Location: Oldsmar , 34677
Do Not Show Listings
509 CYPRESS VIEW DR, OLDSMAR, FL 34677
$624,90024 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,902
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
340 CANAL WAY, OLDSMAR, FL 34677
$184,00046 Days on yellowkey MLS ID: TB8491525
REDUCED by $14,000 (7.1%) on 05/06/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1993Monthly Fee: $50 Tax: $2,288 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$2,288
Remarks: Welcome to easy Florida living in the sought-after 55+ community of Gull-Aire Village in Oldsmar. This well-maintained 2BR/2BA home offers a comfortable, open layout with updated flooring, a spacious living area, and a split-bedroom floor plan that gives both you and your guests privacy. The kitchen and bathrooms are clean and functional with room to make it your own, making this a great opportunity to move right in and update over time to your style. Enjoy the benefits of a covered carport, extra storage, and low-maintenance living in a community where neighbors know each other and there’s always something to do. Gull-Aire Village is a resident-owned 55+ community featuring a clubhouse, heated pool and spa, fitness center, shuffleboard courts, and a full calendar of social activities. Conveniently located near shopping, dining, Gulf beaches, Tampa International Airport, and major highways—everything you need is close by. Land-owned with no lot rent—perfect for a full-time residence or a seasonal Florida escape.
Listing is courtesy of: ACROPOLIS REALTY GROUP LLC (315-396-0493)
Listing Agent: Sal Degaetano (315-396-0493)
475 WOODS LANDING TRL, OLDSMAR, FL 34677
$255,000127 Days on yellowkey MLS ID: A4676723
0 Days Off yellowkey (back on 5/6/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1200 Built: 1984Monthly Fee: $591 Tax: $4,082 (2024)Community: East Lake Woodlands Woods Landing TwnhmsTownhouse
Taxes:$4,082
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
Remarks: Welcome home to this beautifully updated Townhouse in the sought after East Lake Woodlands Gated Community. The views from the enclosed Florida room offering wooded pond view, wildlife and complete serenity. This home features 2 bedroom, 2.5 baths, private driveway with car port and storage shed, updated kitchen with granite countertops and stainless steel appliances. In the kitchen is a sliding door opening up to your private patio with jacuzzi hot tub and access to shed, a perfect spot to enjoy morning coffee or BBQing. Vinyl flooring throughout the first floor for a gorgeous seamless flow offering large living room/dining area combo. All New hurricane proof windows upstairs as well as the slider in the kitchen and in the updated 1/2 bath. Upstairs you will find the Primary suite which has a walk in closet and updated ensuite bath, the guest room also offers an additional walk in closet as well as it's own private bathroom. The laundry closet is conveniently located upstairs between the 2 bedrooms. There is a community pool in the neighborhood, heated and ready to use year round. For an extra fee you can join the Ardea Country Club, which has two – 18-hole golf courses, restaurants, bar, fitness center, tennis courts, pickleball courts, Olympic size pool, splash pads, ping pong and more. Centrally located to shopping, restaurants, airport, excellent schools and Florida’s award-winning Gulf Beaches. All of these features makes East Lake Woodlands the perfect place to call home.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Loren Roye (516-446-3614)
307 COUNTRY CLUB DR, OLDSMAR, FL 34677
$385,95014 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
Elementary School: Oldsmar Elementary-PN
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)
291 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$240,000118 Days on yellowkey MLS ID: TB8463435
REDUCED by $9,900 (4.0%) on 05/06/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1110 Built: 1996Monthly Fee: $454 Tax: $2,205 (2025)Community: Countryside KeyTownhouse
Taxes:$2,205
Remarks: Welcome to the highly sought-after gated community of Countryside Key, ideally located in the heart of Oldsmar! This well-maintained home offers wood laminate flooring, a convenient ground-level laundry closet, and a screened-in lanai with an additional storage closet—perfect for relaxed Florida living. The kitchen opens seamlessly to the dining and living areas, creating an inviting open-concept layout ideal for everyday living and entertaining. Upstairs, you’ll find a desirable split floor plan featuring vaulted ceilings and two spacious, carpeted bedroom suites, each with its own private bath. Residents of Countryside Key enjoy a wealth of amenities, including a secure gated entrance, community pool, tennis courts, and a car wash station. Boat and RV parking are also available. Low monthly HOA fees cover cable, internet, phone, water, sewer, trash, exterior building maintenance, and exterior insurance—offering both convenience and peace of mind. Recent updates include new shut-off valves and a 2024 water heater. Ideally situated near airports, dining, shopping, entertainment, sports venues, and Florida’s award-winning Gulf beaches. Don’t miss this opportunity—schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
200 LEE ST, OLDSMAR, FL 34677
$1,450,0007 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
$570,000209 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
$720,00047 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)
209 CORKWOOD LN, OLDSMAR, FL 34677
$245,408332 Days on yellowkey MLS ID: TB8396745
INCREASED by $508 (0.2%) on 04/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1984Monthly Fee: $268 Tax: $2,960 (2024)Community: Villas Of Forest LakesVilla
Taxes:$2,960
Remarks: Amazing Location, Non Flood Zone, Renovated, New kitchen, New Water heater, New Bathroom Vanity, New flooring, Quartz counter tops and new appliances and there is a Storage room next to the car port and a Privacy back yard area. Good location next to Walmart supercenter Oldsmar and a few minutes away to walk from supermarket Aldi. Great school district. Community has a pool, Tennis Courts, Basketball court. Additional conveniences include a storage room and assign covered parking. The HOA takes care of exterior maintenance and the roof. According to the homeowners, this subdivision has not been flooded from the previous hurricanes in Tampa Bay area. About 20 minutes away from Tampa airport and 20 minutes away from honeymoon island State Park Dunedin Fl Etc...
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Genci Shurdha (727-400-9783)
140 ASHLEY LN, OLDSMAR, FL 34677
$309,90010 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)
10 LESLEY LN, OLDSMAR, FL 34677
$310,00018 Days on yellowkey MLS ID: TB8501611
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1250 Built: 1982Monthly Fee: $451 Tax: $3,869 (2025)Community: Quail Forest Cluster HomesSpa: NoVilla
Taxes:$3,869
Remarks: One or more photo(s) has been virtually staged. Welcome to 10 Lesley Lane, located in the gated community of Quail Forest, nestled within the private country club community of East Lake Woodlands. This beautifully maintained end-unit villa offers serene pond views and a thoughtfully designed split-bedroom floor plan for added privacy and comfort. Major updates provide peace of mind, including a new roof (2022), HVAC (2023), and water heater (2022). The spacious, fully updated kitchen is a true highlight, featuring new cabinetry, sleek quartz countertops, and stainless steel appliances, perfect for both everyday living and entertaining. The layout flows effortlessly into the living and dining areas, all filled with natural light and peaceful water views. Enjoy your morning coffee or unwind in the evening on the charming front patio. Additional conveniences include one assigned carport and plenty of guest parking for visitors. Residents of East Lake Woodlands have access to two championship golf courses, consistently ranked among the top 5 in the entire Tampa Bay area, along with optional country club amenities. Ideally located near shopping, dining, parks, and just a short drive to Tampa International Airport and the Gulf beaches, this home offers the perfect blend of lifestyle and location. Don’t miss your opportunity to own in one of Oldsmar’s most desirable communities!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (813-251-2002)
Listing Agent: Alexis Sollenberger (850-687-2526)
1734 MAPLELEAF BLVD, OLDSMAR, FL 34677
$515,00041 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)
403 E TUSCAN LN E, OLDSMAR, FL 34677
$330,000388 Days on yellowkey MLS ID: TB8376561
1 Days Off yellowkey (back on 1/14/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1525 Built: 2015Monthly Fee: $333 Tax: $5,075 (2024)Community: Tuscany Woods SouthTownhouse
Taxes:$5,075
Remarks: Under contract-accepting backup offers. Welcome home in Oldsmar, FL! This two-story 1,525 square foot townhouse, located in the HIGHLY-desirable gated community of "Tuscany Woods", was built in 2015 and has 3 bedrooms and 2.5 bathrooms. The first floor offers an open floor plan, which seamlessly connects the living, dining, and kitchen areas, making it an ideal space for entertaining friends or simply relaxing. The tile flooring throughout the entire first floor provides both style and ease of cleanup. After a long day, retreat to the second floor, where you can find serenity in either of the large secondary bedrooms, which both share a full bathroom, or the huge primary bedroom, with its own ensuite bathroom and walk-in closet. For convenience, a laundry room, complete with washer and dryer, are also located upstairs. The upstairs and stairs has plush, upgraded wall-to-wall carpeting. The one-car garage offers a secure space for your vehicle and extra storage, and the private driveway provides additional parking. The townhome also has a screened-in lanai. Don't miss out on this incredible opportunity to make this townhouse your home. Located in the desirable Oldsmar area, you'll have convenient access to I-275, and be in close proximity to top-rated public and private schools. You're also only a stone's throw away from various amenities, including shopping centers, restaurants, parks, not to mention Florida's award-winning beaches! Whether you're a nature enthusiast or prefer the hustle and bustle of city life, this location offers the best of both worlds. Contact us today to schedule a viewing and start envisioning your new life in this fantastic home.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Kirk Ray Smith (727-383-1871)
106 LAKESIDE CT, OLDSMAR, FL 34677
$158,000404 Days on yellowkey MLS ID: TB8350281
REDUCED by $2,000 (1.3%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1981 Tax: $2,932 (2024)Community: East Lake Woodlands CondoCondo
Taxes:$2,932
Remarks: Great Value!! This Condo is located within the Gated community of East Lake Woodlands. This unit is on the second floor and features an eat in kitchen, living/dining room with sliders out to the screened lanai, split bedroom plan, the primary suite has a walk-in closet, a secondary closet and a linen closet. The primary bath has a step in shower. The guest suite has a bath off the hallway. The laundry closet is located on the lanai & includes a washer/dryer. Covered parking 1 space under carport. Unit is located across from the Pool! This unit needs your attention & priced to offset reno to make it your own. Great rental, primary residence or winter getaway..No waiting period for a buyer to rent the condo. Excellent opportunity!
Listing is courtesy of: TAMPA BAY SIGNATURE PROPERTIES, LLC (727-692-2847)
Listing Agent: Christi Watson (727-692-2847)
388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$246,00081 Days on yellowkey MLS ID: TB8478422
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1105 Built: 1997Monthly Fee: $433 Tax: $1,771 (2025)Community: Countryside KeyTownhouse
Taxes:$1,771
Elementary School: Curlew Creek Elementary-PN
Remarks: Under contract-accepting backup offers. 2025 HVAC! Assumable FHA Loan! Welcome to 388 Countryside Key, a charming 2-bedroom, 1.5-bathroom townhome located in the highly sought-after Oldsmar, FL community. This delightful two-story residence boasts an open-concept first floor with a spacious kitchen, ample cabinetry, a generous pantry, and a convenient laundry/utility closet with a full-size washer and dryer. The living and dining areas flow seamlessly, enhanced by a kitchen bar and a convenient first-floor half bath. Upstairs, you'll find two generously sized bedrooms, each featuring vaulted ceilings that create an airy ambiance. Step outside to your enclosed screened patio, a serene retreat perfect for unwinding and enjoying the Florida weather year-round. This pet-friendly community offers a wealth of amenities including a secure gate, sparkling pool, tennis courts, sidewalks, and a car-wash station, with recreational storage for your RV, boat, or trailer available for a nominal fee. You'll have an assigned parking spot right at your doorstep with ample guest parking. Monthly HOA fees cover water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Located in an area known for its highly-regarded school districts, buyers are encouraged to verify current school assignments and ratings. Situated near Tampa International Airport, St. Petersburg, and the area's stunning beaches, this gorgeous property offers an exceptional opportunity to create your dream home in a prime location. Don't miss out on this fantastic opportunity! Notable Features & Upgrades: HVAC-2025; Interior Paint-2025; Carpet-2017; Primary Bathroom Renovation-2016; Granite Countertops & Cabinets (Kitchen & Primary Bath)-2013; Upgraded Fixtures & Handles, Lights, Ceiling Fans.
Listing is courtesy of: TROPIC SHORES REALTY (800-775-1302)
Listing Agent: Kevin Baker (352-777-1507)
948 LUCAS LN, OLDSMAR, FL 34677
$475,000102 Days on yellowkey MLS ID: TB8448286
REDUCED by $25,000 (5.0%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1685 Built: 1990Monthly Fee: $575 Tax: $4,086 (2025)Community: Hunters Trail TwnhmsVilla
Taxes:$4,086
Remarks: One or more photo(s) has been virtually staged. Are you done with yard work and exterior maintenance but still would love a 2-car garage and privacy that feels like a house? Welcome to a truly impressive end unit villa set in the East Lake Woodlands nature-filled, and amenity-rich golf community. Private .25 ACRE corner lot - NON-FLOOD zone, SERENE POND VIEWS - Oversized SCREENED-IN PATIO. $60,000 investment of newer top-of-the-line HURRICANE-RATED WINDOWS, DOORS and Garage Door installed 2023. Inside, the home opens up with tons of natural light, cathedral ceilings (no popcorn) and a BRAND NEW 2025 AC with UV-C germicidal lights for better air quality. The spacious living room features a WET BAR and WOOD-BURNING FIREPLACE, creating the perfect backdrop for a dinner event, movie night or just a relaxing evening entertaining. The kitchen has picturesque views through the windows overlooking the lush backyard and pond, yes, deer and owl frequent here! With a 3-bedroom, 2-bath TRUE SPLIT FLOOR PLAN, everyone enjoys their own space, and the full-size washer and dryer are perfectly situated in the hallway laundry closet. Step outside to the SHOWSTOPPER: a HUGE BIRDCAGE PATIO overlooking the tranquil pond - ideal for morning coffee, evening wine, weekend entertaining, or large gatherings. This home also features a 2-car garage, so bring your golf cart as well, and ride or walk to the community pool just at the end of the street. Set among flourishing nature, top-tier amenities, and the prestige of a highly sought-after golf community, this villa delivers an ideal mix of comfort, privacy, and elevated living. No Flood insurance required! The HOA fee includes Cable TV, Internet, Community Pool, Escrow reserves, Maintenance Exterior, Roof, Grounds, Security and Trash. East Lake Woodlands is home to the Adrea Country Club offering a variety of optional memberships for homeowners to join. These exclusive amenities include Two Championship 18-hole Golf Courses, Tennis and Pickleball Courts, Clubhouse Bar, Casual and Fine Dining, Fitness Center, Splash Pad, Swimming Pools, Clubhouse Events and more. Centrally located near trending restaurants, shopping, movies, parks, Tarpon Lake, Gulf Coast beaches, top rated hospitals, Tampa Airport and more, you’ll never run out of activities in town! Come experience it for yourself - schedule your showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Rebecca Norton (727-365-5513)
137 BRENT CIR, OLDSMAR, FL 34677
$799,00046 Days on yellowkey MLS ID: O6394251
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2309 Built: 2002Monthly Fee: $473 Tax: $5,236 (2025)Community: Seaside EstatesTownhouse
Taxes:$5,236
Remarks: **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.** 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, 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.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
502 TIMBER BAY CIR E, OLDSMAR, FL 34677
$419,90098 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)
130 CYPRESS LN #130, OLDSMAR, FL 34677
$160,00014 Days on yellowkey MLS ID: TB8502597
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Monthly Fee: $571 Tax: $2,571 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$2,571
Remarks: One or more photo(s) has been virtually staged. Welcome to this two-bedroom, two-bath condominium in Oldsmar, offering 1,054 square feet and a flexible opportunity for investors, first-time buyers or seasonal residents. This residence is vacant and ready for immediate occupancy or renovation. The interior reflects the original condition, presenting a value-add opportunity for customization. The primary bedroom includes a walk-in closet, and the layout supports functional living and dining spaces. Recent updates include an air-conditioning system installed in 2025, along with a washer, dryer and refrigerator replaced in 2024. This property is well-suited for buyers seeking to personalize a residence or secure an investment with long-term potential. Conveniently near shopping, dining and commuter routes, supporting full-time and seasonal living.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (813-217-5288)
Listing Agent: Maria Azuaje (317-371-0935)
103 CUTLASS WAY, OLDSMAR, FL 34677
$345,00078 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)
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