Location: Oldsmar
Do Not Show Listings
331 SHORE DR E, OLDSMAR, FL 34677
$450,000Listed 07/21/2026 5:00PM MLS ID: TB8531357
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2064 Built: 1959 Tax: $828 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$828
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Florida living at it's best. This fully renovated beautiful solid block home is located in the very desirable Oldsmar Country Club Estates neighborhood and is across the street from the bay and just down the street from three waterfront parks, Veterans Memorial Park, R.E. Olds Park and from Mobbly Bayou Beach Park. This charming house boasts a split bedroom open floor plan. It has a giant sun room/all day room connected to the back of the house with plenty of windows surrounding it. The owner is selling personal items to get ready for the sale of the home and they show as clutter in the pictures, so I might be posting new pictures soon. These pictures don't do this wonderful home justice. Wait till you see this huge kitchen with it's quartz countertops, stainless steel appliances and very spacious wood cabinets. There are fruit trees in the back yard which include mango trees and sweet sop trees. The garage is air conditioned and heated. Conveniently located only 15-20 minutes from Tampa International Airport, near parks and access to boat launches, kayaking and paddleboarding, minutes to downtown Tampa and to some of the best beaches in the US, great restaurants, shopping and theaters.
Listing is courtesy of: THREE PALACES REALTY CORP (813-884-3900)
Listing Agent: Edwin Trinidad (813-731-2554)
2005 HUDSON CT, OLDSMAR, FL 34677
$299,90052 Days on yellowkey MLS ID: W7886259
REDUCED by $10,100 (3.3%) on 07/02/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1170 Built: 1982 Tax: $923 (2025)Community: Bayside Meadows Ph IiSingle Family
Taxes:$923
Remarks: Your dream home in Bayside Meadows Oldsmar, Florida, offers a single-family home with 2 bedrooms plus a garage conversion that could function as a third bedroom with the addition of a closet. The home includes a dining area with French doors leading to a screened lanai, an indoor laundry area, ceramic tile flooring in the main living spaces, and carpet in the bedrooms. You’ll see ceiling fans in every room, and a comforting kitchen that has room to add a center island. Outside, you’ll find a spacious screened lanai, a shed, a tropical oasis of landscaping, and a fenced yard. The property is conveniently close to beaches, parks, nature areas, and nearby airports. Located in northeastern Pinellas County at the top of Old Tampa Bay, Oldsmar features attractions such as Tampa Bay Downs, an ice-skating rink, a flea market, Sheffield Park, the BMX Supercross Track, Mobbly Bayou Beach Park, and Mobbly Wilderness Preserve, which offers hiking trails, kayak launches, and eco tours. The area also offers a variety of dining and shopping options, along with convenient access to medical facilities and a hospital.
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Gail Small (727-455-3057)
380 ROSALIND LN, OLDSMAR, FL 34677
$609,90060 Days on yellowkey MLS ID: TB8510265
REDUCED by $10,099 (1.6%) on 07/21/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2423 Built: 2001Monthly Fee: $100 Tax: $4,811 (2025)Community: Bay ArborSpa: NoSingle Family
Taxes:$4,811
Elementary School: Forest Lakes Elementary-PN
Remarks: One or more photo(s) has been virtually staged. Welcome to your private retreat in the gated community of Bay Arbor! Major Upgrades Include: New Roof (2022), New AC (2026), New Hurricane impact Windows and Doors (2024), New Screen Patio Screen Enclosure (2024), and much more! Nestled on a spacious wooded homesite, this beautifully maintained two-story home offers over 3,000 square feet of thoughtfully designed living space blending comfort, privacy, and everyday convenience. Porcelain tile and wood-like flooring throughout- No carpet. From the moment you step inside, you’re greeted by soaring ceilings, an open staircase, and an abundance of natural light. The formal living and dining rooms create the perfect setting for entertaining guests or hosting holiday gatherings. At the heart of the home, the spacious Updated kitchen with quartz countertops, stainless steel appliances and flows effortlessly into the inviting family room, all overlooking tranquil wooded views that bring a sense of peace and serenity indoors. Whether you're enjoying a quiet evening at home or entertaining, this layout was designed for both relaxation and connection. Upstairs, the primary suite serves as a true escape featuring an updated spa-inspired ensuite bath with dual sink vanity, soaking tub, and a step-in shower. Two additional generously sized bedrooms offer ample closet space and share a beautifully appointed bathroom. A large upstairs bonus room provides endless flexibility, ideal as a media room, second living area, home office, playroom, or gym. Step outside to your screened patio and enjoy the beauty of your private fenced backyard oasis surrounded by mature trees and nature views. It’s the perfect place for morning coffee, evening sunsets, or weekend gatherings. Located just minutes from Tampa, award-winning Gulf beaches, airports, major highways, top-rated schools, shopping, dining, and entertainment, this exceptional home offers the perfect balance of peaceful living and city convenience. Rarely does a home combine space, privacy, location, and lifestyle so effortlessly. Schedule your private showing today! HOA is $600 semi-annually and includes the Community Pool and playground.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Mark Fazzini (727-485-9981)
1745 OAK POND CT, OLDSMAR, FL 34677
$629,0009 Days on yellowkey MLS ID: TB8527516
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2324 Built: 2000 Tax: $8,785 (2025)Community: Eastlake Oaks Ph 4Spa: NoSingle Family
Taxes:$8,785
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to 1745 Oak Pond Court! Welcome to 1745 Oak Pond Court, a beautiful home located in the sought-after East Lake Oaks community. Situated on a quiet street with a premium lot, this home offers comfort, style, and numerous recent upgrades. The interior and exterior have been freshly painted, and the screened lanai has been recently updated. Some major updates include a new water heater installed in 2022, a new air-conditioning system installed in 2023, new carpeting on the stairs completed in May 2026, and stair railings that were sanded and freshly painted in May 2026. The primary bathroom was completely remodeled in 2022 and features a relaxing jetted tub, updated vanity, shower, tile flooring and walls, surround-sound speakers, and mood lighting in the ceiling. A luxurious outdoor kitchen was installed in 2025 and includes a grill, granite countertop, stainless-steel sink, and stainless-steel storage for all your entertaining needs. Additional improvements completed in June 2026 include freshly painted pool patio and garage floor. The kitchen was updated in 2022 with new cabinets and granite countertops, while wood-look laminate flooring was installed throughout the downstairs living areas. Conveniently located near Tampa International Airport, shopping, nature trails, and excellent restaurants, this home is also just twenty minutes from Honeymoon Island Beach. This move-in-ready home combines thoughtful upgrades, a prime location, and Florida living at its best!
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
645 TIMBER BAY CIR E, OLDSMAR, FL 34677
$295,000259 Days on yellowkey MLS ID: TB8443970
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1274 Built: 1984 Tax: $1 (2024)Community: Shoreview Phase 2Single Family
Taxes:$1
Tax Year: 2024
Remarks: Your Renovation Dream Home! This home is in the desirable Shoreview Subdivision situated on 1/3 of an acre of land. After necessary rehab this home will easily be the jewel of the subdivision located a short walking distance from Tampa Bay and Mobbly Beach Park!! The home is priced substantially below market value to attract CASH Buyers understanding the home will require rehabilitation. The homeowner has excess construction material that will convey with the purchase as a cost saving incentive. The home will include refrigerator, dishwasher, HVAC system, and bathroom fixtures to be installed. The home currently has eight (8) new windows already installed and a new back sliding glass door. This is a must see and golden Opportunity to own or invest in this highly desirable community and subdivision!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Michael Eddings (813-480-6026)
355 VENTURA DR, OLDSMAR, FL 34677
$615,00061 Days on yellowkey MLS ID: TB8510293
2 Days Off yellowkey (back on 7/20/2026)
REDUCED by $10,000 (1.6%) on 06/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 2001Monthly Fee: $100 Tax: $5,919 (2025)Community: Bay ArborSingle Family
Taxes:$5,919
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully maintained and completely updated four-bedroom, two-bathroom home located in the gated community of Bay Arbor. Situated on a premium lot with tranquil pond views and no rear neighbors, this exceptional property is directly across the street from the community pool, offering both convenience and scenic surroundings. Thoughtfully renovated from floor to ceiling, this stunning residence blends modern upgrades sparing no expense, to the tune of over $80,000 for comfortable Florida living. Major updates, including a 2020 remodel featuring updated bathrooms, kitchen, Pergo laminate flooring throughout, and upgraded 5 ¼-inch baseboards. Additional enhancements include custom kitchen window seating added in 2020, USB outlets in the kitchen, exterior painting in 2020 with a 10-year warranty, gutters and patio birdcage added in 2020, a 2023 water softener, 2019 water heater, EV outlet, and extensive hurricane protection, including 2025 impact windows, front French door hurricane fabric protection, and a 2011 hurricane impact-rated rear patio French door. The roof was replaced in 2020 and includes a 50-year warranty. Step inside through the inviting foyer entry and immediately notice the high ceilings, abundant natural light, and stylish wood-look flooring flowing throughout the home. The spacious kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances, a beverage fridge, extensive cabinetry for storage, Corian countertops, and a cozy breakfast nook with built-in bench seating. The kitchen opens seamlessly to the dining area and expansive living room highlighted by vaulted ceilings and an open, airy feel. The oversized primary suite offers a relaxing retreat with a large walk-in closet and a beautifully updated private bathroom complete with a dual-sink vanity, soaking tub, glass-enclosed shower, updated fixtures, and private water closet. The additional bedrooms are all generously sized and equipped with ceiling fans for added comfort. Enjoy Florida living year-round from the large screened-in lanai overlooking the fenced backyard and peaceful pond views. Residents of Bay Arbor enjoy access to a community pool and a prime location close to popular dining spots, shopping centers, golf courses, parks, movie theaters, and outdoor recreation. Conveniently situated near Tampa International Airport, Mobbly Bayou Beach Park, Honeymoon Island State Park, Upper Tampa Bay Park Nature Center, AMC Woodlands Square 20, and Tampa Bay Downs, this home offers the perfect blend of privacy, convenience, and lifestyle. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Robert Paolini (727-365-8335)
317 SHORE DR E, OLDSMAR, FL 34677
$484,700173 Days on yellowkey MLS ID: FC315737
REDUCED by $4,970 (1.0%) on 04/21/2026
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)
100 LISA LN, OLDSMAR, FL 34677
$299,0008 Days on yellowkey MLS ID: TB8526300
1 Days Off yellowkey (back on 7/20/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1320 Built: 1977Monthly Fee: $340 Tax: $2,859 (2025)Community: East Lake Woodlands Patio HomesSingle Family
Taxes:$2,859
Remarks: Under contract-accepting backup offers. Escape the winter chill in this fully furnished, turn-key Florida retreat on the greens of Ardea Country Club! Located in the premier gated community of East Lake Woodlands in Oldsmar, this charming home features a stunning view of the 17th hole directly from your private sunroom. Pack your bags and leave the snow shovel behind—everything you need is already here, from stylish furniture to essential housewares. Bring your four-legged family members along, as the community is pet-friendly, allowing up to two dogs or cats. The property includes a spacious two-car garage, perfect for secure vehicle and golf cart storage while you are away. Enjoy resort-style, low-maintenance living just minutes from pristine beaches, premier racquet facilities, and vibrant local dining. This is your ultimate hassle-free seasonal getaway or permanent paradise!. Fully Furnished: Move-in ready with all furniture and housewares included. Golf Course View: Front-row seats to the 17th hole from the bright sun oom. Your new living gives you access to two championship 18-hole courses, tennis, pickleball, and pools via optional membership. Pet-Friendly: Welcome home to your furry companions (up to two dogs or cats allowed). Low Maintenance: Perfect lock-and-leave property for seasonal residents.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-799-2227)
Listing Agent: Joseph Lee Morris (813-300-8486)
2328 WARWICK DR, OLDSMAR, FL 34677
$829,000333 Days on yellowkey MLS ID: TB8419306
REDUCED by $25,000 (2.9%) on 06/23/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3294 Built: 1995Monthly Fee: $127 Tax: $5,742 (2024)Community: Warwick HillsSpa: YesSingle Family
Taxes:$5,742
Elementary School: Cypress Woods Elementary-PN
Remarks: PRICE ADJUSTMENT! Make an offer now, so you can get settled in over the summer! Welcome to Warwick Hills within the Eastlake Woodlands community! Two-story residence awaits on a large corner lot. A stately presence greets you with elegant landscaping. Side-entry 3-car garage & extended driveway. Step inside through double doors into the grand foyer. Formal living and dining rooms, as well as a spacious family room featuring a wood-burning fireplace. Sliding glass doors open up to the lanai and pool. The kitchen and family room blend seamlessly with an open floor plan, highlighted by wood cabinets, granite counter tops, island, wet bar, and multiple pantries. Ideal floor plan for everyday living and entertaining. Relaxing views of the pool & spa with tropical landscaping. A versatile office on the main floor can easily serve as a 5th bedroom. Full-size laundry room.All bedrooms on 2nd floor. Upstairs, the grand primary suite welcomes you with double-door entry and a private sitting area. Two walk-in closets and a renovated bathroom featuring soaking tub, dual vanities, private water closet, and new glass-enclosure. The 2nd floor also features 3 additional bedrooms and 2 more full baths. Property improvements include exterior painted (2023), interior painted (2026) roof (2022), A/C units (2018 & 2019). Hurricane shutters for windows & doors. Ardea Country Club: Residents can take advantage of golf, tennis, dining, and social memberships. With easy access to Hillsborough and Pasco counties, this centrally located home is just minutes to shopping, dining, top-rated schools, and all that the Tampa Bay area has to offer.
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Roberta Celiberti (727-488-1235)
1404 EAST LAKE WOODLANDS PKWY, OLDSMAR, FL 34677
$1,225,00097 Days on yellowkey MLS ID: TB8496474
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 4312 Built: 1990Monthly Fee: $207 Tax: $8,294 (2025)Community: Greenhaven Unit ThreeSpa: NoSingle Family
Taxes:$8,294
Remarks: Located in the highly desirable gated community of East Lake Woodlands, this spacious 4 bedroom, 3 bathroom home offers a versatile layout with 2 bonus rooms and a dedicated office. One of the bonus rooms is located upstairs, providing added flexibility for multi-use living. Pool table will convey with the sale. The home features a solar-heated in-ground pool with a large pool deck, fully enclosed by a screened lanai, creating the perfect space for year-round Florida living and entertaining. The inviting living room includes a fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with abundant wood cabinetry, generous storage, and a center island ideal for cooking and gathering. The split-bedroom floor plan provides privacy, with the primary suite featuring sliding glass doors to the pool, a walk-in closet, and an en-suite bath with dual vanities, a bathtub, and a separate shower. Additional highlights include a 2-car garage, a laundry room, and exceptional interior space throughout. A unique third garage bay has been converted into an interior room, offering even more flexible living options. Residents of East Lake Woodlands enjoy resort-style amenities including a clubhouse, golf courses, country club, heated pools, tennis and pickleball courts, fitness center, dining options, and scenic walking and biking paths within a secure gated community. Conveniently located in Oldsmar, this home provides easy access to Gulf beaches, Tampa International Airport, top-rated schools, dining, and shopping, offering the best of the Tampa Bay lifestyle.
Listing is courtesy of: CONCI, REALTORS (727-405-0005)
Listing Agent: Cyndi Olmstead (727-203-4967)
450 CYPRESS CREEK CIR, OLDSMAR, FL 34677
$625,0005 Days on yellowkey MLS ID: TB8529291
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2139 Built: 1976Monthly Fee: $147 Tax: $4,574 (2025)Community: East Lake WoodlandsSingle Family
Taxes:$4,574
Remarks: Welcome to 450 Cypress Creek Circle, a beautifully renovated single-story home nestled within the prestigious gated community of East Lake Woodlands. Perfectly positioned on the golf course, this exceptional residence enjoys wide-open fairway views of hole #2 on the South Course at Ardea Country club with no homes directly behind, creating a peaceful backdrop for everyday living and entertaining. Thoughtfully updated throughout in 2020, this three-bedroom, two-and-a-half-bath home offers the perfect blend of timeless elegance and modern comfort. The spacious floor plan features formal living and dining rooms, a welcoming family room with a dramatic floor-to-ceiling wood-burning fireplace, and multiple sliding glass doors that seamlessly connect the indoor living spaces to the expansive screened lanai. The beautifully updated kitchen showcases quartz countertops, stainless steel appliances, abundant cabinetry, recessed lighting, and an oversized breakfast bar—perfect for gathering with family and friends. The private primary suite offers direct lanai access, a beautifully renovated bath, and a custom walk-in closet, while the guest bath and powder room have also been tastefully remodeled. Stretching nearly the length of the home, the oversized covered and screened lanai is the perfect place to enjoy your morning coffee, unwind with evening sunsets, or entertain while taking in the panoramic golf course views. The spacious backyard offers plenty of room to add a private pool and create your own private outdoor retreat. Major improvements completed in 2020 include the roof, HVAC system, interior and exterior paint, and extensive interior renovations, providing buyers with added peace of mind. Residents of East Lake Woodlands enjoy beautifully maintained streets, mature landscaping, 24-hour guarded gate access, and optional membership opportunities at the newly renovated Ardea Country Club, featuring 36 holes of championship golf, tennis, pickleball, fitness facilities, swimming pools, exceptional dining, and a vibrant social calendar. Conveniently located just minutes from Boot Ranch shopping, restaurants, parks, Gulf beaches, Tampa International Airport, and everything the Tampa Bay area has to offer, this move-in-ready home delivers the Florida lifestyle you’ve been waiting for.
4931 TURTLE CREEK TRL, OLDSMAR, FL 34677
$1,055,00035 Days on yellowkey MLS ID: TB8518188
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3189 Built: 1995Monthly Fee: $181 Tax: $10,115 (2025)Community: East Lake WoodlandsSpa: YesSingle Family
Taxes:$10,115
Remarks: If you've been searching for a home that checks every box, this one is worth a serious look. Tucked inside the guard-gated East Lake Woodlands community — known for its canopied streets, two championship golf courses, pickle ball and tennis courts, and home to Ardea Country Club — this 4-bedroom, 3-bath pool home sits on nearly a full acre and has been genuinely well cared for. Equipped with a whole-house solar system - means electric bills that are almost laughably low — most months you're paying little more than the base statement fee. Pair that with a whole-home water filtration system, water softener, two brand-new AC units (April 2025 and March 2026), a tile roof replaced in 2019, and two water heaters also replaced in 2019, and you're looking at a home where the expensive stuff has already been done. At 3,189 square feet, the layout gives everyone room to breathe. The great room is the kind of space that feels both impressive and livable, and the split floor plan keeps the primary suite — complete with walk in closets and a sitting area — separate from the other bedrooms. Tile flooring runs throughout the entire home, so there's no carpet to worry about. The kitchen is built for real use: breakfast bar, convection oven, cooktop, and quality appliances, all with stone counters. Out back, the pool and lanai open up to a quiet, private setting that makes it easy to forget the rest of the world exists. Top-rated schools, easy access to Tampa, and a short drive to the Gulf beaches round out a package that's hard to replicate at this price point.
1008 ROBINWOOD DR, OLDSMAR, FL 34677
$675,00039 Days on yellowkey MLS ID: TB8516701
REDUCED by $20,000 (2.9%) on 07/17/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2442 Built: 1997Monthly Fee: $70 Tax: $9,594 (2025)Community: Woods Of Forest Lakes The Ph OneSingle Family
Taxes:$9,594
Remarks: WOW! Big price Drop!! Prime Woods of Forest Lakes!!!This spacious 4-bedroom, 2-bath pool home is situated on a corner lot in the desirable Woods of Forest Lakes. With an expansive living room that features high ceilings and sliding glass doors to the pool area, separate family room, and formal dining area, there's plenty of space for gatherings, game nights, holiday celebrations, or simply spreading out and relaxing. The kitchen is centrally located and features granite countertops, abundant cabinet storage, generous prep space, and a bright breakfast nook surrounded by windows that fill the room with natural light. This is a split bedroom floorplan that features a large primary suite with two walk-in closets and an en-suite bathroom with dual vanities, a garden tub and walk-in shower. There's 3 additional good sized bedrooms and a large separate laundry room. Step outside to a poolside oasis, ideal for entertaining, along with a fully fenced grassy side yard that's a perfect outdoor game area, gathering spot or ideal for your fur babies. The Woods is a well established neighborhood featuring great community amenities including a tennis/pickleball court, playground and a lakefront community picnic area. Walk to the community water park and rec center, take advantage of nearby biking/walking trails, easy access to shops dining and entertainment. Whether you're hosting friends by the pool, enjoying a quiet morning coffee in the breakfast nook, or taking advantage of the community amenities, this home offers comfort, flexibility, and an unbeatable location.
Listing Agent: Joe Koebel (727-410-1455)
586 KINGSMILL CT, OLDSMAR, FL 34677
$600,00047 Days on yellowkey MLS ID: TB8512390
REDUCED by $15,000 (2.4%) on 06/28/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2452 Built: 1998Monthly Fee: $298 Tax: $10,436 (2025)Community: KingsmillSpa: YesSingle Family
Taxes:$10,436
Remarks: Virtually Staged. Welcome to this inviting single-family home in the sought-after Kingsmill neighborhood of East Lake Woodlands—a premier gated community celebrated for its security, lush Florida landscapes, and vibrant lifestyle. Offering 2,453 square feet of living space, this beautifully updated residence features a grand total of three bedrooms, two full bathrooms, and a modernized half bath. Inside, the interior features soaring cathedral ceilings, fresh flooring, and brand-new carpeting. The main level hosts a formal dining room and an open kitchen that flows effortlessly into a spacious great room, complete with a cozy gas-burning fireplace. The primary suite is conveniently situated on the main floor, boasting a stunning, fully remodeled bathroom. Upstairs, discover the remaining bedrooms—including a flexible third bedroom created by walling in the former loft space, making it ideal for a quiet home office or guest room—alongside another full bath. Outside, the large backyard overlooks a peaceful pond and features an inground pool and spa under a brand-new screen enclosure, complemented by a built-in outdoor kitchen setup. Living here means embracing the East Lake Woodlands lifestyle. Residents can enjoy miles of scenic nature and biking trails, while a variety of optional club memberships unlock access to championship golf courses, a premier tennis and pickleball complex, resort-style swimming pools, and a private clubhouse with fine dining and social events. Located in the heart of Oldsmar, this property is also just minutes from excellent shopping, dining, highly rated schools, and pristine Gulf Coast beaches. Don’t miss the opportunity to make this Kingsmill gem your own. Schedule a private tour today to experience this beautiful pond-front retreat firsthand!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Susanne Jones (727-455-0769)
5250 PINEHURST CT, OLDSMAR, FL 34677
$665,0003 Days on yellowkey MLS ID: TB8529582
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2074 Built: 1995Monthly Fee: $518 Tax: $6,099 (2025)Community: Parcel B - The PinnacleSingle Family
Taxes:$6,099
Remarks: RARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. WALK THRU DOUBLE GLASS ENTRY DOORS TO FOYER THAT OPENS TO LIVING ROOM. LIGHT AND BRIGHT EXPANDED FAMILY ROOM AND KITCHEN OFFERS QUIET VIEWS OF CONSERVATION AND GOLF COURSE AREA. NEWLY EXPANDED LANAI WITH PARORAMIC BIRDCAGE SCREENING. KITCHEN OVER LOOKS FAMILY ROOM HAS CENTER ISLAND AND WOOD CABINETRY, BUILT-IN PANTRY, GRANITE COUNTER TOPS AND ALL STAINLESS-STEEL APPLIANCES. SEPARATE DINING ROOM WITH EASY ACCESS FROM THE KITCHEN. MASTER BEDROOM WITH TWO WALK-IN CLOSETS AND MASTER BATH WITH FREE STAND TUB, SEPARATE STALL SHOWER, PRIVATE TOILET CLOSET, DOUBLE SINK VANTY WITH GRANITE COUNTER AND CUSTOM TILE. OFFICE WITH DOUBLE DOOR ENTRY CAN ALSO BE USED AS THIRD BEDROOM WITH CLOSET. SECLUDED SECOND BEDROOM IS PERFECT FOR GUESTS WITH ADJOINING BATH. INSIDE LAUNDRY ROOM WITH UTILITY SINK AND EXTRA STORAGE. GARAGE HAS EXTRA STORAGE AND SPACE FOR TWO CARS. THIS SEPTACULAR HOME LOCATED ON A PRIVATE CUL-DE-SAC. FOR SOCIAL ENJOYMENT YOU CAN RELAX IN THE COMMUNITY POOL. CLUBHOUSE MEMBERSHIP IS ALSO AVAILABLE FOR TENNIS AND GOLF. CLOSE TO BEACHES, SHOPPING, HOSPITALS, AND AIRPORTS. THIS IS WAITING FOR YOU!
Listing Agent: M Sam Mclaughlin (727-647-6767)
402 SHORE DR W, OLDSMAR, FL 34677
$795,000126 Days on yellowkey MLS ID: TB8485835
REDUCED by $54,000 (6.4%) on 07/18/2026
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1711 Built: 1999 Tax: $3,890 (2025)Community: Oldsmar Rev MapSpa: YesSingle Family
Taxes:$3,890
Remarks: One or more photo(s) has been virtually staged. HUGE PRICE ADJUSTMENT JULY 18TH. Gorgeous water views of Old Tampa Bay from this custom-built, original-owner home in a prime Oldsmar location, directly across from popular R.E. Olds Park with its amphitheater, fishing pier, playgrounds, sand volleyball and annual fireworks you can enjoy from your front porch. The resort-style backyard features a large in ground pool with spa, kiddie pool, spillover fountain and fiberoptic lighting, all within a screened enclosure with covered area for dining and parties would cost well over $100k to install today. A spacious concrete pad doubles as a basketball court and offers room to store a boat or add a shed, plus parking for 2 cars under carports and a deep driveway that has accommodated 10+ vehicles, with overflow available at the park. Upstairs, the main living level welcomes you through double hurricane-rated doors to beautiful Brazilian hand-scraped wood floors, abundant windows, and an eat-in kitchen with granite counters and arched opening to the living room, along with a formal dining room. An office or bedroom on this level opens via sliding glass doors to a balcony overlooking the pool, and a convenient half bath completes the floor. The bedroom level begins with a newer washer/dryer closet for easy access to all bedrooms. The primary suite offers stunning water views from sliders, the third-level deck and multiple windows, and its ensuite bath was updated in 2017 with new cabinetry, tile and quartz counters; the second full bath was also updated. Major updates include a 2016 roof and 2023 A/C, making this well-maintained home ideal for both everyday living and large gatherings.
Listing is courtesy of: HOMES BY SANDERS REALTY (727-409-6929)
Listing Agent: Mike Sanders (727-409-8000)
743 WELLINGTON CT, OLDSMAR, FL 34677
$799,00032 Days on yellowkey MLS ID: TB8515327
REDUCED by $16,000 (2.0%) on 07/09/2026
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3058 Built: 2015Monthly Fee: $160 Tax: $6,370 (2025)Community: Wellington EstatesSpa: NoSingle Family
Taxes:$6,370
Remarks: Welcome to luxury living in the highly sought-after Wellington Estates community of Oldsmar. This stunning ENERGY STAR® certified residence offers over 3,000 square feet of thoughtfully designed living space featuring 3 bedrooms, a private den/office, 3.5 bathrooms, and an expansive bonus room that can easily serve as a media room, game room, home gym, or fourth bedroom. The home also includes a spacious 3-car garage and a resort-style outdoor living area. A dramatic two-story foyer with a designer crystal chandelier sets the tone upon entry. The open-concept floor plan showcases soaring ceilings, elegant crown molding, plantation shutters, and abundant natural light throughout. The gourmet kitchen is the centerpiece of the home, featuring rich espresso cabinetry, quartz countertops, stainless steel appliances, double ovens, a large center island, and a spacious dining area that seamlessly connects to the great room—perfect for entertaining. The spacious primary suite offers a luxurious retreat with a custom walk-in closet and spa-inspired bath complete with dual vanities, a soaking tub, and a walk-in shower. Upstairs, the oversized bonus room provides exceptional flexibility for today's lifestyle needs while the additional bedrooms offer comfort and privacy for family and guests. Step outside to your private backyard oasis featuring a screened-in pool with tranquil rock waterfall feature and an impressive outdoor kitchen complete with granite countertops, built-in grill, refrigerator, and ample prep space—ideal for year-round Florida entertaining. Mature landscaping and privacy hedges create a peaceful setting for relaxation and gatherings. Additional highlights include hurricane shutters, reclaimed water irrigation, in-wall pest defense system, abundant storage, and premium finishes throughout. Located just minutes from top-rated schools, shopping, dining, parks, beaches, and Tampa International Airport, this exceptional Wellington Estates home combines luxury, comfort, and convenience in one remarkable package.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
347 COUNTRY CLUB DR, OLDSMAR, FL 34677
$419,000160 Days on yellowkey MLS ID: TB8475491
REDUCED by $10,000 (2.3%) on 06/29/2026
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)
2151 DIAMOND CT, OLDSMAR, FL 34677
$1,350,000267 Days on yellowkey MLS ID: TB8440175
0 Days Off yellowkey (back on 7/18/2026)
REDUCED by $39,000 (2.8%) on 04/21/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3850 Built: 1998Monthly Fee: $142 Tax: $9,378 (2024)Community: Diamond CrestSpa: YesSingle Family
Taxes:$9,378
Remarks: Under contract-accepting backup offers. Turnkey Renovated Home with $200K+ Upgrades | No Major Expenses | Premium View Lot Fully Renovated Luxury Pool Home | New Roof + Impact Windows | Panoramic Water & Conservation Views. Welcome to 2151 Diamond Court, a fully renovated luxury residence located in the gated Diamond Crest community of East Lake Woodlands. This exceptional 4-bedroom, office ,3-bath home offers 3,850 square feet of thoughtfully updated living space, positioned on a premium lot with tranquil water, conservation, with sunrise and sunset views Over $230,000 in recent upgrades provide peace of mind and long-term value, including a new roof (2023-2024) with a 30-year warranty impact-rated hurricane windows(2024) Limited Lifetime warranty panoramic screened lanai enclosure(2024) designed to maximize views and outdoor living updated flooring throughout, a fully renovated kitchen, the result is a truly move-in ready home with no major projects or deferred maintenance. Inside, the home features a desirable split floor plan with a dedicated office, high ceilings, and expansive living spaces that seamlessly connect to the outdoor entertaining area. The updated kitchen with top-of-the-line GE CAFÉ Appliances serves as the centerpiece of the home, offering modern finishes, custom cabinetry, and a functional open layout ideal for everyday living and gatherings. The outdoor living space is equally impressive, panoramic lanai, pool, and spa overlooking peaceful natural surroundings—creating a private retreat perfect for relaxing or entertaining. Unlike many comparable homes, this property offers a rare combination of condition, recent upgrades, and insurance-friendly features, making it one of the best values among renovated homes in East Lake Woodlands. This is a unique opportunity to own a turnkey home in a highly desirable gated community with no major expenses expected for years and Reduced Insurance Premiums
Listing is courtesy of: RE/MAX ELITE REALTY (727-785-7653)
Listing Agent: Michelle Johncola (727-515-2415)
2009 PEPPERTREE CT, OLDSMAR, FL 34677
$380,00083 Days on yellowkey MLS ID: O6403164
REDUCED by $10,000 (2.6%) on 07/06/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1233 Built: 1981 Tax: $927 (2025)Community: Bayside Meadows Ph IiSpa: YesSingle Family
Taxes:$927
Remarks: One or more photo(s) has been virtually staged. Motivated seller!!! Tucked away on a cul-de-sac, this beautifully maintained single-family home offers comfort, space, and thoughtful upgrades perfect for modern family living. Featuring 3 spacious bedrooms and 2 full bathrooms which one has a jacuzzi, the home boasts an open-concept living and dining area filled with natural light—ideal for both relaxing and entertaining. In addition there are 4 hurricane impact windows; 3 energy efficient which come with covers. New roof just placed in June 2026. HVAC/Water Heater 2024. The primary suite is a true retreat, complete with a walk-in closet and a uniquely designed master bathroom featuring a luxurious Jacuzzi tub, separate shower, and elegant double glass sinks. An additional room provides the perfect space for a home office, study, or flex use. Throughout the home, you’ll find a stylish combination of porcelain tile flooring in the main living areas and durable laminate flooring in the bedrooms, offering both beauty and easy maintenance. There is a swim spa in the backyard; a screen porch for relaxation; a shed and some gardening to work on. Also, house has an attached storage that could be turn into office. Also, in the garage there is an 38amp RV plug.
Listing is courtesy of: CFRP REALTY LLC (407-682-8686)
Listing Agent: Ola Lombardi (727-256-7762)
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