Location: Oldsmar
Do Not Show Listings
420 CYPRESS VIEW DR, OLDSMAR, FL 34677
$485,000Listed 05/07/2026 11:41AM MLS ID: TB8505264
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1870 Built: 1998Monthly Fee: $140 Tax: $4,405 (2025)Community: Preserve At Cypress Lakes Ph I TheSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,405
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Welcome to your private slice of paradise in Oldsmar! Updates include a 2026 AC, 2026 Roof, and 2021 Water Heater for peace of mind. This beautifully maintained three-bedroom, three-bathroom pool home offers the perfect blend of comfort and Florida living - nestled on a premium lot with preserve views, no rear or side neighbors, and only one neighboring home for added privacy. Additional updates include whole-house water and air filtration added in 2025, and the home was painted in 2021. From the moment you arrive, you’ll be greeted by easy-to-maintain tropical landscaping that enhances the home’s curb appeal. Step inside to a light and bright interior featuring a welcoming front living room with a cozy fireplace and crown molding that continues throughout the home. High ceilings create an open, airy feel as you move through the thoughtfully designed layout. The spacious kitchen is conveniently located to your right and is well-equipped with abundant cabinetry, a separate pantry for extra storage, and a charming breakfast nook. A laundry room sits just off the kitchen for added convenience. The kitchen opens seamlessly to the main living area, where wood-look vinyl flooring, a ceiling fan, and views of the pool make it the perfect space to relax or entertain. The primary suite is generously sized with high ceilings, wood-look vinyl flooring, and an attached bathroom featuring a dual-sink vanity, soaking tub, and separate glass-enclosed shower. Additional bedrooms are comfortably sized and include ceiling fans, offering flexibility for family, guests, or a home office. Step outside and truly embrace the Florida lifestyle. The screened-in pool area is surrounded by a serene, tree-lined preserve, creating a peaceful and private outdoor retreat. Enjoy a covered space ideal for dining, grilling, or simply lounging poolside year-round. Located near highly rated schools, as well as a variety of dining and shopping options, this home offers both convenience and tranquility in one desirable package. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Jeffrey Borham, Pa (866-308-7109)
382 FOUNTAINVIEW CIR, OLDSMAR, FL 34677
$520,0001 Day on yellowkey MLS ID: TB8499334
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1875 Built: 1995Monthly Fee: $95 Tax: $5,232 (2025)Community: Fountains At Cypress Lakes TheSingle Family
Taxes:$5,232
Remarks: Welcome home to this stunning, move-in ready 4 bedroom, 2 bath split floor plan in one of Oldsmar's most sought-after neighborhoods - and zoned for some of the top-rated schools in the area. From the moment you walk in, you'll notice the difference that thoughtful, high-quality updates make. Soaring vaulted ceilings and elegant columns greet you in the formal living room, while French doors open to a versatile den or 4th bedroom. The heart of the home is a beautifully updated gourmet kitchen featuring shaker-style soft-close cabinetry, quartz countertops, subway tile backsplash, stainless steel appliances, a breakfast bar, and a sunny breakfast nook ... all flowing naturally into the family room and out to the screened porch through a slider, perfect for that indoor-outdoor Florida lifestyle. The primary suite is a true retreat, complete with a spa-inspired bath boasting dual sinks, quartz countertops, and a step-in shower. Two additional bedrooms share a well-appointed bath. Throughout the home you'll find brand new engineered hardwood and LVP flooring, freshly painted interiors, popcorn ceilings removed, and updated baths - every detail has been addressed. And the big ticket items? All taken care of. Brand new roof (May, 2026), newer appliances, new garage door motor, new back pavers, and a fully fenced lot with complete privacy,fresh landscaping, and a freshly painted exterior in warm, natural tones that give the home incredible curb appeal. This is the one you've been waiting for — all the charm, all the updates, and an unbeatable Oldsmar location close to Gulf beaches, parks, golf courses, shopping, and Tampa International Airport.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Marianne Knowles (813-720-9201)
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$449,0009 Days on yellowkey MLS ID: TB8502786
REDUCED by $1,000 (0.2%) on 05/07/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1841 Built: 1940 Tax: $4,298 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$4,298
Elementary School: None
High School: None
Middle School: None
Remarks: Seller is willing to contribute up to $9,000 toward buyer closing costs and/or allowable credits with an acceptable offer. Open House: Saturday, May 9th, from 1:00 PM to 3:00 PM. Fully renovated and move-in ready, this 3-bedroom, 2-bath home features 1,841 square feet of updated living space in a desirable area of Oldsmar. Recent improvements include a brand-new roof, new windows, fresh paint, brand-new appliances, and a fully refurbished HVAC system, creating a true turnkey opportunity. Inside, the home offers a spacious living area filled with natural light, a covered front porch, and an upstairs bonus room that can function well as a home office, playroom, guest area, kids room, or other flexible living space. The upstairs bonus room was not included in the total bedroom count. Situated on a double lot, the property includes ample outdoor space with room for a shed, carport, or future improvements. Conveniently located near parks, schools, shopping, dining, and other local amenities, this home brings together style, comfort, and convenience in one well-updated property. A clean 4-point inspection, wind mitigation report, WDO report, and recent appraisal are available. The recent appraisal came in at $475,000.
Listing is courtesy of: GRAYSTONE REAL ESTATE (727-201-4011)
Listing Agent: Bradley Dreher (863-346-0500)
50 KELLEYS TRL, OLDSMAR, FL 34677
$1,200,0001 Day on yellowkey MLS ID: TB8504781
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3240 Built: 1993Monthly Fee: $185 Tax: $7,792 (2025)Community: Turtle Creek Unit-OneSingle Family
Taxes:$7,792
Remarks: Welcome to an exceptional residence at 50 Kelleys Trail, nestled within the prestigious gated enclave of Turtle Creek within East Lake Woodlands in Oldsmar. This refined home embodies effortless elegance and elevated Florida living, offering a seamless blend of sophistication, comfort, and privacy. From the moment you enter, you’re greeted by soaring ceilings, abundant natural light, and thoughtfully designed living spaces that create an inviting yet upscale atmosphere. The open-concept layout flows beautifully, ideal for both intimate gatherings and grand entertaining. The kitchen serves as the heart of the home, featuring generous workspace, ample cabinetry, and a layout designed for both functionality and style. The primary suite is a true retreat, offering a serene escape with spacious proportions and a well-appointed en-suite bath. Step outside to your private outdoor setting, where you can unwind in tranquility or entertain guests while enjoying Florida’s year-round sunshine. Whether relaxing or hosting, this space offers the perfect backdrop for a luxury lifestyle. Located within one of Oldsmar’s most sought-after golf course communities, residents of East Lake Woodlands have access to optional resort-style amenities, including championship golf, tennis, fitness, and social experiences. Ideally positioned near upscale dining, boutique shopping, top-rated schools, Tampa International Airport, and the Gulf Coast’s renowned beaches, this home offers both convenience and exclusivity. Experience refined living in one of Oldsmar’s premier communities—schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
549 LONGWOOD CIR, OLDSMAR, FL 34677
$525,0001 Day 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)
602 BAY LAKE TRL, OLDSMAR, FL 34677
$375,0007 Days on yellowkey MLS ID: TB8503595
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1554 Built: 1983 Tax: $937 (2025)Community: Shoreview Ph ISingle Family
Taxes:$937
Elementary School: Oldsmar Elementary-PN
Remarks: Located in the Shoreview community of Oldsmar, this home offers a great combination of location, schools, and potential. Zoned for highly rated schools, this home is a smart choice for buyers looking to get into a strong school district while still having the opportunity to make it their own. Set on a peaceful homeowner-owned lake, the property features a private pool and relaxing water views—perfect for everyday living or entertaining. Inside, the home offers a desirable split floor plan for added privacy, a spacious primary suite with a walk-in closet, and an additional flex space/den ideal for a home office, playroom, or second living area. It’s ready for updates, making it ideal for buyers who want to customize and add value over time. You’re just minutes from R.E. Olds Park on Shore Drive, where you can enjoy festivals, outdoor concerts with fireworks over the water, a fishing pier, and beautiful sunset views. The area is also surrounded by waterfront parks offering bike and kayak trails, pickleball, basketball and tennis courts, walking and jogging paths, playgrounds, picnic areas, a small beach, and even a community garden. In addition to all the outdoor amenities, the home is conveniently located near great restaurants, shopping, Tampa International Airport, and the area’s award-winning Gulf beaches. And for peace of mind, the property is high and dry and did not have hurricane flooding or damage. If you’ve been looking for a home in a great location with room to make it your own, this one is definitely worth seeing. Please note: No sight unseen, assignable, or seller financing offers will be considered.
Listing is courtesy of: BRAINARD REALTY (813-922-2891)
Listing Agent: Sandra Santos Garbutt (727-418-1593)
436 LAFAYETTE BLVD, OLDSMAR, FL 34677
$700,000281 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
Tax Year: 2024
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)
509 CYPRESS VIEW DR, OLDSMAR, FL 34677
$624,90020 Days on yellowkey MLS ID: TB8496854
REDUCED by $9,100 (1.4%) on 05/06/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2084 Built: 1998Monthly Fee: $140 Tax: $4,902 (2025)Community: Preserve At Cypress Lakes Ph I TheSingle Family
Taxes:$4,902
Remarks: REDUCED - SELLER MOTIVATED - PRICED TO SELL ... Plus -Enjoy peace of mind with a seller-provided 1-year Home Warranty. OVERSIDED - FULLY FENCED CORNER LOT in highly desirable area/community of Oldsmar - Preserve At Cypress Lake. 4 Bedrooms, 2 Full Bathrooms, no carpeting, only wide-plank flooring & ceramic tile throughout. Separate Living/Dining Room area (currently being used for home Theatre/Office set up). Enjoy another separate Gathering Room. Large Eat-In Kitchen has Breakfast Bar opening to Gathering Room - perfect for entertaining or everyday living. Stainless Steel Appliances, Granite Counters, Pantry, Roll-Out Cabinetry. Connects to inside Laundry Room includes Washer/Dryer. Primary Bedroom large enough for King size Bedding, large Walk-In Closet. Private Ensuite full Bathroom with separate Shower, Garden Tub and Dual Sinks. Other 3 Bedrooms are adequately sized and share another full Bathroom. Closets are equipped with custom closet systems. Plantation Shutters on formal Living Room, Dining Room and Kitchen windows. The outdoors will not disappoint. Screened Lanai features amazing Pool for all your recreation, relaxation & oversized extra Patio space - all under the screened area. Enjoy additional entertaining or everyday living space with grassed area in back yard and another large Paver Patio - perfect for Grilling, Fire Pit, taking in the sun or sitting under an umbrella. Roof installed in 2017. New Hot Water Heater in 2025. Location is SUPBERB ... close to Forest Lakes Elementary, YMCA, Cypress Forest Recreation Center/Waterpark-Spray Park Splash Pad. Enjoy the nearby Nature Trail, Restaurants, Stores, Oldsmar Flea Market, BMX Complex, Oldsmar Hockey Complex, Ball Parks, convenient to Airport, directly down Tampa Road to all the happenings in Dunedin Main Street, Honeymoon Island and all the other Beaches in the area. Enjoy the holiday festivities this community has sponsored - riding on a horse drawn wagon to view neighborhood houses that have decorated. OLDSMAR & Preserve At Cypress Lakes is the place to be !!!
Listing is courtesy of: FLORIDA HOME REALTY GROUP, LLC (813-523-2280)
Listing Agent: Phyllis Clark (813-523-2280)
307 COUNTRY CLUB DR, OLDSMAR, FL 34677
$385,95010 Days on yellowkey MLS ID: TB8502335
REDUCED by $13,950 (3.5%) on 05/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1670 Built: 1960 Tax: $3,567 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$3,567
Remarks: One or more photo(s) has been virtually staged. HONEY STOP THE CAR! THIS IS THE ONE! LOCATION LOCATION LOCATION! Welcome to this FULLY RENOVATED, PRIME OLDSMAR LOCATION. This RARE OPPORTUNITY is a 3 Bed 2 Bath Home that checks every box for buyers looking for a move-in-ready property and investors searching for a smart opportunity in one of Tampa Bay’s fastest-growing hidden gems. This fully updated residence has been transformed from top to bottom with the modern finishes today’s buyers are chasing. From the moment you walk in, you’ll notice the attention to detail from tile flooring, a beautifully renovated kitchen with stylish cabinetry, upgraded countertops, modern fixtures, refreshed bathrooms, and finishes that make this feel like home. Every inch has been thoughtfully improved so the next owner can simply move in and enjoy. The layout offers the perfect blend of functionality and comfort with spacious living areas, generously sized bedrooms, and plenty of natural light throughout. Step outside and you’ll find ample outdoor space perfect for entertaining, relaxing, or creating your own backyard oasis. But what truly makes this property special is location. Situated in the heart of Oldsmar, you’re minutes from everything to love about the area including Waterfront parks and trails including R.E. Olds Park and Veterans Memorial Park, Close to Toronto Blue Jays spring training games at TD Ballpark, Easy access to shopping, dining, and entertainment throughout Oldsmar, Safety Harbor, and Tampa. Convenient commute to Tampa International Airport, Clearwater beaches, and major employers. Near golf courses, pickleball courts, breweries, and the vibrant charm that continues to make Oldsmar one of Tampa Bay’s most desirable places to live. Whether you’re a first-time homebuyer looking for a turnkey home, someone relocating to Florida, or an investor searching for a high-demand rental opportunity in a rapidly appreciating area, this property delivers. Homes this updated in Oldsmar at this price point don’t last. And opportunities like this? They attract attention fast. Schedule your showing before everyone else does, because this one is built to sell quickly.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Mark Fazzini (727-485-9981)
1909 CASTLE BAY CT, OLDSMAR, FL 34677
$374,000210 Days on yellowkey MLS ID: TB8436254
REDUCED by $4,000 (1.1%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1410 Built: 1984 Tax: $2,696 (2024)Community: Sheffield Village Ph Ii At Bayside MeadowsSingle Family
Taxes:$2,696
Remarks: --GORGEOUS HOME--Discover this IMMACULATE 3-bedroom, 2-bath BLOCK home with garage located on a quiet cul-de-sac in the heart of Oldsmar. BEAUTIFUL HIGH GLOSS TILE FLOORING THROUGHOUT Featuring spacious living areas with vaulted ceilings, a primary bedroom with an ensuite, and a split bedroom layout for added privacy and a rear screened porch perfect for relaxing or entertaining. The home has been thoughtfully upgraded with a new electrical panel (2018), roof (2020), air conditioning system (2021), gutters (2022), garage door (2022), water heater (2022), and water softener tank (2024) Exterior Water Line (2025). along with fresh exterior paint. Situated just steps from Sheffield Park, residents enjoy access to hiking and running trails, tennis and basketball courts, a playground, and a covered pavilion for events. Conveniently close to shopping centers, restaurants, downtown Tampa, the international airport, Clearwater beaches, and St. Pete, this neighborhood offers a peaceful environment with NO HOA fees. This turnkey home combines modern comfort with an unbeatable location—great curb appeal, stop by and take a look you wont be disappointed! MOTIVATED SELLER
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Craig Berenger, Jr. (727-772-0772)
200 LEE ST, OLDSMAR, FL 34677
$1,450,0003 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)
1654 BAYHILL DR, OLDSMAR, FL 34677
$570,000205 Days on yellowkey MLS ID: TB8438417
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2320 Built: 1995Monthly Fee: $177 Tax: $5,855 (2024)Community: CreeksideSingle Family
Taxes:$5,855
Elementary School: Cypress Woods Elementary-PN
Remarks: "SELLER OFFERING $6000 TOWARDS CLOSING COSTS" THIS HOME SITS IN THE QUAINT SECLUDED CREEKSIDE COMMUNITY INSIDE THE GATES OF EASTLAKE WOODLANDS, LARGE FAMILY HOME OF 4 BEDROOMS, 2 AND HALF BATHS, 2 CAR GARAGE WITH POOL, YOUR OPEN CONCEPT OF DINING AND LIVING ROOM GREAT FOR THE FAMILY TO GATHER, KITCHEN WITH GRANITE COUNTER TOPS AND UPDATED BACKSPLASH, APPLIANCES TO INCLUDE DISHWASHER OCTOBER 2025, FAMILY ROOM WITH SLIDING GLASS DOORS GOING TO YOUR PERSONAL PARADISE TO ENJOY YOUR SCREENED ENCLOSED PAVED PATIO INGROUND POOL OUT DOORS ANOTHER GREAT ENTERTAINMENT SPACE, THEN OUTSIDE TO SWING AND ENJOY THE WILD LIFE AND DEER AND THE PRIVATE AND QUIET BROOKER CREEK PRESERVE AREA, THEN YOUR BEAUTIFUL STAIRCASE TO YOUR PRIMARY BEDROOM RETREAT WITH LARGE EN-SUITE BATHROOM, INSIDE LAUNDRY ROOM, AC SYSTEM INSTALLED 2021, ROOF 2018. DON'T MISS OUT ON THIS RARE OPPORTUNITY TO OWN THIS MUCH SQUARE FOOTAGE FOR SUCH A GREAT COMMUNITY. POSSIBILITIES ARE ENDLESS!!
Listing is courtesy of: ECKERT REALTY & PROPERTY MGMT (727-240-0668)
Listing Agent: Karen Hutson (727-240-0668)
1384 FORESTEDGE BLVD, OLDSMAR, FL 34677
$720,00043 Days on yellowkey MLS ID: TB8490510
REDUCED by $30,000 (4.0%) on 05/05/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2814 Built: 1991Monthly Fee: $243 Tax: $13,366 (2025)Community: Aberdeen Unit TwoSpa: NoSingle Family
Taxes:$13,366
Remarks: Welcome to refined Florida living in the highly sought-after gated community of Aberdeen within East Lake Woodlands. This exceptional Arthur Rutenberg-built residence offers over 2,814 square feet of thoughtfully designed living space, perfectly positioned on an oversized lot with a private screened pool with lovely water feature. This freshly painted 4-bedroom, 2.5-bath split floor plan is designed for both comfort and sophistication. The expansive primary suite is a true retreat, featuring a spa-inspired bath with a freestanding clawfoot tub, separate shower, water closet, dual vanities, and walk-in closet, along with sliding glass doors leading directly to the pool. The pool bath features a jacuzzi tub and updated finishes. Enter through elegant double front doors into a light-filled interior with soaring ceilings and abundant natural light. The home offers a seamless blend of formal and casual living, including a formal living room with sliders to the pool, a dedicated dining space, and a spacious family room with wood burning fireplace that opens to the kitchen. The refreshed kitchen features an open layout, breakfast nook, with sliders leading to pool/patio making it an easy flow for entertaining. The large laundry room features a wash sink and an ample space for storage. Step outside to your screen-enclosed pool and covered patio, the perfect setting for year-round entertaining, relaxing, and enjoying Florida’s indoor-outdoor lifestyle. Additional highlights include a 3-car garage, new water softener system, 2013 Barrel Tile Roof. HVAC 2019 Located in Flood Zone X500 for added peace of mind, this home is surrounded by top-rated schools and unmatched convenience. Enjoy having an active lifestyle being close to Lake Tarpon, the Gulf beaches, Tampa International Airport, and outdoor destinations like John Chestnut Park, the Pinellas Trail, and the YMCA. Residents also have access to the newly renovated Ardea Country Club, offering two championship 18-hole golf courses, tennis and pickleball courts, fitness center, resort-style pool, and dining, available through optional membership. Don’t miss the rare opportunity to own a magnificent home in one of East Lake’s most desirable gated enclaves.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Kerri Rodriguez (727-385-8823)
140 ASHLEY LN, OLDSMAR, FL 34677
$309,9006 Days on yellowkey MLS ID: TB8504188
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1981Monthly Fee: $440 Tax: $1,408 (2025)Community: East Lake Woodlands Cluster HomesSpa: NoSingle Family
Taxes:$1,408
Remarks: Positioned below two recent appraisals, presenting a compelling opportunity for buyers seeking immediate value. Located within a gated golf course community in North Pinellas County (club and golf memberships optional), this light and bright 4-bedroom, 2-bath villa offers a flexible split-bedroom floor plan and inviting indoor-outdoor living. The great room is the focal point, featuring updated sliding glass doors that frame tranquil pond and fairway views of the 13th hole on the South Course, along with recently installed recessed lighting and wood-look plank tile flooring that enhance both ambiance and overall brightness—creating a warm, open, and inviting living space. New plantation shutters throughout the home add a refined, cohesive look while enhancing light control and privacy. The enclosed lanai extends the living area and opens to an additional patio and deck, ideal for relaxing or entertaining while enjoying the scenic setting. The rear deck is further enhanced by a retractable awning, providing flexible shade and added comfort for outdoor living year-round. The updated kitchen includes wood cabinetry, solid surface countertops, abundant drawer storage, a closet pantry, coordinating wood-look tile flooring, and double sinks. A casual breakfast area offers direct access to a private rear patio, perfect for grilling. Interior laundry closet conveniently located just off the kitchen. The primary suite offers ample closet storage with dual sliding-door closets, along with a large vanity area and separate water closet with a glass-enclosed shower. Both bathrooms feature expansive counter space with room to accommodate dual vanities, offering flexibility for future customization. Three additional bedrooms are well-sized and thoughtfully positioned for privacy, with one offering access to a private side patio—ideal for guests, a home office, or flex space. Well-maintained and move-in ready, this villa delivers a low-maintenance lifestyle with water and golf course views in one of the area’s most desirable communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (727-472-1144)
Listing Agent: Rick Scherer (813-230-5472)
506 FEDERAL ST, OLDSMAR, FL 34677
$1,180,000214 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
Taxes:$1,498
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)
1734 MAPLELEAF BLVD, OLDSMAR, FL 34677
$515,00037 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)
502 TIMBER BAY CIR E, OLDSMAR, FL 34677
$419,90094 Days on yellowkey MLS ID: TB8467897
3 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1658 Built: 1983 Tax: $5,498 (2024)Community: Shoreview Ph ISingle Family
Taxes:$5,498
Remarks: Under contract-accepting backup offers. This beautifully cared-for pool home is tucked away in one of Oldsmar’s most desirable neighborhoods. From the moment you step inside, you’ll feel the space and natural light that make this home so welcoming. The open floor plan flows effortlessly into a spacious living area—perfect for hosting friends, family gatherings, or simply relaxing at the end of the day. The updated kitchen is both stylish and functional, featuring sleek cabinetry, modern appliances, and plenty of counter space for cooking and entertaining. The primary suite offers a true retreat, with generous space to unwind, while the additional bedrooms provide comfort and flexibility for family, guests, or a home office. Step outside and discover your own private backyard oasis. The sparkling pool, framed by lush landscaping, creates the perfect setting for weekend barbecues, quiet mornings, or evening swims. This home has been meticulously maintained and is in excellent condition, with no storm damage from recent events, offering added peace of mind. Located in a quiet, friendly community, you’ll enjoy convenient access to top-rated schools, parks, shopping, dining, and major roadways—making everyday life easy and enjoyable. Whether you’re searching for a place to grow, entertain, or simply relax, this home truly has it all. Don’t miss the chance to make this exceptional Oldsmar pool home your own.
Listing is courtesy of: SELLSTATE LEGACY REALTY (813-542-1224)
Listing Agent: Taylor Cresswell (813-940-0101)
103 CUTLASS WAY, OLDSMAR, FL 34677
$345,00074 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)
4922 EDGEWATER LN, OLDSMAR, FL 34677
$594,00032 Days on yellowkey MLS ID: W7883975
REDUCED by $5,000 (0.8%) on 05/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2390 Built: 1997Monthly Fee: $158 Tax: $9,841 (2025)Community: WorthingtonSingle Family
Taxes:$9,841
Remarks: One or more photo(s) has been virtually staged. Located in the highly desirable Worthington subdivision of the gated East Lake Woodlands Golf Course community, this spacious home offers 3-bedroom, 2.5-bath Pool home with a large loft and 2-car garage offers an exceptional layout and effortless indoor-outdoor living.From the moment you arrive, you’ll be impressed by the custom-designed Brazilian Cherry-stained glass front door. Inside, the home features elegant, rectified porcelain tile and hardwood flooring throughout the lower level, along with a custom open oak staircase that creates a stunning focal point. Designed for both everyday living and entertaining, the home offers a formal sitting area, separate formal dining room, and a large family room with a cozy fireplace. The spacious kitchen and living areas flow seamlessly to the oversized lanai and screened pool area, creating the perfect indoor-outdoor lifestyle. The private backyard retreat includes a sparkling pool and spa, both powered by propane, along with propane service to the fireplace for added comfort and convenience. Upstairs, you’ll find all three bedrooms, each offering generous proportions, along with a large loft ideal for a media room, office, or playroom, and a convenient second-floor laundry room. The spacious primary suite features two walk-in closets and an ensuite bath with a double vanity, separate soaking tub, and ample space to create your own private retreat. Recent upgrades provide peace of mind and energy efficiency, including a new roof installed in 2021, AC replaced in 2022, and solar panels added in 2024. Enjoy life in a premier gated community just steps from championship golf, a new pickleball complex, and resort-style pools. Ideally located near Lake Tarpon and just minutes from top-rated schools, dining, shopping, and beautiful Gulf beaches. East Lake Woodlands Country Club offers optional membership with access to two 18-hole championship golf courses, tennis courts, a fitness center, two community pools, and an on-site restaurant—delivering a true resort-style lifestyle in one of Pinellas County’s most sought-after neighborhoods!
Listing is courtesy of: RE/MAX CHAMPIONS (727-807-7887)
Listing Agent: Eleni Sampson (727-873-8122)
2159 WARWICK DR, OLDSMAR, FL 34677
$800,00056 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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.