptional waterfront townhome, perfectly designed for those who appreciate space, light and direct access to the water. Featuring two private boat slips, this residence offers a RARE opportunity to keep your vessels close and enjoy days on the water at a moment's notice. Inside, the home unfolds into an open, light-filled floor plan enhanced by soaring high ceilings and expansive windows that invite natural light throughout the day. The seemless flow between living, dining, and kitchen spaces creates an ideal setting for both RELAXED everyday LIVING and entertaining. Water views provide a constantly changing backdrop, adding a sense of CALM and CONNECTION to the outdoors. The generous layout offers flexibility for hosting family and guests, while the airy ceiling heights add architectural drama and a sense of openness rarely found in townhome living. Whether you're enjoying quiet mornings with coffee by the water or gathering with friends after a day on the boat, this home adapts effortlessly to your lifestyle. Outdoor living is just as compelling, with immediate access to the waterfront and your own boat slips just steps away - perfect for boating, paddleboarding, or sunset cruises. This is a home that blends convenience and luxury, offering the maintenance ease of a townhome with the experience of a private gated waterfront retreat. Ideally suited as a primary residence or a refined second home, this property delivers the best of waterfront living - space, light, and direct access to the water- all in one elegant package.

119 Brent Circle, Oldsmar
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