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$350,000

Mid Rise (4-7)

One or more photo(s) has been virtually staged, AI generated or rendered. Imagine ending your day with a glass of wine in hand, watching the sun melt into the golf course right from your…

$399,999

Mid Rise (4-7)

Beautifully remodeled and tastefully turnkey furnished 2-bedroom, 2-bath second-floor condo with breathtaking western exposure, delivering spectacular Florida sunsets night after night. This exceptional residence also offers a strong proven rental history, making it an outstanding…

$399,000

Low Rise (1-3)

Enjoy Resort-Style Living with IMMEDIATE GOLF ACCESS! Welcome to Highland Woods Golf & Country Club, one of Bonita Springs most sought after bundled golf communities. The beautifully furnished top-floor Carlton Veranda offers…

$295,000

Mid Rise (4-7)

This is a wonderful opportunity to purchase a condominium in one of the most sought-after gated bundled golf communities in Southwest Florida, Highland Woods Golf and Country Club. This beautiful two-bedroom, two-bath condominium with easy…

$529,000

Villa Attached

This is a wonderful opportunity to own this beautiful villa in one of the sought-after golf communities in Southwest Florida, Highland Woods Golf & Country Club. This impeccably maintained, beautiful two-bedroom, two-bath with a den/office…

$425,000

Low Rise (1-3)

Welcome to effortless Southwest Florida living at 26841 Clarkston Dr #105 in Bonita Springs. This beautifully maintained first-floor residence invites you in with a bright, open layout designed for comfort and ease. Natural light fills…

$225,026

Low Rise (1-3)

Welcome to this light-filled first-floor TURNKEY residence overlooking the golf course in Highland Woods, ready for its new owners. This thoughtfully designed on-bedroom PLUS DEN, two-bath home with a desirable offers both comfort and privacy,…

$675,000

Villa Attached

You found it! Beautiful water/golf-view villa with a 2-car garage in highly desirable Highland Woods Golf & Country Club, ideally located near the convenient US 41 entrance and just moments from the new resort-style pool,…

$375,000

Low Rise (1-3)

Escape the winter blues and find your sanctuary in this stunning two-bedroom, two-bathroom Carlton Veranda, located in the exclusive gated bundled golf community of Highland Woods. This meticulously maintained unit features a desirable split bedroom…

$390,000

Low Rise (1-3)

Explore the stunning Carlton Veranda, a remarkable gem situated in the highly sought-after Highland Woods bundled golf community. This pristine 2-bedroom, 2-bathroom home features a modern kitchen with granite countertops, chic white shaker-style cabinetry, and…

$399,000

Low Rise (1-3)

Welcome home to this stunning first-floor Barrington Veranda in the highly sought-after Highland Woods community! This beautifully appointed residence dazzles with upgrades throughout, including stainless steel appliances, refaced cabinetry, tile flooring in the main living…

$410,000

Low Rise (1-3)

If you’ve been dreaming about an easy, relaxed Southwest Florida lifestyle, this beautifully upgraded first-floor Barrington Veranda in Highland Woods Golf & Country Club might be exactly what you’ve been waiting for. From the moment…

$300,000

Mid Rise (4-7)

Welcome to Your Piece of Paradise - Ideal for Personal Use or Investment!This desirable 2-bedroom 2-bath condo in the prestigious bundled golf community of Highland Woods Golf and Country Club is offered turnkey and has…

$699,999

Villa Attached

Welcome to your dream home in the picturesque and vibrant community of Highland Woods. This beautifully remodeled Cheshire Villa is situated in a coveted bundled golf neighborhood, offering a luxurious and comfortable lifestyle. The heart…

$424,000

Low Rise (1-3)

Discover the allure of this beautifully remodeled Carlton Veranda in the sought-after Highland Woods community. This stunning home showcases an open kitchen concept featuring stainless steel appliances, custom cabinetry, and a granite island, perfect for…

$1,095,000

Single Family Residence

This stunning, remodeled Pinehurst model home in the coveted Highland Woods Golf and Country Club is truly one of a kind. Featuring three spacious bedrooms and three full bathrooms, this residence has been thoughtfully designed…

$349,900

Mid Rise (4-7)

This is your opportunity to own this turnkey impeccably furnished, beautifully renovated second-floor terrace condominium overlooking the 8th fairway with sunset views in the 18-hole bundled golf community of Highland Woods Golf & Country Club.…

$419,000

Low Rise (1-3)

Welcome to your slice of paradise in the highly sought-after gated and bundled golf community of Highland Woods Golf & Country Club in Bonita Springs, FL. This beautifully updated first-floor condo offers a perfect blend…

$445,000

Low Rise (1-3)

Nestled in the heart of the prestigious Highland Woods bundled golf community, this exquisite two-bedroom, two-bathroom plus den carriage home redefines luxurious living. Perfectly positioned in the only true south facing building, this home invites…

$325,000

Low Rise (1-3)

Location Location Location! The lovely two bedroom two bathroom Carlton Veranda is a wonderful winter time retreat. This home just a short walk to everything Highland Woods has to offer. It is light and bright…

$419,000

Low Rise (1-3)

Located in the heart of Bonita Springs, this beautifully updated 2-bedroom, 2-bathroom condo offers 1,256 square feet of living space withe exceptional views of the golf course and lake. Built in 1998, this home seamlessly…

$429,000

Low Rise (1-3)

Your paradise awaits when you arrive at this meticulously maintained 2 bedrooms plus den with detached garage in the St Andrews Verandas! Not only is there the most relaxing and incredible view from your private…

$345,000

Low Rise (1-3)

Light, bright, and beautifully updated! This 2-bedroom, 2-bathroom second-floor end unit in Heathermoor III offers the perfect blend of comfort and convenience and comes mostly furnished! As an end unit, the condo enjoys additional…

$499,900

Low Rise (1-3)

Experience luxury living in this beautifully remodeled Veranda located in the prestigious Highland Woods Golf and Country Club. This exceptional home combines elegance with modern convenience, featuring a remodeled kitchen equipped with custom cabinetry, top-of-the-line…

$430,000

Low Rise (1-3)

Welcome to this charming two-bedroom, two-bathroom plus a den St. Andrews Veranda, nestled in the scenic bundled golf community of Highland Woods. Bathed in natural light and featuring a spacious, open floor plan, this home…

$629,000

Villa Attached

This beautifully maintained 3-bedroom, large kitchen and family room home is ideally situated in one of Naples’ most desirable bundled golf communities, featuring an 18-hole prestige championship course and a vibrant country club lifestyle.Welcome to…

$579,000

Villa Attached

This is your opportunity to purchase a beautiful villa in Highland Woods. This is a two-bedroom, two-bath home with an office/den, all stainless appliances kitchen, ample closet space, dual main bath sinks, with beautiful flooring…

$278,750

Mid Rise (4-7)

Welcome to this beautifully maintained first-floor 2BR/2BA condo in the highly desirable Highland Woods community, offered TURNKEY. The roof was replaced in 2020 and a brand new A/C unit was installed in July 2025. The…

$430,000

Low Rise (1-3)

Discover the charm of the Abbey Model Veranda, nestled on the first floor within the prestigious Highland Woods bundled golf community. This enchanting residence features tile flooring, stunning sunset and golf course views, and a…

$259,900

Low Rise (1-3)

TURNKEY FIRST FLOOR CONDO WITH GOLF COURSE VIEWS & NEW LUXURY VINYL PLANK FLOORING – SELLER IS MOTIVATED!! Discover the perfect blend of comfort and convenience in this meticulously maintained first-floor condo located in Highland…

$1,050,000

Single Family Residence

Welcome to this magnificent single-family home located in the exclusive, gated, bundled golf community of Highland Woods. Rarely on the market, this property offers a 3-car garage and picturesque lake views. It comprises 4 generously…

$414,900

Low Rise (1-3)

Discover this elegant second-floor Barrington Veranda, fully furnished and ready for you to make it your home. The interior is in pristine condition, featuring fresh paint, breathtaking views, ample storage space, a one-car detached garage,…

$430,000

Low Rise (1-3)

Experience the charm of the Abbey Model Veranda, located on the first floor within the esteemed bundled golf community of Highland Woods. This delightful property boasts tile floors, granite countertops, new carpet, a detached one-car…

$675,000

Villa Attached

Rarely available! Being 1 of only 8 two-stories built in the community puts this unit configuration in high demand! This oversized Villa - nearly 2,500 sq. ft - has a great floor plan,…

$390,000

Low Rise (1-3)

Location Location Location! The lovely two bedroom two bathroom plus den Barrington Veranda is a wonderful winter time retreat. This home just a short walk to everything Highland Woods has to offer. It is light…

$479,000

Villa Attached

Discover this quaint Ashmoor Villa, nestled within the prestigious gated community of Highland Woods. This charming property features two bedrooms, two bathrooms, and a versatile den, making it ideal for entertaining. The villa boasts elegant…

$519,000

Villa Attached

This stunning, modern villa is located in the highly desirable Highland Woods community. The home boasts a light-filled, open concept floor plan that is perfect for both everyday living and entertaining. With split bedrooms, the…

$685,000

Villa Attached

Welcome to your dream home in the highly sought-after-gated golf community of Highland Woods in sunny Southwest Florida! This fully remodeled 2 bedroom/2 bathroom villa with den/office offers amazing views of the 13th green &…

$499,900

Villa Attached

BEST PRICED Villa in Highland Woods!! Welcome home to the Ashmoor Villa, a charming retreat nestled in the sought-after gated bundled golf community of Highland Woods. From the moment you step through the front door…

$325,000

Low Rise (1-3)

Welcome home to this charming first-floor condo, located in the serene and sought-after Highland Woods Golf and Country Club in Bonita Springs, FL. This elegant 2-bedroom, 2-bathroom residence is being offered turnkey and offers a…

$999,000

Single Family Residence

This beautifully renovated St. Charles floor plan home in the Highland Woods Golf and Country Club offers an exquisite blend of luxury and convenience. Featuring tile "wood-like" floors throughout, the home boasts a remodeled kitchen…

$405,000

Low Rise (1-3)

This turnkey 2br/2ba condo offers a seamless blend of style, convenience, and resort-style living. Featuring a brand-new roof, hurricane impact windows and sliders, and scheduled for fresh exterior paint in early 2025, this home is…

$499,900

Low Rise (1-3)

Discover your dream home in the vibrant bundled golf community of Highland Woods! This beautifully updated carriage home is located in the heart of Bonita Springs and offers everything you could desire. The property features…

$395,000

Mid Rise (4-7)

All club assessments have been paid by the seller. Immediate Golf available. This rarely available stunning end unit offers 1,408 square feet of beautifully designed living space, featuring 2 spacious bedrooms 2 bathrooms plus a…

$484,900

Low Rise (1-3)

Check out this cozy first-floor Abbey Model Veranda in the gated golfing community of Highland Woods. With two bedrooms, two bathrooms, and a spacious den, there's plenty of room for family and friends. This place…

$499,000

Low Rise (1-3)

Welcome to this stunning second-floor Abbey Veranda, where elegance meets modern comfort. The updated kitchen boasts granite countertops, raised panel cabinetry, and stainless steel appliances, making it a chef's delight. Both the guest and master…

$1,175,000

Single Family Residence

Welcome to this stunning modified York floorplan single-family home, nestled within the spectacular bundled golf community of Highland Woods Golf & Country Club. This expansive residence boasts four bedrooms, three full bathrooms, and a versatile…

$565,000

Villa Attached

Welcome to the stunning Cheshire Villa, located in the exclusive gated community of Highland Woods in Bonita Springs, FL. This delightful home features 2 spacious bedrooms, 2 bathrooms, a den, and a private pool. As…

$399,000

Low Rise (1-3)

Take a look at this charming two-bedroom, two-bathroom with a den Barrington Veranda located in the gated, bundled golf community of Highland Woods. This home is light and bright with stunning preserve views. Upgrades…

$489,000

Low Rise (1-3)

Welcome to your dream home in the picturesque bundled golf community of Highland Woods. This stunning two bedroom/two bathroom plus den carriage home is located in the closest building to the club facilities and has…

$1,049,000

Single Family Residence

Welcome to this beautifully updated Trenton floor plan nestled in the picturesque bundled golf neighborhood of Highland Woods. This three-bedroom, three-bathroom home boasts a recently renovated kitchen with new cabinets, granite countertops, a glass tile…

$470,000

Mid Rise (4-7)

Experience Paradise in Highland Woods! This impeccable fully remodeled and meticulously maintained 2-bedroom, 2-bathroom condo is a rare gem, offering unparalleled elegance and comfort. Every detail has been thoughtfully designed, making this home truly one of…

$344,900

Low Rise (1-3)

Welcome to your dream home nestled in the vibrant Highland Woods community! This delightful two-bedroom, two-bathroom condo features an inviting open floor plan, ideal for entertaining guests. With tasteful decor, new laminate flooring, a…

$449,000

Low Rise (1-3)

Discover your winter sanctuary in this stunning two-bedroom, two-bath Carlton Veranda, situated in the exclusive gated community of Highland Woods, celebrated for its bundled golf amenities. This impeccably maintained home offers a sought-after split bedroom…

$348,500

Low Rise (1-3)

One of the prettiest views in all of Highland Woods! Southwestern, oak trees, palm trees, lake, golf & pool off in the distance frame the private view with no other buildings in sight. This charming…

$599,950

Villa Attached

Experience elevated Florida living in this exceptionally remodeled villa, where modern luxury meets effortless convenience, perfectly situated in the prestigious Highland Woods community. From the moment you step inside, you’ll be captivated by the thoughtfully…

$489,000

2 Story,Low Rise (1-3)

Your new Florida lifestyle awaits! Simply put… a STUNNING main level condo in the St Andrews Verandas Subdivision of Highland Woods. This floor plan features two bedrooms, two full baths and a spacious den area.…

$435,000

Low Rise (1-3)

Welcome to this charming two-bedroom, two-bathroom plus den St Andrews Veranda, nestled in the stunning bundled golf community of Highland Woods. This light-filled, airy residence is ideal for your primary, or vacation home, offering breathtaking…

$319,000

Low Rise (1-3)

Huge price improvement! Top floor residence in the highly sought after Highland Woods Golf and Country Club in Bonita Springs. This two bedroom, two bath home with vaulted ceilings features a large screened lanai with…

$395,000

Mid Rise (4-7)

This beautifully updated condo comes with assigned parking and is turnkey furnished. It features a great room-style layout, with a kitchen that boasts Quartz countertops and stainless steel appliances. Both bathrooms have been renovated with…

$495,900

Low Rise (1-3)

This stunning first-floor Barrington veranda in Highland Woods Golf and Country Club has been meticulously renovated from top to bottom, offering everything you could desire and more. The home features elegant wood-look tile flooring throughout,…

$1,100,000

Ranch,Single Family Residence

Welcome to this exceptional home in the renowned Highland Woods Golf and Country Club! This property offers a spacious layout with 3 bedrooms, a den, and 3.5 bathrooms, including a convenient pool bath. Revel in…

$399,000

Mid Rise (4-7)

Welcome to your dream Florida lifestyle at the Terrace I building in Highland Woods Golf and Country Club. This stunning 2nd-floor condo has been beautifully updated, featuring new tiled floors, sleek granite countertops, and fresh…

$389,900

Mid Rise (4-7)

Welcome to this exquisite two-bedroom, two-bathroom Terrace condo located in the prestigious gated community of Highland Woods. This sophisticated residence showcases tile and engineered wood flooring, granite countertops, and raised panel cabinetry in both the…

$519,000

Low Rise (1-3)

Step into luxury with this gorgeous two-bedroom, two-bathroom plus den Veranda in the gated community of Highland Woods. This end unit is all about style and comfort, featuring high-end designer touches, freshly painted walls, updated…

$429,000

Low Rise (1-3)

This first floor Barrington model with 2bedrooms plus den provides easy access. No stairs to climb. Detached garage just outside yr front door. The views of the wooded preserves in the backdrop, and 4th hole…

$389,900

Low Rise (1-3)

Discover this stunning two-bedroom, two-bathroom Terrace condo located in the prestigious, gated, bundled golf community of Highland Woods. This well-appointed unit features tile floors, granite countertops, and shaker style cabinetry in both the kitchen and…

$492,000

2 Story,Low Rise (1-3)

Stunning dual views from the 2nd floor, this generous end unit condominium is located in a desired gated bundled golf community! Enjoy breathtaking northwesterly sunset views of the lush golf course and splendid, northeasterly views…

$399,000

Low Rise (1-3)

Reduced! - Welcome Home! This is a beautifully updated condo with a detached garage located in the gated golf community of Highland Woods. The condo is turnkey furnished. It features a great-room style layout. You'll…

$399,900

Low Rise (1-3)

Adorable two bedroom two bath first floor unit with beautiful lake and golf course views. GOLF MEMBERSHIP is included with your purchase and offers low dues for exceptional golf on a fantastic par 72 course.…

$549,000

Low Rise (1-3)

Immerse yourself in the epitome of luxury living at this Abbey floor plan carriage home nestled within the prestigious gated bundled golf community of Highland Woods. This fully furnished unit has been meticulously renovated, featuring…

$335,000

Mid Rise (4-7)

This open, light, and bright condo in Highland Woods Golf & Country Club offers breathtaking sunset views and comes fully furnished, including a deeded carport and a large storage closet for bikes, beach gear, and…

$459,000

Low Rise (1-3)

Escape the winter blues in this stunning two-bedroom, two-bath plus den Barrington Veranda nestled in the exclusive gated bundled golf community of Highland Woods. Step into a meticulously maintained space with a lovely split bedroom…

$675,000

Duplex,Villa Attached

Discover the charm of this exceptional Cheshire Villa nestled in the gated bundled golf neighborhood of Highland Woods. Boasting captivating water front views and panoramic golf course vistas from across the lake, this unit offers…