Location: Oldsmar
Do Not Show Listings
1909 CASTLE BAY CT, OLDSMAR, FL 34677
$370,000285 Days on yellowkey MLS ID: TB8436254
REDUCED by $4,000 (1.1%) on 05/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1410 Built: 1984 Tax: $2,696 (2024)Community: Sheffield Village Ph Ii At Bayside MeadowsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,696
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
Remarks: --SERIOUS SELLER-WILLING TO NEGOTIATE--SUBMIT YOUR OFFER ASAP-- Check out this BEAUTIFUL 3-bedroom, 2-bath BLOCK home WITH GARAGE. located on a quiet cul-de-sac in the heart of Oldsmar. BEAUTIFUL HIGH GLOSS TILE FLOORING THROUGHOUT Featuring spacious living areas with vaulted ceilings, a primary bedroom with an ensuite, and a split bedroom layout for added privacy and a rear screened porch perfect for relaxing or entertaining. The home has been thoughtfully upgraded with a new electrical panel (2018), roof (2020), air conditioning system (2021), gutters (2022), garage door (2022), water heater (2022), and water softener tank (2024) Exterior Water Line (2025). along with fresh exterior paint. Situated just steps from Sheffield Park, residents enjoy access to hiking and running trails, tennis and basketball courts, a playground, and a covered pavilion for events. Conveniently close to shopping centers, restaurants, downtown Tampa, the international airport, Clearwater beaches, and St. Pete, this neighborhood offers a peaceful environment with NO HOA fees. This turnkey home combines modern comfort with an unbeatable location—great curb appeal, stop by and take a look you wont be disappointed! MOTIVATED SELLER! SUBMIT YOUR OFFER TODAY!
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Craig Berenger, Jr. (727-847-4444)
4761 STONEBRIAR DR, OLDSMAR, FL 34677
$749,00055 Days on yellowkey MLS ID: TB8509685
REDUCED by $11,000 (1.4%) on 07/06/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2652 Built: 1993Monthly Fee: $117 Tax: $5,832 (2025)Community: StonebriarSingle Family
Taxes:$5,832
Elementary School: None
Tax Year: 2025
Remarks: This is Florida luxury living at its finest in one of the area’s most desirable gated communities. Exclusive executive home located in the highly sought-after Stonebriar community within East Lake Woodlands, a desirable gated golf club community. Zoned for top-rated schools and ideally situated less than 30 minutes from Tampa International Airport and the area’s premier Gulf beaches. This exceptional 4-bedroom luxury residence offers the perfect blend of elegance, comfort, and privacy. Boasting 2,652 square feet of living space with soaring ceilings and abundant natural light, this beautifully updated home features a spacious oversized primary suite complete with a private sitting area overlooking the expansive screened pool, recently resurfaced for years of enjoyment. The gourmet kitchen is designed for both entertaining and everyday living. Newer appliances, newer pool pavers, Plantation shutters added throughout. Roof 2016, Water heater 2019, re screened porch 2017, fresh exterior paint 2019. The private conservation lot provides a tranquil setting ideal for relaxing or entertaining poolside. RECENTLY PASSED 4point and Wind Mitigation.
Listing is courtesy of: PRIME INT'L REAL ESTATE GROUP (877-727-5259)
Listing Agent: Nichole Gaytan (305-323-8108)
438 LAFAYETTE BLVD, OLDSMAR, FL 34677
$575,000138 Days on yellowkey MLS ID: TB8480797
REDUCED by $9,900 (1.7%) on 07/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2138 Built: 1988 Tax: $8,284 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$8,284
Middle School: None
Remarks: Beautiful Custom-built home is situated on ½ acre fenced-in lot (mol) No HOA, No deed restriction, Plenty of room for your Boat and RV! Featuring 4 Bedrooms plus an office, 2 baths and a screened-in heated pool. Circular driveway and etched glass front door welcome you into a wide-open floor plan with vaulted ceilings and lots of windows. Interior freshly painted. The living room offers a beautiful bay window and a cozy fireplace, open to a light and bright dining room. Large, updated kitchen with wood cabinetry, newer stainless-steel appliances, granite countertops, coffee bar and a garden window. The home flows effortlessly from room to room making it ideal for both everyday living and entertaining. Expansive primary suite with 2 large closets, beautiful new bath with a huge walk-in shower and a jetted tub. Additional 3 good size bedrooms plus a great in-home office with built-in shelving and double glass doors leading to the lanai and pool. Beautifully updated 2nd bath, nice size laundry room. 2 Car garage plus a spacious storage room. New top of the line Trane A/C. Roof replaced in 2017. Newer flooring (No Carpet) The huge fenced-in backyard provides privacy and has plenty of space for pets or outdoor entertaining, with a grilling area. Beautiful, heated pool, newly re-screened and new pool heater installed. The beautiful Veterans Memorial waterfront Park is just down the street. Walking distance to downtown Oldsmar. Conveniently located near shopping, fine dining, theatres and golfing. 10-15 Minutes to Philippe Park and Safety Harbor Spa, 15-20 minutes to downtown Dunedin, Honeymoon Island and Pinellas Trails. 20-25 Minutes to Clearwater Beach, Tampa and St Pete airports. Motivated Seller!
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Luigi Kalaj (727-388-4200)
413 COUNTRY CLUB DR, OLDSMAR, FL 34677
$324,90019 Days on yellowkey MLS ID: O6422167
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 1959 Tax: $3,829 (2024)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$3,829
Remarks: Wake up to water views and end your day watching the sun set over the canal. This renovated 3-bedroom, 2-bathroom waterfront home sits on a spacious 0.21-acre lot with no HOA in the established Oldsmar Country Club Estates, and its best feature is right out the back door: direct water access with a scenic trail leading all the way to Tampa Bay. Launch a kayak or paddleboard from your own backyard and be on the water in minutes. Inside, the home is move-in ready with luxury vinyl flooring throughout and an open, light-filled layout. The renovated kitchen features stainless steel appliances, quartz countertops, and generous cabinetry. The primary suite gives a comfortable retreat with an updated bathroom, modern vanity, designer lighting, and a tiled walk-in shower. Sliding doors off the main living area open to an expansive backyard where the waterfront views take center stage. Enjoy morning coffee, evening entertaining, or simply unwind by the water. The location matches the lifestyle. Walk, bike, or take your golf cart to Mobbly Bayou Beach Park, a public boat launch to Tampa Bay, Tampa Bay Pickleball, Veterans Park, Bicentennial Park, and RE Olds Park. You are also close to Empower Adventures Zip Line and the Oldsmar Organic Community Garden, with Tampa International Airport about 20 minutes away. Zoned for well-regarded schools including Oldsmar Elementary, Joseph L. Carwise Middle, and East Lake High. This is a rare opportunity to own a renovated waterfront home with no HOA in one of Oldsmar's most sought-after communities.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
848 CHRISTINA CIR, OLDSMAR, FL 34677
$560,00067 Days on yellowkey MLS ID: TB8509369
1 Days Off yellowkey (back on 7/3/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1756 Built: 1994Monthly Fee: $68 Tax: $4,544 (2025)Community: Bay's EndSpa: YesSingle Family
Taxes:$4,544
Remarks: Under contract-accepting backup offers. Tucked away in the desirable enclave of Bay’s End, this stunning contemporary two-story residence blends upscale coastal living with exceptional indoor-outdoor entertaining. From the moment you enter, soaring ceilings, an open-concept design, and abundant natural light create a warm yet sophisticated atmosphere. Rich wood-look luxury vinyl flooring flows seamlessly throughout the home, enhancing its modern coastal appeal. At the heart of the home is a beautifully designed island kitchen featuring elegant wood cabinetry, gleaming quartz countertops, and stainless steel appliances. The kitchen opens effortlessly to the spacious living and dining areas, highlighted by a striking wood-burning fireplace and views of the tropical pool and spa retreat. The main-level owner’s suite is a private sanctuary complete with a walk-in closet and an expansive spa-inspired bathroom filled with natural light, featuring a luxurious vanity, soaking tub with shower. A convenient half bath, interior laundry room, and attached two-car garage complete the first floor. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile den/media room perfect for a home office, playroom, or entertainment space. Step outside through sliding glass doors to your own private resort-style oasis. The screened lanai surrounds an entertaining-sized pool with waterfall and spa, framed by towering palm trees and lush tropical landscaping. By night, the spectacular pool and landscape lighting transform the backyard into a truly magical setting. Situated on nearly a quarter-acre, the enormous privacy-fenced backyard offers endless possibilities — currently serving as the ultimate playground for soccer, baseball, basketball, and golf. Exceptional savings with the solar panels, installed in 2020. Seller will pay the financing in full at closing. This exceptional Bay’s End home combines style, comfort, and resort-inspired living in one unforgettable package. Opportunities like this don’t last long.
Listing is courtesy of: RIZZO & ASSOCIATES INC (727-894-4400)
Listing Agent: Philip Rizzo (727-656-4400)
1811 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$359,900124 Days on yellowkey MLS ID: TB8488580
REDUCED by $10,100 (2.7%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 1973 Tax: $1,036 (2025)Community: Harbor Palms-Unit TwoSingle Family
Taxes:$1,036
High School: None
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of Oldsmar! Offering 1,248 sq ft of well-designed living space, this move-in-ready property features a functional layout, abundant natural light, and modern updates throughout. Enjoy spacious living and dining areas that flow seamlessly, perfect for both everyday living and entertaining. The kitchen offers ample cabinetry and workspace, while the bedrooms are generously sized for comfort and flexibility. Conveniently located near parks, shopping, dining, and major roadways, this home provides easy access to Tampa, Clearwater, and surrounding areas. Don’t miss this opportunity to own a well-maintained home in a desirable location!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Julio Vasquez (727-404-8889)
1924 MONTEGO CT, OLDSMAR, FL 34677
$359,90042 Days on yellowkey MLS ID: TB8517782
0 Days Off yellowkey (back on 7/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 1980 Tax: $5,005 (2025)Community: Bayside Meadows-Phase ISingle Family
Taxes:$5,005
Remarks: **SUPER STARTER HOME!!** What a fantastic house for the price! From the moment you arrive, you’ll be wowed by the striking curb appeal. The freshly painted exterior is complemented by a newer roof and landscaping, with a 30-year dimensional shingle roof installed in 2024 and a transferable 10-year warranty. Inside, the spacious, open floor plan is just as impressive, starting with a leaded glass front door. This move-in ready home has been updated throughout, featuring a tiled great room with a lighted ceiling fan and a large front window that fills the space with natural light. The eat-in kitchen offers a cozy dinette, updated soft-close cabinetry, stainless steel appliances, recessed lighting, and tile countertops with backsplash. Down the hall are three bedrooms, all with lighted ceiling fans and new carpet. The primary ensuite boasts an updated bathroom with a walk-in shower and new hardware, while the guest bath offers resort-style features. Step through the back sliding glass door to a screened lanai with tile floors—perfect for relaxing or entertaining. The modest fenced backyard has fresh mulch and is easy to maintain. With a new A/C installed in 2022 and a prime location near trendy restaurants, shopping, AMC Woodlands Movies, and just minutes from Tampa, the airport, or the beach, this home truly has it all—don’t miss it! (house has never had any issues with flooding in 20 years owner has owned it)
Listing Agent: Shay Adelman (727-458-3702)
3071 HURON AVE, OLDSMAR, FL 34677
$469,90066 Days on yellowkey MLS ID: TB8507555
1 Days Off yellowkey (back on 6/29/2026)
REDUCED by $30,000 (6.0%) on 06/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1680 Built: 1987 Tax: $5,919 (2025)Community: West Oldsmar Sec 1Single Family
Taxes:$5,919
Remarks: Under contract-accepting backup offers. Must see this amazing home in one of Oldsmar's best kept secret neighborhoods on the sparkling shores of Old Tampa Bay! This 3-bedroom, 2.5-bath multi-level designed home has been FULLY RENOVATED with real class blending coastal charm with PRISTINE UPDATES in every room. Above the Oversized 2-car garage, get ready to be impressed by the high ceilings, all NEW WINDOWS, DOORS & light filled living spaces amongst the refinished oak hardwood & gorgeous porcelain ceramic tile flooring throughout. NEW ROOF 2024! STAIRS & DECKS REFURBISHED! The STUNNING KITCHEN has QUARTZ countertops & stainless steel appliances opening into the living and grand dining rooms with french doors onto the enormous covered deck. It's perfect for entertaining and family time. Upstairs you find 3 good sized bedrooms and 2 full bathrooms. The primary suite features french doors to its own private balcony along with a spa inspired ensuite bathroom featuring a luxurious freestanding tub & separate shower that feels straight from a boutique retreat. Not only is this home perfect for all your year round outdoor activities, you can even cozy up by the wood burning fireplace during cold times. The 2 car garage offers exceptional storage space for all the extras, while the oversized back yard opens the door to endless possibilities to make it your new tropical paradise with room for a pool, gardens, boat or RV parking, and even a potential in-law suite. Just minutes from several Waterfront Parks (R.E. Olds Park is biking distance), Scenic trails, Boat ramps, Fishing, Tennis, Pickle ball, Golfing, Tampa Bay Downs, Shopping, Restaurants, and Top Rated Schools in this location, you truly have it all! Possible owner financing available.
Listing Agent: Diana Beattie (727-417-7021)
200 LEE ST, OLDSMAR, FL 34677
$1,350,00078 Days on yellowkey MLS ID: TB8505047
REDUCED by $100,000 (6.9%) on 06/29/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1250 Built: 1957 Tax: $4,470 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$4,470
Remarks: This is a packaged listing with MLS #TB8504841 for sale & close together. Total land 33,806 sf. A unique prime development opportunity in the heart of The City of Oldsmar with a 350 ft frontage on State St E between SWC of Lee and SEC of Washington Ave with a zoning designation TCCN ( Town Center Commercial Neighborhood District). A dynamic growth opportunity across from the proposed Town Center that includes City hall, 2 business and 4 story apartment building and public area. Near by Oldsmar City Hall, chamber of commerce, The Galleria, Odeon Town Home square and Washington square. Easy access to Tampa Rd, shopping, restaurants, hotels, beaches, hospitals, Tampa Int'l and St Pete/ CLW Int'l airports.
Listing is courtesy of: IDEAL REALTY ADVISORS, LLC (727-647-2814)
Listing Agent: Victor Suhweil (727-647-2814)
5163 PINNACLE DR, OLDSMAR, FL 34677
$635,00062 Days on yellowkey MLS ID: TB8510486
3 Days Off yellowkey (back on 6/28/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1886 Built: 1995Monthly Fee: $482 Tax: $7,853 (2025)Community: Parcel B - The PinnacleSpa: YesSingle Family
Taxes:$7,853
Elementary School: Cypress Woods Elementary-PN
Remarks: Under contract-accepting backup offers. Offering over $23,000 in upgrades! Located in X Flood Zone with no flood insurance required, this beautifully maintained residence offers one of the best values currently available in the highly sought-after gated golf community of East Lake Woodlands. This is one of the newer homes in the community and an exceptional opportunity to own a high-quality property at one of the lowest entry points in ELW. Tucked within the quaint and quiet Pinnacle neighborhood in the desirable north side of East Lake Woodlands, residents enjoy access to a private community pool and peaceful surroundings rarely found at this price point. Welcome to 5163 Pinnacle Drive, a thoughtfully updated 3-bedroom, 2-bath home featuring a desirable split floor plan, soaring ceilings, crown molding, arched openings, decorative column accents, and custom soffit ledge details that create an open, airy feel throughout. Ceramic tile flooring runs throughout the home with no carpet, while abundant natural light enhances the spacious living and dining areas designed for both everyday comfort and entertaining. The kitchen is both functional and stylish with 42-inch cabinetry, stainless steel appliances, a breakfast nook overlooking the lanai, and new custom window treatments. Pocket sliding glass doors fully open to the outdoor living space, seamlessly blending indoor and outdoor living. Enjoy a private screened and covered patio with pavers, an open-air grilling area, lush new landscaping with upgraded irrigation, and a relaxing in-ground spa perfect for unwinding year-round. The oversized primary suite offers three closets and a spacious en-suite bath with double vanities, a garden tub, and a walk-in shower with built-in bench seating. Two additional bedrooms and a full bath are located on the opposite side of the home, offering privacy for guests or family. Extensive updates and improvements include a 2019 roof, 2022 4-ton HVAC system, 2023 spa equipment, 2023–2025 appliances, 2024 exterior paint, whole-house insulation and surge protection, surround sound, garage organization systems, and more. The garage is exceptionally well-equipped with built-in cabinetry, slat-wall storage, overhead storage racks, and a ceiling-mounted air/electric/light station. The home has also been recently inspected by a professional contractor, including both a 4-point inspection and wind mitigation report. Monthly maintenance fees provide low-maintenance living and include lawn care, exterior painting, pressure washing, trash and recycling service, Spectrum cable and internet, and community pool access. Optional membership to the East Lake Woodlands/Ardea Country Club offers two championship golf courses, tennis, pickleball, fitness center, resort-style pools, dining, and year-round social activities. Homes on Pinnacle Drive rarely become available. Don’t miss this opportunity to own a move-in-ready home in one of Oldsmar’s premier gated communities.
Listing Agent: Jenny Neumeyer (727-482-2656)
316 COUNTRY CLUB DR, OLDSMAR, FL 34677
$325,00068 Days on yellowkey MLS ID: TB8508856
2 Days Off yellowkey (back on 6/28/2026)
REDUCED by $3,900 (1.2%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1960 Tax: $616 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$616
Remarks: Under contract-accepting backup offers. Yes! This beautifully renovated mid-century modern block home actually looks this good in person - no AI staging here! Located in the desirable NO HOA community of Oldsmar Country Club Estates. Timeless character with modern upgrades are inside this 3 bedrooms, 2 bathrooms. Under the exposed beams is 1,344 square feet of thoughtfully updated living space. The fully renovated kitchen features elegant quartz countertops, 42” upper cabinets, and stainless steel appliances, creating a stylish and functional space for everyday living and entertaining. Don't let the floor to ceiling windows fool you eco-friendly design allows a low-cost energy bill. Additional highlights and upgrades include: newer vinyl windows, a 2017 roof, 2023 ductless mini-split system, 2023 hot water heater, and updated electrical in 2025 for added peace of mind. Step outside to enjoy the fully fenced backyard, perfect for pets, entertaining, or relaxing in privacy. The attached carport provides convenient covered parking and additional storage flexibility. Ideally situated just yards from the Oldsmar Boat Ramp with direct access to Tampa Bay, this golf cart-friendly community offers the perfect Florida lifestyle. R.E. Olds Park is a 15-acre dog- friendly waterfront park featuring a 400 -foot fishing pier, playgrounds, picnic shelters, an amphitheater, and trails with scenic views of Tampa Bay. Named after automotive pioneer Ransom E. Olds, the park hosts numerous community events and offers amenities like volleyball, tennis & pickleball courts & restrooms. With no HOA restrictions, park the boats, RV’s and work trucks with ease. This property is ideal for a first-time homebuyer, seasonal resident, or as an income-producing short-term rental investment opportunity. Annual Flood quote $2,653.34
Listing is courtesy of: TMWRK BROKERAGE LLC (727-277-9032)
Listing Agent: Faith Walston (813-303-1239)
50 KELLEYS TRL, OLDSMAR, FL 34677
$925,00077 Days on yellowkey MLS ID: TB8504781
REDUCED by $24,000 (2.5%) on 06/28/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3240 Built: 1993Monthly Fee: $185 Tax: $7,792 (2025)Community: Turtle Creek Unit-OneSingle Family
Taxes:$7,792
Remarks: Welcome to an exceptional residence at 50 Kelleys Trail, nestled within the prestigious gated enclave of Turtle Creek within East Lake Woodlands in Oldsmar. This refined home embodies effortless elegance and elevated Florida living, offering a seamless blend of sophistication, comfort, and privacy. From the moment you enter, you’re greeted by soaring ceilings, abundant natural light, and thoughtfully designed living spaces that create an inviting yet upscale atmosphere. The open-concept layout flows beautifully, ideal for both intimate gatherings and grand entertaining. The kitchen serves as the heart of the home, featuring generous workspace, ample cabinetry, and a layout designed for both functionality and style. The primary suite is a true retreat, offering a serene escape with spacious proportions and a well-appointed en-suite bath. Step outside to your private outdoor setting, where you can unwind in tranquility or entertain guests while enjoying Florida’s year-round sunshine. Whether relaxing or hosting, this space offers the perfect backdrop for a luxury lifestyle. Located within one of Oldsmar’s most sought-after golf course communities, residents of East Lake Woodlands have access to optional resort-style amenities, including championship golf, tennis, fitness, and social experiences. Ideally positioned near upscale dining, boutique shopping, top-rated schools, Tampa International Airport, and the Gulf Coast’s renowned beaches, this home offers both convenience and exclusivity. Experience refined living in one of Oldsmar’s premier communities—schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
10 ARBOR LN, OLDSMAR, FL 34677
$669,00047 Days on yellowkey MLS ID: TB8516041
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2318 Built: 1979Monthly Fee: $148 Tax: $9,038 (2025)Community: East Lake WoodlandsSpa: YesSingle Family
Taxes:$9,038
Elementary School: Forest Lakes Elementary-PN
Remarks: Beautiful 4-bedroom, 2-bathroom pool home on a corner lot with views of the 5th hole in East Lake Woodlands. Offering a desirable split-bedroom floor plan, open living areas, and a screened pool and spa, this home combines comfort, functionality, and an exceptional golf course setting. Inside, you'll find a spacious split-bedroom floor plan featuring vaulted ceilings, exposed wood beams, and an open layout designed for both everyday living and entertaining. The inviting living room centers around a cozy fireplace, creating a warm gathering space for family and friends. The kitchen offers abundant teak wood cabinetry with convenient pull-out drawers, stainless steel appliances, a breakfast nook, and thoughtful updates that enhance both style and functionality. The outdoor living area is truly exceptional. A screened-in pool and spa overlook the golf course, while multiple seating and dining areas provide the perfect setting for entertaining guests or enjoying peaceful evenings outdoors. This home has been extensively updated and meticulously cared for. Major improvements include a new roof and gutters in 2022, a new HVAC system in 2025, exterior paint, updated exterior lighting, wired landscape lighting, removal of popcorn ceilings, replacement of eaves with anti-rot wood, and the addition of a skylight. The pool and spa systems have also been upgraded with a new pool filter, pool pump, pool sweep, pool equipment, propane tanks, and a new heater and pump for the spa. Interior enhancements include lifting and leveling the living room floor, installation of waterproof flooring in the living room and laundry room, a new kitchen sink and faucet, updated kitchen electrical, new garbage disposal, dishwasher, refrigerator, laundry room utility tub, and multiple lighting improvements throughout the home. Comfort has been enhanced with six new interior ceiling fans and remote-controlled lanai fans. The primary suite features a beautifully updated bathroom with new cabinetry, countertops, sinks, mirrors, faucet, toilet, lighting, and custom blinds. The guest bathroom has also been refreshed with updated lighting and a new toilet. Additional upgrades throughout the home include new blinds, new door knobs and locks, an outlet for a built-in beverage refrigerator, a new dining room chandelier, and a custom banquette in the kitchen. With its golf course setting, extensive upgrades, resort-style outdoor living, and prime location within East Lake Woodlands, this home offers a rare opportunity to enjoy Florida living at its finest. East Lake Woodlands is a deed-restricted, gated community offering exceptional amenities including golf, pickleball, tennis courts, a community pool, and a clubhouse. Ideally located, this home is approximately 25 minutes from Tampa International Airport, 20 minutes from St. Pete-Clearwater International Airport, 30 minutes from Clearwater Beach, and 35 minutes from Honeymoon Island. Enjoy easy access to a variety of nearby restaurants, shopping, and everyday conveniences. Don’t miss your opportunity to own this exceptional home—schedule your private showing today!
Listing Agent: Julio Morales (813-507-5191)
4878 SHERBROOK DR, OLDSMAR, FL 34677
$650,00048 Days on yellowkey MLS ID: TB8514427
3 Days Off yellowkey (back on 6/25/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2730 Built: 1993Monthly Fee: $142 Tax: $4,924 (2025)Community: Cross PointeSingle Family
Taxes:$4,924
Remarks: Come check out this 4 bed 3 bath 3 car garage pool home in the highly sought after East Lake Woodlands Community. Gated community offering great opportunities for GOLF, Tennis, Clubhouse events and activiites with all kinds of various membership opportunities. This home with a little TLC can be the home of your dreams- great location, great layout and great opportunity to make it yours! This 3 way split plan offers a spacious living/dining combination with sliders leading to your outdoor oasis; the family room is open to the kitchen offering high ceilings, tons of extra windows for the sunshine in; the kitchen has bar space and island space, not to mention a nook space as well - this home is great for entertaining; the Primary suite is on one side offering walk in closest, double vanity, soaking tub, step in shower and private water closet; the one wing of bedrooms offers two spacious bedrooms with a bath in between; the 3rd wing offers a bedroom with an adjacent full bath - the outdoor area has room for that kitchen that makes entertaining a breeze, The 3 car garage offers great space for cars and storage. You will find this gem ready for you to make it your own.
Listing Agent: Vanessa Leonard (727-647-2706)
1007 STATE ST E, OLDSMAR, FL 34677
$695,00047 Days on yellowkey MLS ID: TB8513144
2 Days Off yellowkey (back on 6/24/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2379 Built: 1981 Tax: $5,901 (2025)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$5,901
Remarks: Under contract-accepting backup offers. Tucked away beneath majestic oak trees on over an acre of lush Florida landscape, this one-of-a-kind Oldsmar estate offers the perfect blend of privacy, space, and convenience. If you've been searching for a private pool home with acreage, no HOA, room for all your toys, and a true Florida lifestyle, you've found it. Bring your boat, RV, camper, kayaks, golf cart, tools, and hobbies—there's plenty of room here and no CDD fees or HOA restrictions to hold you back. Every day feels like a vacation when you live in a home like this! From the moment you arrive, you'll feel the charm of Old Florida. A stunning wraparound porch, multiple sundecks, giant in ground pool and peaceful natural surroundings create a setting that feels like your own private retreat. The fenced property provides plenty of space for pets to roam, outdoor entertaining, gardening, or simply enjoying the beauty of nature right outside your door. The spacious open-concept living and dining areas are designed for both everyday comfort and memorable gatherings. The large kitchen features granite countertops, stainless steel appliances, an island overlooking the main living space, and plenty of room for family and friends to gather. Cozy up by the fireplace on cooler evenings or step outside to enjoy the screened deck overlooking your tropical backyard oasis. The large primary suite includes an ensuite bath with dual vanities, soaking tub, and a large walk-in shower. Updated bathrooms feature elegant travertine tile and granite-topped vanities, while thoughtful finishes throughout the home create warmth and character. Downstairs, the possibilities are endless. With over 1800 sq feet of workshop, garage, and flex space complete with electricity, this property is ideal for car enthusiasts, hobbyists, entrepreneurs, contractors, artists, or anyone needing substantial storage and workspace. The lower level also includes additional living space, a fourth bedroom, a pool bath, and a three-car garage (one bay currently a workshop)! Step outside and embrace the Florida lifestyle. Spend sunny afternoons lounging by the pool on the paver patio, hosting backyard barbecues with family and friends, or gather around the fire pit under the stars. This fenced backyard oasis offers the perfect combination of relaxation, recreation, and privacy. Located in one of Oldsmar's beloved equestrian-friendly areas, you'll enjoy the best of both worlds—a peaceful country-like setting just minutes from everyday conveniences. Publix, shopping, restaurants, coffee shops, and entertainment are right around the corner. Outdoor enthusiasts will appreciate nearby Upper Tampa Bay Park, Mobbly Bayou Beach Park, Veterans Memorial Park, hiking trails, kayak launches, dog parks, pickleball and tennis courts, playgrounds, ziplining, and waterfront recreation throughout Tampa Bay. Golf, tennis, and pickleball lovers will appreciate being just minutes from Ardea Country Club. Commuters and travelers will love the central location, approximately 10 miles from Tampa International Airport, 13 miles from St. Pete-Clearwater International Airport, and only 16 miles from the world-famous Clearwater Beach. Properties offering this much land, flexibility, privacy, workshop space, poolside living, and convenience are incredibly rare. Come experience the lifestyle you've been dreaming about and discover why this exceptional Oldsmar property feels like home the moment you arrive. Schedule your tour today!
Listing is courtesy of: KELLER WILLIAMS ST PETE REALTY (727-894-1600)
Listing Agent: Courtney Stein (941-822-4080)
732 SHORE DR E, OLDSMAR, FL 34677
$3,800,00031 Days on yellowkey MLS ID: TB8516635
1 Days Off yellowkey (back on 6/24/2026)
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5675 Built: 2019 Tax: $19,893 (2024)Community: Tampashores Bay SecSpa: NoSingle Family
Taxes:$19,893
Remarks: Custom Waterfront Estate on Old Tampa Bay Set on 1.72 acres with 150 feet of private frontage along Old Tampa Bay, this distinctive custom-built estate offers more than 5,600 square feet of elegant living and water views from nearly every room. A newly constructed 200-foot dock with a 13,000-pound boat lift puts the bay at your doorstep, while an 18-foot elevation keeps the home high and dry with sweeping, unobstructed sunsets. Inside, four bedrooms, four full baths, and two half baths are finished with care. The bayfront primary suite is a retreat of its own — tranquil water views, abundant closet space, and a spa-inspired en-suite with a steam shower. The chef’s kitchen is appointed with top-of-the-line appliances built for both entertaining and everyday ease, and a dedicated media room with projection TV sets the stage for quieter evenings in. Thoughtful upgrades run throughout: impact windows, electric shades, a whole-home pest control system, and central vacuum. Outdoors, a stunning waterfall pool invites you to unwind as the sun drops over the bay — the kind of evening this home was built for.
Listing Agent: Michael Goldstein (727-432-0811)
395 WINGATE CIR, OLDSMAR, FL 34677
$575,000244 Days on yellowkey MLS ID: TB8450027
0 Days Off yellowkey (back on 6/23/2026)
REDUCED by $15,000 (2.5%) on 04/29/2026
Bed: 5 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2827 Built: 2001Monthly Fee: $100 Tax: $9,963 (2025)Community: Bay ArborSingle Family
Taxes:$9,963
Remarks: Under contract-accepting backup offers. Lowest Listed Price Per Square Foot for this community. Picture Perfect Bay Arbor, a gated community. (Approved plans to extend fence in backyard) The School District zoned for this home has two A and one B+ rated schools and zoned for Palm Harbor University IB program. Just a mile walk or golf card ride through the community to just outside the gates brings you to the local First Watch, Beef O' Bradys, Aveda, Tijuanna Flats, and Hot Tuna Sushi. The communities natural surroundings, abundant with community green-space, wildlife, and a community Pool & Playground. A 3 car garage, paver driveway & paver path to the front porch greets you out front. The foyer immediately opens up to high ceilings, filled with natural light. The laundry room and the flex room/5th bedroom, media room, office, and/or den are available on the first level. A Breakfast Bar, generous amounts of counter space, and stainless steel appliances for the kitchen. The Breakfast Nook has a large pantry space and overlooks the fenced backyard. The Primary Bedroom and Bedrooms 2-4 are an easy trip up with the two-side staircase. The Primary Bedroom fits a King Size Bed, 2 Walk-in Closets, Glass shower, Garden Tub, and Dual Vanities. You will appreciate the 240sq.ft. rear screened patio leading to your shady, vinyl fenced yard. Your peace of mind knowing the Roof was installed in 2022 and the dual zone A/C system is 2018 and 2012. Convenient to the Tampa airport, Mobbly Bayou Beach Park, Honeymoon Island, UTBP Nature Center, AMC Woodlands Square 20, Tampa Bay Downs. Come enjoy the true Florida Lifestyle!
Listing is courtesy of: STOFEL & ASSOCIATES REALTY (727-350-0373)
Listing Agent: Joey Torres (727-415-7017)
432 COUNTRY CLUB DR, OLDSMAR, FL 34677
$475,000142 Days on yellowkey MLS ID: A4684573
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1936 Built: 1960 Tax: $3,551 (2025)Community: Oldsmar Country Club Estates Sec 2 Blk 3, Lot 6Single Family
Taxes:$3,551
Remarks: Tucked inside a quiet neighborhood, but only one street away from the magnificent Tampa bay, this 3-bedroom, 3 bath, income- producing residence offers nearly 2000 sf of living space and on a large -size lot with lots of matured trees. With the pool centered in the courtyard, and sliding doors around to maximize the view, this scene will recalibrate your mood every time you walk through it regardless of whether you take a morning swim before work, or just read quietly on the deck with your glass of wine nearby. The house is completely renovated with granite counter tops and stainless -steel appliances, slider doors, and a new pool heater, new pool cage, AC 2025. If you are a person who loves nature and calmness, Oldsmar is for you: R.E. Olds Park, Oldsmar Trail, Veterans Memorial waterfront park are all nearby. The schools are great if this is what required. If you want to invest, the house is already going strong with everything set up. Let's make it your home.
Listing Agent: Phuong Vu Nguyen (941-909-4488)
324 COUNTRY CLUB DR, OLDSMAR, FL 34677
$395,000451 Days on yellowkey MLS ID: TB8379269
INCREASED by $10,000 (2.6%) on 06/23/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1288 Built: 1960 Tax: $3,828 (2024)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$3,828
Remarks: Home Renovated to Perfection!** Welcome to your new home - a stunning, newly renovated home offering comfort and style. Located in a quiet and cozy area, this property is perfect for families looking for space and modernity. - **4 spacious rooms**: Ideal for the comfort of the whole family. - **2 completely renovated bathrooms**: With modern and elegant finishes. - **Large kitchen**: With new appliances and an ideal design to inspire any chef. - **Bright living room**: Perfect space to relax and enjoy pleasant meetings. - **Back garden**: An outdoor area to enjoy and customize to your liking. - **exclusive restaurants**, perfect for enjoying unforgettable dinners. - **Close to stores** and local services, making your daily purchases easier. - Excellent access to transportation and other urban amenities. This house perfectly combines modern design and functionality. Don't miss the opportunity to live in a home that has it all.
Listing is courtesy of: FRIENDS REALTY LLC (813-464-1640)
Listing Agent: Aime Alfonso (813-500-0823)
859 INVERRY DR, OLDSMAR, FL 34677
$649,00030 Days on yellowkey MLS ID: W7886948
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1984 Built: 1994Monthly Fee: $151 Tax: $9,016 (2025)Community: WorthingtonSpa: NoSingle Family
Taxes:$9,016
Remarks: 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!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-847-4444)
Listing Agent: Judson Vanworp (727-512-7533)
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