Location: Oldsmar
Do Not Show Listings
4738 PEBBLE BROOK DR, OLDSMAR, FL 34677
$535,000142 Days on yellowkey MLS ID: TB8460875
2 Days Off yellowkey (back on 5/7/2026)
REDUCED by $14,000 (2.6%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 1996Monthly Fee: $470 Tax: $4,041 (2025)Community: Cross Creek - Unit TwoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,041
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy a Relaxing Lifestyle in the desirable Gated, Golf Community of East Lake Woodlands and the convenience of Less Maintenance responsibilities! This home provides Privacy and Stunning Water Views with a Large, Covered Screened Lanai to enjoy that morning cup of coffee or evening glass of wine. Plus it’s situated in the preferred Zone X so no flood insurance is required. An added bonus is the Cul de Sac location and longer driveway for more parking for family and guests. Volume Ceilings, Crown Molding and an Open Concept highlight a versatile floor plan featuring 2 Bedrooms plus an Office or Den - complete with Custom Paneling, Spacious Desk and Bookcase and even the Luxury of a Wood Burning Fireplace! Open to the generous 28’ x 18’ Great Room, the bright Kitchen features an Eat-In Breakfast Area, Bay Windows with Plantation Shutters, Double Ovens, French Door Fridge and plenty of storage. The Primary Suite features 2 Walk-In Closets complete with Custom Built-in Shelving and Pull-Down Clothing Racks and a Large Bath with Dual Vanities, Large Soaking Tub and Separate Shower. Relax since the reasonable HOA fee includes Lawn Maintenance with Mowing, Fertilizing and Mulching, Cable TV and Internet, Trash and Recycling Collection, a Sparkling Community Pool and Spa for Cross Creek residents, Escrow Reserves, Pressure Cleaning of Roofs and Exterior Painting every 7 years. Home Updates include New Water Heater in Dec. 2025, New Tile Roof in 2019, A/C Unit New in 2018. Washer and Dryer included in the sale plus Manual and Remote-Controlled Exterior Hurricane Shutters and a Generac Generator. This long-time owner had no issues with the 2024 Hurricanes. Enjoy that Gorgeous View and put your touches on this home since this amazing price takes updating into account. All this in a Great Location convenient to Tampa International Airport, beautiful Beaches, Medical Facilities, Professional Sporting Events and Fine Dining. A variety of memberships to Ardea Country Club are available for additional fees and include access to 2 Golf Courses, a Fitness Center, Heated Lap Pool and Freeform Pool, Pickle Ball and Tennis plus Dining and a host of Activities and Events!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
101 DOLPHIN DR N, OLDSMAR, FL 34677
$225,000200 Days on yellowkey MLS ID: TB8444809
REDUCED by $19,900 (8.1%) on 05/07/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1573 Built: 1989Monthly Fee: $70 Tax: $582 (2024)Community: Gull-Aire VillageSpa: NoManufactured Home
Taxes:$582
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
Remarks: Welcome Home! Your move-in ready and partially furnished Florida retreat with a warm, contemporary flair awaits you in the heart of Oldsmar. This spacious 2-bedroom, 2-bath home is situated on a rare DOUBLE LOT (7,854 sq. ft.), that YOU OWN offering privacy and flexibility. The open and inviting floor plan features cathedral ceilings and newer laminate flooring throughout the family room, kitchen, laundry room and hallway. The kitchen is well-appointed with a spacious island/snack bar, newer refrigerator and a convenient pantry closet - perfect for entertaining. The generous primary suite includes access to the over sized (10.75' x 31') enclosed Florida room, a walk-in closet, an en-suite bath with a walk-in shower and relaxing garden tub. The Florida room features glass windows overlooking the beautifully landscaped backyard and provides an ideal space for entertaining or just enjoying Florida's indoor-outdoor lifestyle! More recent updates include a newer A/C system (2020), a spacious 2 car garage with a large workshop with ample storage space (2003) and a newer high-quality sliding glass door. Nestled in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers exceptional resort-style amenities, including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. This home sits on land you own and features a low monthly HOA fee of just $70 with one pet of any size permitted. The location is truly unbeatable! You're less than a mile from Woodlands Square, offering Bealls, Marshall’s, Ulta, PetSmart, AMC Theatres, Craft Street Kitchen, Shaker & Peel, Eve’s Family Restaurant, and more. Everyday conveniences such as Publix, Target, Walmart Neighborhood Market, and Mease Countryside Hospital are just 2 miles away. Honeymoon Island Beach is approximately 9 miles away, and Tampa International Airport is a easy 15-mile drive. An adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, providing the perfect setting to enjoy Florida’s outdoor beauty. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply enjoying the peaceful surroundings, you’ll fall in love with the friendly, welcoming lifestyle of Gull-Aire Village. (Room dimensions are approximate and should be verified by Buyer.)
Listing is courtesy of: AH REALTY SERVICES, LLC (727-275-3512)
Listing Agent: Anne Hode (813-545-1960)
400 SHORE DR E, OLDSMAR, FL 34677
$1,000,00095 Days on yellowkey MLS ID: TB8478151
3 Days Off yellowkey (back on 5/7/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1890 Built: 1957 Tax: $3,995 (2025)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$3,995
Remarks: Under contract-accepting backup offers. The Ultimate Waterfront Canvas: 150ft of Panoramic Bay Frontage. Secure a legacy-grade homesite on one of the most expansive waterfront lots in Oldsmar. Situated on almost ¾ acre on the prettiest street in Oldsmar, 400 Shore Drive E offers a rare 150 feet of direct, unobstructed frontage on Safety Harbor. This is a premier opportunity for a visionary buyer or elite builder to bypass the limitations of existing construction and design a bespoke custom estate from the ground up. While the current structure is a teardown (sold as-is), its presence provides a significant footprint and potential impact fee advantages for your new architectural masterpiece. Experience total privacy and some of the most breathtaking, wide-water sunset views found anywhere in the Tampa Bay region. Just minutes from the refined trails of RE Olds Park and the area’s top dining, this location perfectly balances secluded coastal living with urban convenience. Don’t just buy a home—build a landmark on the water’s edge.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Crystal Tipton, Mrs (813-436-7229)
1802 CHINABERRY DR, OLDSMAR, FL 34677
$375,000219 Days on yellowkey MLS ID: TB8439498
5 Days Off yellowkey (back on 5/7/2026)
INCREASED by $6,000 (1.6%) on 04/30/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1358 Built: 1972 Tax: $865 (2024)Community: Harbor Palms-Unit OneSpa: NoSingle Family
Taxes:$865
Remarks: Easily 3 Bedroom (EVEN 4) - Total Renovation - Block/Slab Home - Large Indoor Laundry - 2 Car Garage - New Roof - New AC - New Water Heater - New Kitchen - Solid Wood Cabinets - Solid Surface Counters - New Bathrooms - New Floors - Interior and Exterior Paint - Landscaping - Large Fenced Yard -
Listing is courtesy of: FOXX AND ASSOCIATES (877-538-6868)
Listing Agent: Dan Nease (727-354-2222)
124 LOBLOLLY CT #D, OLDSMAR, FL 34677
$155,00071 Days on yellowkey MLS ID: TB8487484
REDUCED by $5,000 (3.1%) on 05/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1986Monthly Fee: $665 Tax: $2,239 (2025)Community: Gardens Of Forest Lakes Condo TheCondo
Taxes:$2,239
Remarks: Unit tottaly Renovated New Kitchen Bath Bathrooms and flooring at the Garden of Forest lakes 2 Bedroom 2 bath
Listing is courtesy of: LYN PROPERTIES (813-951-3083)
Listing Agent: Meir Barack (813-951-3083)
403 BLUE MARLIN DR, OLDSMAR, FL 34677
$184,000210 Days on yellowkey MLS ID: TB8442487
REDUCED by $5,000 (2.6%) on 05/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1993Monthly Fee: $70Community: Gull-Aire VillageManufactured Home
Taxes:$0
Remarks: Assumable VA Loan at 2.8% for Qualified Veteran Available! Welcome to your new home in the highly sought-after 55+ Gull-Aire Village! Perfectly situated on a spacious corner lot, this charming Jacobsen manufactured residence offers both comfort and convenience within walking distance to the community pool and clubhouse. Constructed in 1993, it features durable ¾ inch plywood subfloors with laminate, carpet, and tile flooring throughout. Enjoy the versatility of the enclosed Florida room, equipped with central air and heat as well as a custom fan system—ideal for hobbies and creative projects. Recent upgrades include a new hot water heater installed in 2018 and beautifully renovated bathrooms completed in 2020. Further improvements include new windows, a front door, siding, and insulation added in 2013.The kitchen is outfitted with sleek 2019 stainless-steel appliances including a refrigerator and dishwasher. A new air conditioning system installed in 2016. Unique to this home is an electric custom ramp capable of lifting to 600 lbs., offering exceptional accessibility for those with mobility needs. A roof-over was added in 2005, and an inside laundry area comes complete with a washer and dryer for your convenience. The vibrant clubhouse is the heart of the community, hosting monthly events and providing amenities such as a pool table, shuffleboard, bocce ball court, and a heated pool and spa. There are also regular activities to keep you engaged and active, including yoga, bingo, cards, and line dancing. The golf cart-friendly streets make getting around a breeze! With HOA fees at just $70 per month, you will enjoy affordable living in a wonderfully maintained neighborhood. This pet-friendly community allows one pet of any size, and a second pet is permitted with a doctor's note for emotional support. Best of all, ownership includes the land—no lot rent! Everyday conveniences are just steps away, with AMC Theatres, Bealls, Marshalls, PetSmart, Five Below, and Dollar Store across the street, as well as popular dining options like Shaker & Peel, Craft Street Kitchen, Mandola's, Country Pizza Italian Grill, and Eve's Family Restaurant. Major retailers such as Super Walmart and Publix, along with Countryside Hospital, are only minutes from your door. For outdoor enthusiasts, the stunning beaches of Honeymoon Island and Caladesi State Park are just ten miles away, and a scenic biking and walking trail along the canal offers easy access from within the community. Room sizes are approximate. Do not miss your chance to enjoy the best of Oldsmar living in one of the area's most desirable communities!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
549 LONGWOOD CIR, OLDSMAR, FL 34677
$525,00021 Days on yellowkey MLS ID: A4692285
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1344 Built: 1984Monthly Fee: $30 Tax: $5,336 (2025)Community: Manors Of Forest Lakes TheSingle Family
Taxes:$5,336
Remarks: Welcome to your private retreat in the heart of Oldsmar. Located in the desirable Longwood community, this beautifully maintained home offers the perfect blend of comfort, charm, and Florida living. Surrounded by mature landscaping and peaceful streets, 549 Longwood Circle features spacious living areas, abundant natural light, and an inviting layout ideal for both entertaining and everyday living. Step outside to enjoy a relaxing backyard setting with room to unwind, host gatherings, or create your own outdoor oasis. Conveniently located near top-rated schools, parks, shopping, dining, and the Gulf beaches, this home delivers both privacy and accessibility. Whether you're looking for a full-time residence or a seasonal getaway, this property is an incredible opportunity to own a piece of paradise in one of Tampa Bay’s most sought-after communities.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Susan Kolesnikov (916-272-9177)
121 LOBLOLLY CT #C, OLDSMAR, FL 34677
$161,90021 Days on yellowkey MLS ID: A4692680
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1987Monthly Fee: $635 Tax: $2,263 (2025)Community: Gardens Of Forest Lakes Condo TheCondo
Taxes:$2,263
Remarks: Owner remodeled for family member but family member chose other living arrangements. Here is your chance to have a fully updated unit fit for higher end living without the cost.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
436 LAFAYETTE BLVD, OLDSMAR, FL 34677
$700,000300 Days on yellowkey MLS ID: TB8412856
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2695 Built: 1994 Tax: $10,665 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$10,665
Remarks: One or more photo(s) has been virtually staged. Must see this 4 bedroom/2.5 bath home with almost 2700 Sq/Ft on one of the highest/majestic lots in downtown Oldsmar! Relax by the wood fireplace with your family in the comfortable living room! Entertain guests, make a fire-pit area, or start your own garden in the expansive backyard with Lanai! Lot is almost a half acre! Fantastic kitchen with granite countertops, stainless steel appliances, plenty of wood cabinets/countertop space and breakfast bar! Large master bedroom with enormous walk-in closet and newly updated master bath with soaking tub, his-and-her sinks and high end stone tile throughout! Take the private glass vacuum elevator to the second floor! Also a dining area, family room and office! Some additional upgrades include: High ceilings, sprinkler system, hurricane windows, whole house instant hot water, water softener/filter system, updated flooring throughout, vinyl fencing, smart-home switches/recessed lighting, updated 2 car garage, block home. Short walk to Bicentennial Park that has a dog park, playground, tennis/basketball/pickleball courts. Also near boat launch, hiking/biking trails, library, fishing pier, museum and schools. Home had no hurricane/water damage! Oldsmar is located centrally in north Pinellas County and is a short drive to world class gulf beaches, Tampa International Airport, sporting venues, theater, shopping, restaurants and much, much more!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Dillon Currier (727-919-4214)
200 LEE ST, OLDSMAR, FL 34677
$1,450,00022 Days on yellowkey MLS ID: TB8505047
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)
1734 MAPLELEAF BLVD, OLDSMAR, FL 34677
$515,00056 Days on yellowkey MLS ID: TB8492116
3 Days Off yellowkey (back on 5/5/2026)
REDUCED by $10,000 (1.9%) on 04/23/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2428 Built: 2000Monthly Fee: $13 Tax: $4,787 (2025)Community: Eastlake Oaks Ph 4Single Family
Taxes:$4,787
Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! Welcome to 1734 Mapleleaf Boulevard, a beautifully maintained two-story home in the heart of Oldsmar offering the perfect blend of space, comfort, and peace of mind. With 4 generously sized bedrooms and 2.5 bathrooms, this home is designed for both everyday living and effortless entertaining. As you step through the elegant glass front door with sidelight, you’re welcomed into a bright, inviting interior filled with natural light, highlighted by a large picture window that frames the serene backyard. The main level flows seamlessly between the living, dining, and kitchen areas, creating a functional and open feel without sacrificing warmth or character. Upstairs, all four bedrooms are thoughtfully positioned for privacy, including a spacious primary suite featuring a walk-in closet, double vanity, soaking tub, separate shower, and a private water closet—creating a true retreat at the end of the day. The additional bedrooms are all well-sized, offering flexibility for family, guests, or a home office. Step outside to your extended screened-in paver patio, a standout feature that makes outdoor living easy and enjoyable year-round. Whether you’re sipping your morning coffee or hosting friends and family, this space is built to be enjoyed. The backyard offers privacy and a peaceful setting with minimal maintenance required. This home has never flooded, even through recent storms, and includes a transferable flood policy—an incredible value that adds an extra layer of confidence for the next owner. Additional features include a 2-car garage, ample storage, and a well-cared-for condition that makes this home truly move-in ready. Ideally located near parks, shopping, dining, and with easy access to Tampa, this home offers the lifestyle you’ve been looking for in one of Oldsmar’s most desirable areas.
Listing is courtesy of: LPT REALTY, LLC. (877-366-2213)
Listing Agent: Ashley Mason (813-735-2495)
403 E TUSCAN LN E, OLDSMAR, FL 34677
$330,000403 Days on yellowkey MLS ID: TB8376561
1 Days Off yellowkey (back on 1/14/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1525 Built: 2015Monthly Fee: $333 Tax: $5,075 (2024)Community: Tuscany Woods SouthTownhouse
Taxes:$5,075
Remarks: Under contract-accepting backup offers. Welcome home in Oldsmar, FL! This two-story 1,525 square foot townhouse, located in the HIGHLY-desirable gated community of "Tuscany Woods", was built in 2015 and has 3 bedrooms and 2.5 bathrooms. The first floor offers an open floor plan, which seamlessly connects the living, dining, and kitchen areas, making it an ideal space for entertaining friends or simply relaxing. The tile flooring throughout the entire first floor provides both style and ease of cleanup. After a long day, retreat to the second floor, where you can find serenity in either of the large secondary bedrooms, which both share a full bathroom, or the huge primary bedroom, with its own ensuite bathroom and walk-in closet. For convenience, a laundry room, complete with washer and dryer, are also located upstairs. The upstairs and stairs has plush, upgraded wall-to-wall carpeting. The one-car garage offers a secure space for your vehicle and extra storage, and the private driveway provides additional parking. The townhome also has a screened-in lanai. Don't miss out on this incredible opportunity to make this townhouse your home. Located in the desirable Oldsmar area, you'll have convenient access to I-275, and be in close proximity to top-rated public and private schools. You're also only a stone's throw away from various amenities, including shopping centers, restaurants, parks, not to mention Florida's award-winning beaches! Whether you're a nature enthusiast or prefer the hustle and bustle of city life, this location offers the best of both worlds. Contact us today to schedule a viewing and start envisioning your new life in this fantastic home.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Kirk Ray Smith (727-383-1871)
106 LAKESIDE CT, OLDSMAR, FL 34677
$158,000419 Days on yellowkey MLS ID: TB8350281
REDUCED by $2,000 (1.3%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1981 Tax: $2,932 (2024)Community: East Lake Woodlands CondoCondo
Taxes:$2,932
Remarks: Great Value!! This Condo is located within the Gated community of East Lake Woodlands. This unit is on the second floor and features an eat in kitchen, living/dining room with sliders out to the screened lanai, split bedroom plan, the primary suite has a walk-in closet, a secondary closet and a linen closet. The primary bath has a step in shower. The guest suite has a bath off the hallway. The laundry closet is located on the lanai & includes a washer/dryer. Covered parking 1 space under carport. Unit is located across from the Pool! This unit needs your attention & priced to offset reno to make it your own. Great rental, primary residence or winter getaway..No waiting period for a buyer to rent the condo. Excellent opportunity!
Listing is courtesy of: TAMPA BAY SIGNATURE PROPERTIES, LLC (727-692-2847)
Listing Agent: Christi Watson (727-692-2847)
388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$246,00096 Days on yellowkey MLS ID: TB8478422
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1105 Built: 1997Monthly Fee: $433 Tax: $1,771 (2025)Community: Countryside KeyTownhouse
Taxes:$1,771
Elementary School: Curlew Creek Elementary-PN
Remarks: Under contract-accepting backup offers. 2025 HVAC! Assumable FHA Loan! Welcome to 388 Countryside Key, a charming 2-bedroom, 1.5-bathroom townhome located in the highly sought-after Oldsmar, FL community. This delightful two-story residence boasts an open-concept first floor with a spacious kitchen, ample cabinetry, a generous pantry, and a convenient laundry/utility closet with a full-size washer and dryer. The living and dining areas flow seamlessly, enhanced by a kitchen bar and a convenient first-floor half bath. Upstairs, you'll find two generously sized bedrooms, each featuring vaulted ceilings that create an airy ambiance. Step outside to your enclosed screened patio, a serene retreat perfect for unwinding and enjoying the Florida weather year-round. This pet-friendly community offers a wealth of amenities including a secure gate, sparkling pool, tennis courts, sidewalks, and a car-wash station, with recreational storage for your RV, boat, or trailer available for a nominal fee. You'll have an assigned parking spot right at your doorstep with ample guest parking. Monthly HOA fees cover water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Located in an area known for its highly-regarded school districts, buyers are encouraged to verify current school assignments and ratings. Situated near Tampa International Airport, St. Petersburg, and the area's stunning beaches, this gorgeous property offers an exceptional opportunity to create your dream home in a prime location. Don't miss out on this fantastic opportunity! Notable Features & Upgrades: HVAC-2025; Interior Paint-2025; Carpet-2017; Primary Bathroom Renovation-2016; Granite Countertops & Cabinets (Kitchen & Primary Bath)-2013; Upgraded Fixtures & Handles, Lights, Ceiling Fans.
Listing is courtesy of: TROPIC SHORES REALTY (800-775-1302)
Listing Agent: Kevin Baker (352-777-1507)
130 CYPRESS LN #130, OLDSMAR, FL 34677
$160,00029 Days on yellowkey MLS ID: TB8502597
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Monthly Fee: $571 Tax: $2,571 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$2,571
Elementary School: Forest Lakes Elementary-PN
Remarks: One or more photo(s) has been virtually staged. Welcome to this two-bedroom, two-bath condominium in Oldsmar, offering 1,054 square feet and a flexible opportunity for investors, first-time buyers or seasonal residents. This residence is vacant and ready for immediate occupancy or renovation. The interior reflects the original condition, presenting a value-add opportunity for customization. The primary bedroom includes a walk-in closet, and the layout supports functional living and dining spaces. Recent updates include an air-conditioning system installed in 2025, along with a washer, dryer and refrigerator replaced in 2024. This property is well-suited for buyers seeking to personalize a residence or secure an investment with long-term potential. Conveniently near shopping, dining and commuter routes, supporting full-time and seasonal living.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (813-217-5288)
Listing Agent: Maria Azuaje (317-371-0935)
103 CUTLASS WAY, OLDSMAR, FL 34677
$345,00093 Days on yellowkey MLS ID: TB8479354
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 2016Monthly Fee: $255 Tax: $6,017 (2025)Community: Hayes Park VillageSingle Family
Taxes:$6,017
Remarks: Welcome to this impeccably maintained 3 bedroom, 2.5 bath residence in the highly sought-after Hayes Park Village in Oldsmar. Offering approximately 1,392 square feet of thoughtfully designed living space, this home showcases a beautifully renovated kitchen with contemporary finishes, ceramic flooring on the first floor, and carpet flooring on the second floor. The split-bedroom floor plan and abundant natural light create a bright, open atmosphere that is both welcoming and functional. Step outside to a covered porch overlooking a breathtaking pond and a serene conservation area behind it —providing exceptional privacy. Combining generous living space, peaceful privacy, and an unbeatable location, this exceptional home is ready to welcome YOU!
Listing is courtesy of: FLORIDA COMMERCIAL GROUP (813-935-9600)
Listing Agent: Leyla Mohebbi (813-359-7999)
2159 WARWICK DR, OLDSMAR, FL 34677
$800,00075 Days on yellowkey MLS ID: TB8486224
1 Days Off yellowkey (back on 5/4/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2673 Built: 1996Monthly Fee: $133 Tax: $6,682 (2025)Community: Warwick HillsSpa: NoSingle Family
Taxes:$6,682
Elementary School: Cypress Woods Elementary-PN
Remarks: Under contract-accepting backup offers. It's time to buy in Eastlake Woodlands! Settle in to your dream home in the coveted subdivision of Warwick Hills within Eastlake Woodlands. Eastlake Woodlands is a renowned golf and tennis community that offers a full range of amenities for an additional membership including the fully remodeled Ardea Country Club, championship golf courses, tennis, pickle ball, resort style pools and more. This stunning 4bedroom, 3 bath pool home spans 2,673 sf and offers a bevy of upgrades. Step into the fully updated kitchen, featuring beautiful quartz counters, newer stainless steel appliances, updated cabinetry and large center island- perfect for any culinary enthusiast. The 3 way split floor plan boasts brand new wood floors throughout the main living area and primary suite, providing a warm and inviting atmosphere. Relax on the outdoor screened patio that faces a serene conservation area, where you can enjoy watching deer and other wildlife or splash in the cool pool. The spacious lot, over 8,000 sq. ft., offers plenty of room for outdoor activities and entertainment. Modern upgrades include a tankless water heater installed in 2024, new impact windows (except for the sliding door and corner windows) in 2023, and fresh exterior paint in 2024. The house also features a suburban propane tank and the patio is plumbed for gas, making it ready for an outdoor kitchen. Don‘t miss out on this incredible opportunity to own a meticulously maintained home in a desirable location. Schedule your showing today and experience all that this Eastlake Woodlands gem has to offer!
Listing is courtesy of: PALERMO REAL ESTATE PROF. INC. (813-637-0117)
Listing Agent: Cristina Lorenzo (813-451-4055)
405 HOLLY HILL RD, OLDSMAR, FL 34677
$660,00027 Days on yellowkey MLS ID: TB8503763
0 Days Off yellowkey (back on 5/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2311 Built: 1979Monthly Fee: $149 Tax: $3,606 (2026)Community: East Lake WoodlandsSpa: YesSingle Family
Taxes:$3,606
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Welcome to your private retreat in the highly sought-after gated community of East Lake Woodlands in Oldsmar. This beautifully updated 3-bedroom, 2-bathroom home features a thoughtfully designed open split floor plan that provides both comfort and privacy. Step inside to a stunning living room with vaulted ceilings and exposed beams, creating a warm yet spacious atmosphere. Entertain with ease at the bar, or open the French doors to seamlessly extend your living space onto the re-screened lanai. Outside, enjoy your own slice of Florida paradise with a sparkling PebbleTec pool and spa overlooking the scenic golf course. The home has been fully updated, including a modern updated kitchen equipped with granite countertops, stainless steel appliances, and soft-close drawers. Both bathrooms have been tastefully renovated, with the spacious primary suite offering dual sinks with granite counters and two walk-in closets. ADDITIONAL RECENT UPGRADES INCLUDE THE REMOVAL OF POPCORN CEILINGS, NEW ATTIC INSULATION, REPLACEMENT OF ALL INTERIOR DOORS, A NEW POOL MOTOR, AND BEAUTIFUL PAVERS INSTALLED IN THE DRIVEWAY, WALKWAY, AND PORCH. Major improvements such as a NEW ROOF (2025) and HVAC system (2017) add even more value and peace of mind. Further enhancements include HURRICANE RATED WINDOWS IN ALL BEDROOMS AND THE BATHROOM, a WATER SOFTNER SYSTEM, NEW WINDOW TREATMENTS, NEW OUTDOOR LIGHTING, ADDED LAUNDRY ROOM FEATURES, UPDATED BASEBOARDS THROUGHOUT, —just to name a few. Additional highlights include a cozy fireplace, a 240 sq ft BONUS ROOM perfect for a home office or gym, with flex space that offers endless possibilities. 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 is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Jan Thomas-Smith (727-492-7825)
124 LOBLOLLY CT #H, OLDSMAR, FL 34677
$157,00075 Days on yellowkey MLS ID: TB8481313
REDUCED by $3,000 (1.9%) on 05/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1986Monthly Fee: $666 Tax: $2,517 (2025)Community: The Gardens Of Forest Lakes CondoCondo
Taxes:$2,517
Remarks: Investor-friendly opportunity: This turn-key property currently has a cash flowing year-long tenant in place, making it an excellent 1031 exchange option for investors seeking immediate rental income with a low-maintenance property. Welcome to this beautifully fully remodeled 2-bedroom, 2-bathroom condo located at 124 Loblolly Ct, Unit H in desirable Oldsmar. This move-in-ready home has been thoughtfully updated from top to bottom, featuring brand new carpet, fresh interior paint, and new appliances, creating a clean and modern living space ready for its next owner. The spacious layout offers comfortable living with two well-appointed bedrooms, including a primary suite with a private bathroom. The open living and dining area provides a comfortable setting for relaxing or entertaining, while the fresh upgrades throughout give the home a bright, refreshed feel. Located in a quiet, well-maintained community, residents enjoy the convenience of nearby parks, swimming pool, playground, tennis, basketball and racquetball courts, shopping, dining, and easy access to major commuting routes. The location provides quick connectivity to both Tampa and Clearwater, while still enjoying the charm and waterfront lifestyle of Oldsmar along Tampa Bay. Whether you're looking for an investment property or a future personal residence, this fully updated condo offers comfort, convenience, and long-term value in a highly desirable Tampa Bay location.
Listing is courtesy of: HOMESMART (407-476-0461)
Listing Agent: Nikki Pagoria (314-221-6810)
140 HUNTER LAKE DR #G, OLDSMAR, FL 34677
$174,94532 Days on yellowkey MLS ID: TB8501829
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1987 Tax: $2,836 (2025)Community: Gardens Of Forest Lakes Condo TheSpa: YesCondo
Taxes:$2,836
Remarks: Welcome home - this modern 2-Bedroom/2-Bathroom condo offers convenient location between Palm Harbor & Tampa, and maintenance free living at The Gardens of Forrest Lakes community. Located on the second floor, the condo is bright with natural light and offers a spacious balcony. It is fully renovated with granite countertops; glass backsplash; newer cabinets, appliances and flooring; new (2024) water heater. The two bedrooms are spacious: the primary offers a walk-in closet and en-suite with a walk-in shower and a single vanity; the second bedroom has a built-in closet with sliding mirror doors. Guest bathroom has a bathtub with shower and a single vanity. There is a laundry room in the unit. The community offers a pool, tennis court, basketball hoop, playground, lake access with a fishing pier and picnic area. Owner financing available.
Listing is courtesy of: 1 REALTY GROUP LLC (727-888-4286)
Listing Agent: Gergana Kosturkova (727-698-6095)
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