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 natural beauty meets suburban charm. This vibrant city, located just a stone's throw from the stunning Gulf Coast, offers residents a perfect blend of tranquility and convenience. With its rich history dating back to the early 1900s, Oldsmar boasts a unique character that sets it apart from other Florida communities.

One of the standout features of Oldsmar is its picturesque landscapes, particularly the homes that offer breathtaking views of lush trees and serene woods. Imagine waking up each morning to the gentle rustling of leaves and the soothing sounds of nature right outside your window. These homes provide not just a place to live, but a sanctuary where the beauty of the outdoors becomes an integral part of your daily life.

The city is known for its commitment to preserving green spaces, making it an ideal location for those who appreciate nature. The nearby parks, such as the expansive Mobbly Bayou Preserve, offer endless opportunities for hiking, biking, and enjoying the great outdoors. Whether you're sipping coffee on your deck surrounded by towering pines or taking a leisurely stroll through a wooded trail, the natural beauty of Oldsmar is sure to captivate you.

With a thriving community, excellent schools, and a variety of recreational activities, Oldsmar is not just a place to live; it’s a place to thrive. Discover your dream home with a view of the trees and woods in this enchanting city and experience the perfect balance of nature and modern living. Welcome home to Oldsmar!

Newest Oldsmar Homes with Trees/Woods View

$1,099,000
4 Beds ⋅ 3 Baths ⋅ Greenhaven Unit Two SubDv. ⋅ 34677 Zip Code
Homes of this caliber rarely become available in the highly sought-after gated community of East Lake Woods. Completely remodeled and set on over a quarter acre, this residence offers an extraordinary blend of luxury, comfort, and thoughtful functionality. Featuring over 3,000 sq ft., single story, 4 beds, 3 full bathrooms, 3 car garage, a large POOL, hot tub & serene pond views- making this a rarity in the Cul-de-sac. From the moment you arrive, the home makes a striking impression with its expansive driveway, and commanding curb appeal. Approaching the grand double-door entrance you will see soaring 12-foot ceilings immediately as they establish the sense of scale and elegance that defines the interior. Upon entry, your gaze is drawn straight to the sparkling pool and tranquil pond beyond—an unforgettable first impression. Freshly painted inside and out, the home showcases new luxury waterproof vinyl plank flooring throughout, creating a seamless and modern aesthetic. Designed for both everyday living and elevated entertaining, the desirable three-way split floor plan ensures privacy for family and guests alike. The spacious primary suite is a true sanctuary, featuring high ceilings, plantation shutters, and a spa-inspired ensuite. Indulge in the freestanding soaking tub or the oversized walk-in shower with a rainfall showerhead and body jets. Dual vanities, a dedicated makeup station, and an illuminated LED mirror complete this luxurious retreat. At the heart of the home is a breathtaking open-concept kitchen and a family room. The fully remodeled kitchen boasts brand-new solid wood soft-close cabinetry, hand selected Taj Mahal quartz countertops, a cooktop with pot filler, new stainless-steel appliances, and an exceptional workspace for the home chef. A bright breakfast nook overlooks the pool, while the separate butler’s pantry offers the perfect space for a coffee bar, beverage station, or additional storage. Entertaining is effortless with the beautifully redesigned wet bar, featuring rich dark cabinetry, ambient lighting, a sink, and a built-in wine refrigerator. The family room layout provides space to host all gatherings. A beautifully renovated guest bathroom off the kitchen showcases designer tile, a modern vanity, and an LED mirror. Toward the rear of the home, two additional spacious bedrooms are accompanied by another fully remodeled bathroom with dual sinks, LED mirrors, and convenient pool access. Step outside to your private backyard oasis. The oversized screened lanai surrounds and offers an ideal setting for year-round Florida living. The impressive outdoor kitchen features stunning brown fantasy granite countertops, a new built-in grill, and a beverage refrigerator. The finishing touch: your very own private putting green—perfect for practicing, entertaining guests, or simply enjoying the peaceful views. Every detail of this remarkable home has been meticulously updated, creating a truly move-in-ready opportunity in one of the area’s most desirable gated communities. Residents also have the option to join the on-site Ardea Country Club, with memberships offering access to championship golf, tennis, pickleball, a resort-style lap pool, a state-of-the-art fitness center, and dining. All of this is ideally located just minutes from top-rated schools, Tampa International Airport, award-winning Gulf beaches, professional sports teams, and more. Homes like this don't last long, secure your private showing today!

35 Greenhaven Trail, Oldsmar
$469,900
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Welcome Home! Your beautifully updated move-in-ready Florida retreat with a warm, contemporary style awaits you in the heart of Oldsmar. This spacious 2-bedroom, 2-bath home with a den, (possible 3rd bedroom), 2-car garage home is situated on a beautifully landscaped lot, offering privacy, flexibility and plenty of space to enjoy the Florida lifestyle. The open and inviting floor plan features cathedral ceilings and newer, high quality laminate flooring throughout the living room, dining area, foyer, bedrooms, den and hallway. Ceramic tile flooring is featured in the kitchen, dinette, Florida room, laundry room and bathrooms. The well-appointed kitchen is designed for both everyday living and entertaining, featuring quartz countertops, stylish cabinetry, an island, stainless steel appliances - including a refrigerator, range, range hood and microwave - and a convenient pantry closet. The generous primary suite offers two walk-in closets and a private en-suite bathroom with a double sink vanity, walk-in shower and linen closet. The spacious Florida room overlooks the beautifully landscaped private backyard and can be accessed from the dinette area, living room or the primary bedroom. Plantation shutters throughout the dinette area and on the primary bedroom sliding glass door provides privacy. The covered screened-in porch features sleek aluminum railings and durable composite deck flooring providing both style and additional space for relaxing or entertaining. More recent upgrades include a roof replacement (2024), newer A/C system (2022), screened-in porch (2022), and water heater (2022). Nestled in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers exceptional 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.This home features a low monthly HOA fee of just $70 with one pet of any size permitted.The location is truly unbeatable! You're less than a mile from Woodlands Square, offering Bealls, Marshall’s, Ulta, PetSmart, AMC Theatres, Craft Street Kitchen, Shaker & Peel, Eve’s Family Restaurant, and more. Everyday conveniences such as Publix, Target, Walmart Neighborhood Market, and Mease Countryside Hospital are just 2 miles away. Honeymoon Island Beach is approximately 9 miles away, and Tampa International Airport is an easy 15-mile drive.An adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, providing the perfect setting to enjoy Florida’s outdoor beauty. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply enjoying the peaceful surroundings, you’ll fall in love with the friendly, welcoming lifestyle of Gull-Aire Village.(Room dimensions are approximate and should be verified by Buyer.)

603 Canal Way, Oldsmar
$275,000
2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome home to this beautiful END UNIT & FULLY UPDATED 2BR/1.5BA townhome in the gated Countryside Key community, offering the rare benefit of an extra-large side yard for addl. outdoor space & privacy. Even better, assoc. fees include water, trash, cable & internet! With extensive improvements, an enclosed patio, reserved parking directly in front, & an outstanding Pinellas County location (NON-FLOOD ZONE), this home is truly move-in ready. Step inside to an inviting open first floor designed for comfortable everyday living & entertaining. The kitchen features quartz countertops, custom cabinetry installed in '22, including larger cabinets providing excellent storage. The owners thoughtfully removed the upper cabinetry around the sink & counter area, creating a more open feel and better connection between the kitchen & adjoining living space. Updated appliances, lighting & ceiling fans complement the space, while no popcorn ceilings on either the first or second floor give the home a clean, updated look. Fresh interior paint was completed in August '26. Just beyond the main living area, the enclosed patio creates additional flexible space to relax, entertain, work from home, or just enjoy throughout the year. As an end unit, this home also possesses an extra-large side yard, providing additional outdoor space & separation rarely found with townhome living. Upstairs, the spacious primary suite features large dual closets, built-in bookshelves (providing both character & functional storage), while the generous windows bring an abundance of natural light into the space. Relax in the large private upgraded bathroom to complete the suite! The home has also benefited from an impressive list of improvements. HVAC, water heater & appliances were replaced in '22, along with new attic insulation in '22, washer & dryer in '24, & new light fixtures & ceiling fans. A new impact-rated rear door window was added in '22 for enhanced security, & exterior doorknobs, deadbolts & keys were also replaced. More recently, the home received new exterior paint in '26 & new interior paint in '26. Enjoy the everyday convenience of reserved parking directly in front of the unit's door, along with ample guest parking throughout the gated community & specifically near this unit! Countryside Key also offers a community pool overlooking the pond, tennis courts, & a designated storage area for camper vehicles, boats, trailers, &/or commercial vehicles (subject to association requirements - see HOA). This INCREDIBLE LOCATION is conveniently positioned near the Hillsborough County line & just minutes from the charm, restaurants, waterfront parks & activities of Safety Harbor. You're also only 8.7 miles from beautiful Honeymoon Island State Park and its Gulf beaches, with convenient access to Tampa International Airport, shopping, dining, entertainment and major roadways connecting you throughout the Tampa Bay area (all points). This Countryside Key townhome offers an exceptional combination of privacy, convenience, value & move-in-ready living.

279 Countryside Key Boulevard, Oldsmar
$719,000
4 Beds ⋅ 2 Baths ⋅ East Lake Woodlands SubDv. ⋅ 34677 Zip Code
Tucked away in the highly desirable gated community of East Lake Woodlands, this one-of-a-kind 4-bedroom, 2-bath waterfront retreat offers a rare opportunity to experience the timeless beauty of Old Florida. With an extraordinary 180-degree view of lush natural surroundings and a tranquil waterway, this private setting feels like a world of its own—where trees, abundant wildlife, and peaceful water views create a backdrop that is both breathtaking and serene. A large circular driveway welcomes you to the home, where a new double-door entry opens to vaulted ceilings and an inviting, light-filled interior. The formal living room features French doors leading to the screened lanai, while the dining room is accented by a beautiful Tiffany-style light fixture. Throughout the home, tile flooring and roller shades provide a clean, timeless aesthetic. The updated kitchen features granite countertops and opens naturally to the family room, where one of two fireplaces creates a warm and inviting gathering space. The primary suite offers its own featured fireplace, creating a cozy retreat, along with an updated private bathroom featuring an oversized glass-enclosed shower and soaking tub. An updated guest bathroom provides additional modern convenience sandwiched between two of the additional bedrooms. Step outside and discover what truly sets this property apart. The expansive screened lanai surrounds a beautiful saltwater pool and spa, with a painted cool-deck surface and lush tropical landscaping creating your own private resort-style escape. Beyond the pool, a Trex dock and completely renovated seawall (2020) provide the perfect vantage point to take in the incredible natural setting and 180-degree views of Old Florida. Thoughtfully maintained and updated, the home features impact and double-pane windows with galvanized storm shutters, a hybrid water heater, water softener, new shingle roof (2024), gutters, French drains extending to the lake and exterior paint completed in August 2026. The wrought-iron fenced yard adds privacy and enhances the beautifully landscaped grounds. Located outside a flood zone and within a top-rated A-rated school zone, this exceptional home also offers the opportunity to become a social, golf, or tennis member at Ardea Country Club, adding an optional lifestyle component to an already remarkable property. Private waterfront, resort-style amenities, thoughtful updates, and an unmatched Old Florida setting—this is more than a home; it’s a rare opportunity to own your own piece of paradise in East Lake Woodlands.

80 Foxfire Lane, Oldsmar
$195,000
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
$129,900
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
$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.

704 Lemonwood Drive, 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 from the 3 skylights, 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 water heater, new epoxy garage floor, remote blinds, water softener 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
$589,000
4 Beds ⋅ 3 Baths ⋅ Eastlake Oaks Ph 4 SubDv. ⋅ 34677 Zip Code
Welcome to 1745 Oak Pond Court! Welcome to 1745 Oak Pond Court, a beautiful home located in the sought-after East Lake Oaks community. Situated on a quiet street with a premium lot, this home offers comfort, style, and numerous recent upgrades. The interior and exterior have been freshly painted, and the screened lanai has been recently updated. Some major updates include a new water heater installed in 2022, a new air-conditioning system installed in 2023, new carpeting on the stairs completed in May 2026, and stair railings that were sanded and freshly painted in May 2026. The primary bathroom was completely remodeled in 2022 and features a relaxing jetted tub, updated vanity, shower, tile flooring and walls, surround-sound speakers, and mood lighting in the ceiling. A luxurious outdoor kitchen was installed in 2025 and includes a grill, granite countertop, stainless-steel sink, and stainless-steel storage for all your entertaining needs. Additional improvements completed in June 2026 include freshly painted pool patio and garage floor. The kitchen was updated in 2022 with new cabinets and granite countertops, while wood-look laminate flooring was installed throughout the downstairs living areas. Conveniently located near Tampa International Airport, shopping, nature trails, and excellent restaurants, this home is also just twenty minutes from Honeymoon Island Beach. This move-in-ready home combines thoughtful upgrades, a prime location, and Florida living at its best!

1745 Oak Pond Court, 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
$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
$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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