Oldsmar, FL Homes for Sale with Pool

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  /40

  $195,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  83 Pelican Dr N, Oldsmar, FL 34677

  Discover exceptional value in Gull-Aire Village, a vibrant 55+ community, with this meticulously maintained home ready for its next owner. Move right in! this sale includes all furnishings and contents, including a 60-inch TV, for a seamless transition. Enjoy peace of mind with a host of recent upgrades: In March of 2024 a brand-new shingle roof, 11 new hurricane windows, and 11 new solar panels

  Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

  83 Pelican Dr N, Oldsmar, FL 34677
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  /46

  $524,000

  $41K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,065 Sq Ft

  854 Christina Cir, Oldsmar, FL 34677

  Priced to the Ridiculous!! Welcome to Bays End, a hidden gem community offering a peaceful setting with convenient access to everything the area has to offer. This well-maintained 3-bedroom, 2-bathroom home features a spacious and inviting layout. Enter to an open living room that flows into the dining area. The updated kitchen showcases beautiful cabinetry, generous storage, and plenty of

  Joseph Koebel RE/MAX REALTEC GROUP INC

  854 Christina Cir, Oldsmar, FL 34677
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  /2

  Price To Be Determined

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,341 Sq Ft

  Alto Plan at Odeon Square, Oldsmar, FL 34677

  Introducing the stunning Alto townhome at Odeon Square — a modern, flexible three-story home designed for the way you live, work, and entertain.Located in the heart of vibrant Oldsmar, the Alto offers a thoughtfully crafted layout with stylish contemporary living spaces, private retreats, and versatile rooms to fit every lifestyle.The first floor welcomes you with a spacious two-car

  DRB Homes Builder

  504 St Petersburg Dr St E Unit 40570367, Oldsmar, FL 34677
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  /60

  $734,900

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,652 Sq Ft

  4761 Stonebriar Dr, Oldsmar, FL 34677

  Motivated SELLER!! This is Florida luxury living at its finest in one of the area’s most desirable gated communities. Exclusive executive home located in the highly sought-after Stonebriar community within East Lake Woodlands, a desirable gated golf club community. Zoned for top-rated schools and ideally situated less than 30 minutes from Tampa International Airport and the area’s premier Gulf

  Nichole Gaytan PRIME INT'L REAL ESTATE GROUP

  4761 Stonebriar Dr, Oldsmar, FL 34677
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  /57

  $585,000

  $30K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,452 Sq Ft

  586 Kingsmill Ct, Oldsmar, FL 34677

  Virtually Staged. Welcome to this inviting single-family home in the sought-after Kingsmill neighborhood of East Lake Woodlands—a premier gated community celebrated for its security, lush Florida landscapes, and vibrant lifestyle. Offering 2,453 square feet of living space, this beautifully updated residence features a grand total of three bedrooms, two full bathrooms, and a modernized half bath.

  Susanne Jones REDFIN CORPORATION

  586 Kingsmill Ct, Oldsmar, FL 34677
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  /51

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,471 Sq Ft

  258 Pelican Dr N, Oldsmar, FL 34677

  Now available in the sought-after 55+ Gull-Aire Village: a meticulously maintained 1995 Jacobsen home, offering over 1,400 square feet of comfortable living space. This inviting residence features three spacious bedrooms and two full bathrooms, with a split floor plan that provides privacy for guests. The home boasts a newly installed TPO roof (2024) that covers the main unit, Florida room, and

  Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

  258 Pelican Dr N, Oldsmar, FL 34677
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  /30

  $150,000

  $60K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,094 Sq Ft

  110 Lakeside Ct Unit 74, Oldsmar, FL 34677

  Nestled within the highly desirable East Lake Woodlands community of Oldsmar is this beautiful 1094 sq ft 2 bedroom 2 bath 2nd floor condominium. The kitchen has been updated with granite countertops and contemporary white cabinets that have been professionally resurfaced. There is also a laundry closet with a washer and dryer inside that is accessed from the lanai. This unit has closets galore!

  Barry Rothstein DALTON WADE INC

  110 Lakeside Ct Unit 74, Oldsmar, FL 34677
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  /82

  $129,000

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 915 Sq Ft

  140 Hunter Lake Dr Unit 8C, Oldsmar, FL 34677

  Location, Location, Location!!! Welcome to the carefree living community of Gardens of Forest Lakes in fabulous Oldsmar! Move-in ready... ALL BRAND NEW in this magnificent home that combines style and functionality. Be the first to live in this magnificent COMPLETELY REBUILT condo! Just under 1,000 sq. ft. with 2 bedrooms and 2 bathrooms plus a screened balcony. Beautiful luxury vinyl flooring

  Nancy Leslie RE/MAX REALTEC GROUP INC

  140 Hunter Lake Dr Unit 8C, Oldsmar, FL 34677
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  /38

  $188,000

  $7K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 879 Sq Ft

  204 Windward Place Unit 36, Oldsmar, FL 34677

  Welcome to 204 Windward Place #36, a move-in-ready condominium located in the gated community of East Lake Woodlands, one of Oldsmar's most established residential communities. Offering low-maintenance living in the heart of Tampa Bay, this well-maintained residence combines comfort, convenience, and easy access to everything Florida's Gulf Coast has to offer. Designed with functionality and

  Robert Dinan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  204 Windward Place Unit 36, Oldsmar, FL 34677
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  /44

  $160,000

  • 2 Beds
  • 2 Baths
  • 915 Sq Ft

  134 Sycamore Ln Unit H, Oldsmar, FL 34677

  This beautifully maintained 2 bedroom, 2 bath condo in fantastic Gardens of Forest lakes, offers perfect blend of comfort and convenience. As you step inside, you will be greeted by an open floor plan that seamlessly connects the living and kitchen areas. Kitchen features granite countertops, wood cabinets. The dining area opens to a charming balcony overlooking trees and it is perfect for

  Tatiana Russu FUTURE HOME REALTY INC

  134 Sycamore Ln Unit H, Oldsmar, FL 34677
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  /2

  Price To Be Determined

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,259 Sq Ft

  Tenor Plan at Odeon Square, Oldsmar, FL 34677

  The Tenor is an elegant three-story townhome that combines spacious living, modern design, and exceptional flexibility to fit today’s lifestyle. Thoughtfully designed with open-concept gathering spaces, private bedroom retreats, and versatile bonus areas, the Tenor offers the perfect balance of comfort, convenience, and contemporary style.The first floor welcomes you with a charming covered

  DRB Homes Builder

  504 St Petersburg Dr St E Unit 40570349, Oldsmar, FL 34677
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  /64

  $525,000

  • 3 Beds
  • 3 Baths
  • 1,834 Sq Ft

  119 Brent Cir, Oldsmar, FL 34677

  Are you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from everywhere you want to be? Experience effortless coastal living in this exceptional waterfront townhome, perfectly designed for those who appreciate space, light and direct access to the water. Featuring two private boat slips, this residence offers a RARE opportunity to keep your vessels close and enjoy days

  Darren Booth COMPASS FLORIDA LLC

  119 Brent Cir, Oldsmar, FL 34677
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  /62

  $229,900

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  480 Trout Ln, Oldsmar, FL 34677

  Just listed in Gull-Aire Village! This beautifully furnished 1993 Jacobsen is nestled in a peaceful location and eagerly awaits its new owner. Boasting 1,521 square feet, the open floor plan invites you to enjoy spacious living and effortless entertaining. An expansive 11x19 (209 square feet) Florida room, which adjoins the kitchen and family room, provides even more space for relaxation and

  Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

  480 Trout Ln, Oldsmar, FL 34677
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  /26

  $180,000

  • 2 Beds
  • 2 Baths
  • 879 Sq Ft

  115 Windward Place Unit 15, Oldsmar, FL 34677

  LOCATION, LOCATION, LOCATION! Close to entertainment, shopping, restaurants, airports, and world-famous beaches, this beautiful ground floor, end unit condo is waiting for you! Located in the highly desirable, gated community Meadows of Eastlake Woodlands, this home has it all! Gorgeous granite countertops highlight the kitchen as does the impressive cabinet space and closet pantry. The inviting

  Millie Jackson FLORIDA PREMIERE REALTY

  115 Windward Place Unit 15, Oldsmar, FL 34677
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  /25

  $239,000

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft

  104 E Cypress Ct Unit 104, Oldsmar, FL 34677

  Located in East Lake Woodlands this quiet private second-story unit offers serene views overlooking the golf course and has a bright welcoming interior. Thoughtfully remodeled throughout, the home features abundant cabinet space, newer appliances, and major system upgrades including air conditioner and furnace. The unit has been tastefully finished with beautiful Florida-style decor, creating a

  Stephen Hachey FLAT FEE MLS REALTY

  104 E Cypress Ct Unit 104, Oldsmar, FL 34677
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  /29

  $175,000

  • 2 Beds
  • 2 Baths
  • 1,266 Sq Ft

  410 Dolphin Dr S, Oldsmar, FL 34677

  Welcome to Gull-Aire Village, one of Pinellas County's most desirable and active 55+ communities! Don't miss this opportunity to own a home in the highly sought-after Gull-Aire Village, where you own the land and enjoy an incredibly affordable HOA fee of just $70 per month. Whether you're looking for a full-time residence, seasonal retreat, or future investment property, this community offers

  David Mayhew CHARLES RUTENBERG REALTY INC

  410 Dolphin Dr S, Oldsmar, FL 34677
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  /32

  $475,000

  • 3 Beds
  • 3 Baths
  • 1,834 Sq Ft

  117 Brent Cir, Oldsmar, FL 34677

  Come and tour this cozy 3 bedroom, 3 bathroom waterfront townhouse and you will quickly see how easy it is to embrace the lifestyle that makes Florida living so desirable. This 1834 sq ft, 3 level townhouse delivers comfortable maintenance free living in a space where you can be in for years to come. Soak in endless water views as you sip your morning coffee or unwind with a good book, from 2

  Jaybee Racaza-Benitez BLAKE REAL ESTATE INC

  117 Brent Cir, Oldsmar, FL 34677
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  /65

  $1,124,900

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,098 Sq Ft

  35 Greenhaven Trail, Oldsmar, FL 34677

  Homes like this rarely become available in the highly sought-after gated community of East Lake Woods. Completely remodeled and situated on over a quarter acre overlooking a tranquil pond, this exceptional residence offers the perfect blend of luxury, comfort, and functionality. From the moment you arrive, you'll appreciate the expansive driveway, oversized three car garage, and impressive curb

  David Ares CHARLES RUTENBERG REALTY INC

  35 Greenhaven Trail, Oldsmar, FL 34677
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  /34

  $247,000

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  407 Dolphin Dr S, Oldsmar, FL 34677

  Experience the charm of Gull-Aire Village 55+ in this beautifully renovated home, ready for its next owners. Boasting a spacious 1,320 square feet with stylish laminate flooring throughout, this residence is perfect for entertaining and comfortable living. The split-bedroom layout ensures privacy for both you and your guests, while both bathrooms feature luxurious walk-in showers for added

  Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

  407 Dolphin Dr S, Oldsmar, FL 34677
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  /36

  $429,500

  $21K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  2410 Arch Ave, Oldsmar, FL 34677

  Imagine coming home to breathtaking waterfront surroundings, resort-style amenities, and maintenance-free living in one of Tampa Bay's most desirable gated communities. Welcome to Bayside Terrace, where this beautifully upgraded 3-bedroom, 2.5-bath townhome with a 1-car garage offers the perfect blend of luxury, convenience, and coastal lifestyle.Ideally situated just steps from the community

  Joseph Richards KELLER WILLIAMS TAMPA PROPERTIES

  2410 Arch Ave, Oldsmar, FL 34677
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  /80

  $419,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  347 Country Club Dr, Oldsmar, FL 34677

  "Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths with plenty of storage space, vehicles, boat and golf cart(s) parking. Luxury vinyl flooring throughout this split plan homes interior, picturesque French Door views to the pool and lanai deck, all new kitchen appliances and home systems installed. An expansive corner lot

  Frank Fundora PEOPLE'S CHOICE REALTY SVC LLC

  347 Country Club Dr, Oldsmar, FL 34677
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  /57

  $189,999

  $9K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,096 Sq Ft

  130 Nancy Dr Unit 37, Oldsmar, FL 34677

  "RESORT STYLE LIVING" in East Lake Woodlands! This beautifully maintained 2-bedroom,2-bath condominium offers approximately 1,151 sq ft of comfortable living space in one of Oldsmar’s most desirable gated communities. Major updates provide peace of mind, including flooring, A/C system, hot water heater, dishwasher, washer and dryer, and bedroom carpeting all approximately 3 years old, plus a

  Steve DeMatos RE/MAX ALLIANCE GROUP

  130 Nancy Dr Unit 37, Oldsmar, FL 34677
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  /31

  $165,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  278 Pelican Dr N, Oldsmar, FL 34677

  Don't miss this desirable and very active community of Gull-Aire Village! This is one of the most highly sought-after 55+ communities in Pinellas County. With HOA fees at only $60/mo and the ability to rent out your home after only 1 year of ownership, the possibilities are endless. This home includes a rare LARGE GARAGE! You own your own land. The owner has just replaced the range and

  Jon Dant RE/MAX ACTION FIRST OF FLORIDA

  278 Pelican Dr N, Oldsmar, FL 34677
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  /17

  $220,000

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,024 Sq Ft

  2034 Montego Ct, Oldsmar, FL 34677

  Welcome to this spacious 1,028 sq ft villa in the desirable Bayside Meadows community of Oldsmar. This beautifully updated home offers the comfort and privacy of villa living with a one-car garage, fenced backyard, and screened lanai—perfect for enjoying Florida’s year-round outdoor lifestyle.The thoughtfully designed interior features a kitchen overlooking the living area, a cozy

  Jerry Hills RE/MAX ELITE REALTY

  2034 Montego Ct, Oldsmar, FL 34677
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  /43

  $118,900

  $11K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 915 Sq Ft

  123 Loblolly Ct Unit B, Oldsmar, FL 34677

  Virtually Staged. GROUND FLOOR ~ NON - FLOOD ZONE. 2 Bedrooms, 2 Bathroom and move in ready in the heart of Oldsmar! Community amenities include a pool, playground, basketball court, tennis courts and beautiful lake with a dock! Bring your fishing pole. Freshly painted and move-in ready, tile floor throughout, making it an ideal canvas for a buyer looking to add personal touches and build equity.

  Christina Paolillo CHARLES RUTENBERG REALTY INC

  123 Loblolly Ct Unit B, Oldsmar, FL 34677
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  /34

  $437,500

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  1309 Sunset Wind Loop, Oldsmar, FL 34677

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome (NEVER FLOODED) in one of Oldsmars most desirable waterfront gated communities. This move-in-ready home offers comfort, convenience and low-maintenance resort style living. The open-concept layout is designed for both everyday comfort and effortless entertaining, featuring a spacious living and dining area filled with natural

  Anabel Ottersbach DALTON WADE INC

  1309 Sunset Wind Loop, Oldsmar, FL 34677
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  /35

  $680,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,290 Sq Ft

  2456 Appaloosa Trail, Palm Harbor, FL 34685

  Location, Location, Location says it all. This large 4 bedroom, 3 bath Executive waterfront pool home in the much desired Bridlewood subdivision is waiting for you. Relax in the Solar heated pool as you look out over the peaceful waters of the pond. Fenced in back yard to keep your little ones from wandering off. Lots of room for your autos and toys in the 3 car garage and large driveway. Kitchen

  Frank George CHARLES RUTENBERG REALTY INC

  2456 Appaloosa Trail, Palm Harbor, FL 34685
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  /87

  $664,000

  $36K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,839 Sq Ft

  3421 Brian Rd S, Palm Harbor, FL 34685

  SELLERS MOTIVATED! OFFERING 15k towards updates or closing costs. Hurry out to see this spacious 5-bedroom, 3-bath home offers over 2,800 square feet of thoughtfully designed living space, combining timeless character, quality craftsmanship, and many valuable updates.Step inside to discover a functional and inviting layout that has been meticulously maintained over the years. The kitchen is

  Amy Garzaro CHARLES RUTENBERG REALTY INC

  3421 Brian Rd S, Palm Harbor, FL 34685
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  /95

  $1,399,900

  New Construction

  • 4 Beds
  • 4 Baths
  • 3,433 Sq Ft

  3426 Channelside Ct, Safety Harbor, FL 34695

  Virtually Staged. Welcome to one of Pinellas County’s most exceptional values in luxury new construction. Completed in 2025 and never occupied, this extraordinary waterfront pool home combines timeless architecture, impeccable craftsmanship, and designer finishes typically found in homes at a substantially higher price point. Situated on an oversized waterfront homesite, enjoy breathtaking

  John LaRocca FUTURE HOME REALTY INC

  3426 Channelside Ct, Safety Harbor, FL 34695

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