Location: Oldsmar
Do Not Show Listings
2151 DIAMOND CT, OLDSMAR, FL 34677
$1,350,000212 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,378
Elementary School: Cypress Woods Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
Remarks: Welcome to 2151 Diamond Court ~ Where luxury meets everyday comfort and style. This beautifully updated residence in the exclusive, gated community of Diamond Crest at East Lake Woodlands offers stunning water and conservation views and a thoughtfully designed 3-way split floor plan with a dedicated front office. From the moment you step inside, you’ll notice the meticulous attention to detail. The spacious, NEWLY RENOVATED GOURMET KITCHEN features custom cabinetry, quartz countertops, Café Platinum Collection appliances (including double wall ovens with air fryer and 36” induction cook-top), and a show-stopping triple frosted glass pantry door. The kitchen opens seamlessly to the expansive great room where a 60”, three-sided glass linear fireplace and floor-to-ceiling picture window frame the serene natural backdrop. Nearly every major improvement has already been completed for peace of mind — including a BRAND NEW TILE ROOF, PGT LOW-E IMPACT WINDOWS, luxury plank flooring throughout, and a NEW PANORAMIC-VIEW SCREENED LANAI enclosure that beautifully extends your indoor living outdoors. Enjoy unobstructed views of lush conservation and tranquil water, making this home perfect for both relaxing and entertaining. The primary suite is generously sized with large windows that bring the outdoors in, while each guest wing offers privacy and comfort. All bathrooms have been tastefully remodeled, and remote-operated window treatments and ceiling fans add to the home’s thoughtful conveniences. Outside your front door, discover the newly re-imagined Ardea Country Club, offering championship golf, state-of-the-art racquet facilities, expanded dining, resort-style amenities, and engaging spaces for all ages. Membership is optional — simply visit the clubhouse for details. Location is unbeatable — tucked in a quiet, private setting yet just 20–25 minutes to Tampa International Airport, award-winning Gulf beaches, and the vibrant dining and shopping of both Tampa and Clearwater. This home truly has it all — luxury, convenience, and a view you’ll never tire of. Come experience it in person.
Listing is courtesy of: RE/MAX ELITE REALTY (727-785-7653)
Listing Agent: Michelle Johncola (727-515-2415)
1744 MAPLELEAF BLVD, OLDSMAR, FL 34677
$610,00082 Days on yellowkey MLS ID: W7883065
0 Days Off yellowkey (back on 5/12/2026)
REDUCED by $15,000 (2.4%) on 04/20/2026
Bed: 6 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3124 Built: 2000Monthly Fee: $12 Tax: $4,563 (2025)Community: Eastlake Oaks Ph 4Spa: NoSingle Family
Taxes:$4,563
Elementary School: Oldsmar Elementary-PN
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Perfection and CHARM has arrived in popular Oldsmar, FL. This south east facing- AMAZING 6 bedroom, 3 full bathroom two-story corner lot home is nothing short of dreamy. With a full privacy fence, new exterior paint and new carpet upstairs, a spacious screened in lanai WITH HURRICANE/SAFE ROOM, you can not let this pass you by. Step inside to a majestic entryway and a floor plan with a purpose. Front door has a slider screen on it so you can open the front door all year. To your right, you have a Florida room and dining room combo perfect for entertaining or enjoying the picturesque views. This connects to the dining space that can accommodate a rather large setting. Once through this space, you get to the heart of the home. This GORGEOUS kitchen is jam-packed with positives! Center island with electricity, ample counter space, tons of cabinetry, a separate bar/serving area with pass through to the living room, a quaint dinette with views into the backyard, large pantry, and stainless steel appliances. The living offers great space and is cozy and bright. There is a GUEST ROOM on the main level tucked in the back that has a full bathroom near it; an absolute necessity in today's market. Upstairs, take note of the wide hallways. There are 5 MORE spacious bedrooms here! The primary retreat is separated for privacy and the ensuite has NEW luxury vinyl flooring and walk-in shower and garden tub. Huge owners closet. The third FULL bathroom is shared for the other rooms and has been tastefully updated with modern tile details and shiplap. Smart technology for day time and night time lighting or play some music while getting ready! The outdoor oasis is open to whatever your lifestyle desires. The hurricane/safe room has independent air flow and electricity. NEWER WINDOWS! UV system for AC unit. EastLake Oaks does provide a COMMUNITY POOL for all to enjoy. This home is close to medical, grocery, restaurants, parks, easy travel to Tampa/Clearwater and the beaches/airports. PRIME location and popular schools. No CDD fees, low HOA, and low flood insurance. 5 years warranty on AC units. Click on both links for a two tours!
Listing is courtesy of: RE/MAX CHAMPIONS (727-807-7887)
Listing Agent: Kristy Thurber (904-271-1950)
435 LAKEVIEW DR, OLDSMAR, FL 34677
$475,00062 Days on yellowkey MLS ID: TB8489554
REDUCED by $14,000 (2.9%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1570 Built: 1984Monthly Fee: $35 Tax: $6,675 (2025)Community: Manors Of Forest Lakes TheSpa: YesSingle Family
Taxes:$6,675
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to Forest Lakes and this beautifully appointed, immaculately maintained 3-bedroom, 2-bath, 2-car garage home offering 1,569 square feet of living space. Nestled in an exceptional school district, this home has been lovingly cared for and is truly immaculate. It features soaring vaulted ceilings, a cozy fireplace, and French doors leading to a large backyard retreat. The gorgeous kitchen with granite, newer stainless steel appliances, and pantry overlooks both the living room and the pool, which is fully screened and features a child-proof fence for added security. The master bedroom offers a private en-suite bath, providing a tranquil retreat. Other highlights for this house include a new 200 amp electrical panel with whole home surge protector, new switches and recepticals throughout and a dedicated 50 amp E.V. car charger. A four-year-old roof, with newer windows, and a new garage door, makes Florida living a breeze. Outside, enjoy the large pool area and spa with a new pump, timer, and automatic cleaner, a fire pit, and a host of amenities. An oversized garage also features a dedicated electric outlet for your vehicle, a washer and dryer, and a newer water heater. The community offers a lakefront playground, a barbecue area, a fishing dock, and courts for basketball, tennis, and racquetball. With very low monthly HOA fees and a large community pool, this move-in-ready home is a true gem. Don’t miss out! Nothing else to do but move in!
Listing is courtesy of: COLDWELL BANKER REALTY (727-581-9411)
Listing Agent: Kim Krenek (727-262-3181)
50 WILLOWOOD LN, OLDSMAR, FL 34677
$1,499,900103 Days on yellowkey MLS ID: TB8475420
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4172 Built: 1987Monthly Fee: $240 Tax: $8,709 (2024)Community: Deerpath Unit OneSingle Family
Taxes:$8,709
Remarks: Tucked away on a quiet lane in the highly desirable East Lake Woodlands community, this beautifully updated residence at 50 Willowood Ln offers exceptional space, flexibility, and privacy—perfect for today’s modern lifestyle. Featuring 4-6 bedrooms: 4 true bedrooms PLUS a dedicated office (5th bedroom) and an additional flex room with its own private entrance (ideal as a 6th bedroom, guest suite, or in-law space), this home provides endless possibilities. Of note, two bedrooms are located upstairs, with a jack-and-jill bath and massive loft area, also with infinite uses for entertaining, studying, working, gaming or an additional family room. Step inside to discover a light-filled, open-concept layout with generous living and dining areas designed for both everyday comfort and entertaining. The spacious kitchen flows seamlessly into the main living space and offers ample cabinetry, counter space, and a functional layout for the home chef. The primary suite is a private retreat, complete with an en-suite bath and ample closet space, while the secondary bedrooms are well-sized and thoughtfully positioned. The separate office provides the perfect work-from-home setup, and the versatile flex room—with its own entrance—adds incredible value and adaptability. Enjoy Florida living outdoors with a serene backyard setting, with almost 2,000sf of screened-in pool/lounge space, perfect for relaxing or entertaining, and a full bath! Located within the gated East Lake Woodlands community, residents enjoy access to golf, tennis, and country club amenities (optional membership), all while being just minutes from top-rated schools, shopping, dining, and Gulf Coast beaches. Key Highlights include 4 Bedrooms + Office (5th Bedroom Option) + Flex Room (6th Bedroom Option with Private Entrance), a Flexible floor plan with a multitude of options. This home is located in a sought-after double-gated community, convenient to beaches, airports, shopping, and dining. This is a rare opportunity to own a highly adaptable home in one of Oldsmar’s most coveted neighborhoods—schedule your private showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Melissa Pranzo (646-509-7350)
504 FEDERAL ST, OLDSMAR, FL 34677
$1,180,000233 Days on yellowkey MLS ID: TB8427180
REDUCED by $90,000 (7.1%) on 04/25/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2961 Built: 2026 Tax: $1,498 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$1,498
Remarks: This stunning new three-story residence by Danva Construction perfectly blends modern luxury with resilient, high-end design. Located at 504 Federal Street in the desirable waterfront community of Oldsmar, this home is built for peace of mind with a solid concrete block structure, pilings, impact-resistant windows, and a durable TPO roof, all backed by a comprehensive builder warranty. The exterior is finished in Sherwin Williams Chantilly Lace, creating a clean, modern curb appeal enhanced by professional landscaping and a signature magnolia tree. Inside, the open-concept layout features soaring ceilings, porcelain tile flooring, and a gourmet kitchen that serves as a true showpiece. The kitchen is complete with a waterfall island, designer backsplash, and premium Bosch 800-series appliances. The luxurious primary suite offers a spa-inspired retreat with a freestanding soaking tub and porcelain tiled walls. Indoor-outdoor living shines with a second-floor porcelain tile balcony and a covered lanai. Note that some images are virtually staged to show the home's potential. Perfectly positioned just one block from Tampa Bay and five minutes to Mobbly Bayou Beach Park, this home offers a lifestyle of privacy and convenience. Oldsmar is a charming waterfront community known for its parks and trails, with effortless access to Tampa International Airport (under 20 mins), Downtown Tampa (30 mins), and the world-famous beaches of Clearwater. The location is a true paradise for outdoor enthusiasts and urban commuters alike. You are steps away from the Upper Tampa Bay Trail, offering miles of scenic cycling and jogging paths. Just minutes away, the historic downtown Oldsmar district provides an array of boutique dining, local craft breweries, and community events like the annual Oldsmar Days. For shopping, the International Plaza and Bay Street are a short drive away, offering world-class retail experiences. Nature lovers will appreciate being adjacent to the Mobbly Bayou Wilderness Preserve, featuring over 400 acres of kayaking, hiking, and even a zip-line adventure park. Golfers can enjoy proximity to several championship courses including the nearby East Lake Woodlands Country Club. Whether you are catching a flight for business or spending a Saturday at Honeymoon Island State Park, this central location puts the very best of the Florida Gulf Coast right at your doorstep. This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location.This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location. All financing information is for illustrative purposes only and not a commitment to extend credit.
Listing is courtesy of: ENGEL & VOLKERS TAMPA DOWNTOWN (813-863-1986)
Listing Agent: Virginia Torres Bond (813-352-2933)
387 TAVERNIER CIR, OLDSMAR, FL 34677
$459,90089 Days on yellowkey MLS ID: TB8480272
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1808 Built: 1997Monthly Fee: $75 Tax: $2,383 (2025)Community: Fountains At Cypress Lakes Ii-B TheSingle Family
Taxes:$2,383
Remarks: You've found your Florida dream home in the heart of Oldsmar. This spacious 1808 sq ft 3 bedroom 2 bath home offers many extras including a large primary bedroom suite with a bathroom that boasts a garden tub with a separate shower to relax at the end of a long day. The 2nd Bathroom is strategically located between Bedroom 2 and 3. The kitchen & both bathrooms have wooden cabinets with matching luxurious granite. Home has an extra room that can be used as a study or office and a separate laundry room. Perfect for pets or kids with its large fenced back yard. Make this beautiful home that is well situated yours and take advantage of all that the City of Oldsmar has to offer including the multiple festivals and events the Cypress Forest Center where there is a splash park, various sports activities less than a mile away. The elementary school is less than half a mile. Shopping is nearby. Beaches, parks, dining, hospitals as well as both airports - Tampa International and Clearwater. Come see this home before it's too late!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Alan Prather (813-400-5345)
506 FEDERAL ST, OLDSMAR, FL 34677
$1,180,000233 Days on yellowkey MLS ID: TB8434625
REDUCED by $90,000 (7.1%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2961 Built: 2025 Tax: $1,498 (2024)Community: Oldsmar Rev MapSingle Family
Remarks: One or more photo(s) has been virtually staged. This stunning new three-story residence by Danva Construction perfectly blends modern luxury with resilient, high-end design. Located at 504 Federal Street in the desirable waterfront community of Oldsmar, this home is built for peace of mind with a solid concrete block structure, pilings, impact-resistant windows, and a durable TPO roof, all backed by a comprehensive builder warranty. The exterior is finished in Sherwin Williams Chantilly Lace, creating a clean, modern curb appeal enhanced by professional landscaping and a signature magnolia tree. Inside, the open-concept layout features soaring ceilings, porcelain tile flooring, and a gourmet kitchen that serves as a true showpiece. The kitchen is complete with a waterfall island, designer backsplash, and premium Bosch 800-series appliances. The luxurious primary suite offers a spa-inspired retreat with a freestanding soaking tub and porcelain tiled walls. Indoor-outdoor living shines with a second-floor porcelain tile balcony and a covered lanai. Note that some images are virtually staged to show the home's potential. Secure a 1% rate buy-down when using our preferred lender, Revolution Mortgage. Perfectly positioned just one block from Tampa Bay and five minutes to Mobbly Bayou Beach Park, this home offers a lifestyle of privacy and convenience. Oldsmar is a charming waterfront community known for its parks and trails, with effortless access to Tampa International Airport (under 20 mins), Downtown Tampa (30 mins), and the world-famous beaches of Clearwater. The location is a true paradise for outdoor enthusiasts and urban commuters alike. You are steps away from the Upper Tampa Bay Trail, offering miles of scenic cycling and jogging paths. Just minutes away, the historic downtown Oldsmar district provides an array of boutique dining, local craft breweries, and community events like the annual Oldsmar Days. For shopping, the International Plaza and Bay Street are a short drive away, offering world-class retail experiences. Nature lovers will appreciate being adjacent to the Mobbly Bayou Wilderness Preserve, featuring over 400 acres of kayaking, hiking, and even a zip-line adventure park. Golfers can enjoy proximity to several championship courses including the nearby East Lake Woodlands Country Club. Whether you are catching a flight for business or spending a Saturday at Honeymoon Island State Park, this central location puts the very best of the Florida Gulf Coast right at your doorstep. This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location.This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location. All financing information is for illustrative purposes only and not a commitment to extend credit.
Listing is courtesy of: URBAN REAL ESTATE US (786-322-9729)
Listing Agent: Jessica Scialletti (754-217-9348)
470 HICKORYNUT AVE, OLDSMAR, FL 34677
$765,00077 Days on yellowkey MLS ID: TB8485715
REDUCED by $30,000 (3.8%) on 05/08/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2922 Built: 1987Monthly Fee: $110 Tax: $10,515 (2025)Community: East Lake WoodlandsSpa: YesSingle Family
Taxes:$10,515
Elementary School: Forest Lakes Elementary-PN
Remarks: One or more photo(s) has been virtually staged. Located inside the highly desirable gated community of East Lake Woodlands, this spacious 4-bedroom, 2.5-bath residence offers an expansive 2,922 sq ft of living space on an oversized lot with peaceful water views. Step inside to soaring ceilings and an open, light-filled floor plan designed for both everyday living and entertaining. The home features expansive living areas including a formal living and dining room and a large family room with fireplace. New Luxury Vinyl Plank flooring installed in 2026 runs throughout the main living areas, creating a modern and cohesive look, while new carpet installed in 2026 adds comfort to the guest bedrooms. The updated kitchen features granite countertops and stainless-steel appliances, flowing seamlessly into the main living space and breakfast area—perfect for gatherings and everyday living. The spacious primary suite offers direct access to the pool area along with a private bath and generous closet space. Enjoy Florida living at its best with a screened pool and lanai overlooking a tranquil pond, providing both privacy and relaxing water views. The home also features fresh exterior paint completed in 2026 and a 3-car garage, all situated on a generous homesite within this established golf-course community. Residents of East Lake Woodlands have the option to join the Ardea Country Club, a recently renovated club offering two championship golf courses, tennis and pickleball courts, fitness facilities, resort-style pool, and multiple dining venues. The club provides a vibrant social calendar and family-friendly amenities, creating a true country club lifestyle right inside the community. Located just minutes from shopping, dining, top-rated schools, and major commuter routes, this home offers convenient access to Tampa International Airport, Gulf beaches, and the best of the Tampa Bay area. Close to all the Tampa Bay Area has to offer; Championship golf courses, Tampa International Airport, NHL, NFL, MLB events, Grand Prix, PGA events, fine dining, concerts, parks, biking trails, BMX events, and more. Begin Your Paradise Life Today.
Listing is courtesy of: PARADISE LIFE REALTY (727-698-2996)
Listing Agent: Lou Tutko (727-698-2996)
204 BENGAL CIR, OLDSMAR, FL 34677
$715,00082 Days on yellowkey MLS ID: O6388593
REDUCED by $20,000 (2.7%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2429 Built: 2013Monthly Fee: $65 Tax: $5,728 (2025)Community: Bungalow Bay EstatesSpa: YesSingle Family
Taxes:$5,728
Remarks: Stunning custom home with luxury upgrades, thoughtful design, and handicap-friendly features throughout. Perfectly designed for entertaining, this home blends elegant finishes with comfortable indoor-outdoor living. A grand foyer welcomes you into the spacious great room where a wall of three-pane sliding glass doors fully tucks away, seamlessly connecting the living space to the covered patio and pool area. The gourmet chef’s kitchen features granite countertops, high-end appliances, custom cabinetry, designer lighting, and a large island with seating and additional storage. A generous walk-in pantry closet provides excellent storage and functionality. The home is wired for sound with built-in surround speakers in the living room and screened porch, plus audio ports throughout the house so speakers can easily be connected in every room. The luxurious primary suite features a tray ceiling and three oversized walk-in closets, one currently used as a private office. The spa-like primary bath includes wraparound dual vanities, an air-jetted soaking tub, and a spacious shower with rain shower head and therapy jets. The suite also offers direct access to the patio and pool. Designed with accessibility in mind, the home includes extra-wide doorways for wheelchair access and a zero-threshold primary shower. Step outside to your private backyard retreat with a heated saltwater pool and spa featuring PebbleTec finish and a self-cleaning pop-up system, all set within a beautiful paver deck and screened porch with generous ceiling fans—perfect for year-round Florida living. Additional highlights include central vacuum, oversized laundry room, an oversized two-car garage with workshop space and service door, PVC privacy fencing, and irrigation on reclaimed water. Major updates provide peace of mind: New AC (March 2026), roof replaced late 2025, and water heater replaced late 2025. Conveniently located near waterfront parks, shopping, Tampa International Airport, and the beautiful Pinellas County beaches. Home has never flooded-high and dry!
Listing is courtesy of: GILLEN & ASSOCIATES (321-947-0912)
Listing Agent: Cynthia Weclew (813-507-7818)
4738 PEBBLE BROOK DR, OLDSMAR, FL 34677
$535,000142 Days on yellowkey MLS ID: TB8460875
2 Days Off yellowkey (back on 5/7/2026)
REDUCED by $14,000 (2.6%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 1996Monthly Fee: $470 Tax: $4,041 (2025)Community: Cross Creek - Unit TwoSingle Family
Taxes:$4,041
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy a Relaxing Lifestyle in the desirable Gated, Golf Community of East Lake Woodlands and the convenience of Less Maintenance responsibilities! This home provides Privacy and Stunning Water Views with a Large, Covered Screened Lanai to enjoy that morning cup of coffee or evening glass of wine. Plus it’s situated in the preferred Zone X so no flood insurance is required. An added bonus is the Cul de Sac location and longer driveway for more parking for family and guests. Volume Ceilings, Crown Molding and an Open Concept highlight a versatile floor plan featuring 2 Bedrooms plus an Office or Den - complete with Custom Paneling, Spacious Desk and Bookcase and even the Luxury of a Wood Burning Fireplace! Open to the generous 28’ x 18’ Great Room, the bright Kitchen features an Eat-In Breakfast Area, Bay Windows with Plantation Shutters, Double Ovens, French Door Fridge and plenty of storage. The Primary Suite features 2 Walk-In Closets complete with Custom Built-in Shelving and Pull-Down Clothing Racks and a Large Bath with Dual Vanities, Large Soaking Tub and Separate Shower. Relax since the reasonable HOA fee includes Lawn Maintenance with Mowing, Fertilizing and Mulching, Cable TV and Internet, Trash and Recycling Collection, a Sparkling Community Pool and Spa for Cross Creek residents, Escrow Reserves, Pressure Cleaning of Roofs and Exterior Painting every 7 years. Home Updates include New Water Heater in Dec. 2025, New Tile Roof in 2019, A/C Unit New in 2018. Washer and Dryer included in the sale plus Manual and Remote-Controlled Exterior Hurricane Shutters and a Generac Generator. This long-time owner had no issues with the 2024 Hurricanes. Enjoy that Gorgeous View and put your touches on this home since this amazing price takes updating into account. All this in a Great Location convenient to Tampa International Airport, beautiful Beaches, Medical Facilities, Professional Sporting Events and Fine Dining. A variety of memberships to Ardea Country Club are available for additional fees and include access to 2 Golf Courses, a Fitness Center, Heated Lap Pool and Freeform Pool, Pickle Ball and Tennis plus Dining and a host of Activities and Events!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
400 SHORE DR E, OLDSMAR, FL 34677
$1,000,00095 Days on yellowkey MLS ID: TB8478151
3 Days Off yellowkey (back on 5/7/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1890 Built: 1957 Tax: $3,995 (2025)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$3,995
Remarks: Under contract-accepting backup offers. The Ultimate Waterfront Canvas: 150ft of Panoramic Bay Frontage. Secure a legacy-grade homesite on one of the most expansive waterfront lots in Oldsmar. Situated on almost ¾ acre on the prettiest street in Oldsmar, 400 Shore Drive E offers a rare 150 feet of direct, unobstructed frontage on Safety Harbor. This is a premier opportunity for a visionary buyer or elite builder to bypass the limitations of existing construction and design a bespoke custom estate from the ground up. While the current structure is a teardown (sold as-is), its presence provides a significant footprint and potential impact fee advantages for your new architectural masterpiece. Experience total privacy and some of the most breathtaking, wide-water sunset views found anywhere in the Tampa Bay region. Just minutes from the refined trails of RE Olds Park and the area’s top dining, this location perfectly balances secluded coastal living with urban convenience. Don’t just buy a home—build a landmark on the water’s edge.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Crystal Tipton, Mrs (813-436-7229)
1802 CHINABERRY DR, OLDSMAR, FL 34677
$375,000219 Days on yellowkey MLS ID: TB8439498
5 Days Off yellowkey (back on 5/7/2026)
INCREASED by $6,000 (1.6%) on 04/30/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1358 Built: 1972 Tax: $865 (2024)Community: Harbor Palms-Unit OneSpa: NoSingle Family
Taxes:$865
Remarks: Easily 3 Bedroom (EVEN 4) - Total Renovation - Block/Slab Home - Large Indoor Laundry - 2 Car Garage - New Roof - New AC - New Water Heater - New Kitchen - Solid Wood Cabinets - Solid Surface Counters - New Bathrooms - New Floors - Interior and Exterior Paint - Landscaping - Large Fenced Yard -
Listing is courtesy of: FOXX AND ASSOCIATES (877-538-6868)
Listing Agent: Dan Nease (727-354-2222)
549 LONGWOOD CIR, OLDSMAR, FL 34677
$525,00021 Days on yellowkey MLS ID: A4692285
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1344 Built: 1984Monthly Fee: $30 Tax: $5,336 (2025)Community: Manors Of Forest Lakes TheSingle Family
Taxes:$5,336
Remarks: Welcome to your private retreat in the heart of Oldsmar. Located in the desirable Longwood community, this beautifully maintained home offers the perfect blend of comfort, charm, and Florida living. Surrounded by mature landscaping and peaceful streets, 549 Longwood Circle features spacious living areas, abundant natural light, and an inviting layout ideal for both entertaining and everyday living. Step outside to enjoy a relaxing backyard setting with room to unwind, host gatherings, or create your own outdoor oasis. Conveniently located near top-rated schools, parks, shopping, dining, and the Gulf beaches, this home delivers both privacy and accessibility. Whether you're looking for a full-time residence or a seasonal getaway, this property is an incredible opportunity to own a piece of paradise in one of Tampa Bay’s most sought-after communities.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Susan Kolesnikov (916-272-9177)
436 LAFAYETTE BLVD, OLDSMAR, FL 34677
$700,000300 Days on yellowkey MLS ID: TB8412856
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2695 Built: 1994 Tax: $10,665 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$10,665
Remarks: One or more photo(s) has been virtually staged. Must see this 4 bedroom/2.5 bath home with almost 2700 Sq/Ft on one of the highest/majestic lots in downtown Oldsmar! Relax by the wood fireplace with your family in the comfortable living room! Entertain guests, make a fire-pit area, or start your own garden in the expansive backyard with Lanai! Lot is almost a half acre! Fantastic kitchen with granite countertops, stainless steel appliances, plenty of wood cabinets/countertop space and breakfast bar! Large master bedroom with enormous walk-in closet and newly updated master bath with soaking tub, his-and-her sinks and high end stone tile throughout! Take the private glass vacuum elevator to the second floor! Also a dining area, family room and office! Some additional upgrades include: High ceilings, sprinkler system, hurricane windows, whole house instant hot water, water softener/filter system, updated flooring throughout, vinyl fencing, smart-home switches/recessed lighting, updated 2 car garage, block home. Short walk to Bicentennial Park that has a dog park, playground, tennis/basketball/pickleball courts. Also near boat launch, hiking/biking trails, library, fishing pier, museum and schools. Home had no hurricane/water damage! Oldsmar is located centrally in north Pinellas County and is a short drive to world class gulf beaches, Tampa International Airport, sporting venues, theater, shopping, restaurants and much, much more!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Dillon Currier (727-919-4214)
200 LEE ST, OLDSMAR, FL 34677
$1,450,00022 Days on yellowkey MLS ID: TB8505047
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1250 Built: 1957 Tax: $4,470 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$4,470
Remarks: This is a packaged listing with MLS #TB8504841 for sale & close together. Total land 33,806 sf. A unique prime development opportunity in the heart of The City of Oldsmar with a 350 ft frontage on State St E between SWC of Lee and SEC of Washington Ave with a zoning designation TCCN ( Town Center Commercial Neighborhood District). A dynamic growth opportunity across from the proposed Town Center that includes City hall, 2 business and 4 story apartment building and public area. Near by Oldsmar City Hall, chamber of commerce, The Galleria, Odeon Town Home square and Washington square. Easy access to Tampa Rd, shopping, restaurants, hotels, beaches, hospitals, Tampa Int'l and St Pete/ CLW Int'l airports.
Listing is courtesy of: IDEAL REALTY ADVISORS, LLC (727-647-2814)
Listing Agent: Victor Suhweil (727-647-2814)
1734 MAPLELEAF BLVD, OLDSMAR, FL 34677
$515,00056 Days on yellowkey MLS ID: TB8492116
3 Days Off yellowkey (back on 5/5/2026)
REDUCED by $10,000 (1.9%) on 04/23/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2428 Built: 2000Monthly Fee: $13 Tax: $4,787 (2025)Community: Eastlake Oaks Ph 4Single Family
Taxes:$4,787
Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! Welcome to 1734 Mapleleaf Boulevard, a beautifully maintained two-story home in the heart of Oldsmar offering the perfect blend of space, comfort, and peace of mind. With 4 generously sized bedrooms and 2.5 bathrooms, this home is designed for both everyday living and effortless entertaining. As you step through the elegant glass front door with sidelight, you’re welcomed into a bright, inviting interior filled with natural light, highlighted by a large picture window that frames the serene backyard. The main level flows seamlessly between the living, dining, and kitchen areas, creating a functional and open feel without sacrificing warmth or character. Upstairs, all four bedrooms are thoughtfully positioned for privacy, including a spacious primary suite featuring a walk-in closet, double vanity, soaking tub, separate shower, and a private water closet—creating a true retreat at the end of the day. The additional bedrooms are all well-sized, offering flexibility for family, guests, or a home office. Step outside to your extended screened-in paver patio, a standout feature that makes outdoor living easy and enjoyable year-round. Whether you’re sipping your morning coffee or hosting friends and family, this space is built to be enjoyed. The backyard offers privacy and a peaceful setting with minimal maintenance required. This home has never flooded, even through recent storms, and includes a transferable flood policy—an incredible value that adds an extra layer of confidence for the next owner. Additional features include a 2-car garage, ample storage, and a well-cared-for condition that makes this home truly move-in ready. Ideally located near parks, shopping, dining, and with easy access to Tampa, this home offers the lifestyle you’ve been looking for in one of Oldsmar’s most desirable areas.
Listing is courtesy of: LPT REALTY, LLC. (877-366-2213)
Listing Agent: Ashley Mason (813-735-2495)
103 CUTLASS WAY, OLDSMAR, FL 34677
$345,00093 Days on yellowkey MLS ID: TB8479354
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 2016Monthly Fee: $255 Tax: $6,017 (2025)Community: Hayes Park VillageSingle Family
Taxes:$6,017
Remarks: Welcome to this impeccably maintained 3 bedroom, 2.5 bath residence in the highly sought-after Hayes Park Village in Oldsmar. Offering approximately 1,392 square feet of thoughtfully designed living space, this home showcases a beautifully renovated kitchen with contemporary finishes, ceramic flooring on the first floor, and carpet flooring on the second floor. The split-bedroom floor plan and abundant natural light create a bright, open atmosphere that is both welcoming and functional. Step outside to a covered porch overlooking a breathtaking pond and a serene conservation area behind it —providing exceptional privacy. Combining generous living space, peaceful privacy, and an unbeatable location, this exceptional home is ready to welcome YOU!
Listing is courtesy of: FLORIDA COMMERCIAL GROUP (813-935-9600)
Listing Agent: Leyla Mohebbi (813-359-7999)
2159 WARWICK DR, OLDSMAR, FL 34677
$800,00075 Days on yellowkey MLS ID: TB8486224
1 Days Off yellowkey (back on 5/4/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2673 Built: 1996Monthly Fee: $133 Tax: $6,682 (2025)Community: Warwick HillsSpa: NoSingle Family
Taxes:$6,682
Remarks: Under contract-accepting backup offers. It's time to buy in Eastlake Woodlands! Settle in to your dream home in the coveted subdivision of Warwick Hills within Eastlake Woodlands. Eastlake Woodlands is a renowned golf and tennis community that offers a full range of amenities for an additional membership including the fully remodeled Ardea Country Club, championship golf courses, tennis, pickle ball, resort style pools and more. This stunning 4bedroom, 3 bath pool home spans 2,673 sf and offers a bevy of upgrades. Step into the fully updated kitchen, featuring beautiful quartz counters, newer stainless steel appliances, updated cabinetry and large center island- perfect for any culinary enthusiast. The 3 way split floor plan boasts brand new wood floors throughout the main living area and primary suite, providing a warm and inviting atmosphere. Relax on the outdoor screened patio that faces a serene conservation area, where you can enjoy watching deer and other wildlife or splash in the cool pool. The spacious lot, over 8,000 sq. ft., offers plenty of room for outdoor activities and entertainment. Modern upgrades include a tankless water heater installed in 2024, new impact windows (except for the sliding door and corner windows) in 2023, and fresh exterior paint in 2024. The house also features a suburban propane tank and the patio is plumbed for gas, making it ready for an outdoor kitchen. Don‘t miss out on this incredible opportunity to own a meticulously maintained home in a desirable location. Schedule your showing today and experience all that this Eastlake Woodlands gem has to offer!
Listing is courtesy of: PALERMO REAL ESTATE PROF. INC. (813-637-0117)
Listing Agent: Cristina Lorenzo (813-451-4055)
405 HOLLY HILL RD, OLDSMAR, FL 34677
$660,00027 Days on yellowkey MLS ID: TB8503763
0 Days Off yellowkey (back on 5/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2311 Built: 1979Monthly Fee: $149 Tax: $3,606 (2026)Community: East Lake WoodlandsSpa: YesSingle Family
Taxes:$3,606
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Welcome to your private retreat in the highly sought-after gated community of East Lake Woodlands in Oldsmar. This beautifully updated 3-bedroom, 2-bathroom home features a thoughtfully designed open split floor plan that provides both comfort and privacy. Step inside to a stunning living room with vaulted ceilings and exposed beams, creating a warm yet spacious atmosphere. Entertain with ease at the bar, or open the French doors to seamlessly extend your living space onto the re-screened lanai. Outside, enjoy your own slice of Florida paradise with a sparkling PebbleTec pool and spa overlooking the scenic golf course. The home has been fully updated, including a modern updated kitchen equipped with granite countertops, stainless steel appliances, and soft-close drawers. Both bathrooms have been tastefully renovated, with the spacious primary suite offering dual sinks with granite counters and two walk-in closets. ADDITIONAL RECENT UPGRADES INCLUDE THE REMOVAL OF POPCORN CEILINGS, NEW ATTIC INSULATION, REPLACEMENT OF ALL INTERIOR DOORS, A NEW POOL MOTOR, AND BEAUTIFUL PAVERS INSTALLED IN THE DRIVEWAY, WALKWAY, AND PORCH. Major improvements such as a NEW ROOF (2025) and HVAC system (2017) add even more value and peace of mind. Further enhancements include HURRICANE RATED WINDOWS IN ALL BEDROOMS AND THE BATHROOM, a WATER SOFTNER SYSTEM, NEW WINDOW TREATMENTS, NEW OUTDOOR LIGHTING, ADDED LAUNDRY ROOM FEATURES, UPDATED BASEBOARDS THROUGHOUT, —just to name a few. Additional highlights include a cozy fireplace, a 240 sq ft BONUS ROOM perfect for a home office or gym, with flex space that offers endless possibilities. East Lake Woodlands is a deed-restricted, gated community offering exceptional amenities including golf, pickleball, tennis courts, a community pool, and a clubhouse. Ideally located, this home is approximately 25 minutes from Tampa International Airport, 20 minutes from St. Pete-Clearwater International Airport, 30 minutes from Clearwater Beach, and 35 minutes from Honeymoon Island. Enjoy easy access to a variety of nearby restaurants, shopping, and everyday conveniences. Don’t miss your opportunity to own this exceptional home—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Jan Thomas-Smith (727-492-7825)
347 COUNTRY CLUB DR, OLDSMAR, FL 34677
$429,000105 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)
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