Home & Condo Listings in Oldsmar, FL by Century 21 Coast to Coast

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

PRICE REDUCED!! Call to schedule your private showing of this beautifully furnished 2-bedroom, 2-bath upstairs condominium in the highly desirable gated community of East Lake Woodlands. TOTALLY TURNKEY if you desire Perfectly positioned in a quiet setting, this light-filled home welcomes you with soaring vaulted ceilings and an abundance of natural light streaming through the upper windows, creating a bright and spacious atmosphere you'll love coming home to. Designed for comfortable Florida living, this FULLY FURNISHED condo is move-in ready. Snowbirds and seasonal residents can simply bring their clothes and groceries—everything else is already here, making your Florida getaway effortless. Enjoy refreshing breezes from two private screened patios. Sip your morning coffee as the sun rises or relax in the evening with your favorite beverage while taking in the peaceful surroundings. The screened balcony is accessible from both the spacious living room and the primary bedroom, creating a seamless indoor-outdoor lifestyle. The split-bedroom floor plan offers privacy for both owners and guests. The generous primary suite features a large walk-in closet and a private en-suite bathroom, while the guest bedroom is thoughtfully separated by the guest bath and closets, making it ideal for family and visitors. A convenient laundry closet with a washer and dryer is located on the screened kitchen patio and is easily accessible from both the kitchen and the guest bedroom. East Lake Woodlands is a beautifully maintained 24-hour guard-gated golf community where residents enjoy secure access with resident vehicle passes and a peaceful country club atmosphere. Optional memberships offer golf, tennis, fitness, dining, and social activities. Located at the corner of Tampa Road and East Lake Road, you'll be just minutes from grocery stores, shopping, restaurants, medical facilities, and entertainment, with beautiful Gulf beaches and Tampa International Airport only a short drive away. Whether you're looking for a seasonal retreat or a full-time Florida residence, this exceptional condo offers comfort, convenience, and the carefree lifestyle you've been dreaming about.

124 Woodlake Wynde, Oldsmar

$514,900

3 Beds ⋅ 2 Baths ⋅ Bays End SubDv. ⋅ 34677 Zip Code

Priced to the Ridiculous!! Welcome to Bays End, a hidden gem community offering a peaceful setting with convenient access to everything the area has to offer. This well-maintained 3-bedroom, 2-bathroom home features a spacious and inviting layout. Enter to an open living room that flows into the dining area. The updated kitchen showcases beautiful cabinetry, generous storage, and plenty of workspace. The heart of the home is the family room, with vaulted ceilings and a fireplace create a warm and open space. The spacious primary suite offers walk-in closets and a tastefully updated en-suite bathroom. Split plan with two bedrooms and a bathroom. Step outside to your own private backyard retreat featuring a pool, spa, paver patio, and fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine. Roof 2026!! There is NOTHING wrong with this home!!

854 Christina Circle, Oldsmar

$775,000

4 Beds ⋅ 4 Baths ⋅ Wellington Estates SubDv. ⋅ 34677 Zip Code

Welcome to luxury living in the highly sought-after Wellington Estates community of Oldsmar. This stunning ENERGY STAR® certified residence offers over 3,000 square feet of thoughtfully designed living space featuring 4 bedrooms, a private den/office, 3.5 bathrooms, and an expansive bonus room that can easily serve as a media room, game room, home gym, or fourth bedroom. The home also includes a spacious 3-car garage and a resort-style outdoor living area. A dramatic two-story foyer with a designer crystal chandelier sets the tone upon entry. The open-concept floor plan showcases soaring ceilings, elegant crown molding, plantation shutters, and abundant natural light throughout. The gourmet kitchen is the centerpiece of the home, featuring rich espresso cabinetry, quartz countertops, stainless steel appliances, double ovens, a large center island, and a spacious dining area that seamlessly connects to the great room—perfect for entertaining. The spacious primary suite offers a luxurious retreat with a custom walk-in closet and spa-inspired bath complete with dual vanities, a soaking tub, and a walk-in shower. Upstairs, the bonus room provides exceptional flexibility for today's lifestyle needs while the additional bedrooms, 1 with en suite bath, offer comfort and privacy for family and guests. Step outside to your private backyard oasis featuring a screened-in pool with tranquil rock waterfall feature and an impressive outdoor kitchen complete with granite countertops, built-in grill, refrigerator, and ample prep space—ideal for year-round Florida entertaining. Mature landscaping and privacy hedges create a peaceful setting for relaxation and gatherings. Additional highlights include hurricane shutters, reclaimed water irrigation, in-wall pest defense system, abundant storage, and premium finishes throughout. Located just minutes from top-rated schools, shopping, dining, parks, beaches, and Tampa International Airport, this exceptional Wellington Estates home combines luxury, comfort, and convenience in one remarkable package.

743 Wellington Court, Oldsmar

$179,950

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

Welcome to 106 Windward Place, a two bedroom two bathroom condominium located in the Meadows at East Lake Woodlands. One of Oldsmar‘s most sought after gated communities. This is a bank owned (REO) property, an excellent opportunity for homeowners, investors, or buyers looking to customize a home of their own taste. The functional floor plan features a spacious, living and dining area, split bedroom, layout, and a private setting within the community. The Meadows offers beautifully maintained grounds, mature landscaping, and a peaceful residential atmosphere. Residents enjoy convenient access to shopping, dining, golf, parks, Tampa International Airport and the Beautiful Gulf beaches. Whether you are searching for a primary residence, seasonal getaway or investment property 106 Windward Place offers outstanding value and the chance to own within the desirable East Lake Woodlands community. Property is being sold as is.

106 Windward Place, Oldsmar

$115,000

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

Virtually Staged. GROUND FLOOR ~ NON - FLOOD ZONE. 2 Bedrooms, 2 Bathroom and move in ready in the heart of Oldsmar! Community amenities include a pool, playground, basketball court, tennis courts and beautiful lake with a dock! Bring your fishing pole. Freshly painted and move-in ready, tile floor throughout, making it an ideal canvas for a buyer looking to add personal touches and build equity. Investor friendly, no wait to rent it out right away. Enjoy the patio outside the sliding doors for morning coffee. Storage shed also included for extras with lock and key. Ideally located near shopping, dining, parks, waterfront trails, and major commuter routes, you’ll enjoy easy access to Tampa, Clearwater, and everything the Gulf Coast has to offer. Opportunities to purchase in this sought-after area at an affordable price point are becoming increasingly rare. Call today for your private showing!

123 Loblolly Court Unit B, Oldsmar

$190,000

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

Welcome to a condo that feels like home the moment you step inside. Beautifully updated and meticulously maintained in the highly sought-after guard-gated East Lake Woodlands community. Light, bright, crisp, and spotless, this 2-bedroom, 2-bath residence is truly move-in ready. The kitchen is the centerpiece of the home, featuring solid wood cabinetry, quartz countertops, stainless steel appliances, porcelain tile flooring, a spacious pantry, breakfast bar, coffee bar area, and an updated tray ceiling with LED lighting that adds a modern, elevated feel. Gorgeous laminate flooring flows throughout the main living areas, creating a seamless and stylish design. The open-concept living and dining space leads to a private screened balcony overlooking a peaceful, natural greenspace. The primary suite offers dual walk-in closets and a beautifully updated en-suite bath with quartz countertops. The secondary bedroom is comfortably sized, and the guest bath is clean, bright, and tastefully updated. Additional features include a 2023 LG front-load washer and dryer, updated lighting and fixtures throughout, and a roof that was replaced approximately two years ago. The covered carport is conveniently located as the first space closest to the building entrance. Every detail reflects pride of ownership and consistent care. Residents of East Lake Woodlands appreciate the natural beauty, walkable setting, and convenient access to all that Tampa Bay has to offer. Community amenities include a heated pool, scenic walking paths, and an optional membership to Ardea Country Club with championship golf, tennis, pickleball, fitness, resort-style pools, dining, and year-round activities. Ideally located just minutes from Tampa International Airport, Gulf beaches, bike trails, parks, shopping, Westfield Countryside Mall, restaurants, and the charming downtowns of Dunedin, Tarpon Springs, and Safety Harbor. No flood insurance required (Flood Zone X500). Monthly dues include exterior maintenance, cable, internet, water, sewer, trash, and roof maintenance. Clean, updated, and move-in ready, this home stands out for its warmth, condition, and effortless livability—an opportunity buyers immediately recognize and appreciate.

110 Cypress Ct Unit 3-82, Oldsmar

$349,900

3 Beds ⋅ 2 Baths ⋅ Harbor Palms Unit Eleven Lot 451 SubDv. ⋅ 34677 Zip Code

Welcome to 442 Evergreen Drive, nestled in one of Oldsmar's most desirable neighborhoods! This beautifully updated 3 bedroom, 2-bath residence offers the perfect blend of comfort, style, and Florida living. Filled with abundant natural light, the thoughtfully designed floor plan creates an inviting atmosphere ideal for both everyday living and effortless entertaining. Step outside to your private backyard retreat featuring a spacious screened-in porch—the perfect place to enjoy your morning coffee, host family and friends, or simply relax while enjoying Florida's beautiful weather. Freshly painted inside and out, this move-in-ready home reflects pride of ownership from the moment you arrive. Enjoy added peace of mind with numerous updates, including a Roof (2018), HVAC System (2018), Kitchen (2024), New Flooring (2024), Remodeled Primary Bathroom, and Impact Windows & Doors (2021). The property is located in Flood Zone AE and offers the benefit of updated impact windows and doors for added peace of mind. The oversized backyard provides plenty of room to add a outdoor kitchen, or create your own tropical oasis, while the spacious garage offers excellent storage and functionality. Conveniently located near beautiful parks, shopping, dining, entertainment, and the stunning Gulf beaches, this exceptional home offers the very best of the Florida lifestyle. Whether you're searching for your first home, a place to grow, or your next chapter, 442 Evergreen Drive is a rare opportunity to own a beautifully maintained, move-in-ready home in a prime Oldsmar location.

442 Evergreen Drive, Oldsmar

$1,055,000

4 Beds ⋅ 3 Baths ⋅ Turtle Creek Unit-Three SubDv. ⋅ 34677 Zip Code

If you've been searching for a home that checks every box, this one is worth a serious look. Tucked inside the guard-gated East Lake Woodlands community — known for its canopied streets, two championship golf courses, pickle ball and tennis courts, and home to Ardea Country Club — this 4-bedroom, 3-bath pool home sits on nearly a full acre and has been genuinely well cared for. Equipped with a whole-house solar system - means electric bills that are almost laughably low — most months you're paying little more than the base statement fee. Pair that with a whole-home water filtration system, water softener, two brand-new AC units (April 2025 and March 2026), a tile roof replaced in 2019, and two water heaters also replaced in 2019, and you're looking at a home where the expensive stuff has already been done. At 3,189 square feet, the layout gives everyone room to breathe. The great room is the kind of space that feels both impressive and livable, and the split floor plan keeps the primary suite — complete with walk in closets and a sitting area — separate from the other bedrooms. Tile flooring runs throughout the entire home, so there's no carpet to worry about. The kitchen is built for real use: breakfast bar, convection oven, cooktop, and quality appliances, all with stone counters. Out back, the pool and lanai open up to a quiet, private setting that makes it easy to forget the rest of the world exists. Top-rated schools, easy access to Tampa, and a short drive to the Gulf beaches round out a package that's hard to replicate at this price point.

4931 Turtle Creek Trail, Oldsmar

$291,000

2 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 34677 Zip Code

Welcome home to a beautifully refreshed property where all the big-ticket items are already taken care of. A 2025 roof, 2023 A/C, and 2022 water heater ensure years of worry-free living. Inside, the home feels bright and airy with vaulted smooth ceilings and walls and brand-new engineered wood flooring installed in 2025. The fenced in backyard area is a private & a personal space for your enjoyment all year round. Spacious and well-kept inside & out! The primary bathroom features a double sink, while the guest bathroom offers a relaxing Jacuzzi tub — perfect for unwinding after a long day. Newer garage door and motor installed in 2021. This home is designed for comfort and convenience. Located near shops, movie theater, Sheffield Park & Eastlake. Low HOA fees or $160/month! A truly move-in-ready space with thoughtful upgrades throughout. Schedule your viewing today!

2013 Dover Court, Oldsmar

$175,000

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo Unit 7 SubDv. ⋅ 34677 Zip Code

This adorable 2nd floor, 2 bedroom, 2 bathroom condo in the guarded/gated community of East Lake Woodlands! An open and airy front balcony welcomes you in to the unit. NO REAR NEIGHBORS! Just views of the lovely back yard wooded area and daily deer sightings from your 2nd balcony which is private and screened-in! A big picture window, recessed lighting, solid wood cabinets and tiled backsplash accent the kitchen. The kitchen has a floor to ceiling pantry and is open to living / dining with an breakfast bar. An elegant, 2 tiered chandelier, crown molding and new modern ceiling fan grace the ceiling. Newer laminate flooring installed in the living /dining and both bedrooms. Step through the living room sliding doors and onto the screened-in balcony where the true Florida lifestyle begins. Roller shades on the balcony create privacy while still allowing the cool breezes to flow through. This unit features a split bedroom plan with NO CARPET! Master bedroom has its own bath en suite with separate shower/commode area, 3 walk in closets (YES! 3), tropical ceiling fan with palm leaf blades, double picture window with beautiful views of the wooded back yard! It is spacious enough for a king bedroom furniture set and also has a set of sliding doors out to the balcony! Guest bedroom features a large closet and an adjacent full bathroom with tub/shower in the hall. No lack of storage here with a coat closet in the main entry hall and a full wall to wall reach in closet in the guest hallway. A side by side washer and dyer are conveniently located in the balcony closet. Your assigned covered parking spot is right in front of the entrance (#108). Plenty of extra guests spots for a 2nd car too. Heated pool just steps away! Love to golf? East Lake Woodlands County Club will become your new favorite spot with (2) 18 hole championship courses, upscale restaurant, fitness center, clubhouse, tennis courts, 2 pools and a multimillion dollar renovation underway! Located just around the corner from Oldsmar sports complex on Tampa Rd with a playground, ball hockey rink, BMX supercross track and fields for baseball football and soccer. Adjacent to the complex is Woodlands Square Mall with an IMAX movie theater, gourmet restaurants and shopping. East Lake Rd houses 2 large shopping centers with Target, Walmart, and an assortment of fast food chains. Short drive to Countryside mall, Tampa Airport, and the sugar sands of the Gulf’s finest beaches. Bring your furry friends! Two cats or dogs allowed under 20 lbs each (or a total of 40 lbs between the 2). Low condos fees with water, sewer, trash and basic cable included. Make your appointment to see today!

108 Woodlands Court Unit 108, Oldsmar

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