Oldsmar, FL Homes

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  $199,900

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

  229 Mary Dr Unit 45, Oldsmar, FL 34677

  Discover Gated Serenity in East Lake Woodlands.Welcome home to this beautifully renovated 2-bedroom, 2-bath condo offering 1,094 square feet of comfortable, light-filled living at 229 Mary Dr, Oldsmar, FL—nestled within the guard-gated East Lake Woodlands community, one of Tampa Bay’s most desirable enclaves.From the moment you arrive, you’ll feel the peace of mind that comes with 24-hour

  Gary Jones, Jr EZ CHOICE REALTY

  229 Mary Dr Unit 45, Oldsmar, FL 34677
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  /21

  $2,995 per month

  • 4 Beds
  • 2 Baths
  • 1,911 Sq Ft
  • House for Rent

  405 Arlington Ave E, Oldsmar, FL 34677

  Spectacular Open Layout, Great Location and Large Backyard! Welcome to this spacious single-family home featuring an open floor plan with four bedrooms and two bathrooms. A large entryway leads into the living room with vaulted ceilings, which flows seamlessly into a Florida room overlooking the expansive fenced backyard. The home features a combination of tile and gleaming wood floors

  Steven Godoy RENT SOLUTIONS

  405 Arlington Ave E, Oldsmar, FL 34677
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  $395,000 Sold Mar 21, 2025

  1002 Vineyard Ln, Oldsmar, FL 34677

  • 3 Beds
  • 2.5 Baths
  • 1,773 Sq Ft
  • Built 2017

  Last Sold Summary

  • 1% Below List Price
  • $223/SF
  • 4 Days On Market

  Current Estimated Value $398,435

  Last Listing Agent Stella Giudicelli DALTON WADE INC

  1002 Vineyard Ln, Oldsmar, FL 34677
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  /42

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  142 Blue Marlin Dr, Oldsmar, FL 34677

  142 Blue Marlin Dr, Oldsmar, FL 34677
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  /31

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft

  271 Hemingway Dr, Oldsmar, FL 34677

  One or more photo(s) has been virtually staged. Welcome to this inviting 3-bedroom, 2.5-bath townhome with a private garage, perfectly set on a premier conservation lot, in the quaint Oldsmar community of Sun Ketch Townhomes of Cypress Lakes. Step inside to find brand-new luxury vinyl plank flooring and a bright, open layout. The spacious great room features sliding glass doors leading to a

  Marcy Daniels COLDWELL BANKER REALTY

  271 Hemingway Dr, Oldsmar, FL 34677
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  /35

  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft
  • Apartment for Rent

  204 Hemingway Dr, Oldsmar, FL 34677

  Call to see this Sun Ketch Villa and your private showing. Welcome home to this beautifully maintained 2-bedroom, 2-bath villa filled with natural sunlight throughout. The vaulted ceiling in the living room features a skylight, enhancing the bright and open feel of the space. A wall mount for your TV is already installed, and the living and dining areas showcase stunning hardwood floors. The

  Fonda Dillard BHHS FLORIDA PROPERTIES GROUP

  204 Hemingway Dr, Oldsmar, FL 34677
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  /2

  $425,000 Sold Feb 11, 2025

  3132 Phoenix Ave, Oldsmar, FL 34677

  • 2 Beds
  • 1 Bath
  • 1,178 Sq Ft
  • Built 1963

  Last Sold Summary

  • 9% Below List Price
  • $361/SF
  • 24 Days On Market

  Current Estimated Value $420,627

  Last Listing Agent Pamela Leitch UNKNOWN FIRM

  3132 Phoenix Ave, Oldsmar, FL 34677
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  /53

  Est $538,952 Not Listed For Sale

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

  162 Brent Cir, Oldsmar, FL 34677

  162 Brent Cir, Oldsmar, FL 34677
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  /15

  $359,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  1223 Clays Trail, Oldsmar, FL 34677

  This property is one of a kind and the seller is motivated! This spacious 2600 square foot, 4 bedrooms, 2.5 bath, 1 car garage townhome is located in the very popular, highly sought after Eastlake Woodlands Golf and Country Club community. With an open floor plan, custom lighting in the great room, and double master bedrooms,-one on each floor with bay windows and plantation blinds, this

  Stephen Hachey REALTY OF RIVERVIEW LLC

  1223 Clays Trail, Oldsmar, FL 34677
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  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 2,109 Sq Ft
  • House for Rent

  314 Fountainview Cir, Oldsmar, FL 34677

  Charming Oldsmar home with an open floor plan and peaceful water and conservation views. The spacious kitchen overlooks the living and dining areas, creating a bright and inviting space. The split-bedroom layout features a large primary suite with private bath on one side of the home, and two additional bedrooms with a full bath on the other.The garage has been converted into a storage

  Michele Ranjbar COLDWELL BANKER REALTY

  314 Fountainview Cir, Oldsmar, FL 34677
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  /2

  $190,000 Sold Dec 23, 2025

  117 Cypress Ct Unit 117, Oldsmar, FL 34677

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Built 1980

  Last Sold Summary

  • 27% Below List Price
  • $180/SF
  • 132 Days On Market

  Last Listing Agent Marya Morrison, MBA BELLE ISLE REALTY, LLC

  117 Cypress Ct Unit 117, Oldsmar, FL 34677
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  Est $174,286 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 915 Sq Ft

  137 Hunter Lake Dr Unit C, Oldsmar, FL 34677

  137 Hunter Lake Dr Unit C, Oldsmar, FL 34677
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  /58

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  513 Oakwood Blvd, Oldsmar, FL 34677

  Welcome home to this beautifully remodeled 3-bedroom, 2-bath pool home in the heart of Oldsmar. Recently updated and truly move-in ready, this home offers modern finishes, comfortable living spaces, and an ideal location close to the waterfront. Step inside to an inviting open layout featuring new luxury vinyl flooring throughout and a beautifully updated kitchen with new cabinets, countertops,

  Marissa Barrett EXP REALTY LLC

  513 Oakwood Blvd, Oldsmar, FL 34677
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  /10

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,053 Sq Ft
  • Condo for Rent

  144 Cypress Ln, Oldsmar, FL 34677

  This Condo is a second floor unit loacted in Gated Community of East Lake Woodlands.. Cypress Estates One - New Carpet and Fresh Paint - This unit comes with water/sewer/trash, basic cable and basic internet. One space under carport. Open floor plan with Split bedroom layout, good closet space, screened Lanai - use of washer/dryer located in closet on Lanai. Near Beautiful Clearwater Beaches,

  Christi Watson TAMPA BAY SIGNATURE PROPERTIES, LLC

  144 Cypress Ln, Oldsmar, FL 34677
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  /33

  $240,000 Sold Mar 17, 2025

  345 Country Club Dr, Oldsmar, FL 34677

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 1959

  Last Sold Summary

  • 44% Below List Price
  • $159/SF
  • 134 Days On Market

  Current Estimated Value $272,867

  Last Listing Agent Mark Fazzini RE/MAX REALTEC GROUP INC

  345 Country Club Dr, Oldsmar, FL 34677
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  /42

  Est $189,696 Not Listed For Sale

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

  215 Palmetto Ct Unit 215, Oldsmar, FL 34677

  215 Palmetto Ct Unit 215, Oldsmar, FL 34677
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  /30

  $539,900

  • 3 Beds
  • 2.5 Baths
  • 2,143 Sq Ft

  423 Cypress View Dr, Oldsmar, FL 34677

  Location! Homes in this quiet community sell quickly. 2,143 sf two story with Florida room and awesome view of the huge pond on a cul-de-sac. Roof only 3 years old. House has updated white shaker cabinet kitchen with marble-look composite countertops and backsplash, updated flooring and fresh paint throughout. Updated owner’s bathroom shower enclosure, double vanity, and garden tub. Stainless

  James Maiorano MARK SPAIN REAL ESTATE

  423 Cypress View Dr, Oldsmar, FL 34677
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  /18

  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Condo for Rent

  208 Cypress Ct Unit 208, Oldsmar, FL 34677

  Fantastic 2br/2ba FURNISHED/YEARLY condo in East Lake Woodlands Cypress in Oldsmar! Gated community with guard gate. 2nd floor no elevator. Sorry no pets. Available Now with HOA approval. Enjoy Florida's lifestyle living at its best. Home is fully equipped with full size bed and queen size bed. Open floor plan with natural lighting has a dining room/living room combo which opens to wall of

  Lisa Connors RENT SOLUTIONS

  208 Cypress Ct Unit 208, Oldsmar, FL 34677
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  /2

  $260,000 Sold Feb 28, 2025

  1922 Sheffield Ct, Oldsmar, FL 34677

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Below List Price
  • $278/SF
  • 24 Days On Market

  Current Estimated Value $261,837

  Last Listing Agent Teri Pecoroni COLDWELL BANKER REALTY

  1922 Sheffield Ct, Oldsmar, FL 34677
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  /50

  Est $192,247 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  116 Mary Dr Unit 16, Oldsmar, FL 34677

  116 Mary Dr Unit 16, Oldsmar, FL 34677
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  /39

  $380,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,667 Sq Ft

  2208 Sunset Wind Loop, Oldsmar, FL 34677

  Under contract-accepting backup offers. This beautiful 3 bedroom, 2.5 bathroom townhome located in the heart of Oldsmar and is ready for a new owner. This spacious open concept has tile throughout the first floor. The stunning kitchen features white cabinets and granite countertops, a breakfast bar that seats 6 comfortably, pendant lighting, stainless appliances, and large pantry. The living room

  Yael Hatfield KELLER WILLIAMS TAMPA PROP.

  2208 Sunset Wind Loop, Oldsmar, FL 34677
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  /5

  $1,495 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  3648 Meriden Ave, Oldsmar, FL 34677

  CALL TODAY ABOUT OUR DECEMBER MOVE IN SPECIAL2 Bedroom, 1 1/2 bathroom apartment centrally located in Oldsmar, FL. Pet fees apply.

  Nabil Basta BASTA REALTY SOLUTIONS

  3648 Meriden Ave, Oldsmar, FL 34677
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  /2

  $700,000 Sold May 20, 2025

  501 Pinewood Dr, Oldsmar, FL 34677

  • 4 Beds
  • 3 Baths
  • 2,236 Sq Ft
  • Built 2000

  Last Sold Summary

  • $313/SF
  • 7 Days On Market

  Current Estimated Value $691,524

  Last Listing Agent Paul E. Klink RE/MAX ACTION FIRST OF FLORIDA

  501 Pinewood Dr, Oldsmar, FL 34677
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  /2

  Est $195,824 Not Listed For Sale

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

  106 Mary Dr Unit 6, Oldsmar, FL 34677

  106 Mary Dr Unit 6, Oldsmar, FL 34677
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  /55

  $200,000

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

  103 Camille Ct Unit 51, Oldsmar, FL 34677

  This East Lake Woodlands gem is a must-see. This renovated two-bedroom, two-bath downstairs condo offers comfort, convenience, and a beautiful natural setting. Enjoy a peaceful backyard view overlooking green space and a conservation area where wildlife is often seen. As you enter the front door, the renovated kitchen is to your left, featuring stone countertops and abundant storage. The entire

  Bob McCaffery BHHS FLORIDA PROPERTIES GROUP

  103 Camille Ct Unit 51, Oldsmar, FL 34677
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  /30

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 2,404 Sq Ft
  • House for Rent

  5107 Pinnacle Dr, Oldsmar, FL 34677

  Annual fully furnished rental home located in the Pinnacle area of the gated community of East Lake Woodlands Country Club! This inviting three bedroom home offers large scale comfort and charm within its efficient design. You will appreciate the many finer details, beautiful entrance foyer into the formal living room and dining area or just enjoy the open kitchen with pleasant eating nook and

  Becki Joyal CENTURY 21 INTEGRA

  5107 Pinnacle Dr, Oldsmar, FL 34677
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  /2

  $333,000 Sold Dec 26, 2025

  150 Poole Place, Oldsmar, FL 34677

  • 4 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1979

  Last Sold Summary

  • 17% Below List Price
  • $215/SF
  • 124 Days On Market

  Last Listing Agent Kristin Hallamek ENGEL & VOLKERS BELLEAIR

  150 Poole Place, Oldsmar, FL 34677
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  /17

  Est $290,509 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,237 Sq Ft

  205 Clays Trail Unit 205, Oldsmar, FL 34677

  205 Clays Trail Unit 205, Oldsmar, FL 34677
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  /86

  $199,500

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

  107 Mary Dr Unit 107, Oldsmar, FL 34677

  One or more photo(s) has been virtually staged. Move-In Ready Ground Floor Condo in Gated East Lake Woodlands Community!Step into this beautiful updated ground floor condo, where comfort meets convenience in a secure gated environment. The kitchen and bathrooms were thoughtfully renovated in 2017, and brand-new luxury vinyl plank flooring flows seamlessly throughout the living, dining, hall,

  Rachel Friesema BHHS FLORIDA PROPERTIES GROUP

  107 Mary Dr Unit 107, Oldsmar, FL 34677
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  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Condo for Rent

  211 Pine Ct, Oldsmar, FL 34677

  2 bedroom, 2 bathroom 1st floor condo just steps from the community pool, available for rent! Vinyl plank flooring throughout the entire home – no carpet here! Living room/dining room combo with space for a cozy breakfast nook in the kitchen. The kitchen also boasts stainless steel appliances, gleaming quartz counters, and a pantry. Ceiling fans in the living room, patio, and both bedrooms. The

  Brittany Medina WEICHERT REALTORS EXCLUSIVE PROPERTIES

  211 Pine Ct, Oldsmar, FL 34677
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  /2

  $745,000 Sold Aug 21, 2025

  4749 Stoneview Cir, Oldsmar, FL 34677

  • 4 Beds
  • 3 Baths
  • 2,763 Sq Ft
  • Built 1993

  Last Sold Summary

  • 7% Below List Price
  • $270/SF
  • 87 Days On Market

  Current Estimated Value $744,261

  Last Listing Agent Jo Anne Locascio LANDSHARK REALTY

  4749 Stoneview Cir, Oldsmar, FL 34677
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  /2

  Est $195,311 Not Listed For Sale

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

  123 W Cypress Ct Unit 2-95, Oldsmar, FL 34677

  123 W Cypress Ct Unit 2-95, Oldsmar, FL 34677
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  /42

  $494,900

  • 4 Beds
  • 2 Baths
  • 2,122 Sq Ft

  3073 Duane Ave, Oldsmar, FL 34677

  This beautifully remodeled, move-in-ready home is packed with features and ready for its next owner. It has a spacious master bedroom with an en-suite bathroom and a large walk-in closet. Outside, you’ll find a large detached porch with big storage, perfect for storing a golf cart, bikes, kayaks, or motorcycles—or transform it into a bedroom, gym, or office or a party place . The backyard is a

  Madelin Martinez S P O R T REALTY GROUP INC.

  3073 Duane Ave, Oldsmar, FL 34677
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  /16

  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,053 Sq Ft
  • Condo for Rent

  244 Cypress Ln Unit 244, Oldsmar, FL 34677

  2nd Floor Condo with Pond View in Cypress Estates of gated East Lake Woodlands......... Comfortable lifestyle in this second-floor condo with wonderful pond view of 2-acre lake in Cypress Estates of East Lake Woodlands Country Club Community. Walk into living room/dining room combination with sliders out to screen enclosed lanai overlooking pond. Spacious kitchen with breakfast bar to living

  Sandra Harris PREFERRED REALTY GROUP, LLC

  244 Cypress Ln Unit 244, Oldsmar, FL 34677
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  /2

  $235,000 Sold Dec 09, 2025

  367 Countryside Key Blvd, Oldsmar, FL 34677

  • 2 Beds
  • 1.5 Baths
  • 1,105 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $213/SF
  • 135 Days On Market

  Last Listing Agent Stephanie Quarles BHHS FLORIDA PROPERTIES GROUP

  367 Countryside Key Blvd, Oldsmar, FL 34677
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  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  39 Pelican Dr S, Oldsmar, FL 34677

  39 Pelican Dr S, Oldsmar, FL 34677
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  /51

  $515,000

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  948 Lucas Ln, Oldsmar, FL 34677

  One or more photo(s) has been virtually staged. Welcome to a truly impressive villa set in the East Lake Woodlands nature-filled, and amenity-rich golf community. Tucked away on an expansive .25 ACRE corner lot in a NON-FLOOD zone, this quiet end-unit property offers the kind of peaceful setting buyers crave - mature trees, backyard privacy, and a serene pond view right outside your massive

  Rebecca Norton COLDWELL BANKER REALTY

  948 Lucas Ln, Oldsmar, FL 34677
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  /2

  $353,000 Sold Mar 21, 2025

  553 Dove Terrace W, Oldsmar, FL 34677

  • 2 Beds
  • 2 Baths
  • 1,478 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $239/SF
  • 1 Day On Market

  Current Estimated Value $358,585

  Last Listing Agent Cathy McCarthy RE/MAX REALTEC GROUP INC

  553 Dove Terrace W, Oldsmar, FL 34677
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  Est $218,135 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  112 Woodlake Ln Unit 112, Oldsmar, FL 34677

  112 Woodlake Ln Unit 112, Oldsmar, FL 34677
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  $475,000

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  440 Lakeview Dr, Oldsmar, FL 34677

  Price Reduced -This is a rare lakefront opportunity with unmatched Views & Value in Oldsmar NON FLOOD ZONE—schedule your private showing today before it’s gone.3bed/2bath/2car garage home with separate family and living room offers a truly one-in-a-million view overlooking the lake and peaceful conservation area, where egrets, deer, and abundant birdlife are regular visitors. Situated on an

  Nicole Smith-Pellegatti RMS ELITE PROPERTIES

  440 Lakeview Dr, Oldsmar, FL 34677

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