Highland Woods Homes

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  /49

  $424,900

  • 2 Beds
  • 2 Baths
  • 1,414 Sq Ft

  26290 Sunderland Dr Unit 6104, Bonita Springs, FL 34135

  Major Price Reduction, Owner says bring all reasonable offers! Golf Membership is included! This meticulously maintained first-floor carriage home in Highland Woods offers over 1,400 sq ft of living space. Featuring 2 bedrooms plus a den, it boasts an open, airy layout, 2 screened lanais, a detached garage, and stunning views of the golf course. Recent upgrades include new tile flooring in the

  Ronald Delfino Royal Shell Real Estate, Inc.

  26290 Sunderland Dr Unit 6104, Bonita Springs, FL 34135
• 

  

  

  /15

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,162 Sq Ft
  • Condo for Rent

  9500 Highland Woods Blvd Unit 207, Bonita Springs, FL 34135

  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 new large community pool with cabana bar as well as a beautiful clubhouse offering dining as well. Located conveniently near beaches, shopping and excellent restaurants.

  Gregory Manchester Coldwell Banker Realty

  9500 Highland Woods Blvd Unit 207, Bonita Springs, FL 34135
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  /35

  $307,500 Sold Jun 12, 2025

  • 1,125 Sq Ft
  • $273/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  9200 Highland Woods Blvd Unit 1103, Bonita Springs, FL 34135

  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 harmonious blend of comfort and sophistication. Step inside to discover an inviting living space adorned with wood-like flooring throughout the main living areas and

  Dennis Bowers Compass Florida LLC

  9200 Highland Woods Blvd Unit 1103, Bonita Springs, FL 34135
• 

  

  

  /31

  Est $318,323 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft

  9200 Highland Woods Blvd Unit 1201, Bonita Springs, FL 34135

  9200 Highland Woods Blvd Unit 1201, Bonita Springs, FL 34135
• 

  

  

  /24

  $499,000

  • 2 Beds
  • 2 Baths
  • 1,333 Sq Ft

  26901 Clarkston Dr Unit 106, Bonita Springs, FL 34135

  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 culinary enthusiasts. The bathrooms have been elegantly redesigned with custom vanities and walk-in showers with glass enclosures, complemented

  Taylor Stewart Compass Florida LLC

  26901 Clarkston Dr Unit 106, Bonita Springs, FL 34135
• 

  

  /18

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  9450 Highland Woods Blvd, Bonita Springs, FL 34135

  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, March 2026 already rented. Off season months available at discounted rates.

  Gregory Manchester Coldwell Banker Realty

  9450 Highland Woods Blvd, Bonita Springs, FL 34135
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  /36

  $970,000 Sold Jun 03, 2025

  • 1,974 Sq Ft
  • $491/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  26280 Summer Greens Dr, Bonita Springs, FL 34135

  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 complete with new white shaker cabinetry, quartzite countertops, convection cooktop, wall oven, and a large 10 ft island with seating for six. The bathrooms have

  Taylor Stewart Compass Florida LLC

  26280 Summer Greens Dr, Bonita Springs, FL 34135
• 

  

  /19

  Est $368,256 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /23

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft

  26691 Clarkston Dr Unit 206, Bonita Springs, FL 34135

  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 blends modern comfort with resort-style living, providing the ideal backdrop for relaxation and recreation. As part of the prestigious Highland Woods Country Club, you'll have

  Jennifer Naples John R. Wood Properties

  26691 Clarkston Dr Unit 206, Bonita Springs, FL 34135
• 

  

  /20

  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,327 Sq Ft
  • Condo for Rent

  26190 Clarkston Dr Unit 104, Bonita Springs, FL 34135

  This spacious veranda is offered as an off-season rental with a one-month rental minimum. The owner prefers a 3-month rental minimum. Available May 2025, June 2025, July 2025, August 2025, September 2025, October 2025. The unit sleeps up to 6. 2 bedrooms + office (with sleeper sofa). 2- full size bathrooms. The first-floor unit has two lanai’s, and an outdoor parking space located very close to

  Erika Koscal Royal Shell Real Estate, Inc.

  26190 Clarkston Dr Unit 104, Bonita Springs, FL 34135
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  /32

  $380,000 Sold Jun 02, 2025

  • 1,333 Sq Ft
  • $285/SF
  • 142 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  26781 Clarkston Dr Unit 103, Bonita Springs, FL 34135

  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 move-in ready with peace of mind for years to come!The updated kitchen boasts granite countertops, stainless-steel appliances and updated light fixtures and ceiling

  Tracie Martin Coldwell Banker Realty

  26781 Clarkston Dr Unit 103, Bonita Springs, FL 34135
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  /33

  Est $349,820 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  9350 Highland Woods Blvd Unit 4307, Bonita Springs, FL 34135

  9350 Highland Woods Blvd Unit 4307, Bonita Springs, FL 34135
• 

  

  /40

  $390,000

  • 2 Beds
  • 2 Baths
  • 1,414 Sq Ft

  26490 Sunderland Dr Unit 1104, Bonita Springs, FL 34135

  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 and bright with spectacular golf course, lake and sunset views. Upgrades include tiled floors, tiled lanais, electric storm shutters, brand new high impact windows. Also, this unit offers

  Taylor Stewart Compass Florida LLC

  26490 Sunderland Dr Unit 1104, Bonita Springs, FL 34135
• 

  

  /25

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Condo for Rent

  26751 Clarkston Dr Unit 102, Bonita Springs, FL 34135

  Beautifully furnished first floor residence in gated golf course community of Highland Woods. This two bedroom, two bath condominium is absolutely adorable. The owner has thought of everything! The kitchen is fully equipped if you like to cook while on vacation! Enjoy 2 screened lanai's at this condo! The ideal spot for outdoor lounging. Beautiful golf course view from the lanai. When renting,

  Holly Gregor Royal Shell Real Estate, Inc.

  26751 Clarkston Dr Unit 102, Bonita Springs, FL 34135
• 

  

  /43

  $385,000 Sold May 27, 2025

  • 1,408 Sq Ft
  • $273/SF
  • 110 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  9500 Highland Woods Blvd Unit 108, Bonita Springs, FL 34135

  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 den. Take in the picturesque golf course views with desirable western exposure and get immediate access to a golf membership at Highland Woods Golf & Country Club.Step

  Rick Conly III Compass Florida LLC

  9500 Highland Woods Blvd Unit 108, Bonita Springs, FL 34135
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  /29

  Est $317,302 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  9200 Highland Woods Blvd Unit 1109, Bonita Springs, FL 34135

  9200 Highland Woods Blvd Unit 1109, Bonita Springs, FL 34135
• 

  

  /45

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft

  26841 Clarkston Dr Unit 105, Bonita Springs, FL 34135

  COME AND VIEW THIS BEAUTIFUL VERANDA HOME IN HIGHLAND WOODS OVERLOOKING THE GOLF COURSE! THIS HOME HAS HAD LONG TIME OWNERS FROM THE MIDWEST SO IT HAS BEEN VERY LIGHTLY USED. HIGHLAND WOODS OFFERS GREAT VALUE AND IS HIGHLY DESIRED FOR IT'S MANY AMENITIES AND REPUTATION. VERY CLOSE BY THERE IS AN ABUNDANCE OF DINING, SHOPPING, MEDICAL, BANKING, AND A SHORT DRIVE TO THE WEST WILL TAKE YOU TO WHITE

  Gerald Mathusek Downing Frye Realty Inc.

  26841 Clarkston Dr Unit 105, Bonita Springs, FL 34135
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  /34

  $7,875 per month

  • 2 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • Condo for Rent

  26991 Clarkston Dr Unit 8106, Bonita Springs, FL 34135

  AVAILABLE JAN-MARCH 2026 SEASON. Stunning 2 bedroom plus den, 2 bath End Unit in highly sought after Highland Woods community. Enjoy this meticulously renovated condo with beautiful new wood floors, open concept design with exquisite quartz countertops, stainless steel appliances, stylish kitchen island, custom woodwork, subway tile backsplash, and elegant 42-inch cabinets. Relax in the private

  Kay Tarnowski DomainRealty.com LLC

  26991 Clarkston Dr Unit 8106, Bonita Springs, FL 34135
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  /28

  $430,000 Sold May 19, 2025

  • 1,791 Sq Ft
  • $240/SF
  • 191 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  26751 Clarkston Dr Unit 201, Bonita Springs, FL 34135

  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 bathrooms have been tastefully updated with quartz countertops and new fixtures. Luxury vinyl flooring runs throughout the property, adding a touch of

  Taylor Stewart Compass Florida LLC

  26751 Clarkston Dr Unit 201, Bonita Springs, FL 34135
• 

  

  /29

  Est $321,164 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,125 Sq Ft

  9200 Highland Woods Blvd Unit 1203, Bonita Springs, FL 34135

  9200 Highland Woods Blvd Unit 1203, Bonita Springs, FL 34135
• 

  

  /27

  $470,000

  • 2 Beds
  • 2 Baths
  • 1,556 Sq Ft

  26180 Clarkston Dr Unit 201, Bonita Springs, FL 34135

  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 is ideal as either a primary residence or a vacation getaway. Enjoy breathtaking views of the golf course and lake, complemented by thoughtful updates such as high-end

  Drew Fagan Royal Shell Real Estate, Inc.

  26180 Clarkston Dr Unit 201, Bonita Springs, FL 34135
• 

  

  /20

  $9,500 per month

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • House for Rent

  26343 Clarkston Dr, Bonita Springs, FL 34135

  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 and features an open and spacious floor plan with large outdoor screened lanai overlooking picturesque golf course views. Highland Woods Golf &

  Kimberly Costantini Premier Sotheby's Int'l Realty

  26343 Clarkston Dr, Bonita Springs, FL 34135
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  /38

  $1,090,750 Sold May 05, 2025

  • 2,336 Sq Ft
  • $467/SF
  • 6 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1996

  26351 Summer Greens Dr, Bonita Springs, FL 34135

  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 den space. Designed with a modified open concept, the home offers unobstructed views from the front door through to the main living space and out to the

  Taylor Stewart Compass Florida LLC

  26351 Summer Greens Dr, Bonita Springs, FL 34135
• 

  

  /45

  Est $395,922 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,333 Sq Ft

  26781 Clarkston Dr Unit 15103, Bonita Springs, FL 34135

  26781 Clarkston Dr Unit 15103, Bonita Springs, FL 34135
• 

  

  /33

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,414 Sq Ft

  26370 Sunderland Dr Unit 4102, Bonita Springs, FL 34135

  Welcome to this delightful 2-bedroom plus den Barrington model located in the esteemed bundled golf community of Highland Woods Golf & Country Club. This first-floor unit offers unobstructed western exposure views of the serene lake and the 2nd hole of the golf course. This is the perfect spot for enjoying an evening cocktail while watching breathtaking sunsets from your spacious covered lanai,

  John Foley Jr Coldwell Banker Realty

  26370 Sunderland Dr Unit 4102, Bonita Springs, FL 34135
• 

  

  /48

  $530,000 Sold May 01, 2025

  • 1,756 Sq Ft
  • $302/SF
  • 60 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  26550 Clarkston Dr, Bonita Springs, FL 34135

  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 you step inside, you'll find an open living and dining area filled with natural light, perfect for both entertaining and relaxation. The villa is elegantly appointed with plantation

  Taylor Stewart Compass Florida LLC

  26550 Clarkston Dr, Bonita Springs, FL 34135
• 

  

  /29

  Est $445,436 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,414 Sq Ft

  26691 Clarkston Dr Unit 18207, Bonita Springs, FL 34135

  26691 Clarkston Dr Unit 18207, Bonita Springs, FL 34135
• 

  

  /31

  $339,900

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft

  9350 Highland Woods Blvd Unit 4304, Bonita Springs, FL 34135

  BRAND NEW AIR CONDITIONER INSTALLED !!! This is a great opportunity to enjoy immediate golf and avoid the waitlist, when you purchase this turnkey third floor 2 BR/2 BA condo. This condo overlooks the golf course in this highly sought after Highland Woods Community. The condo has new luxury vinyl plank flooring installed in the second bedroom and the full condo had been freshly painted. This

  Kathleen Malley Five Star Real Estate of FL

  9350 Highland Woods Blvd Unit 4304, Bonita Springs, FL 34135
• 

  

  /38

  $385,000 Sold Apr 30, 2025

  • 1,414 Sq Ft
  • $272/SF
  • 51 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  26170 Clarkston Dr Unit 102, Bonita Springs, FL 34135

  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 include tiled floors throughout, including the lanais, electric storm shutters and a BRAND NEW WATER HEATER. Also, this unit offers a one-car detached garage for extra storage.

  Taylor Stewart Compass Florida LLC

  26170 Clarkston Dr Unit 102, Bonita Springs, FL 34135
• 

  

  /29

  Est $330,516 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  9200 Highland Woods Blvd Unit 1105, Bonita Springs, FL 34135

  9200 Highland Woods Blvd Unit 1105, Bonita Springs, FL 34135
• 

  

  /30

  $274,900

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  9300 Highland Woods Blvd Unit 3105, Bonita Springs, FL 34135

  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 Woods. With an included golf membership and stunning views of the first fairway, this turnkey home is move-in ready, featuring granite countertops, stainless steel

  Claire Gogan EXP Realty LLC

  9300 Highland Woods Blvd Unit 3105, Bonita Springs, FL 34135
• 

  

  /19

  $475,000 Sold Apr 29, 2025

  • 1,414 Sq Ft
  • $336/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  26330 Sunderland Dr Unit 5203, Bonita Springs, FL 34135

  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 been meticulously maintained. Featuring a modern kitchen with granite countertops and stainless steel appliances, as well as updated bathrooms with elegant glass shower enclosure,

  Taylor Stewart Compass Florida LLC

  26330 Sunderland Dr Unit 5203, Bonita Springs, FL 34135
• 

  

  /17

  Est $310,096 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  9250 Highland Woods Blvd Unit 2106, Bonita Springs, FL 34135

  9250 Highland Woods Blvd Unit 2106, Bonita Springs, FL 34135
• 

  

  /39

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  9200 Highland Woods Blvd Unit 1309, Bonita Springs, FL 34135

  Discover our charming penthouse condo in the highly desired Highland Woods Golf & Country Club. This 2 bed / 2 bath unit features brand new luxury vinyl flooring, new baseboards, fresh paint, and updated light fixtures and fans throughout, newer stainless steel appliances, a brand new washer and dryer, plus a newer AC (2023) and water heater (2022). Impact-resistant windows and sliders provide

  Ellen Boyce Keller Williams Elite Realty

  9200 Highland Woods Blvd Unit 1309, Bonita Springs, FL 34135
• 

  

  /38

  $1,025,000 Sold Apr 23, 2025

  • 2,202 Sq Ft
  • $465/SF
  • 37 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1996

  26380 Summer Greens Dr, Bonita Springs, FL 34135

  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 backsplash, and new appliances. The bathrooms have been upgraded with new vanities, fixtures, retiled showers, and glass enclosure. Bedrooms

  Taylor Stewart Compass Florida LLC

  26380 Summer Greens Dr, Bonita Springs, FL 34135
• 

  

  /28

  Est $332,974 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft

  9400 Highland Woods Blvd Unit 5404, Bonita Springs, FL 34135

  9400 Highland Woods Blvd Unit 5404, Bonita Springs, FL 34135
• 

  

  /44

  $850,000

  • 2 Beds
  • 2 Baths
  • 1,529 Sq Ft

  26036 Clarkston Dr, Bonita Springs, FL 34135

  Absolutely stunning two bedroom plus den pool home with a refreshing full home renovation offering the absolute best in today's living comforts with a fresh and sophisticated flare. FULL GOLF MEMBERSHIP IS INCLUDED WITH THE HOME! The open kitchen was redesigned and totally rebuilt in 2024 with the highest end quartz counters, top of the line cabinetry and upgraded appliances that include an

  Gregory Manchester Coldwell Banker Realty

  26036 Clarkston Dr, Bonita Springs, FL 34135
• 

  

  /50

  $450,000 Sold Apr 21, 2025

  • 1,162 Sq Ft
  • $387/SF
  • 17 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  9400 Highland Woods Blvd Unit 5402, Bonita Springs, FL 34135

  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 a kind.The open and inviting living space boasts luxury vinyl flooring throughout, stylish plantation shutters, and a sleek

  Tracie Martin Coldwell Banker Realty

  9400 Highland Woods Blvd Unit 5402, Bonita Springs, FL 34135
• 

  

  /31

  Est $318,323 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft

  9200 Highland Woods Blvd Unit 1201, Bonita Springs, FL 34135

  9200 Highland Woods Blvd Unit 1201, Bonita Springs, FL 34135
• 

  

  /30

  $359,000

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft

  9500 Highland Woods Blvd Unit 107, Bonita Springs, FL 34135

  This is a wonderful opportunity to purchase a condominium in one 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 first-floor living, with sunset and golf course views and is in short distance to the immense amenities consisting of seven community pools including a new resort

  James Duda Premier Sotheby's Int'l Realty

  9500 Highland Woods Blvd Unit 107, Bonita Springs, FL 34135

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