Three Oaks Homes under $500,000

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Newest Three Oaks Homes under $500,000

$474,000

3 Beds ⋅ 2 Baths ⋅ 226026350 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Set on an oversized .34-acre homesite with coveted western rear exposure, this 3-bedroom, 2-bath pool home offers the space, privacy, and laid-back Florida lifestyle that make Southwest Florida living so appealing. The single-story split-bedroom floor plan provides comfortable separation between the primary suite and guest rooms, while vaulted ceilings enhance the sense of openness throughout the main living areas. Large glass doors create an easy connection between the interior and the screened outdoor living space, drawing the eye toward the private pool and landscaped backyard beyond. The eat-in kitchen offers abundant cabinetry and counter space, stainless steel appliances, and convenient access to the surrounding living and dining areas, while the primary suite includes direct access to the lanai, a spacious walk-in closet, and an en-suite bath. Outside, the expansive screened lanai and private in-ground pool create a wonderful setting for morning coffee, afternoon swims, casual dinners, entertaining friends, and unwinding at the end of the day. With western exposure, evenings bring beautiful skies and colorful sunsets right from your own backyard. Recent improvements include a roof replaced in 2023, a new A/C air handler and compressor in 2026, and extensive 2026 irrigation updates including a new timer, pipes, valves, rotors, pop-ups, and nozzles. An attached two-car garage adds storage and everyday convenience, while extremely low HOA fees make this an especially appealing option for buyers looking to keep ongoing ownership costs down. The location is hard to beat, with I-75 less than five minutes away and Southwest Florida International Airport approximately 10 minutes from home, plus convenient access to Miromar Outlets, Hertz Arena, Florida Gulf Coast University, Coconut Point, world-class healthcare, Gulf beaches, shopping, dining, entertainment, and everyday essentials. Whether you’re searching for a full-time residence, seasonal retreat, or investment opportunity, this home brings together an oversized lot, private pool, sunset exposure, meaningful recent improvements, low HOA fees, and an exceptionally convenient Southwest Florida location.

19112 Pine Run LN, Fort Myers

$439,000

3 Beds ⋅ 2 Baths ⋅ 226032891 MLS

Discover the perfect blend of privacy and charm in the highly sought-after Cypress Chase community in Three Oaks. Nestled in a peaceful neighborhood lined with mature oak trees, this three-bedroom, two bath home offers low HOA fees, an X flood zone for reduced insurance costs, family-friendly charm and quiet walkable streets. Whether you are looking for a perfect place to raise your family, a quiet place to retire, or a winter snowbird get- away without the high expenses… this home… in this community… delivers 100%. Step outside to a peaceful 38’ screened-in lanai, heavily landscaped, offering plenty of space to relax and enjoy the in-ground heated hot tub. Conveniently located only 1 block to the LeeTran Bus Stop on Pine Chase Dr, within walking distance to an A-rated elementary school, and only a short drive to Three Oaks Middle School and Three Oaks Academy, Gulf Coast Town Center, Miromar Outlets, Three Oaks Parks, RSW International Airport, Florida Gulf Coast University, fine restaurants and world-famous beaches. This home will not last long so schedule your private showing today.

18895 Cypress View DR, Fort Myers

$454,500

3 Beds ⋅ 2 Baths ⋅ 2026030597 MLS

Less time driving …more time living. This pool home in Three Oaks is close to everything! 3 bedrooms, 2 Bath, Pool home with screened enclosure is walking distance to community park, and a short drive to Gulf Coast Town Center or Bonita Beach. This family friendly neighborhood offers a community pool, tennis courts, underground utilities with decorative street nights for those evening walks. There is a screened front entry with LPV flooring throughout. The kitchen offers plenty of counter space and breakfast bar with white shaker cabinets and stainless steel appliances. The primary bedroom has vaulted ceilings, 2 walk in closets, with sliding glass door access to back porch. The primary bathroom has a separate soaking tub and stand up shower, dual sinks with quartz counter top and recessed lighting. Step outside to the screened in patio with electric heated pool making it great for entertaining the kids all year long. Recent updates include a new pool pump, new screen doors, pool heater replaced in 2021. Close to shopping, dinning, and entertainment, come check out all this homes has to offer. Seller carries flood insurance by choice and is paying $857/year. This policy is also assumable. Motivated sellers welcome all offers!!

17791 Castle Harbor DR, Fort Myers

$465,000

3 Beds ⋅ 2 Baths ⋅ 2026030057 MLS

PRIME S FT MYERS/ESTERO area location Near Everything! Great Value for POOL home with 3 Bedrooms and 2 Full Baths on LARGE LOT near end of Cul-de-sac (no thru traffic) with Tree-Lined Street & Sidewalks. Stainless Steel Appliances, Wood Cabinetry and Granite Countertops. NO Carpet. Spacious Floor Plan with entry to Living and Dining Areas and Additional Large Family Room and Breakfast Nook. Sliders from Living and Family Room to Pool and Screened Lanai. Primary Suite with Slider to Pool, Separate Vanities, Walk0in Closets, Garden Tub and Walk-in Shower. Split Bedroom Plan with Full Bath, 2 More Bedrooms, 1 with Walk-in Closet. Laundry Room with Washer & Dryer. Garage has partial air conditioned space perfect for Workshop or Hobby Area. Close to Areas Best Shopping, Restaurants, Parks, Schools, FGCU, I-75, Highway 41/Tamiami Trail, RSW Airport, Bonita Springs, Estero and Naples. Low fees and NO CDD fees.

17341 Stepping Stone DR, Fort Myers

$425,000

3 Beds ⋅ 2 Baths ⋅ 226022608 MLS

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home in the highly desirable Pine Run community within Three Oaks! Offering the perfect combination of comfort, convenience, and value, this home features a **brand-new roof (2026)** and is located in a **low HOA fee** community. Step inside to discover a bright, open floor plan designed for everyday living and effortless entertaining. The highlight of the home is the stunning outdoor living space, featuring a **gorgeous screened-in pool**, spacious covered lanai, and large pool cage—your own private Florida oasis perfect for relaxing or hosting family and friends year-round. Ideally situated in one of Southwest Florida's most convenient locations, you're just minutes from **Miromar Outlets, Coconut Point Mall, Gulf Coast Town Center**, and an endless selection of shopping, dining, and entertainment. Commuting is a breeze with **I-75 less than 5 minutes away**, **Southwest Florida International Airport (RSW) just 10 minutes away**, and the area's beautiful Gulf beaches less than **20 minutes** from your doorstep. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional home delivers an unbeatable location, desirable features, and the Florida lifestyle you've been looking for.

19028 Pine Run LN, Fort Myers

$480,000

4 Beds ⋅ 2.5 Baths ⋅ 226022324 MLS

Welcome to this beautifully updated two-story home in the highly desirable Islands at Three Oaks community! Offering nearly 2,300 square feet of living space, this LAKEFRONT move-in-ready residence features 4 bedrooms, 2.5 bathrooms, and a floorpan to fit many lifestyles. From the moment you enter, you'll be impressed by the soaring ceilings and abundance of natural light that create an open and inviting atmosphere. The home has been extensively updated with fresh interior and exterior paint, brand-new carpeting, stylish light fixtures, updated hardware, and a stunning new kitchen featuring white shaker cabinetry with soft-close doors and drawers, gorgeous Corian countertops, and stainless-steel appliances. The spacious first-floor primary suite offers a private retreat with dual updated vanities, a relaxing jetted soaking tub, separate walk-in shower, and ample closet space. Upstairs, you'll find additional bedrooms and living space to accommodate family and guests comfortably. Step outside to the oversized screened lanai, offering plenty of room for outdoor dining, entertaining, and relaxing while enjoying the beautifully landscaped backyard. Lush tropical landscaping surrounds the home, enhancing its curb appeal and creating a peaceful setting. Located in one of South Fort Myers' most sought-after communities, this home is conveniently situated near shopping, dining, entertainment, RSW International Airport, and schools. With school starting soon, now is the perfect time to make your move and enjoy everything this exceptional home has to offer!

17911 Bermuda Dunes DR, Fort Myers

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.