Tanglewood Homes under $500,000

Welcome to Tanglewood, a charming subdivision nestled in the heart of Florida, where tranquility meets convenience. This vibrant community offers an inviting atmosphere, perfect for families, retirees, and anyone seeking a serene lifestyle without compromising on accessibility to urban amenities. Tanglewood is renowned for its lush landscapes, picturesque streets, and a friendly neighborhood vibe that makes it feel like home from the moment you arrive.

One of the standout features of Tanglewood is its diverse selection of homes priced under $500,000. Whether you're a first-time homebuyer, looking to downsize, or seeking an investment opportunity, you'll find a variety of options that cater to different tastes and needs. From cozy single-family homes to modern townhouses, each property is designed with comfort and style in mind, making it easy to envision your life here.

The community is not just about beautiful homes; it also boasts an array of amenities that enhance the quality of life for its residents. Enjoy leisurely strolls through well-maintained parks, engage in community events, or take advantage of the nearby shopping and dining options that are just a stone's throw away. With excellent schools and convenient access to major highways, Tanglewood is ideally situated for those who appreciate both peaceful living and urban convenience.

Discover the charm of Tanglewood today, where your dream home awaits at an affordable price. Experience the perfect blend of community spirit and modern living in this delightful Florida subdivision!

Newest Tanglewood Homes under $500,000

$409,900

3 Beds ⋅ 2 Baths ⋅ 226033441 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to this beautifully maintained 3-bedroom, 2-bath attached villa in Tanglewood at Lely Country Club, ideally located in the heart of Naples. From the moment you enter, cathedral ceilings and an open, airy layout create a welcoming sense of space, while freshly painted interiors offer a bright, move-in-ready feel. The spacious primary suite features vaulted ceilings and a walk-in closet, providing a comfortable private retreat. Step outside to the screened-in lanai and open patio, where a peaceful, landscaped setting creates the perfect backdrop for morning coffee, outdoor dining, or relaxing after a day at the beach. Enjoy the best of Naples with Downtown Naples, Fifth Avenue South, world-class dining, shopping, beautiful beaches, and everyday conveniences all just minutes away. Whether you are searching for a full-time residence, seasonal getaway, or income-producing property, this villa offers a wonderful combination of comfort, location, and lifestyle. A fantastic opportunity to own in one of Naples’ established and sought-after communities—come see all this charming villa has to offer!

430 Saint Andrews BLVD Unit 6, Naples

439 Saint Andrews BLVD Unit 145-0, Naples

$460,000

3 Beds ⋅ 2 Baths ⋅ 226031969 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Beautiful and well-maintained 3-bedroom, 2-bathroom home in a highly desirable location with stunning lake views! This inviting property offers the perfect combination of comfort, style, and the Florida lifestyle. Enjoy peaceful water views from your private swimming pool, creating the ideal setting for relaxing and entertaining year-round. The home features newly renovated bathrooms and a new A/C system, providing modern comfort and peace of mind. Bright and welcoming living spaces make this home feel inviting from the moment you walk in. Conveniently located near shopping, dining, schools, and major roadways. Don't miss the opportunity to own this beautiful pool home with lake views in a fantastic location!

439 Saint Andrews BLVD Unit 145-0, Naples

$475,000

3 Beds ⋅ 2 Baths ⋅ 226030035 MLS ⋅ Tanglewood BLDG.

Beautifully updated3-bedroom,2-bath villa in Tanglewood I at Lely Country Club. Features a recently remodeled kitchen with modern finishes, a new roof installed in 2024, an attached garage, screened lanai with tranquil lake view. Open, functional layout with peaceful surroundings. Convenient to shopping, dining, golf, downtown Naples, and Gulf beaches. Low maintenance living in a well-established community.

561 Saint Andrews, Naples

$445,000

2 Beds ⋅ 2 Baths ⋅ 226028185 MLS

Welcome to this beautiful 2-bedroom, 2-bath home tucked away in the desirable Tanglewood neighborhood, just off the palm tree-lined McGregor Boulevard. This charming home offers a wonderful combination of comfort, style, and location. Step inside to a spacious living area featuring elegant French doors that open to a stunning pool and beautifully landscaped backyard. The screened-in lanai provides the perfect setting for relaxing or entertaining while enjoying the Florida lifestyle. The kitchen is a standout, with a unique “fishbowl” style window offering beautiful views of the pool and lanai. Welcome to this beautiful 2-bedroom, 2-bath home tucked away in the desirable Tanglewood neighborhood, just off the palm tree-lined McGregor Boulevard. This charming home offers a wonderful combination of comfort, style, and location. Step inside to a spacious living area featuring elegant French doors that open to a stunning pool and beautifully landscaped backyard. The screened-in lanai provides the perfect setting for relaxing or entertaining while enjoying the Florida lifestyle. This home features ceramic tile in the kitchen creating a clean and cohesive look, while the windows fill the space with plenty of natural light.. The kitchen is a standout, with a unique “fishbowl” style window offering beautiful views of the pool and lanai. Wood flooring is featured in the rest of the home. The spacious primary bedroom includes a walk-in closet, while the additional bedroom and bath provide comfortable accommodations for family or guests. The air-conditioned 2-car garage offers exceptional versatility and can easily be used as a bonus room, home office, hobby space, or additional living area. You’ll be close to restaurants, shopping, and everyday conveniences, while Fort Myers Beach and Sanibel Island are approximately 20 minutes away. Recent updates include a roof replaced in 2020 and an A/C system and ductwork that are approximately two years old. A wonderful opportunity to enjoy a beautiful home, private pool, lush landscaping, and an excellent Fort Myers location!. The spacious primary bedroom includes a walk-in closet, while the additional bedroom and bath provide comfortable accommodations for family or guests. The air-conditioned 2-car garage offers exceptional versatility and can easily be used as a bonus room, home office, hobby space, or additional living area. Located in a great neighborhood within walking distance of Tanglewood Elementary School, this home is conveniently situated off McGregor Boulevard between College Parkway and Colonial Boulevard. You’ll be close to restaurants, shopping, and everyday conveniences, while Fort Myers Beach and Sanibel Island are approximately 20 minutes away. Recent updates include a roof replaced in 2020 and an A/C system and ductwork that are approximately two years old. A wonderful opportunity to enjoy a beautiful home, private pool, lush landscaping, and an excellent Fort Myers location!

1352 Oaklawn CT, Fort Myers

$380,000

3 Beds ⋅ 2 Baths ⋅ 226026670 MLS

Step into this home featuring new luxury vinyl flooring throughout and soaring vaulted ceilings in both the great room and primary bedroom, creating a bright, open, and spacious feel. The remodeled kitchen has been enhanced with an expanded pass-through, newer stainless-steel appliances, granite countertops, a tiled backsplash, and a sunny breakfast area with a large window that fills the space with natural light. The primary suite offers an updated bath with dual sinks and a generous walk-in closet. A standout feature is the oversized enclosed lanai complete with its own air conditioner, providing comfortable year-round living space. Outdoors, enjoy a private brick paver patio surrounded by mature fruit trees, perfect for relaxing or entertaining. With low HOA fees, this home offers exceptional value and is conveniently located just minutes from wonderful downtown Naples, world-class shopping, dining, and our beautiful Gulf beaches.

510 Saint Andrews BLVD Unit 16, Naples

$469,990

3 Beds ⋅ 2 Baths ⋅ 2026027151 MLS

Welcome to this beautifully maintained, NO FLOOD ZONE, two-owner home in the highly desirable Tanglewood community bordering Whiskey Creek. Offering approximately 2,085 square feet, this spacious split-bedroom floor plan features luxury 9” vinyl plank flooring throughout, fresh interior paint, contemporary LED lighting, and elegant 5” baseboards. All rooms have custom window treatments- including wall and vertical blinds. The heart of the home is the updated kitchen with a tray ceiling, breakfast area, generous bar seating, and an open layout overlooking the expansive family room—perfect for everyday living and entertaining. A formal dining room and inviting foyer provide additional gathering space, while the functional brick fireplace adds warmth and character on cooler Florida evenings. The primary suite offers a large walk-in closet, and both bathrooms have been tastefully updated with Kohler toilets. Step outside to enjoy the newly screened lanai with a bronze locking security door, overlooking the private fenced backyard with plenty of room to add a pool or spa. Recent improvements provide peace of mind, including a 2022 roof with third nail, Storm Smart hurricane protection with Storm Catcher screen system, updated electrical with GFCI receptacles, 4-ton Rheem heat pump, 2023 submersible irrigation well pump, programmable thermostat, new exterior lighting, matte stainless, irrigation system with Hunter X-Core controller, and a spacious oversized garage featuring an epoxy floor and utility sink. Located in a quiet, established neighborhood with convenient access to shopping, dining, beaches, downtown Fort Myers, and Southwest Florida International Airport. While Tanglewood does not have its own golf course, optional membership to Whiskey Creek Country Club offers golf, social amenities, and golf cart access for an additional membership fee. The oversized circular driveway provides ample parking for multiple vehicles while enhancing the home’s curb appeal. Move-in ready and meticulously maintained, this home combines timeless quality, thoughtful updates, and an unbeatable location.

1442 Woodwind CT, Fort Myers

$493,000

3 Beds ⋅ 2 Baths ⋅ 226021315 MLS

Welcome to this beautifully renovated, move-in-ready villa where the expensive updates have already been completed for you. Thoughtfully remodeled from top to bottom, this exceptional home features a new high-definition shingle roof, hurricane-impact windows, new water lines throughout the home, a recently replaced A/C system and water heater, new gutters, fresh exterior paint, professionally cleaned HVAC ducts, and fresh interior paint on the walls, ceilings, and trim—providing peace of mind and significantly reducing future maintenance costs. The stunning kitchen has been completely redesigned with custom Amish-built soft-close cabinetry, elegant quartz countertops, a marble backsplash, new Samsung smart appliances, a wall oven, refrigerator with dual ice makers, new sinks, and LED lighting above and below the cabinetry. Luxury vinyl plank flooring flows throughout the home, complemented by new window blinds, updated light fixtures, smoke detectors, a Wi-Fi smart thermostat, and a redesigned primary bedroom closet. Both bathrooms have been tastefully updated with new vanities, a completely remodeled primary shower, new toilets, and new exhaust fans. Additional improvements include laundry and garage cabinetry, a new interior garage access door, a new garage door opener, and replaced rollers on the living room sliding glass doors. Outdoor living is equally impressive with epoxy-coated garage, lanai, and front entry floors, a garage screen enclosure, a motorized hurricane-rated lanai screen, manual hurricane shutters, and professionally updated landscaping, creating an ideal space to enjoy Southwest Florida living year-round. This is far more than a home with cosmetic improvements—it’s a property where the major systems and big-ticket items have already been addressed. From the impact windows and newer roof to the updated plumbing, HVAC, kitchen, and bathrooms, this home offers exceptional value, quality, and peace of mind. Combined with its desirable Lely Country Club location, golf course setting, low HOA fees, vaulted ceilings, and close proximity to downtown Naples, Gulf beaches, shopping, and dining, this is truly one of the most move-in-ready and competitively updated homes available in the community.

657 Saint Andrews BLVD, Naples

$495,000

4 Beds ⋅ 3 Baths ⋅ 2026016775 MLS

Welcome to 5148 Fairfield Dr, a spacious 4-bedroom, 3-bath home offering 2,259 sq. ft. of living space on a beautiful oversized corner lot in the highly desirable Tanglewood community of Fort Myers. This Michigan-built home is known for its solid construction and quality craftsmanship, offering a wonderful combination of character, space and potential. Located just off the iconic, Royal Palm-lined McGregor Boulevard, the home features dedicated interior laundry room with utility sink, NEWER ROOF (2020), HURRICANE IMPACT WINDOWS AND GARAGE DOOR, a 3-ZONE HVAC SYSTEM, manual hurricane shutters, central air purifier system and a new stove. The flexible floor plan includes four bedrooms, with one that can easily serve as a home office, den, hobby room or guest space. Enjoy the charm of an established neighborhood with mature landscaping where GOLF CARTS ARE PERMITTED, and Tanglewood Elementary School is conveniently located just down the street! Ideally located near shopping, dining, Downtown Fort Myers, Fort Myers Beach, Sanibel Island and many of Southwest Florida's favorite attractions. Whether you're enjoying a peaceful sunrise stroll or an evening sunset walk, Tanglewood is a wonderful neighborhood to call home. If you're looking for a primary residence, seasonal Florida getaway or a home you can update and make your own, this property offers tremendous potential. SELLER IS MOTIVATED AND READY TO REVIEW OFFERS! Schedule your private showing today!

5148 Fairfield DR, Fort Myers

$450,000

3 Beds ⋅ 2 Baths ⋅ 226013766 MLS

Beautifully fully renovated and move-in ready, this stunning 3-bedroom, 2-bath attached villa with a 2-car garage. The home has been completely rehabbed and features a brand-new roof, offering peace of mind and modern finishes throughout. This bright and spacious residence offers an open floor plan with abundant natural light and thoughtfully updated living spaces. The upgraded kitchen flows seamlessly into the main living and dining areas, creating the perfect setting for both everyday living and entertaining. The primary suite provides a comfortable retreat with a private bath and generous closet space, while two additional bedrooms offer flexibility for guests, a home office, or additional living space. Offered fully furnished, this home is truly turnkey—perfect for seasonal residents, investors, or anyone looking to enjoy the Naples lifestyle immediately.

480 Saint Andrews BLVD Unit 14, Naples

$422,000

3 Beds ⋅ 2 Baths ⋅ 226006515 MLS

Move-in ready 3-bedroom, 2-bath attached villa with an attached 2-car garage, Split bedrooms, ideally located in the Tanglewood community of Lely Country Club. This light-filled, single-story home features a desirable split floor plan, vaulted ceilings, and an open living and dining area perfect for everyday living or entertaining. The spacious primary suite offers a walk-in closet and private bath, while two additional bedrooms provide flexibility for guests, a home office, or seasonal living. Enjoy the Florida lifestyle from the screened lanai, just steps from the community pool. Additional highlights include electric storm shutters, breakfast bar, ample storage, and a low-maintenance lifestyle with low HOA fees. Conveniently located minutes from downtown Naples, 5th Avenue South, beaches, Marco Island, shopping, dining, and golf (no mandatory membership). Ideal as a full-time residence, seasonal retreat, or investment opportunity.

494 Saint Andrews BLVD Unit 14, Naples

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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.