Location: Oldsmar
Do Not Show Listings
208 HEMINGWAY DR, OLDSMAR, FL 34677
$314,90023 Days on yellowkey MLS ID: TB8490712
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1207 Built: 1997Monthly Fee: $265 Tax: $4,507 (2025)Community: Sun Ketch Twnhms At Cypress LakesVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,507
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: This beautifully maintained end-unit villa offers the perfect combination of comfort, privacy, and modern upgrades along with water views from most rooms. Step inside to high-volume ceilings that create a bright and spacious atmosphere throughout. The home features all-new luxury flooring, giving every room a sleek and cohesive look. The thoughtful layout includes a separate living and dining area, ideal for both everyday living and entertaining guests. From here, step out onto your private screened lanai with an epoxy floor, overlooking a serene pond—a perfect spot for morning coffee or relaxing evenings. The back yard is fenced for extra privacy. The split-bedroom floorplan has a spacious primary suite boasting a large walk-in closet and an en suite bathroom with a walk-in shower and dual sink vanity. The open, tiled kitchen is a chef’s delight, offering ample counter space and a convenient breakfast bar. Additional highlights include a 2-car garage with extra driveway space, French drains, rain gutters, and the added privacy of an end unit. Conveniently located near shopping, airports, schools, beaches, and the community pool, this villa truly combines style, convenience, and tranquility. Your new home awaits—move in and enjoy the perfect blend of comfort and elegance!
Listing is courtesy of: RE/MAX MARKETING SPECIALISTS (727-853-7801)
Listing Agent: Lisa Heberlein Pa (727-432-8769)
340 CANAL WAY, OLDSMAR, FL 34677
$198,00022 Days on yellowkey MLS ID: TB8491525
REDUCED by $12,000 (5.7%) on 04/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1993Monthly Fee: $50 Tax: $2,288 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$2,288
Remarks: Welcome to easy Florida living in the sought-after 55+ community of Gull-Aire Village in Oldsmar. This well-maintained 2BR/2BA home offers a comfortable, open layout with updated flooring, a spacious living area, and a split-bedroom floor plan that gives both you and your guests privacy. The kitchen and bathrooms are clean and functional with room to make it your own, making this a great opportunity to move right in and update over time to your style. Enjoy the benefits of a covered carport, extra storage, and low-maintenance living in a community where neighbors know each other and there’s always something to do. Gull-Aire Village is a resident-owned 55+ community featuring a clubhouse, heated pool and spa, fitness center, shuffleboard courts, and a full calendar of social activities. Conveniently located near shopping, dining, Gulf beaches, Tampa International Airport, and major highways—everything you need is close by. Land-owned with no lot rent—perfect for a full-time residence or a seasonal Florida escape.
Listing is courtesy of: ACROPOLIS REALTY GROUP LLC (315-396-0493)
Listing Agent: Sal Degaetano (315-396-0493)
4766 STONEVIEW CIR, OLDSMAR, FL 34677
$645,00022 Days on yellowkey MLS ID: TB8487161
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2114 Built: 1993Monthly Fee: $108 Tax: $3,755 (2025)Community: StonebriarSingle Family
Taxes:$3,755
Elementary School: Cypress Woods Elementary-PN
High School: East Lake High-PN
Middle School: Carwise Middle-PN
Remarks: Welcome to an exceptional opportunity in the highly desirable Stonebriar enclave of East Lake Woodlands—where timeless design meets effortless Florida living. This impeccably maintained four-bedroom, two-bath pool home showcases true pride of ownership and offers a seamless blend of comfort, functionality, and style. From the moment you arrive, the home’s pristine condition and inviting curb appeal set the tone. Step through the front door and be immediately captivated by a stunning sightline that draws your eye through the living space to the screened lanai and sparkling pool beyond—an ideal introduction to the indoor-outdoor lifestyle that defines this residence. To the right, the formal dining room offers generous proportions, perfect for hosting gatherings both intimate and grand. Straight ahead, the formal living room provides direct access to the lanai, creating a fluid transition for entertaining and allowing you to fully embrace Florida’s beautiful weather year-round. Privately positioned to the left of the entry, the primary suite is a serene retreat featuring its own access to the lanai. The en suite bath is thoughtfully appointed with a deep soaking tub, step-in shower, and a spacious walk-in closet—delivering both comfort and convenience. At the heart of the home, the updated kitchen is a standout, boasting white shaker cabinetry, stone countertops, and an elegant tile backsplash. A breakfast bar and optional nook space add flexibility, while the open layout flows effortlessly into the family room, complete with a cozy wood-burning fireplace—perfect for relaxed evenings at home. The split-bedroom floor plan enhances privacy, with three additional generously sized bedrooms located toward the rear of the home, each offering ample closet space. The secondary bath features a tub/shower combination and provides direct access to the laundry room and lanai, functioning perfectly as a pool bath. Step outside to your private oasis—an expansive screened lanai featuring a solar heated saltwater pool, ideal for year-round enjoyment. The covered area offers the perfect setting for outdoor dining and lounging, and select patio furnishings are available for purchase, making this space move-in ready for immediate enjoyment. A spacious backyard completes the outdoor experience. With its thoughtful layout, stylish updates, and inviting indoor-outdoor flow, this home is truly ready for its next chapter. Roof 2013, HVAC 2024, Hurricane rated impact windows throughout, new gutters and pool cage rescreening. Don’t miss the opportunity to experience everything this exceptional property has to offer—schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
235 WOODS LANDING TRL #235, OLDSMAR, FL 34677
$279,90062 Days on yellowkey MLS ID: TB8474969
REDUCED by $20,000 (6.7%) on 04/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1201 Built: 1984Monthly Fee: $591 Tax: $4,279 (2024)Community: East Lake Woodlands Woods Landing TwnhmsTownhouse
Taxes:$4,279
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Move-in ready and tucked inside one of Oldsmar’s most established gated communities, East Lake Woodlands, this townhome offers low-maintenance living with peaceful pond views and thoughtful updates throughout. The kitchen features updated cabinetry, crisp white quartz countertops (2025), stainless steel appliances, and a dining area that flows seamlessly into the living space. The split-bedroom floor plan provides privacy, with both bedrooms offering wide-plank luxury vinyl flooring, built-in closet shelving, and brand-new doors. The primary suite includes a private en-suite bath with a fully tiled walk-in shower and glass enclosure. Neutral finishes and a pedestal sink create a clean, bright, and easy-to-maintain space. Large windows and sliding glass doors bring in natural light, while the enclosed lanai overlooking the pond offers a quiet spot for morning coffee or relaxed evenings. Located near the community pool and close to everything Oldsmar residents love; parks, restaurants, shopping, with convenient access to Tampa and Clearwater. Optional membership at Ardea Country Club provides access to championship golf, tennis, pickleball, fitness facilities, pools, and clubhouse dining.
Listing is courtesy of: SOUTHERN LIFE REALTY (727-642-1758)
Listing Agent: Kelsi Ward (727-488-7032)
1654 BAYHILL DR, OLDSMAR, FL 34677
$570,000185 Days on yellowkey MLS ID: TB8438417
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2320 Built: 1995Monthly Fee: $177 Tax: $5,855 (2024)Community: CreeksideSingle Family
Taxes:$5,855
Remarks: THIS HOME SITS IN THE QUAINT SECLUDED CREEKSIDE COMMUNITY INSIDE THE GATES OF EASTLAKE WOODLANDS, LARGE FAMILY HOME OF 4 BEDROOMS, 2 AND HALF BATHS, 2 CAR GARAGE WITH POOL, YOUR OPEN CONCEPT OF DINING AND LIVING ROOM GREAT FOR THE FAMILY TO GATHER, KITCHEN WITH GRANITE COUNTER TOPS AND UPDATED BACKSPLASH, APPLIANCES TO INCLUDE DISHWASHER OCTOBER 2025, FAMILY ROOM WITH SLIDING GLASS DOORS GOING TO YOUR PERSONAL PARADISE TO ENJOY YOUR SCREENED ENCLOSED PAVED PATIO INGROUND POOL OUT DOORS ANOTHER GREAT ENTERTAINMENT SPACE, THEN OUTSIDE TO SWING AND ENJOY THE WILD LIFE AND DEER AND THE PRIVATE AND QUIET BROOKER CREEK PRESERVE AREA, THEN YOUR BEAUTIFUL STAIRCASE TO YOUR PRIMARY BEDROOM RETREAT WITH LARGE EN-SUITE BATHROOM, INSIDE LAUNDRY ROOM, AC SYSTEM INSTALLED 2021, ROOF 2018. DON'T MISS OUT ON THIS RARE OPPORTUNITY TO OWN THIS MUCH SQUARE FOOTAGE FOR SUCH A GREAT COMMUNITY. POSSIBILITIES ARE ENDLESS!!
Listing is courtesy of: ECKERT REALTY & PROPERTY MGMT (727-240-0668)
Listing Agent: Karen Hutson (727-240-0668)
1734 MAPLELEAF BLVD, OLDSMAR, FL 34677
$525,00017 Days on yellowkey MLS ID: TB8492116
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
Elementary School: Oldsmar Elementary-PN
Remarks: One or more photo(s) has been virtually staged. 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 at just $900 per year—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)
800 SAINT PETERSBURG DR W, OLDSMAR, FL 34677
$409,00028 Days on yellowkey MLS ID: TB8489139
REDUCED by $10,000 (2.4%) on 04/06/2026
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: 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)
347 COUNTRY CLUB DR, OLDSMAR, FL 34677
$429,00066 Days on yellowkey MLS ID: TB8475491
REDUCED by $20,000 (4.5%) on 04/05/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 1967 Tax: $1,515 (2024)Community: Oldsmar Country Club Estates Sec 1 RepSingle Family
Taxes:$1,515
Remarks: "Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths with plenty of storage space, vehicles, boat and golf cart(s) parking. Luxury vinyl flooring throughout this split plan homes interior, picturesque French Door views to the pool and lanai deck, all new kitchen appliances and home systems installed. An expansive corner lot property with plenty of green space, fenced yard and mature landscaping. Enjoy your Florida Lifestyle with family and social gatherings within the updated interior decor or outside in the screened pool and lanai deck area. We'll look forward to your visit.
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Frank Fundora (813-361-2505)
101 DOLPHIN DR N, OLDSMAR, FL 34677
$244,900161 Days on yellowkey MLS ID: TB8444809
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1573 Built: 1989Monthly Fee: $70 Tax: $582 (2024)Community: Gull-Aire VillageManufactured Home
Taxes:$582
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 a walk-in closet and an en-suite bath with a walk-in shower and relaxing garden tub. The over sized enclosed porch features, complete with glass windows overlooking the beautifully landscaped backyard, 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 $60 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)
501 LAKEVIEW DR, OLDSMAR, FL 34677
$499,90078 Days on yellowkey MLS ID: TB8470254
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1667 Built: 1983Monthly Fee: $35 Tax: $4,306 (2024)Community: Manors Of Forest Lakes TheSingle Family
Taxes:$4,306
Elementary School: Forest Lakes Elementary-PN
Remarks: Fabulous...Location! Location! Location! This stunning pool home in the sought after community of Forest Lakes sits on an oversized corner lot and offers tranquil water and conservation views.; Move-in ready, delightfully updated home of nearly 1,700 sq.ft. features 3 bedrooms in a desirable split floorplan layout, 2 brilliantly renovated baths and an oversized 2 car garage. Enter thru the double leaded glass doors to the fabulous main living area featuring luxury vinyl flooring (2023) and centered by an elegant decorative stone and granite accented wood burning fireplace and offering views of your gorgeous pool side lanai thru large sliders. The spacious formal dining room also features luxury vinyl flooring and is an ideal space for entertaining. The extended galley kitchen boasts raised panel cabinetry, epoxy coating countertops, tile backsplash, dual stainless-steel sinks, large built in cabinet pantry including butler pull out drawers and plenty of storage and counter space for family meals and entertaining. Appliances include ceran top range, built in microwave, side by side refrigerator and dishwasher. The built-in desk is convenient and ideal for office space or homework area. The spacious eat in area offers tranquil serenity overlooking the lanai and pool. A perfectly situated laundry room is located just off the kitchen. The seller is generously including the washer and dryer with the sale of the home. Large primary suite features a walk-in closet and spectacular remodeled ensuite bath (2023). The magnificent, spa like bathroom boasts gorgeous tile flooring, designer vanity with quartz counter, undermount sink, spacious full walk-in shower with decorative tile accents and a bench seat... absolutely stunning! The secondary bedrooms and bath are conveniently situated on the other side of the home offering ultimate privacy. The spectacular remodeled second bath (2023) boasts dual vanities with undermount sinks, granite countertop, an enormous walk-in shower with fashionable frameless glass, floor to ceiling designer tilework, dual shower heads, corner bench seat and niche. Gorgeous!!! Entertaining and family living space is extended outdoors with a covered lanai accented by river rock decking and a vaulted screen enclosed saltwater pool (2023). Florida living at its best… enjoy a morning cup of coffee or afternoon cocktail watching the turkeys and deer graze while overlooking the tranquil pond and serene conservation views. Outdoor Jacuzzi, Trampoline and Zip line may convey. Furnishings are negotiable. Other notable updates include interior paint 2023, Roof 2015, AC Jan 2016, Impact windows and sliding glass doors. Forest Lakes Community offers basketball, racquetball, tennis and pickle ball courts, community pool, playground and picnic area. Zoned for top rated schools! Quick drive to Tampa International Airport & minutes from shopping, restaurants and a short drive to Dunedin’s Honeymoon Island. Florida living… can’t beat it!
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Nancy Leslie (727-789-5555)
317 SHORE DR E, OLDSMAR, FL 34677
$489,67079 Days on yellowkey MLS ID: FC315737
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1660 Built: 2000 Tax: $6,929 (2024)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$6,929
Remarks: STUNNING TAMPA BAY VIEWS! UPDATED OLDSMAR SPLIT-LEVEL WITH RV/BOAT PAD! Breathtaking Tampa Bay views await in this updated, elevated home in one of Oldsmar’s most desirable neighborhoods! Just steps from the water, this 3-bedroom, 2-bath residence offers the perfect blend of peace of mind and outdoor living. The split-level design ensures durability, with a spacious 2-car garage on the ground level and all living areas elevated. Major upgrades include a new roof, a newer water heater (<5 years), and a renovated primary suite featuring a walk-in closet. The kitchen shines with stylish quartz countertops, and a large first floor laundry room. Step outside to your fully fenced, level backyard—ideal for entertaining or relaxing in the screened-in porch. The property includes a dedicated RV or Boat pad. Enjoy an incredible lifestyle within walking distance or take your golf cart to the waterfront parks, nature trails, pickleball courts, a fishing pier, and playgrounds. Located in a top-rated school district. This home is the complete package.
Listing is courtesy of: ADAMS, CAMERON & CO., REALTORS (386-445-5595)
Listing Agent: Charles Kelly (203-610-3091)
1802 CHINABERRY DR, OLDSMAR, FL 34677
$369,000180 Days on yellowkey MLS ID: TB8439498
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1358 Built: 1972 Tax: $865 (2024)Community: Harbor Palms-Unit OneSingle 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)
129 CAMPHOR CIR #C, OLDSMAR, FL 34677
$180,00067 Days on yellowkey MLS ID: TB8474438
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1986 Tax: $170 (2025)Community: Gardens Of Forest Lakes Condo TheCondo
Taxes:$170
Remarks: Welcome to The Gardens of Forest Lakes, one of Oldsmar’s well-kept secret communities. This 2 bedroom 2 bathroom condo is a true move-in ready home. The features and amenities are apparent upon entering this well-decorated unit. The newer luxury vinyl flooring set the stage for a great showing. The living room/dining room combination offers an open & spacious area you can call home. The kitchen was updated to include custom wood cabinets with hydraulic drawers; led area lighting; newer appliances including a brand new refrigerator & a double oven; deep double steel sink; tile backsplash; granite-looking Formica countertops; Both bathrooms were updated to include wood-like tile; the guest bathroom offers a deep soaker tub; Enjoy the beautiful pond view from both bedrooms and the private balcony; An inside laundry room with a newer washer/dryer combo for your convenience; The master bedroom offers a walk-in closet; The balcony has a storage room for your extra stuff; The community has a recreation center that includes a swimming pool, tennis & racquetball courts, a playground and a fishing pier. Close to shopping, dining, entertainment and more. Schedule your private showing today. You’ll be glad you did.
Listing is courtesy of: KELLER WILLIAMS REALTY PORTFOLIO COLLECTION (727-489-0800)
Listing Agent: Garrett Grimes (727-403-8723)
219 PALMETTO CT, OLDSMAR, FL 34677
$182,00096 Days on yellowkey MLS ID: TB8463698
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,045 (2024)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$3,045
Remarks: Easy, low-maintenance living in the heart of East Lake Woodlands. This affordable ground-floor, end-unit 2-bedroom, 2-bath condo offers comfort, privacy, and a peaceful setting surrounded by greenery. Inside, you’ll find a bright great room overlooking open green space, a desirable split-bedroom floor plan, and an open kitchen that flows seamlessly into the dining and living areas—ideal for both everyday living and entertaining. Recent updates include fresh interior paint (November 2025), new carpet, tile flooring in the kitchen and living room, and a new AC and heat system installed in 2024 with a 10-year warranty. The home also includes a washer and dryer, stove, and a storage room with laundry hookups. The primary suite features two walk-in closets, plus a hallway linen closet for additional storage. Enjoy Florida living with two sets of sliding doors leading to a screened lanai, a paver patio beyond, and tranquil green space between buildings. The community pool is just steps from the back door, set beyond the greenery for a sense of separation. Convenience continues with covered carport parking directly out front, ample guest parking, and a resident-only rear entrance providing quick access to shopping and dining along East Lake Road and Tampa Road. Located in East Lake Woodlands, a gated community bordered by the 8,700-acre Brooker Creek Preserve, residents are surrounded by mature trees, lakes, and natural beauty. Optional memberships are available at the East Lake Woodlands Country Club, featuring two championship golf courses, tennis and pickleball courts, dining, a fitness center, and a resort-style pool. Monthly fees include exterior building maintenance, roof, building insurance, water, sewer, trash, basic cable, grounds maintenance, and the community pool, making ownership simple and predictable. Whether you’re searching for a primary residence, seasonal retreat, or investment opportunity, this move-in-ready home offers comfort, convenience, and a setting that feels calm yet connected to everything Tampa Bay has to offer. (One or more photos have been virtually staged)
Listing is courtesy of: KINEST REALTY (727-212-0021)
Listing Agent: Stephanie Person (727-212-0021)
375 WELLINGTON AVE, OLDSMAR, FL 34677
$1,299,00015 Days on yellowkey MLS ID: TB8492687
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2624 Built: 1993 Tax: $14,951 (2025)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$14,951
Remarks: Welcome to your modern dream home—completely reimagined with a full 2024 designer remodel where no detail was overlooked. From the baseboards to the custom designer air vents, every finish has been thoughtfully curated and impeccably executed. The gourmet kitchen is a true showpiece, featuring full custom cabinetry with lighted drawers, newer appliances, and stunning high-end Essenza Quartzite waterfall countertops—an architectural statement rarely found outside luxury homes. Throughout the second and third floors, you’ll find polished 32x32 porcelain Onyx tile, complemented by sleek single-panel glass interior doors, designer chrome hardware, and all-new outlets, switches, and striking modern glass light fixtures and chandeliers. Every bathroom has been fully renovated with floating vanities, vessel sinks, LED mirrors, smart toilets, and all new fixtures and finishes. The primary suite offers a true retreat, featuring a dramatic three-sided gas fireplace that flows into a spa-inspired en suite with a custom concrete vanity by a local artist, freestanding soaking tub, and walk-in shower. The staircase is a statement in itself, finished with Calacatta Sunset quartz and floating frameless glass railings with chrome accents, echoed throughout the home’s balconies. Anchoring the main living space is a breathtaking 20-foot LED-lit accent wall—an unforgettable focal point that defines the home’s modern design. Situated on a full acre in the heart of Oldsmar, this property offers both luxury and freedom with no HOA. Flood insurance is approximately $800/year and transferable. The ground level features a versatile game room, gym, or flex space that opens to an expansive 1,400 sq ft paver pool deck with a two-story screened enclosure, outdoor kitchen & gorgeous pool & spa combo—perfect for entertaining and enjoying Florida living year-round. AC(2023), ROOF (2022), ELECTRIC PANEL (2023), HURRICANE RATED WINDOWS & SLIDERS (2017), POOL PUMP (2024), TANKLESS WATER HEATER (2018). Store your boat or RV on your one acre fully fenced and gated private lot. Close proximity to three waterfront parks, Pickleball, boat and kayak launch, fishing pier, restaurants, Tampa, International Airport, and the most beautiful beaches in the world. This home was meticulously designed and must be seen to be appreciated.
Listing Agent: Jenny Neumeyer (727-482-2656)
2020 DOVER CT, OLDSMAR, FL 34677
$255,00025 Days on yellowkey MLS ID: TB8486084
3 Days Off yellowkey (back on 4/3/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1143 Built: 1983Monthly Fee: $160 Tax: $588 (2025)Community: Bayside Meadows Ph IiVilla
Taxes:$588
Remarks: Under contract-accepting backup offers. Updated Villa in Oldsmar with Low HOA, 2024 HVAC, updated kitchen and baths, Hurricane impact window and sliders & heated Community Pool. Welcome to 2020 Dover Ct in Oldsmar, Florida—an updated 2-bedroom, 2-bath villa with a 1-car garage, ideally positioned on a quiet cul-de-sac in one of Oldsmar’s most convenient locations. Offering 1,143 square feet of thoughtfully designed living space, this home blends comfort, functionality, and low-maintenance Florida living. Recent updates provide peace of mind, including a 2024 A/C system, new duct work 2022, hurricane-rated sliders 2022, updated hurricane-rated windows 2019, garage door 2023, and beautifully refreshed kitchen and flooring with new tile extending through the hallway and into the bathrooms, updated bathrooms. Step inside through the welcoming foyer to find a light and bright interior with volume ceilings and a spacious great room with Luxury Vinyl Plank flooring is centered around a charming wood-burning fireplace—perfect for cozy Florida evenings. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring abundant counter space, a flat cooktop range, stainless steel refrigerator, breakfast bar, large cabinet pantry, and the added convenience of an under-counter washer and dryer. The split-bedroom layout offers privacy, with the secondary bedroom and full bath located near the front of the home, while the primary suite is tucked away and features sliding glass doors leading to the Florida room, a large linen closet, and an updated en-suite bath with a step-in shower. Enjoy relaxing mornings or evening breezes on your Florida room that overlooking your backyard—ideal for enjoying Florida’s year-round outdoor lifestyle. With low HOA fees of just $160/month, residents enjoy true maintenance-free living including lawn care, community pool access, annual tree trimming, pressure washing of sidewalks once a year, maintenance of the rear fence behind the villa, and reclaimed water for irrigation—saving you both time and money while keeping the community beautifully maintained. Location is everything, and this home delivers—just minutes from shopping, dining, movie theaters, hospitals, medical facilities and everyday conveniences, with easy access to Tampa Road, US-19, and McMullen Booth Road for quick commutes to Tampa, Clearwater, and St. Petersburg. Outdoor enthusiasts will appreciate nearby parks, trails, and waterfront areas, including Upper Tampa Bay Park, the Oldsmar Trail, and quick access to the Courtney Campbell Causeway. World-famous Gulf beaches, Tampa International Airport, and St. Pete-Clearwater Airport are all within an easy drive. This is your opportunity to own an updated villa in Oldsmar with low maintenance, strong value, and a prime location—schedule your private showing today and start living the Florida lifestyle.
Listing is courtesy of: EXP REALTY (727-449-9276)
Listing Agent: Kathie Lea (727-422-9455)
465 HOLLY HILL RD, OLDSMAR, FL 34677
$650,00033 Days on yellowkey MLS ID: TB8486777
0 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2324 Built: 1985Monthly Fee: $148 Tax: $3,265 (2025)Community: East Lake WoodlandsSingle Family
Taxes:$3,265
Remarks: Under contract-accepting backup offers. Stunning 3BR/2BA + Bonus Room, Pool Home in Gated East Lake Woodlands – Move-In Ready Resort-Style Living Beautifully updated, turnkey pool residence in the prestigious gated golf community of East Lake Woodlands, Oldsmar, FL. This highly desirable Tampa Bay suburb offers tree-lined streets, top-rated schools (zoned for East Lake area schools), optional private club access (championship golf, tennis, pickleball, fitness, dining & social events), and quick access to TPA airport (~15 min), pristine beaches (~10 miles to Honeymoon Island), shopping, and dining. -FEATURES & RECENT UPDATES - Fully remodeled kitchen (2026): soft-close solid wood white shaker cabinets, Carrera AZe quartz counters, under-cabinet lighting - Fresh Benjamin Moore interior paint throughout (2026); exterior paint (2024) - Luxury vinyl plank flooring in main living areas (2025) - Popcorn ceilings removed (2025) - New roof (2025) - Miami-Dade skylights (2025) - New appliances: dishwasher (2026), washer/dryer (2025), refrigerator (2023) - New A/C (2020) with new compressor (2025) - Screened lanai resurfaced (2024) - RainBird irrigation serviced (2025) - Hurricane-rated garage door & opener (2022) and impact-resistant sliding glass doors (2020) Step into your private backyard oasis featuring a sparkling pool and spacious screened lanai—perfect for year-round Florida entertaining and relaxation. Flood Zone: X (no flood insurance required) Community: Gated, golf & social club optional, top-rated schools. A rare combination of thoughtful recent renovations, timeless appeal, and unbeatable location. Don't miss this paradise in one of Tampa Bay's most sought-after communities!
1001 STARBOARD CT, OLDSMAR, FL 34677
$534,90017 Days on yellowkey MLS ID: TB8492967
0 Days Off yellowkey (back on 4/3/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1928 Built: 2019Monthly Fee: $580 Tax: $5,109 (2025)Community: Bayside TerraceTownhouse
Taxes:$5,109
Remarks: Under contract-accepting backup offers. WATERFRONT CORNER UNIT with very LOW, TRANSFERABLE Flood Policy! Don’t miss this once-in-a-lifetime opportunity to own the highly sought-after SANTA ROSA CORNER MODEL in the gated waterfront community of Bayside Terrace. This is the only model of its kind currently available, offering stunning water views of Tampa Bay, unmatched privacy, and an abundance of natural light throughout. This upgraded 3 bedroom, 2.5 bathroom, 2 car garage townhome has been meticulously maintained with attention to every detail. As a corner unit, it enjoys extra windows and sunlight, creating a bright and inviting atmosphere from the moment you walk in. Soaring 18 foot ceilings and an open floor plan showcase breathtaking water and sunset views from the entire main living area. The modern kitchen is both functional and elegant, featuring granite countertops, stainless steel appliances, under cabinet lighting, ample cabinetry, a large island, and a spacious walk-in pantry. Tile flooring spans the main living areas, while upgraded luxury vinyl plank flooring flows through the primary suite, stairs, and entire upstairs, combining style with easy maintenance. Additional upgrades include plantation shutters, sliding blinds, and a water filtration system. Step outside to your private screened lanai and enjoy spectacular sunsets over the bay, all while watching dolphins swim by. The first floor primary suite is a true retreat, offering coffered ceilings, serene water views, a spacious walk-in closet, and a conveniently located laundry area inside the master closet. The spa-like en suite includes dual sinks, a granite vanity, and a walk in shower. Upstairs, a large loft provides a flexible space for a game room, media room, home office, or family room, with partial water views. The two additional bedrooms are generously sized, each with walk-in closets, and share a beautifully updated full bathroom that is perfect for family or guests. The two car garage includes extra shelving and space for kayak storage. Hurricane shutters are included, and this home has never experienced storm surge or water damage from Hurricane Helene, offering rare peace of mind on the water. Bayside Terrace offers resort-style, maintenance-free living with a heated salt water infinity pool, fitness center, clubhouse, fire pit, BBQ area, and a waterfront dock with kayak and canoe launch. Ideally located near Tampa International and St Pete airports, award winning beaches, shopping, dining, and just minutes from Safety Harbor, Dunedin, and Honeymoon Island. Washer and dryer convey. This is a rare, one-of-a-kind opportunity, and the only Santa Rosa Corner Model currently available with the master room downstairs. Schedule your private showing today and secure your dream waterfront home before it’s gone.
Listing is courtesy of: TOM TUCKER REALTY (727-692-3997)
Listing Agent: Dave Doherty (727-639-2371)
240 CYPRESS LN #240, OLDSMAR, FL 34677
$254,90050 Days on yellowkey MLS ID: TB8481270
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,193 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$3,193
Remarks: Welcome to 240 Cypress Lane in Oldsmar, where effortless Florida living meets refined, turnkey luxury with tranquil water views and a premier golf lifestyle just moments away. This fully furnished, completely renovated second-floor residence offers the perfect blend of comfort, style, and security, high and dry with no flood insurance required. Step inside to a bright, open-concept layout enhanced by brand-new high-impact windows and sliders, allowing natural light to pour in while providing peace of mind year-round. The heart of the home is a stunning, fully updated kitchen, complete with modern cabinetry, sleek countertops, and all-new appliances, ideal for both entertaining and everyday living. Every detail has been thoughtfully upgraded, including new flooring, designer lighting, new electrical panel, and a New A/C system delivering a truly move-in ready experience. Enjoy peaceful pond and water views from your living space, creating a relaxing and private setting that captures the essence of Florida living. Residents also enjoy access to a heated community pool, offering a resort-style atmosphere just steps from your door, perfect for unwinding any time of year. The home also includes dedicated covered carport parking, adding both convenience and value. Perfectly positioned, this home is nestled near East Lake Woodlands Country Club, now known as Ardea Country Club, a premier golf destination in Oldsmar. The club features two newly renovated 18-hole championship courses, the North and South Courses, and recently completed an $11 million transformation, enhancing every aspect of the experience, including the golf courses, tennis facilities, and clubhouse. Located less than 30 minutes from world-class Gulf beaches, as well as Tampa International Airport (TPA) and St. Pete-Clearwater International Airport (PIE), this home offers both convenience and an unbeatable lifestyle. HOA dues provide exceptional value and convenience, including Cable TV, Internet, Community Pool, exterior maintenance, grounds maintenance, sewer, trash, and water, allowing for truly low-maintenance living. Whether you’re seeking a full-time residence, seasonal retreat, or investment opportunity, this home delivers low-maintenance living with high-end upgrades in one of Oldsmar’s most desirable locations. You’ve seen the rest, now own the best.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nick Wimperis (651-472-1506)
416 COUNTRY CLUB DR, OLDSMAR, FL 34677
$385,00063 Days on yellowkey MLS ID: TB8475710
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1293 Built: 1959 Tax: $644 (2025)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$644
Remarks: Nestled in the highly deisrable City of Oldsmar, this home has been tastefuly renovated. You'll love the updated kitchen with new stainless steel appliances, stone counter top and lovely build in desk. This modern kitchen has beautiful black cabinets, double sink, new range, refrigerator, dishwasher, and microwave. There are new ceiling fans throughout the home and plenty of decorator lighting. The master suite has it's own bath and modern shower. It is a beauty. The secondary bath is very modern with decorator fixtures and lighted mirror, all done very tastefully. This shower has beautiful ceramic tile and modern features. There is spacious great room and separate dining room which is leading to the perfect entertaining back yard. There are 2 decks, brick pavers and it features a jacuzzi tub. You'll love the separate shed for storage and fenced in yard. There is plenty of room for your toys with gated entry to the back yard. No CDD or HOA fees here but there are several parks and a boat ramp in the neighborhood. Move in ready and a must see.
Listing is courtesy of: MURRAY BELL REAL ESTATE LLC (813-629-8202)
Listing Agent: Jenny Meers (813-748-8112)
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