Location: Oldsmar
Do Not Show Listings
442 EVERGREEN DR, OLDSMAR, FL 34677
$352,50035 Days on yellowkey MLS ID: TB8517079
REDUCED by $2,000 (0.6%) on 07/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1190 Built: 1979 Tax: $5,386 (2025)Community: Harbor Palms Unit Eleven Lot 451Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,386
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Welcome to 442 Evergreen Drive, nestled in one of Oldsmar's most desirable neighborhoods! This beautifully updated 4-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 taking in 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 (2020), HVAC System (2021), Kitchen (2024), New Flooring (2024), Remodeled Primary Bathroom, Impact Windows & Doors (2023), and energy-efficient solar panels that help reduce utility costs. Located in Flood Zone X, flood insurance is currently not required, offering even greater value and peace of mind. The oversized backyard provides plenty of room to add a pool, 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.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Sheri Boesch (727-776-3422)
854 CHRISTINA CIR, OLDSMAR, FL 34677
$555,50029 Days on yellowkey MLS ID: TB8521571
REDUCED by $9,500 (1.7%) on 07/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2065 Built: 1994Monthly Fee: $68 Tax: $8,686 (2025)Community: Bays EndSpa: YesSingle Family
Taxes:$8,686
Remarks: Roof 2026!! 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.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Joe Koebel (727-410-1455)
1469 RIVERDALE DR, OLDSMAR, FL 34677
$599,99917 Days on yellowkey MLS ID: TB8521939
REDUCED by $25,000 (4.0%) on 07/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1890 Built: 1992Monthly Fee: $470 Tax: $4,870 (2025)Community: Cross CreekSingle Family
Taxes:$4,870
Elementary School: Forest Lakes Elementary-PN
Remarks: HUGE PRICE IMPROVEMENT!!! Welcome to your dream home nestled in the coveted Cross Creek of Eastlake Woodlands, where tranquil living meets modern convenience! This charming 3-bedroom, 2-bathroom house is a true gem, boasting stunning water views that will take your breath away. As you step inside, you’ll be greeted by tall, soaring ceilings and a light-filled living space that seamlessly blends modern aesthetics with cozy charm. The heart of this home is undoubtedly the kitchen, featuring beautiful wood cabinets equipped with convenient pullout shelves and exquisite Corian countertops, perfect for culinary adventures or casual gatherings with family and friends. The spacious living area is accentuated by a cozy wood-burning fireplace and the en-suite bedroom is a true retreat, complete with sliding doors that lead to an enclosed lanai, where you can soak in serene pond views while sipping your morning coffee or unwinding after a long day. The en-suite bathroom comes equipped with a walk-in shower, walk-in bath and dual sinks. This property goes beyond aesthetics; it’s loaded with practical features too. Enjoy the benefits of a tankless water heater, new AC and a water treatment system that ensure your comfort and peace of mind. Plus, the home is scheduled to be freshly painted in October and the roof was replaced in 2013, providing you with years of worry-free living. Step outside and discover a world of leisure just across the street. A heated pool and spa await, offering the perfect escape to relax and rejuvenate. Nestled in a vibrant golf community, you’ll find yourself just moments away from an array of shops, delightful restaurants, and the stunning beaches that the area is known for. The proximity to the airport adds an extra layer of convenience for those who love to travel. This exquisite home in Cross Creek of Eastlake Woodlands is not just a house; it’s a lifestyle waiting to be embraced. Don’t miss your chance to own this enchanting property that beautifully combines luxurious living with the serenity of nature. Schedule your private tour today and step into the life you’ve always imagined!
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Phil Evans (304-617-3384)
1745 OAK POND CT, OLDSMAR, FL 34677
$629,0009 Days on yellowkey MLS ID: TB8527516
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2324 Built: 2000 Tax: $8,785 (2025)Community: Eastlake Oaks Ph 4Spa: NoSingle Family
Taxes:$8,785
Elementary School: None
High School: None
Middle School: None
Remarks: 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!
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
3138 PHOENIX AVE, OLDSMAR, FL 34677
$1,525,00012 Days on yellowkey MLS ID: TB8527279
0 Days Off yellowkey (back on 7/11/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3218 Built: 2021 Tax: $17,105 (2025)Community: West Oldsmar Sec 1Single Family
Taxes:$17,105
Remarks: Under contract-accepting backup offers. Experience the best of Florida waterfront living in this exceptional custom estate built in 2021. Perfectly positioned on a private .42-acre lot with no rear neighbors, this luxurious retreat blends timeless design with everyday comfort. Soaring ceilings, abundant natural light, porcelain flooring, marble bathrooms, and designer finishes complement an open-concept layout centered around a stunning chef's kitchen with custom cabinetry, premium appliances, granite countertops, an oversized island, and wine cooler. Step outside to your own private oasis featuring a saltwater pool, expansive covered lanai, fruit trees, and peaceful water views. Boaters will love the private dock with a 13,000-pound boat lift offering direct access to Tampa Bay and the Gulf. An incredible 2,200+ sq. ft. garage, circular driveway, RV/boat parking, and no HOA provide unmatched flexibility. Located on a quiet waterfront street just minutes from Tampa, both airports, near top-rated schools, shopping, dining, Gulf beaches, and more, this one-of-a-kind home delivers the ultimate Florida lifestyle.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-799-2227)
Listing Agent: Christina Cox (727-337-0123)
415 COUNTRY CLUB DR, OLDSMAR, FL 34677
$350,00041 Days on yellowkey MLS ID: TB8517638
REDUCED by $19,000 (5.1%) on 07/17/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1748 Built: 1959 Tax: $3,505 (2024)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$3,505
Tax Year: 2024
Middle School: John Hopkins Middle-PN
Remarks: Seller is offering a contribution toward the buyer’s closing costs! Beautiful waterfront-view home overlooking the water from the backyard, located in the desirable Oldsmar Country Club Estates community. This fully renovated property features 4 bedrooms and 2 bathrooms and sits on a 0.21-acre lot with no HOA restrictions, offering comfort, functionality, and an excellent location. The home features new flooring throughout, a renovated kitchen with quartz countertops, stainless steel appliances, and ample cabinet space, along with updated bathrooms with modern finishes. The spacious backyard provides access to a canal leading to Tampa Bay, making it ideal for kayaking, paddleboarding, and other outdoor activities. It also offers the perfect setting to relax or entertain family and friends. Conveniently located near parks, recreational areas, public boat launches, Tampa Bay Pickleball, restaurants, shopping, and more. Additionally, Tampa International Airport is approximately 20 minutes away, providing excellent convenience and connectivity.
Listing is courtesy of: FRIENDS REALTY LLC (813-464-1640)
Listing Agent: Madelin Artigas (713-384-5600)
1806 FOREST DR, OLDSMAR, FL 34677
$418,000264 Days on yellowkey MLS ID: TB8442794
1 Days Off yellowkey (back on 4/30/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1539 Built: 1973 Tax: $4,086 (2024)Community: Harbor PalmsSingle Family
Taxes:$4,086
Remarks: Under contract-accepting backup offers. Welcome to this beautifully remodeled home filled with natural light and modern charm. The open-concept floor plan features a spacious living area with brand new windows throughout the house, the new designed kitchen offers new cabinetry beautiful countertops, new stainless-steel appliances, and a breakfast bar the flows seamlessly into the dining and living spaces, interior laundry room with new cabinets and new washer & dryer. New central air condition and ductwork, new ceiling lights and fans, new flooring throughout the house. The primary bedroom includes a large closet and a stylish new bathroom with a glass - enclosed shower-tub combo, modern finishes. Two additional bedrooms provide versatility for guess, a home office, and the second new full bath is bright and modern. All interior doors are new so it is the front door and garage door, new interior and exterior paint, new wood fence, new landscape. this home is a perfect blend of comfort and value.
Listing Agent: Mena Reyes (727-789-5555)
1319 FORESTEDGE BLVD, OLDSMAR, FL 34677
$1,100,00039 Days on yellowkey MLS ID: TB8517867
REDUCED by $50,000 (4.3%) on 07/02/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3849 Built: 1991Monthly Fee: $243 Tax: $8,986 (2025)Community: Aberdeen Unit TwoSpa: NoSingle Family
Taxes:$8,986
Remarks: Welcome to this beautifully updated Arthur Rutenberg estate, perfectly positioned on a premium corner homesite with partial pond views and exceptional privacy in the sought-after Aberdeen enclave of East Lake Woodlands. This move-in-ready residence offers 5 bedrooms, a versatile bonus room with a wet bar, and 3.5 bathrooms, providing the ideal blend of luxury, comfort, and functionality. Extensively remodeled in 2021, the home showcases timeless design, quality craftsmanship, and modern finishes throughout. Upon entering, you are greeted by an abundance of natural light, soaring ceilings, and gorgeous Mohawk engineered wood flooring that flows throughout the main living areas. The heart of the home is the fully renovated kitchen, featuring a massive waterfall-edge island, crisp white shaker cabinetry, quartz countertops, high-end stainless steel appliances, and stylish Pottery Barn pendant lighting. The kitchen opens seamlessly to the breakfast nook and inviting family room, where a redesigned brick fireplace and custom mantle create a warm and elegant focal point. Designed for the Florida lifestyle, the living spaces transition effortlessly to the spectacular outdoor oasis. The expansive, recently rescreened pool enclosure showcases a sparkling PebbleTec pool with a tranquil rock waterfall, all surrounded by upgraded pavers. Whether hosting family and friends or enjoying a peaceful evening at home, this outdoor retreat is perfectly suited for both entertaining and relaxation. The primary suite serves as a private sanctuary, offering direct lanai access, custom-built closet organizers, and a spa-inspired en-suite bathroom complete with a soaking tub, dual vanities, and elegant finishes. The highly adaptable bonus room provides the perfect space for a game room, media center, home office, or multi-generational living area, complete with its own wet bar. Practical upgrades and peace of mind abound throughout the home. A brand-new HVAC system was installed in March of this year, and the property also features a 5-year-old water heater, a newer water softener, and fresh interior paint completed during the 2021 renovation. The oversized 3-car garage provides ample storage and showcases a sleek, durable epoxy floor. Aberdeen is a tranquil oasis featuring quiet streets, mature tropical landscaping, and abundant wildlife within the gated East Lake Woodlands community. Residents enjoy convenient access to top-rated schools, world-class beaches including Clearwater Beach and Honeymoon Island, major medical facilities, shopping, dining, and both Tampa International Airport and St. Pete-Clearwater International Airport. Optional Ardea Country Club memberships provide access to two championship 18-hole golf courses, premier tennis facilities, resort-style swimming, fitness amenities, dining venues, and a vibrant social calendar. Combining timeless Arthur Rutenberg craftsmanship, extensive modern updates, resort-style outdoor living, and an exceptional East Lake Woodlands location, this remarkable residence offers a rare opportunity to enjoy the very best of Florida living. Schedule your private showing today.
Listing Agent: Mark Fazzini (727-485-9981)
4953 POINTE CIR, OLDSMAR, FL 34677
$865,00085 Days on yellowkey MLS ID: TB8502016
REDUCED by $20,000 (2.3%) on 05/12/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2513 Built: 1997Monthly Fee: $142 Tax: $11,677 (2025)Community: Cross PointeSpa: YesSingle Family
Taxes:$11,677
Elementary School: Cypress Woods Elementary-PN
Remarks: This newly renovated 4 bedroom 3 bath home is nestled in a quiet, cozy part of the elite Cross Pointe neighborhood located in the highly sought after Eastlake Woodlands development. From the moment you walk through the door, you’ll notice the attention to detail and inviting atmosphere that make this home truly special. Natural light, functional spaces, and stylish touches create a setting that’s both elegant and comfortable. Enjoy the amenities of Ardea Golf, Tennis, and Social club. This gem will not last long - schedule a viewing today.
Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)
Listing Agent: Camilo Perez (833-700-2782)
800 SAINT PETERSBURG DR W, OLDSMAR, FL 34677
$399,000122 Days on yellowkey MLS ID: TB8489139
4 Days Off yellowkey (back on 7/6/2026)
REDUCED by $10,000 (2.4%) on 04/20/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1712 Built: 1949 Tax: $3,631 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$3,631
Elementary School: Oakhurst Elementary-PN
Remarks: Under contract-accepting backup offers. BACK ON THE MARKET. PREVIOUS BUYER HAD FINANCING ISSUES. APPRAISAL AND HOME INSPECTION WERE GOOD. Completely Renovated Oldsmar Home on Oversized Fenced Lot – Move-In Ready! Welcome to this beautifully updated home located in the City of Oldsmar, situated on a generously sized, fully fenced lot with an expansive backyard—perfect for entertaining, pets, or future outdoor enhancements. This turnkey property has been fully renovated from top to bottom, offering modern finishes and a flexible layout. The home features two primary bedroom suites (or use one as a spacious family room), along with three fully updated bathrooms, each showcasing custom tile showers and high-end fixtures. Enjoy 24” tile flooring throughout, providing a clean, contemporary look with easy maintenance. The gourmet kitchen is designed for both function and style, complete with a center island, Frigidaire appliance package, and upgraded fixtures. Additional highlights include a washer and dryer, updated systems and finishes throughout, and a layout that accommodates a variety of living arrangements. Everything has been updated—just move in and enjoy. HVAC 2025, Roof November 2025, Water Heater 2026, plumbing and electrical updates 2026. City Water and Sewer.
Listing is courtesy of: TAM BAY REALTY LLC (813-493-2913)
Listing Agent: Stephanie Brubaker (813-475-1696)
219 BAY ARBOR BLVD, OLDSMAR, FL 34677
$540,00095 Days on yellowkey MLS ID: TB8498550
REDUCED by $10,000 (1.8%) on 07/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1873 Built: 2000Monthly Fee: $100 Tax: $7,973 (2025)Community: Bay Arbor Unit 1ASingle Family
Taxes:$7,973
Remarks: Virtually Staged. NO MORE CARPET!!! BRAND NEW VINYL FLOORING INSTALLED and a NEW, HOT PRICE!!! We are the LOWEST-PRICED four-bedroom home around in a gated community!! Vaulted ceilings and an open floorplan welcome you as you step inside. The Living Room is HUGE, a wonderful place for family gatherings and entertaining for holidays and parties. The large Kitchen opens up to the Living Room for an expansion on entertaining space, featuring solid wood cabinets, matching Stainless Steel Frigidaire Appliances, and a large Breakfast Nook. The Formal Dining Room is set right across from the Kitchen, and is the perfect space for formal gatherings and family dinners. It even has a 4.5' x 2.5' nook that would house a China Cabinet or dry bar if desired. This home offers a split plan, providing maximum privacy to the Master Suite, as well as to the "Guest Wing" and other guest bedrooms. The Master Bedroom features a walk-in closet, access to the back patio, and a large en-suite Bathroom with dual vanities, a jetted tub and a standing shower. The "Guest Wing" or "Home Office Wing" is a wonderful layout to suit any needs. It has a bathroom located right off of the Bedroom, and is set apart from the rest of the bedrooms for added privacy. The other 2 Bedrooms are Jack-and-Jill style, both accessing the 3rd Full Bathroom. Large sliders in the Living Room open up to the peaceful back patio, laced in Slate Tile and fully covered. This space is a sanctuary, overlooking a small pond and greenery instead of facing a rear neighbor. The sun rises in the front of this home, so it is easy to enjoy your morning coffee at sun-up, as well as enjoy the sunsets thanks to the shade provided by the natural greenery. The Roof and Water Heater are NEW 2022, and the A/C was replaced in 2021! LOW HOA FEES only $100/month. This community is gated, with a playground and a community pool, as well as sidewalks for your morning jogs or evening walks! What's not to love?? Move right in and make this home your own!! Only a 30-minute drive to Tampa Int'l Airport, a 25-minute drive to Honeymoon Island, and just minutes from shopping, dining, and all you need to live your Florida dream to its fullest! Located in X Zone! That's right, NO FLOOD ZONE!
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Jessica Jurek (727-487-4957)
3858 SHORE BLVD, OLDSMAR, FL 34677
$1,100,00070 Days on yellowkey MLS ID: TB8506221
REDUCED by $50,000 (4.3%) on 07/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1594 Built: 1986 Tax: $8,857 (2025)Community: West Oldsmar Sec 1Single Family
Taxes:$8,857
Remarks: Experience the laid back lifestyle of Oldsmar, a sought-after community nestled between the urban hubs of Tampa and Clearwater. This serene, waterfront property offers the perfect balance of peaceful living and convenient access to local attractions. Residents here enjoy a tranquil, private environment, starting mornings with fresh coastal breezes on a private porch or deck, and spending evenings watching sunsets from a kayak or boat. This elevated, two-story home, topped with a 2025 roof, showcases an expansive layout filled with radiant natural light and soaring vaulted ceilings. The interior ambiance is both airy and welcoming, anchored by a charming wood-burning fireplace. The heart of the home is a sun-drenched, open-concept great room and kitchen, equipped with stainless steel appliances, granite surfaces, a propane stove, and a tankless water heater, all showcased by floor-to-ceiling windows. The generous primary suite acts as a private retreat, featuring an ensuite bathroom with a garden tub, dual vanities, and a separate shower, alongside a private deck offering stunning vistas. Functionality meets flexibility in the lower level, which houses a spacious two-car garage and a versatile 600-square-foot accessory dwelling unit. With its own entrance, bathroom, and kitchen facilities, this suite is perfectly suited for guests or extended family. The exterior features substantial paver parking, ready to accommodate RVs, boats, and other recreational vehicles. Nature enthusiasts will delight in the local wildlife, including dolphins and manatees, viewable directly from home. The property’s private floating dock and boat ramp provide effortless access to Tampa Bay without worrying about the tides. Elevated construction ensures peace of mind during inclement weather, while the property’s location—situated on a private, oversized lot on a quiet cul-de-sac—secures absolute seclusion. Located in a premier school district and just 20 to 30 minutes from the region’s best beaches and downtown centers, this home also offers residents easy access to the festive R.E. Olds Park and the vibrant dining scenes of nearby Safety Harbor. Both Mobbly Beach Park and the picturesque Phillippe Park are situated within a three-mile radius, making them a breeze to reach via cycling or boat. Oldsmar stands out for several unique reasons: it operates its own reverse osmosis water filtration system, houses the Tampa Bay Skating Academy Ice Rink, and maintains a higher density of parks per square mile than any other municipality in the state, with roughly 40% of its total area reserved for green spaces and conservation. Those who love the outdoors can take advantage of the ten-mile Oldsmar Trail, which winds through eight of the city's ten parks, providing endless chances for recreation and immersion in nature. Don't wait—secure your chance to live out your ideal Florida dream by booking your private viewing of this exceptional property today!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Mark Yorke, Llc (727-481-2165)
50 WILLOWOOD LN, OLDSMAR, FL 34677
$1,499,900158 Days on yellowkey MLS ID: TB8475420
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4475 Built: 1987Monthly Fee: $240 Tax: $8,709 (2024)Community: Deerpath Unit OneSpa: YesSingle Family
Taxes:$8,709
Remarks: **6 Bedrooms | Private In-Law Suite | 4.5 Baths | 1.4 Acres | Gated East Lake Woodlands** If you've been searching for a home with room for everyone—this is one you need to see in person. Set on a private 1.4-acre cul-de-sac lot in the gated East Lake Woodlands community, this expansive home offers 6 total bedrooms, 4.5 baths, including a dedicated in-law suite with its own private entrance, and an oversized upstairs loft perfect for a media room, playroom, or home office. Designed for entertaining, the nearly 2,000-square-foot screened lanai creates an incredible extension of the home's living space. The space features a newly updated pool, outdoor kitchen, bar, and a full, dedicated, poolside bath complete with shower. Inside, soaring 25-foot ceilings, beautiful herringbone Turkish tile flooring, a spacious family room with a wet bar, and a chef-inspired kitchen with custom wood cabinetry, large island, prep sink, breakfast bar, and generous dining space make everyday living as enjoyable as hosting family and friends. Located just minutes from top-rated schools, shopping, dining, Tampa International Airport, and the Gulf beaches, this home also offers optional access to East Lake Woodlands' golf, tennis, fitness, and country club amenities. Homes offering this much space, flexibility, and outdoor living are rare. Schedule your private tour today and experience 50 Willowood Lane for yourself!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Melissa Pranzo (646-509-7350)
392 TAVERNIER CIR, OLDSMAR, FL 34677
$558,90029 Days on yellowkey MLS ID: TB8521472
REDUCED by $10,100 (1.8%) on 07/15/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1656 Built: 1996Monthly Fee: $75 Tax: $2,635 (2025)Community: Fountains At Cypress Lakes Ii-BSpa: NoSingle Family
Taxes:$2,635
Remarks: 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.
Listing is courtesy of: RE/MAX ELITE REALTY (727-785-7653)
Listing Agent: Jean Rodgers (727-647-1374)
1704 SPLIT FORK DR, OLDSMAR, FL 34677
$599,0009 Days on yellowkey MLS ID: TB8527058
1 Days Off yellowkey (back on 7/15/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2166 Built: 1997Monthly Fee: $12 Tax: $9,642 (2025)Community: Eastlake Oaks Ph 1Spa: NoSingle Family
Taxes:$9,642
Remarks: Under contract-accepting backup offers. Virtually Staged. If you've been searching for a home with room to spread out, a private pool, in an amazing neighborhood, this is it. Tucked in Eastlake Oaks, this beautifully maintained 4-bedroom, 2.5-bath home with a 2-car garage has over 2,000 square feet of updated living space and a backyard designed for enjoying Florida year round. Step inside to soaring ceilings, abundant natural light, and a floor plan that brings flexibility for everyday living. The main living areas flow seamlessly together, creating comfortable spaces for entertaining and daily life. The timeless kitchen features crisp white shaker cabinetry, quartz countertops, a farmhouse sink, stainless steel appliances, subway tile backsplash, floating wood shelving, recessed lighting, and a statement brick accent wall that adds warmth and character. Overlooking the living areas, it's the perfect gathering place whether you're hosting friends or enjoying a quiet evening at home. The spacious primary suite designed as a true retreat. The beautifully renovated en-suite bath is complete with dual vanities, quartz countertops, a freestanding soaking tub, walk-in shower with frameless glass, designer tile, modern black fixtures, and a custom walk-in closet complete with built-in shelving and drawers. The secondary bedrooms offer a comfortable and inviting feel with generous space for guests. Need additional space? The bonus room has endless flexibility as a home office, playroom, media room, or second living area.. Outside, the screened heated saltwater pool creates your own private escape. Surrounded by a paver patio, lush landscaping, privacy fencing, and multiple seating areas, the backyard is ready for weekend gatherings, or relaxing after a long day. Additional improvements include select Windows (2023), New Water Heater (2025), Refrigerator and Range (2024), HVAC (2022), in-home Water Softener, screened enclosure, fencing, and additional outdoor living enhancements. Beyond the home, Eastlake Oaks residents enjoy a community pool and playground, while a neighborhood nature trail provides direct access to Sheffield Park. You're just minutes from shopping, restaurants including Craft Street Kitchen and Shaker & Peel, AMC Theatre, and beautiful local parks including R.E. Olds Park. Schedule your showing today and experience everything this outstanding Oldsmar home has to offer. **Use the seller’s preferred lender and receive a no cost 1-point permanent rate buy down.
Listing is courtesy of: SOUTHERN LIFE REALTY (727-642-1758)
Listing Agent: Kelsi Ward (727-488-7032)
435 LAKEVIEW DR, OLDSMAR, FL 34677
$475,000117 Days on yellowkey MLS ID: TB8489554
0 Days Off yellowkey (back on 7/14/2026)
REDUCED by $14,000 (2.9%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1570 Built: 1984Monthly Fee: $35 Tax: $6,675 (2025)Community: Manors Of Forest Lakes TheSpa: YesSingle Family
Taxes:$6,675
Remarks: Under contract-accepting backup offers. Welcome to Forest Lakes and this beautifully appointed, immaculately maintained 3-bedroom, 2-bath, 2-car garage home offering 1,569 square feet of living space. Nestled in an exceptional school district, this home has been lovingly cared for and is truly immaculate. It features soaring vaulted ceilings, a cozy fireplace, and French doors leading to a large backyard retreat. The gorgeous kitchen with granite, newer stainless steel appliances, and pantry overlooks both the living room and the pool, which is fully screened and features a child-proof fence for added security. The master bedroom offers a private en-suite bath, providing a tranquil retreat. Brand NEW HVAC system to be installed July 8! Other highlights for this house include a new 200-amp electrical panel with whole-home surge protector, new switches and receptacles throughout, and a dedicated 50-amp E.V. car charger. A four-year-old roof, with newer windows and a new garage door, makes Florida living a breeze. Outside, enjoy the large pool area and spa with a new pump, timer, and automatic cleaner, a fire pit, and a host of amenities. An oversized garage also features a dedicated electric outlet for your vehicle, a washer and dryer, and a newer water heater. The community offers a lakefront playground, a barbecue area, a fishing dock, and courts for basketball, tennis, and racquetball. With very low monthly HOA fees and a large community pool, this move-in-ready home is a true gem. Don’t miss out! Nothing else to do but move in!
Listing is courtesy of: COLDWELL BANKER REALTY (727-581-9411)
Listing Agent: Kim Krenek (727-262-3181)
416 MAPLEWOOD DR, OLDSMAR, FL 34677
$460,00011 Days on yellowkey MLS ID: TB8527873
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1395 Built: 1977 Tax: $1,408 (2026)Community: Harbor Palms-Unit OneSpa: NoSingle Family
Taxes:$1,408
Tax Year: 2026
Remarks: Welcome to one of Oldsmar's hidden gems! This beautifully maintained 3-bedroom, 2-bath pool home is nestled in the highly desirable Harbor Palms neighborhood, offering the perfect combination of location, comfort, and the Florida lifestyle. The bright split-floor plan features premium laminate and tile flooring, a spacious living room with French doors leading to your private backyard oasis, a formal dining room with a picture window, and a beautifully appointed kitchen with granite countertops, wood cabinetry, and stainless-steel appliances, to include a Point of use Reverse Osmosis Water Purification System. The interior laundry room includes the washer, dryer, and ample storage cabinets. The spacious primary suite offers dual walk-in closets and a beautifully updated en-suite bath with quartz countertops, soft-close cabinetry, and a custom-tiled walk-in shower. Step outside to the screened, covered lanai overlooking a sparkling pool with a tranquil waterfall. The pool is equipped with a child safety fence, which is included with the home. The oversized, fully fenced backyard offers plenty of room to entertain, relax, or enjoy Florida's year-round sunshine. Ideally located just a short walk or bike ride to the neighborhood's beloved Sheffield Park, featuring playgrounds. You'll also enjoy being just 25 minutes from Honeymoon Island and Tampa International and St. Pete-Clearwater airports, and only minutes from shopping, dining, and everyday conveniences. Opportunities like this in Oldsmar are rare—don't miss your chance to own this move-in-ready Florida retreat.
Listing Agent: Frank Gomez (813-695-1247)
1811 FOREST DR, OLDSMAR, FL 34677
$429,00032 Days on yellowkey MLS ID: TB8520312
REDUCED by $10,000 (2.3%) on 07/14/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2142 Built: 1973 Tax: $1,463 (2024)Community: Harbor Palms-Unit ThreeSpa: NoSingle Family
Taxes:$1,463
Remarks: Nestled in the heart of Oldsmar, this location offers the perfect blend of small-town charm, outdoor recreation, and everyday convenience that makes living in Harbor Palms so desirable. Situated HIGH AND DRY with NO history of flooding, residents enjoy being just minutes from the waterfront parks and trails along Tampa Bay, including R.E. Olds Park, Veterans Memorial Park, and the scenic Upper Tampa Bay Trail. Whether you're spending the day kayaking, biking, fishing, or enjoying one of the area's many community events, Oldsmar embraces an active Florida lifestyle while maintaining a welcoming neighborhood feel. This beautifully renovated 3-bedroom, 2-bathroom POOL home offers over 2,100 square feet of thoughtfully designed living space. From the moment you arrive, the inviting curb appeal sets the stage for the upgrades found throughout the home. Luxury vinyl plank flooring flows seamlessly from room to room, creating a modern and cohesive feel. The front living room transitions effortlessly into the dining area and spacious family room, where a cozy fireplace flanked by built-in shelving serves as the focal point. The centrally located galley-style kitchen is sure to impress with quartz countertops, stainless steel appliances, a statement vent hood, crisp white cabinetry, and a stylish backsplash. The oversized owner's suite offers a private retreat complete with a large walk-in closet and an ensuite bathroom featuring floor-to-ceiling tile and a walk-in shower. Two additional bedrooms are conveniently located near the beautifully updated guest bathroom. A dedicated mudroom with washer and dryer hookups adds extra functionality and storage space. Step outside to the screened-in lanai overlooking the sparkling in-ground pool, creating the perfect setting for relaxing or entertaining guests. Major updates include a new roof and AC in 2024, providing peace of mind for years to come. One of the biggest advantages of living here is the incredible convenience and abundance of nearby amenities. Harbor Palms Nature Park is just steps away and features a kayak launch, scenic boardwalk, walking trails, and an 18-hole disc golf course. Sheffield Park is also nearby with basketball and tennis courts, baseball and softball fields, and a dog park. Centrally located between Tampa, Clearwater, and Palm Harbor, residents enjoy easy access to Tampa International Airport, award-winning Gulf beaches, shopping, dining, entertainment, Mease Countryside Hospital, Tampa Bay Downs, and the Oldsmar BMX Supercross Track. With beautiful parks, a strong sense of community, and a prime Tampa Bay location, it's easy to see why Oldsmar continues to be one of the area's most sought-after places to call home. Schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Tiana Lake (727-688-5565)
2055 DIAMOND CT, OLDSMAR, FL 34677
$1,150,00032 Days on yellowkey MLS ID: TB8520799
0 Days Off yellowkey (back on 6/23/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3237 Built: 1996Monthly Fee: $142 Tax: $8,014 (2025)Community: Diamond CrestSpa: YesSingle Family
Taxes:$8,014
Remarks: Under contract-accepting backup offers. Welcome to 2055 Diamond Court, an exceptional residence located in the highly sought after guard gated community of Eastlake Woodlands. Situated on a rare trifecta lot with views of the pond, conservation and the golf course. Updated well-appointed home with 3 spacious bedrooms and a dedicated office that could also be an exercise or nursery room. A circular drive leads to the portico entrance. The views immediately greet you upon entering. The generous formal living and dining areas, high ceilings, abundant natural light and multiple gathering spaces create a warm and inviting atmosphere. Entertain easily in the updated gourmet kitchen and expansive family room that overlook the views and pool area. The primary suite is a retreat with pool and spa access, ensuite bath and walk-in closet. Beautifully remodeled primary bath includes a walk in shower, double sinks with quartzite counters and a relaxing stand-alone tub. Additional bedrooms are spacious with entry to the second and third remodeled baths. Enjoy the outdoor view on the travertine pool deck. Take a dip in the solar heated pool or relax in the spa. The expanded pool deck allows for several dining arrangements on the patio. Updates include a 2018 tile roof, 2021 HVAC, exterior and interior paint, updated kitchen and all baths. Located in the subdivision of Diamond Crest, a small one street community inside Eastlake Woodlands. Residents enjoy a beautifully maintained setting with convenient access to shopping, dining, parks, highly rated schools, Tampa International Airport and the area’s award winning Gulf Coast beaches. Eastlake Woodlands is home to the prestigious Ardea Country Club with two championship golf courses, tennis, pickle ball, fitness center, restaurant and banquet room. There are various memberships to choose from to fit your lifestyle. This is a rare opportunity to enjoy Florida’s year round sunshine, private home oasis and a premier Oldsmar location. Please be sure to watch the video for more photos and drone photography.
Listing Agent: Debra Gross (727-463-2271)
1815 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$427,50067 Days on yellowkey MLS ID: W7885693
REDUCED by $500 (0.1%) on 07/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1855 Built: 1972 Tax: $2,731 (2025)Community: Harbor Palms-Unit TwoSingle Family
Taxes:$2,731
Remarks: This beautifully remodeled three-bedroom, two-bath home is perfectly located in Oldsmar at the top of Tampa Bay. Completely updated from top to bottom, it features a stunning new kitchen with stainless steel appliances, soft-close cabinetry, leather-finished quartz countertops, and a cozy breakfast nook. One of the standout features is how all three bedrooms are nicely separated for added privacy. The spacious master suite boasts a huge California-style walk-in closet, peaceful backyard views, and a gorgeous bathroom with a walk-in shower. The open-concept living space extends into a roomy bonus area at the back of the house, accented by tandem ceiling fans. From here, French doors lead to a fully fenced backyard, complete with a poured slab ready for a shed. A generous laundry room with a utility sink connects to the two-car garage, featuring a new hurricane-rated door and opener. Oldsmar offers unmatched access to the Pinellas Beaches, all that Tampa has to offer, plus its own great dining, excellent schools and shopping scene. Don’t miss the opportunity to check out this beautiful home!
Listing is courtesy of: SNAP REALTY LLC (727-457-5453)
Listing Agent: Dean Glicos (727-509-9296)
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