Search Listings

$259,000

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…

$425,000

Low Rise (1-3)

This Barrington model Veranda has been recently painted and offers a beautiful view of Hole 17 and offers bundled golf in Highland Woods Golf & Country Club. This turnkey 2 bedroom + den/2 bath…

$384,500

Low Rise (1-3)

Discover your perfect winter retreat in this exquisite turnkey two-bedroom, two-bath Carlton Veranda, located in the prestigious gated community of Highland Woods. Known for its bundled golf amenities, this impeccably maintained home boasts a desirable…

$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…

$699,900

Villa Attached

Step into the epitome of Florida living with this exquisite Cheshire Villa, nestled in the coveted gated, bundled golf community of Highland Woods. This home is a true retreat, featuring a spacious paver lanai with…

$450,000

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…

$475,000

Low Rise (1-3)

If you’ve been dreaming about a place in Southwest Florida that feels like a true escape, this beautifully updated Abbey end unit in Highland Woods Golf & Country Club might be the one. From the…

$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…

$350,900

Mid Rise (4-7)

FIRST FLOOR! Why buy a 2 bedroom when you can buy a 2 bedroom plus a den. Super clean end unit with a FABULOUS view! Completely turnkey furnished and ready for a new owner. Highland…

$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…

$325,000

Low Rise (1-3)

Check out this fantastic top floor unit in the Heathermoor's at Highland Woods! It's got everything you need with wood floors, quartz kitchen countertops, granite counters in the bathrooms, a remodeled guest bath, custom woodwork,…

$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…

$269,000

Low Rise (1-3)

Discover your perfect winter retreat in this charming 2-bedroom, 2-bathroom Heathermoor condo, ideally located on the 1st fairway within the gated and bundled golfing community of Highland Woods. This delightful condo offers a slice of…

$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…

$7,875

Low Rise (1-3)

AVAILABLE 2027 SEASON JAN–MARCH. Stunning REMODELED 2 BEDROOM PLUS DEN, 2 BATH END UNIT in the highly sought-after Highland Woods BUNDLED GOLF community. This meticulously renovated condo features beautiful new wood floors and an open-concept…

$525,000

Low Rise (1-3)

Discover an exquisite second-floor Barrington veranda located in the prestigious Highland Woods Golf and Country Club. This stunning home features two bedrooms, two bathrooms, and a versatile den, all beautifully revamped within the last two…

$440,000

Mid Rise (4-7)

Rarely available and exquisitely renovated, this top-floor, end-unit Colonnade floor plan in the Terraces is a true gem. Boasting two bedrooms, two bathrooms, and a versatile den, this home has been thoughtfully updated from top…

$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.…

$379,000

Mid Rise (4-7)

Welcome to your dream retreat in the Terraces of Highland Woods Golf and Country Club! This stunning third-floor end unit combines elegance, comfort, and breathtaking views, making it the perfect place to call home. Featuring…

$479,000

Low Rise (1-3)

iscover 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 and wood flooring, crown molding, electric storm shutter and…

$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…

$410,000

Low Rise (1-3)

Wake up to tranquil lake views, swaying palms, and manicured fairways just beyond your lanai. This first-floor Barrington model in Highland Woods Golf & Country Club delivers the effortless Southwest Florida lifestyle buyers are searching…

$6,000

Mid Rise (4-7)

Stunning sunset views overlooking the golf course in this 2-2, 2nd floor condo located in Highland Woods. This resort style community is very social and active, offering bocce ball, tennis, pickleball, fitness center, a…

$319,000

Mid Rise (4-7)

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

$405,000

Low Rise (1-3)

Nestled in the prestigious Highland Woods Golf and Country Club, this Carlton Veranda is the perfect blend of elegance, comfort, and lifestyle. Featuring a sought-after split-bedroom floor plan, this home boasts two spacious bedrooms and…

$269,900

Mid Rise (4-7)

Move in and immediately embrace the ultimate Southwest Florida lifestyle! Only minutes from pristine Gulf beaches, this beautiful gated community places you at the center of dynamic dining, shopping, arts, and fitness options. The residence…

$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…

$339,000

Mid Rise (4-7)

This stunning fourth-floor condo in the highly sought-after Highland Woods community offers a lifestyle as elevated as its views. Picture this: a championship golf course rolling out beneath you with views of five different golf…

$349,900

Mid Rise (4-7)

Welcome to your slice of paradise! This absolutely stunning condo in the sought-after Highland Woods community offers a perfect blend of modern updates, luxurious amenities, and an unbeatable location. Step inside to find a beautifully…

$395,000

Low Rise (1-3)

Location, lifestyle, and luxury—this two-bedroom, two-bathroom Carlton Veranda is the ultimate winter retreat! Just steps from all that Highland Woods has to offer, this home is flooded with natural light and boasts breathtaking views of…

$335,000

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…

$1,125,000

Single Family Residence

Nestled in the prestigious Highland Woods Golf and Country Club, this stunning home is a true masterpiece of style, comfort, and functionality. From the moment you pull up, the curb appeal will captivate you—custom lighting,…

$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…

$469,000

Low Rise (1-3)

Discover the charm of the Abbey Model Veranda, nestled on the second floor within the prestigious Highland Woods bundled golf community. Being sold turnkey this well appointed residence features tile flooring, granite countertops, updated vanities…

$374,900

Mid Rise (4-7)

Welcome to your dream home in the esteemed Highland Woods Golf and Country Club! Presenting a magnificent top-floor end unit, this two-bedroom, two-bathroom Brookside model condo offers the perfect retreat from colder climates. Step inside…

$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…

$659,000

Villa Attached

This stunning Cheshire Villa, nestled within the exclusive gated community of Highland Woods, perfectly marries luxury with comfort. From the moment you step inside, you'll be captivated by the thoughtful upgrades and elegant details throughout.…

$638,000

Villa Attached

Discover the ultimate bundled golf and resort-style lifestyle in the highly sought-after gated community of Highland Woods Golf & Country Club! This vibrant community offers everything you need to enjoy the full Southwest Florida experience…

$424,900

Low Rise (1-3)

Rare opportunity to own this highly sought-after Barrington Veranda in the exclusive, gated Highland Woods community. Your Bundled Golf Membership starts the moment you close! This meticulously maintained 2-bedroom, 2-bath plus den home offers the…

$6,000

Mid Rise (4-7)

Gorgeous two bedroom two bath turnkey furnished second floor condo with elevator available monthly short term. Western sunset exposure. Fantastic location within minutes drive to Barefoot Beach, restaurants, shopping, theater, airport. Gated community. Jan, Feb,…

$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…

$599,900

Villa Attached

This exquisite Cheshire Villa, located in the prestigious gated community of Highland Woods, offers a perfect blend of luxury and comfort. The villa boasts an updated kitchen featuring quartz countertops and refaced cabinetry, complemented by…

$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…

$285,000

Mid Rise (4-7)

Step into the effortless elegance of Highland Woods Golf & Country Club with this beautifully updated 2-bedroom, 2-bath luxury condominium overlooking lush golf-course vistas. Located in one of Bonita Springs’ most desirable bundled-golf communities, this…

$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…

$5,750

Low Rise (1-3)

BUNDLED GOLF INCLUDED! Beautiful 2 Bedroom, 2 Bath condo. Step into easy Florida living with this inviting 3rd-floor end-unit condo in the sought-after Heathermoor I enclave of Highland Woods. This residence offers a fantastic blend…

$6,000

Low Rise (1-3)

BUNDLED GOLF AVAILABLE: APRIL 2027 SEASON Available $6000. Off-Season $2500. This beautiful first-floor corner-unit condo in the desirable Heathermoor I building offers exceptional natural light and stunning views of Hole 1 of the Highland Woods…

$9,500

Single Family Residence

Exceptional 3 bedroom, 2 bath, 2 car garage, single family home with private heated pool in the highly desirable Bundled Golf Community of Highland Woods. This beautifully maintained and thoughtfully updated residence is tastefully furnished…

$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…