Location: Oldsmar , 34677
Do Not Show Listings
4761 STONEBRIAR DR, OLDSMAR, FL 34677
$749,00050 Days on yellowkey MLS ID: TB8509685
REDUCED by $11,000 (1.4%) on 07/06/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2652 Built: 1993Monthly Fee: $117 Tax: $5,832 (2025)Community: StonebriarSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,832
Elementary School: None
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: This is Florida luxury living at its finest in one of the area’s most desirable gated communities. Exclusive executive home located in the highly sought-after Stonebriar community within East Lake Woodlands, a desirable gated golf club community. Zoned for top-rated schools and ideally situated less than 30 minutes from Tampa International Airport and the area’s premier Gulf beaches. This exceptional 4-bedroom luxury residence offers the perfect blend of elegance, comfort, and privacy. Boasting 2,652 square feet of living space with soaring ceilings and abundant natural light, this beautifully updated home features a spacious oversized primary suite complete with a private sitting area overlooking the expansive screened pool, recently resurfaced for years of enjoyment. The gourmet kitchen is designed for both entertaining and everyday living. Newer appliances, newer pool pavers, Plantation shutters added throughout. Roof 2016, Water heater 2019, re screened porch 2017, fresh exterior paint 2019. The private conservation lot provides a tranquil setting ideal for relaxing or entertaining poolside. RECENTLY PASSED 4point and Wind Mitigation.
Listing is courtesy of: PRIME INT'L REAL ESTATE GROUP (877-727-5259)
Listing Agent: Nichole Gaytan (305-323-8108)
506 SHORE DR E, OLDSMAR, FL 34677
$900,00060 Days on yellowkey MLS ID: TB8509618
4 Days Off yellowkey (back on 7/6/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1313 Built: 1955 Tax: $9,895 (2025)Community: Tampashores Bay SecSingle Family
Taxes:$9,895
Elementary School: Oldsmar Elementary-PN
Remarks: Under contract-accepting backup offers. Exceptional waterfront opportunity on one of Oldsmar’s most desirable streets. Situated on a 75x205 (.33 acre) waterfront homesite overlooking beautiful Old Tampa Bay, this property presents a rare opportunity to create a custom luxury estate in an area experiencing significant redevelopment and impressive new construction. Currently utilized as a vacation rental, the home offers income producing potential while future plans take shape, though the true value lies in the land and its exceptional waterfront setting. For water enthusiasts, the lifestyle possibilities are endless. Launch a kayak or paddleboard from your backyard, enjoy boating and jet skiing on the Bay, or simply unwind while taking in panoramic water views and breathtaking sunset skies. With no HOA or deed restrictions, there is added flexibility and ample room for boat and RV parking. Ideally located approximately 20 minutes from Tampa International Airport and about 25 minutes to the Gulf beaches, the property is also just down the street from RE Olds Park and offers convenient access to pickleball, Mobbly Beach, Veterans Memorial Park, scenic biking and walking trails, dining, shopping, and everyday conveniences. Offering a unique blend of waterfront serenity and exceptional accessibility, this is a rare opportunity to create a one of a kind coastal retreat where the lifestyle is just as remarkable as the setting.
Listing is courtesy of: WESTWARD REAL ESTATE (813-285-4456)
Listing Agent: John Pestalozzi Jr Llc (813-285-4456)
438 LAFAYETTE BLVD, OLDSMAR, FL 34677
$575,000133 Days on yellowkey MLS ID: TB8480797
REDUCED by $9,900 (1.7%) on 07/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2138 Built: 1988 Tax: $8,284 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$8,284
Middle School: None
Remarks: Beautiful Custom-built home is situated on ½ acre fenced-in lot (mol) No HOA, No deed restriction, Plenty of room for your Boat and RV! Featuring 4 Bedrooms plus an office, 2 baths and a screened-in heated pool. Circular driveway and etched glass front door welcome you into a wide-open floor plan with vaulted ceilings and lots of windows. Interior freshly painted. The living room offers a beautiful bay window and a cozy fireplace, open to a light and bright dining room. Large, updated kitchen with wood cabinetry, newer stainless-steel appliances, granite countertops, coffee bar and a garden window. The home flows effortlessly from room to room making it ideal for both everyday living and entertaining. Expansive primary suite with 2 large closets, beautiful new bath with a huge walk-in shower and a jetted tub. Additional 3 good size bedrooms plus a great in-home office with built-in shelving and double glass doors leading to the lanai and pool. Beautifully updated 2nd bath, nice size laundry room. 2 Car garage plus a spacious storage room. New top of the line Trane A/C. Roof replaced in 2017. Newer flooring (No Carpet) The huge fenced-in backyard provides privacy and has plenty of space for pets or outdoor entertaining, with a grilling area. Beautiful, heated pool, newly re-screened and new pool heater installed. The beautiful Veterans Memorial waterfront Park is just down the street. Walking distance to downtown Oldsmar. Conveniently located near shopping, fine dining, theatres and golfing. 10-15 Minutes to Philippe Park and Safety Harbor Spa, 15-20 minutes to downtown Dunedin, Honeymoon Island and Pinellas Trails. 20-25 Minutes to Clearwater Beach, Tampa and St Pete airports. Motivated Seller!
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Luigi Kalaj (727-388-4200)
124 WOODLAKE WYNDE #0, OLDSMAR, FL 34677
$215,00016 Days on yellowkey MLS ID: TB8523772
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 924 Built: 1983 Tax: $3,053 (2025)Community: East Lake Woodlands Woodlake RunSpa: NoCondo
Taxes:$3,053
Elementary School: Forest Lakes Elementary-PN
Remarks: Call to schedule your private showing of this beautifully furnished 2-bedroom, 2-bath upstairs condominium in the highly desirable gated community of East Lake Woodlands. Perfectly positioned in a quiet setting, this light-filled home welcomes you with soaring vaulted ceilings and an abundance of natural light streaming through the upper windows, creating a bright and spacious atmosphere you'll love coming home to. Designed for comfortable Florida living, this fully furnished condo is move-in ready. Snowbirds and seasonal residents can simply bring their clothes and groceries—everything else is already here, making your Florida getaway effortless. Enjoy refreshing breezes from two private screened patios. Sip your morning coffee as the sun rises or relax in the evening with your favorite beverage while taking in the peaceful surroundings. The screened balcony is accessible from both the spacious living room and the primary bedroom, creating a seamless indoor-outdoor lifestyle. The split-bedroom floor plan offers privacy for both owners and guests. The generous primary suite features a large walk-in closet and a private en-suite bathroom, while the guest bedroom is thoughtfully separated by the guest bath and closets, making it ideal for family and visitors. A convenient laundry closet with a washer and dryer is located on the screened kitchen patio and is easily accessible from both the kitchen and the guest bedroom. East Lake Woodlands is a beautifully maintained 24-hour guard-gated golf community where residents enjoy secure access with resident vehicle passes and a peaceful country club atmosphere. Optional memberships offer golf, tennis, fitness, dining, and social activities. Located at the corner of Tampa Road and East Lake Road, you'll be just minutes from grocery stores, shopping, restaurants, medical facilities, and entertainment, with beautiful Gulf beaches and Tampa International Airport only a short drive away. Whether you're looking for a seasonal retreat or a full-time Florida residence, this exceptional condo offers comfort, convenience, and the carefree lifestyle you've been dreaming about.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-847-4444)
Listing Agent: Robert Mccaffery (727-364-8530)
205 WOODS LANDING TRL, OLDSMAR, FL 34677
$264,00014 Days on yellowkey MLS ID: TB8524916
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1200 Built: 1984Monthly Fee: $591 Tax: $2,130 (2025)Community: East Lake Woodlands Woods Landing TwnhmsTownhouse
Taxes:$2,130
Remarks: From the welcoming entrance foyer, visitors are immediately drawn to the peaceful wooded views at the rear of the home, creating a warm and inviting first impression. Welcome to this beautifully maintained two-bedroom, two-and-a-half-bath townhome in the gated community of East Lake Woodlands, one of Pinellas County's most sought-after neighborhoods. Offering maintenance-free living in a non-flood zone at an exceptional price, this home combines comfort, convenience, and value. The spacious great room and dining area provide a versatile, open floor plan that can easily accommodate both casual everyday living and entertaining. Upstairs, two generously sized bedrooms each feature their own en-suite bathroom and walk-in closet (closets in the primary bedroom are fully customizable with the IKEA BOAXEL system), offering privacy and comfort for family members or guests. A convenient first-floor powder room adds extra functionality for everyday living and entertaining. The bright and cheerful kitchen is filled with natural light and features a breakfast bar overlooking the dining area, a closet pantry, and sliding glass doors leading to a private front patio—an ideal spot to enjoy your morning coffee or dine outdoors. The open living and dining areas are enhanced by large windows and sliding glass doors that overlook the enclosed tiled Florida room, where you can relax while taking in tranquil wooded views and watching the local wildlife. This flexible space is perfect as a sunroom, home office, or additional entertaining area. Recently installed laminate flooring extends throughout the main level, adding both style and durability. Additional features include a private driveway with covered carport, storage shed, and an upstairs laundry closet conveniently located between the bedrooms and equipped with a full-size washer and dryer. The a/c in 2022 and the hw heater new in 2025. As a resident of East Lake Woodlands, you'll have the opportunity to join the recently renovated Ardea Country Club, offering two championship 18-hole golf courses, pickleball and tennis courts, a fitness center, a full-service restaurant and bar, and an active calendar of social events. The HOA fee provides outstanding value by including roof maintenance, cable & internet at discounted rates, exterior grounds maintenance, garbage, exterior pest and termite control, exterior insurance (owner's still need to have HO6 policy) along with a community heated pool and more. East Lake Woodlands offers the perfect balance of convenience and tranquility, with easy access to shopping, dining, beautiful Gulf beaches, Tampa International Airport, and everything the Tampa Bay area can provide—all while enjoying the charm and serenity of one of Pinellas County's premier gated communities. Don't miss this opportunity to own an affordable home in this exclusive community and enjoy the Florida lifestyle you've been dreaming of!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Karen Sewell (727-542-4467)
160 JAMES CT, OLDSMAR, FL 34677
$350,00077 Days on yellowkey MLS ID: TB8503480
1 Days Off yellowkey (back on 7/4/2026)
REDUCED by $13,900 (3.8%) on 06/03/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1445 Built: 1981Monthly Fee: $451 Tax: $5,927 (2025)Community: Quail Forest Cluster HomesVilla
Taxes:$5,927
High School: None
Remarks: Under contract-accepting backup offers. Virtually Staged. Fantastic Price - Welcome to this beautifully Updated One-Story Villa nestled in the Gated, Golf Community of East Lake Woodlands, boasting 1,445 sq. ft. with 3 Bedrooms and 2 Full Baths and a Maintenance-Free Lifestyle. This Much-Sought-After End Unit provides the advantages of More Natural Light and More Privacy - plus a true Open Concept with Soaring Ceilings, Wood Beams and a Spacious Great Room that flows to the Dining Area and has Open Access to the Stunning Kitchen with white Shaker Cabinetry, gleaming Granite Countertops, Stainless Steel Appliances and Eat-In Breakfast Area. Glass sliders lead to a Large Screened Patio overlooking a Peaceful Water View that spans the entire length of the home. Enjoy a second outdoor space with a patio at the front of the home with Glass Sliders leading from both the Kitchen and Dining Area – perfect for that morning cup of coffee. The Primary Suite features Serene Water Views, Walk-In Closet and an Updated Bath with spacious Granite Countertops with Double Sinks and Beautifully Tiled Shower. This Split Floor Plan provides privacy with the 2nd and 3rd Bedrooms separated from the Primary Suite with access to the second Updated Bath. The Screened Lanai extends the living space and includes a Large Storage Closet for those extra items. Front Loading Washer and Dryer off the Breakfast Area are included in the sale. And best of all, you can Simplify Your Life and Relax with Maintenance-Free Living since Lawn Care and Exterior Building Maintenance including the Roof (replaced in 2025) is included in the HOA fees along with a sparkling Community Heated Pool, Basic Cable and Trash and Recycling Collection. Plus for additional fees, take advantage of a wide array of amenities with Ardea Country Club optional memberships featuring 2 Golf Courses, Tennis and Pickle Ball, Fitness Center, Lap and Freeform Pools, Dining and Social Events. All this in a Premier Location Convenient to Tampa International Airport, Medical Facilities, A-rated Schools, Award-Winning Beaches as well as Professional Sporting Events, Concerts, Fine Dining and more in the Tampa Bay Area. Discover Comfort and Convenience in this inviting villa and a Fabulous Lot located in the preferred Zone X so no flood insurance is required!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
413 COUNTRY CLUB DR, OLDSMAR, FL 34677
$324,90014 Days on yellowkey MLS ID: O6422167
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 1959 Tax: $3,829 (2024)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$3,829
Tax Year: 2024
Remarks: Wake up to water views and end your day watching the sun set over the canal. This renovated 3-bedroom, 2-bathroom waterfront home sits on a spacious 0.21-acre lot with no HOA in the established Oldsmar Country Club Estates, and its best feature is right out the back door: direct water access with a scenic trail leading all the way to Tampa Bay. Launch a kayak or paddleboard from your own backyard and be on the water in minutes. Inside, the home is move-in ready with luxury vinyl flooring throughout and an open, light-filled layout. The renovated kitchen features stainless steel appliances, quartz countertops, and generous cabinetry. The primary suite gives a comfortable retreat with an updated bathroom, modern vanity, designer lighting, and a tiled walk-in shower. Sliding doors off the main living area open to an expansive backyard where the waterfront views take center stage. Enjoy morning coffee, evening entertaining, or simply unwind by the water. The location matches the lifestyle. Walk, bike, or take your golf cart to Mobbly Bayou Beach Park, a public boat launch to Tampa Bay, Tampa Bay Pickleball, Veterans Park, Bicentennial Park, and RE Olds Park. You are also close to Empower Adventures Zip Line and the Oldsmar Organic Community Garden, with Tampa International Airport about 20 minutes away. Zoned for well-regarded schools including Oldsmar Elementary, Joseph L. Carwise Middle, and East Lake High. This is a rare opportunity to own a renovated waterfront home with no HOA in one of Oldsmar's most sought-after communities.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
848 CHRISTINA CIR, OLDSMAR, FL 34677
$560,00062 Days on yellowkey MLS ID: TB8509369
1 Days Off yellowkey (back on 7/3/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1756 Built: 1994Monthly Fee: $68 Tax: $4,544 (2025)Community: Bay's EndSpa: YesSingle Family
Taxes:$4,544
Remarks: Under contract-accepting backup offers. Tucked away in the desirable enclave of Bay’s End, this stunning contemporary two-story residence blends upscale coastal living with exceptional indoor-outdoor entertaining. From the moment you enter, soaring ceilings, an open-concept design, and abundant natural light create a warm yet sophisticated atmosphere. Rich wood-look luxury vinyl flooring flows seamlessly throughout the home, enhancing its modern coastal appeal. At the heart of the home is a beautifully designed island kitchen featuring elegant wood cabinetry, gleaming quartz countertops, and stainless steel appliances. The kitchen opens effortlessly to the spacious living and dining areas, highlighted by a striking wood-burning fireplace and views of the tropical pool and spa retreat. The main-level owner’s suite is a private sanctuary complete with a walk-in closet and an expansive spa-inspired bathroom filled with natural light, featuring a luxurious vanity, soaking tub with shower. A convenient half bath, interior laundry room, and attached two-car garage complete the first floor. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile den/media room perfect for a home office, playroom, or entertainment space. Step outside through sliding glass doors to your own private resort-style oasis. The screened lanai surrounds an entertaining-sized pool with waterfall and spa, framed by towering palm trees and lush tropical landscaping. By night, the spectacular pool and landscape lighting transform the backyard into a truly magical setting. Situated on nearly a quarter-acre, the enormous privacy-fenced backyard offers endless possibilities — currently serving as the ultimate playground for soccer, baseball, basketball, and golf. Exceptional savings with the solar panels, installed in 2020. Seller will pay the financing in full at closing. This exceptional Bay’s End home combines style, comfort, and resort-inspired living in one unforgettable package. Opportunities like this don’t last long.
Listing is courtesy of: RIZZO & ASSOCIATES INC (727-894-4400)
Listing Agent: Philip Rizzo (727-656-4400)
115 WINDWARD PL #15, OLDSMAR, FL 34677
$180,000111 Days on yellowkey MLS ID: TB8490824
0 Days Off yellowkey (back on 7/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1984Monthly Fee: $431 Tax: $2,768 (2025)Community: Meadows Condo At East Lake WoodlandsCondo
Taxes:$2,768
Remarks: Under contract-accepting backup offers. LOCATION, LOCATION, LOCATION! Close to entertainment, shopping, restaurants, airports, and world-famous beaches, this beautiful ground floor, end unit condo is waiting for you! Located in the highly desirable, gated community Meadows of Eastlake Woodlands, this home has it all! Gorgeous granite countertops highlight the kitchen as does the impressive cabinet space and closet pantry. The inviting open living space makes time together comfortable, yet the split bedroom floor plan offers privacy when needed. The primary bedroom is generous and offers two walk-in closets, an ensuite bath with step-in shower, and patio access. HVAC 2021. The HOA fees include water, sewer, trash, cable, community pool, exterior maintenance including the roof, and grounds maintenance. There is a community golf course that owners may access for an additional fee.
Listing is courtesy of: FLORIDA PREMIERE REALTY (727-437-0261)
Listing Agent: Millie Jackson (828-337-9468)
1811 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$359,900119 Days on yellowkey MLS ID: TB8488580
REDUCED by $10,100 (2.7%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 1973 Tax: $1,036 (2025)Community: Harbor Palms-Unit TwoSingle Family
Taxes:$1,036
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of Oldsmar! Offering 1,248 sq ft of well-designed living space, this move-in-ready property features a functional layout, abundant natural light, and modern updates throughout. Enjoy spacious living and dining areas that flow seamlessly, perfect for both everyday living and entertaining. The kitchen offers ample cabinetry and workspace, while the bedrooms are generously sized for comfort and flexibility. Conveniently located near parks, shopping, dining, and major roadways, this home provides easy access to Tampa, Clearwater, and surrounding areas. Don’t miss this opportunity to own a well-maintained home in a desirable location!
Listing Agent: Julio Vasquez (727-404-8889)
360 S WOODLANDS DR, OLDSMAR, FL 34677
$399,90040 Days on yellowkey MLS ID: TB8515718
REDUCED by $15,000 (3.6%) on 07/02/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1590 Built: 1979Monthly Fee: $340 Tax: $5,335 (2025)Community: East Lake Woodlands Patio HomesVilla
Taxes:$5,335
Remarks: Welcome to 360 S Woodlands Drive, a beautifully renovated 2-bedroom, 2-bath patio home nestled within the prestigious gated community of East Lake Woodlands in Oldsmar. Offering 24-hour guarded security and a maintenance-free lifestyle, this move-in ready residence combines modern upgrades with exceptional privacy and comfort. NEW ROOF + FLAT ROOF (2025)! NEW AC (2025)! Extensively updated throughout, the home features luxury vinyl plank flooring installed in 2022, a completely remodeled kitchen with granite countertops, premium cabinetry, and stainless steel appliances, along with two beautifully renovated bathrooms featuring updated tilework, granite countertops, and stylish vanities. The spacious primary suite serves as a private retreat with a custom-designed closet and an oversized soaking tub perfect for relaxation. Additional improvements include IMPAC impact windows, a new flat roof installed in December 2021, updated interior doors, and a custom 45-foot paver walkway that extends from the front entrance to the private rear patio, creating an ideal outdoor space for entertaining or enjoying Florida's beautiful weather. The HVAC system was replaced in 2025 for added peace of mind.The monthly HOA fee provides true maintenance-free living and includes lawn care, irrigation, Spectrum cable and internet service with two cable boxes, and exterior painting every five years. Residents also have the option to join East Lake Woodlands Country Club, offering two championship golf courses, tennis courts, swimming pools, fitness facilities, dining, and a vibrant social calendar. Ideally located near shopping, dining, parks, Tampa International Airport, and some of the area's most beautiful Gulf Coast beaches, this exceptional home offers the perfect blend of luxury, convenience, and Florida living. Schedule your private showing today.
Listing Agent: Mark Fazzini (727-485-9981)
2005 HUDSON CT, OLDSMAR, FL 34677
$299,90048 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)
1924 MONTEGO CT, OLDSMAR, FL 34677
$359,90037 Days on yellowkey MLS ID: TB8517782
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 1980 Tax: $5,005 (2025)Community: Bayside Meadows-Phase ISingle Family
Taxes:$5,005
Remarks: **SUPER STARTER HOME!!** What a fantastic house for the price! From the moment you arrive, you’ll be wowed by the striking curb appeal. The freshly painted exterior is complemented by a newer roof and landscaping, with a 30-year dimensional shingle roof installed in 2024 and a transferable 10-year warranty. Inside, the spacious, open floor plan is just as impressive, starting with a leaded glass front door. This move-in ready home has been updated throughout, featuring a tiled great room with a lighted ceiling fan and a large front window that fills the space with natural light. The eat-in kitchen offers a cozy dinette, updated soft-close cabinetry, stainless steel appliances, recessed lighting, and tile countertops with backsplash. Down the hall are three bedrooms, all with lighted ceiling fans and new carpet. The primary ensuite boasts an updated bathroom with a walk-in shower and new hardware, while the guest bath offers resort-style features. Step through the back sliding glass door to a screened lanai with tile floors—perfect for relaxing or entertaining. The modest fenced backyard has fresh mulch and is easy to maintain. With a new A/C installed in 2022 and a prime location near trendy restaurants, shopping, AMC Woodlands Movies, and just minutes from Tampa, the airport, or the beach, this home truly has it all—don’t miss it! (house has never had any issues with flooding in 20 years owner has owned it)
Listing Agent: Shay Adelman (727-458-3702)
2024 SHEFFIELD CT, OLDSMAR, FL 34677
$239,99044 Days on yellowkey MLS ID: TB8510499
REDUCED by $10,000 (4.0%) on 06/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1986Monthly Fee: $110 Tax: $3,568 (2025)Community: Sheffield Village At Bayside MeadowsVilla
Taxes:$3,568
Remarks: Welcome home to this charming villa in the heart of Oldsmar! Filled with natural light and featuring soaring cathedral ceilings, this inviting home offers laminate and tile flooring throughout, stainless steel appliances, and a bright, low-maintenance interior. Relax with your morning coffee or unwind in the evening on the screened porch overlooking your private backyard, and enjoy the convenience of two assigned parking spaces located just outside your front door. Residents have access to the community pool, while nearby Sheffield Park provides additional opportunities for recreation and outdoor activities. Located within a highly sought-after school district and just minutes from shopping, dining, the sports complex, and the AMC movie theater, this villa offers the perfect combination of comfort, convenience, and the Florida lifestyle.
Listing is courtesy of: WEICHERT REALTORS EXCLUSIVE PROPERTIES (813-426-2669)
Listing Agent: Christopher Webb (813-297-1435)
645 TIMBER BAY CIR E, OLDSMAR, FL 34677
$295,000255 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
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)
304 WOODLAKE WYNDE #304, OLDSMAR, FL 34677
$154,90078 Days on yellowkey MLS ID: TB8498051
0 Days Off yellowkey (back on 7/1/2026)
REDUCED by $5,000 (3.1%) on 06/30/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 674 Built: 1985Monthly Fee: $418 Tax: $2,403 (2025)Community: East Lake Woodlands Woodlake RunCondo
Taxes:$2,403
Remarks: Under contract-accepting backup offers. Great Buy reduced 25,000 from original listing price. If you’re looking for a waterfront location in a non-flood zone and an exceptional condominium, this scenic residence in Woodlake Run at East Lake Woodlands is the perfect fit. Set within a gated, very well-maintained community, the condo offers outstanding curb appeal, tranquil water views, mature landscaping, and a peaceful natural setting that defines one of Pinellas County’s most desirable areas Just steps from the front door, the heated pool provides year-round enjoyment and adds to the effortless lifestyle this property delivers. Reserved parking space in front of your unit for easy access. Inside, the comfortable living area features a soaring ceiling and opens to a screened-in lanai overlooking the lake, The adorable kitchen includes shaker-style wood cabinetry and granite countertops, with the dining area conveniently positioned just off the kitchen for easy everyday living and entertaining. The spacious primary bedroom features lovely water views, new flooring and a generously sized walk-in closet. Major improvements include a 2023 A/C system, 2026 water heater, a 2022 electrical panel and the roof replacement in 2017 provided by the HOA. A full-size washer and dryer are also included with the unit. The owner is conveying everything with the unit, including a new leather sofa, leather accent chair, king-size bedroom set, Smart TV, décor, artwork, and all household items, making this a turnkey opportunity. The maintenance-free lifestyle is impressively comprehensive and reasonable, covering the heated pool, exterior maintenance, roof, internet, cable, water, sewer, pest control, waste services, grounds maintenance, and gated entry. East Lake Woodlands is known for its scenic surroundings, two golf courses, and optional country club, tennis, and swimming amenities. The location is ideal, close to shopping, dining, and outdoor recreation, approximately fifteen minutes to Honeymoon Island State Park for stunning beaches and Gulf sunsets, and about thirty minutes to Tampa International Airport for convenient travel. The property is also located in zone x- no-flood zone. Whether you’re seeking a primary residence, seasonal retreat, or investment property, this waterfront condo offers outstanding value in a highly sought-after community and is priced significantly below the comparable sales. This opportunity won't last long
Listing is courtesy of: SELECT PROPERTIES INC (727-934-4099)
Listing Agent: Frank Acerra (727-410-9849)
137 BRENT CIR, OLDSMAR, FL 34677
$749,900112 Days on yellowkey MLS ID: O6394251
1 Days Off yellowkey (back on 7/1/2026)
REDUCED by $25,000 (3.2%) on 06/25/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2309 Built: 2002Monthly Fee: $473 Tax: $5,236 (2025)Community: Seaside EstatesTownhouse
Taxes:$5,236
Remarks: Under contract-accepting backup offers. Set within a gated, waterfront community in Oldsmar, this expansive townhouse at 137 Brent Circle offers a rare combination of space, thoughtful upgrades, and true Florida coastal living, complete with your own private, recently upgraded boat slip just steps out the back door. Featuring 3 bedrooms, 2 bathrooms, and approximately 2,300 square feet, this is one of the largest units in the neighborhood, ideally positioned at the end of a cul-de-sac for added privacy. The layout is both functional and versatile, offering expansive living areas, a large dining room, and flexible spaces perfect for a rec room, home office, or art studio, all enhanced by abundant natural light and gorgeous water views throughout. What truly sets this home apart is its direct connection to Upper Tampa Bay, where dolphins, manatees, and native wildlife are often seen. Enjoy ridiculously beautiful water views from dual balconies, perfectly positioned for both sunrise and sunset, because here, the lifestyle is just as important as the home itself. The kitchen has been professionally remodeled and architecturally designed, with renovations thoughtfully planned by an architect and interior designer, serving as a stunning focal point of the home. Additional interior upgrades include luxury flooring throughout, fresh interior paint, custom stair railing, and beautiful ceiling fans that elevate both style and comfort. The primary suite features a dramatic bath with travertine tile and oversized closets, while a generous laundry room adds everyday convenience. Practical upgrades provide peace of mind, including a new air conditioning system exceeding current codes and hurricane shutters on every window. The home also features a 3-car tandem garage, offering ample space for vehicles, storage, or recreational gear, with the option to add an elevator in the future if desired. Step outside to enjoy freshly painted balconies and a newly updated screened enclosure, creating the perfect setting to relax, entertain, and take in the views, because yes, wine really does taste better out here. The community enhances the lifestyle even further with a pool and hot tub, kayak launch, lighted boardwalk, and an active social committee. Located just minutes from the Safety Harbor boat launch, as well as a variety of restaurants, bars, parks, and entertainment, this home offers both tranquility and convenience. Oldsmar itself is known for its abundance of parks and natural beauty, making it a hidden gem along the Gulf Coast. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
138 BLUE MARLIN DR, OLDSMAR, FL 34677
$349,900217 Days on yellowkey MLS ID: TB8452561
2 Days Off yellowkey (back on 7/1/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1364 Built: 2016Monthly Fee: $120 Tax: $4,005 (2025)Community: Gull-Aire VillageModular Home
Taxes:$4,005
Remarks: Under contract-accepting backup offers. Opportunities like this rarely come along. Set on a true double lot, this 2016 Skyline home offers an exceptional combination of space, privacy, and quality upgrades that are nearly impossible to replicate. With 3 bedrooms, 2 bathrooms, a one-car garage, and a massive carport with workshop, this property delivers flexibility and functionality rarely found in the community. Inside, vaulted ceilings and fresh paint create an open, airy feel, while a glass-enclosed living room addition off the dining area adds a sun-filled space perfect for entertaining or relaxing year-round. The kitchen is a showpiece, featuring custom white shaker cabinetry and stunning quartzite countertops that read more like artwork than stone. The bedroom layout provides privacy for guests, with two bedrooms sharing a full bath, while the primary suite offers a walk-in closet and a private bath with walk-in shower. Step outside and you’ll find what truly sets this property apart: rare outdoor space and privacy, enhanced by pavers ideal for grilling, gathering, and enjoying Florida living. Located in the sought-after Gull Aire community, residents enjoy a heated pool, golf-cart-friendly streets, and a vibrant social calendar featuring craft shows, dances, and live music at the community center. HOA is just $120 per month for both lots, and the land is owned—making this an exceptional and increasingly rare opportunity in today’s market. Across the street and within walking distancefrom restaurants, shopping and movies. Close to award winning golf courses, tampa international airport, beaches, recreation facilities and sporting events.
131 SABAL CT #E, OLDSMAR, FL 34677
$145,00059 Days on yellowkey MLS ID: TB8509741
REDUCED by $15,000 (9.4%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1987 Tax: $2,319 (2025)Community: Gardens Of Forest Lakes Condo TheCondo
Taxes:$2,319
Remarks: Welcome to this beautifully maintained condo in the heart of desirable East Lake Woodlands! Offering a spacious and inviting layout, this residence provides the perfect blend of comfort, convenience, and relaxed Florida living. LOW HOAs and fantastic amenities that include a full size pool, a kiddy pool, tennis/basketball/raquetball courts, and a playground. This light and bright unit features an open floor plan with generous living and dining areas, perfect for entertaining or relaxing at home. The kitchen offers ample cabinet and counter space with a functional layout ideal for everyday living. The primary suite includes a private bath and spacious closet space, while additional bedrooms provide flexibility for guests, family, or a home office. Great location near Honeymoon Island, RE Olds Park, Tampa International Airport, bike and walking trails, dog parks, shopping, restaurants, live theater, museums, and activities in downtown St. Pete and Tampa.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Paul Ly (813-841-4655)
2151 DIAMOND CT, OLDSMAR, FL 34677
$1,350,000263 Days on yellowkey MLS ID: TB8440175
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
Elementary School: Cypress Woods Elementary-PN
Remarks: 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)
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