Location: Oldsmar
Do Not Show Listings
340 CANAL WAY, OLDSMAR, FL 34677
$184,00040 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,288
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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
$255,000121 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
$385,9508 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
$240,000112 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)
382 FOUNTAINVIEW CIR, OLDSMAR, FL 34677
$520,000Listed 05/06/2026 8:33AM 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)
417 DOLPHIN DR S, OLDSMAR, FL 34677
$269,0005 Days on yellowkey MLS ID: TB8504194
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1253 Built: 1985Monthly Fee: $70 Tax: $3,616 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$3,616
Remarks: Welcome to this beautifully renovated home in the desirable 55+ Gull-Aire Village where comfort, style, and convenience seamlessly come together. Step inside to discover luxury vinyl flooring throughout, a modern kitchen featuring elegant shaker cabinetry, granite countertops, a convenient pot filler, premium stainless-steel appliances, smooth ceilings, and five-inch baseboards. The custom kitchen island comfortably seats three, perfect for casual dining or entertaining. The primary bathroom has been thoughtfully designed for both style and accessibility, boasting a fully updated, wheelchair-friendly walk-in shower. The guest bathroom is also refreshed, offering a versatile tub/shower combination. The spacious laundry room includes newly installed custom cabinetry and a sink, with the potential to serve as a second kitchen for those who enjoy cooking. Enjoy Florida living year-round in the expansive glass-enclosed, air-conditioned Florida room, complete with durable vinyl plank flooring. Upgrades include a new air conditioning system installed with permit in November 2018, a permitted TPO roof added in August 2012, and a whole-house Generac generator that guarantees uninterrupted power during any weather. Additional storage is available in the handy shed. The vibrant clubhouse is the heart of the community, hosting monthly events and providing amenities such as a pool table, shuffleboard, bocce ball courts, a heated pool, and spa. Residents can take part in regular activities like bingo, card games, and line dancing, fostering an active, social lifestyle. The golf cart-friendly streets make getting around the neighborhood both easy and fun. Enjoy affordable living with HOA fees of just $70 per month in this meticulously maintained community. Pet owners are welcome—one pet of any size is allowed, and a second pet may be permitted with an emotional support letter from a physician. Ownership includes the land, so there is no lot rent. Everyday conveniences are right across the street, with options like AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store. Dining choices abound including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Major retailers such as Super Walmart and Publix, along with Countryside Hospital, are about ten minutes away. Outdoor enthusiasts will love being just ten miles from the stunning beaches at Honeymoon Island and Caladesi State Park, plus direct access to a scenic biking and walking trail along the canal. Room measurements are approximate.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
1909 CASTLE BAY CT, OLDSMAR, FL 34677
$374,000208 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
$1,450,0001 Day 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
$570,000203 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
$720,00041 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
$245,408326 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)
2031 DOVER CT, OLDSMAR, FL 34677
$289,00015 Days on yellowkey MLS ID: TB8500444
REDUCED by $11,000 (3.7%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1215 Built: 1982Monthly Fee: $135 Tax: $4,212 (2025)Community: Bayside Meadows Ph IiVilla
Taxes:$4,212
Remarks: Welcome to your peaceful retreat! This beautifully updated 2-bedroom, 2-bathroom, 1-car garage villa combines comfort, charm, and convenience in a quiet, sidewalk-lined neighborhood ideal for leisurely strolls and a true sense of community. Step inside to a spacious living area, featuring a large primary suite with a walk-in closet and private en suite bathroom. Enjoy Florida living with two large lanais, perfect for relaxing or entertaining. As an end unit tucked into a private cul-de-sac, this home boasts the largest yard in the community—a rare and valuable feature. Updates include new HVAC, fenced in backyard, luxury vinyl plank through out, fresh paint, water heater 2 years old, and roof is just 4 years old. Take advantage of the inviting community pool, or enjoy a short walk to Sheffield Park just 0.4 miles away. You'll love the unbeatable location—just minutes from Publix grocery (1.8 miles), shopping, dining, and Starbucks (1 mile), and a quick drive to the beach (9 miles) and Tampa International Airport (13 miles). With low HOA fees and easy access to everything you need, this villa is perfect as a full-time residence or a seasonal getaway. Don't miss your chance to enjoy effortless living in a prime location!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Jay Umboh (813-539-3105)
140 ASHLEY LN, OLDSMAR, FL 34677
$309,9004 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)
433 SAILFISH BLVD, OLDSMAR, FL 34677
$256,00065 Days on yellowkey MLS ID: TB8481608
REDUCED by $3,000 (1.2%) on 04/06/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 960 Built: 1987Monthly Fee: $70 Tax: $1,585 (2025)Community: Gull-Aire VillageSpa: NoManufactured Home
Taxes:$1,585
Remarks: SPECTACULAR VIEWS! Welcome home to your quaint, cozy - yet surprisingly spacious - cottage nestled along a serene pond directly across from a peaceful tropical bird sanctuary in the heart of Oldsmar, Florida! This beautifully updated 2-bedroom, 2-bathroom home features cathedral ceilings, along with a bright open-concept layout with a generous living room and dining area – perfect for entertaining guests or enjoying quiet evenings in comfort. Thoughtfully upgraded throughout, the home showcases charming barn wood accent walls, and newer luxury vinyl flooring that flows seamlessly from room to room. The spacious primary suite is a true retreat, complete with a large walk-in closet accented by stylish barn doors and a private en-suite bathroom featuring a separate walk-in shower and enclosed toilet area for added privacy. Recent improvements provide peace of mind and modern appeal, including newer vinyl siding, double-pane windows, fresh interior and exterior paint, ungraded doors with stylish hardware, and much more - making this home truly move-in ready. Located in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers resort-style amenities including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. Enjoy the rare benefit of owning the land with a low monthly HOA fee of just $70 and one pet of any size is welcomed. You’ll love the unbeatable location—less than a mile from Woodlands Square and just minutes to everyday conveniences. Honeymoon Island Beach is approximately 9 miles away, Mease Countryside Hospital among other health facilities are approximated 2 miles away and Tampa International Airport is a quick 15-mile drive. An adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, the perfect spot to enjoy Florida’s outdoor lifestyle. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply soaking in the tranquil water views, you’ll fall in love with the welcoming charm and vibrant lifestyle of Gull-Aire Village. Schedule your private tour today! (Room dimensions are approximate and should be verified by Buyer.)
Listing is courtesy of: AH REALTY SERVICES, LLC (727-275-3512)
Listing Agent: Anne Hode (813-545-1960)
10 LESLEY LN, OLDSMAR, FL 34677
$310,00012 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)
506 FEDERAL ST, OLDSMAR, FL 34677
$1,180,000212 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
$515,00035 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
$330,000382 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
$158,000398 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
$246,00075 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)
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