Winter Haven, FL Homes for Sale in a Senior Community

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  /70

  $199,000

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft

  352 Siberian Cypress Cir, Winter Haven, FL 33881

  STOP and TAKE A LOOK INSIDE! LOW LOT FEE $604/month, 55 Plus Active Lifestyle Community in Cypress Creek Village. 3 bedroom/3 bath home. The beautiful double wide home is spacious, has a Water Filtration System, is sold with all appliances, MOVE IN READY, Central Air, Storage Shed, Sunroom, Ceiling Fans, Walk In Closet, Ensuite Bathroom, Tray Ceiling, Removable Electric Fireplace, Gutters, Newer

  Daniel Butler Sun Realty of Florida

  352 Siberian Cypress Cir, Winter Haven, FL 33881
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  /63

  $145,000

  • 2 Beds
  • 2 Baths
  • 1,014 Sq Ft

  6204 Knotty Pine Drive South E, Winter Haven, FL 33884

  R E D U C E D - R E D U C E D ... DON'T WAIT TO OWN THIS 2BR-2BA MFG HOME ON THIS LARGE CORNER LOT IN SE COMMUNITY WITH LOW MONTHLY FEES, OWNING YOUR OWN LAND AND GREAT AMENITIES. CLUBHOUSE WITH LARGE ENTERTAINMENT ROOM, FULL KITCHEN, LIBRARY, BILLIARDS ROOM, SPA, OVERSIZED POOL OVERLOOKING WATERFRONT PEACE POND WITH COOKOUT ROOM OFF POOL AREA AND EVEN SHUFFLEBOARD, THIS COMMUNITY OFFERS SO MUCH

  Glenda Pruitt FLORIDA HOME CHOICE REALTY

  6204 Knotty Pine Drive South E, Winter Haven, FL 33884
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  /25

  $136,900

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1201 Cypress Vine Rd, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #297 - 2BED / 2 BATH / 1,200 SF. / $136,900 POND VIEW HOME with Double Driveway! Golf cart included! This MODERN, TURNKEY HOME is furnished and move-in-ready for you! This immaculately maintained home is only 5 years old! It features an open floor plan, air-conditioned four-season Florida Room and lower screened lanai - all of which have a tranquil pond view. This home has a

  Jennifer Meyers CRF Communities

  1201 Cypress Vine Rd, Winter Haven, FL 33881
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  /13

  $49,900

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  4155 Rolling Oaks Dr, Winter Haven, FL 33880

  Cash Only, This home has a new roof, but needs a lot of work.priced accordingly! If you are allergic to smoke do not go in this home, because smoke smell is very strong. But would be a beautiful home with some rehab work.

  Rita Stead SOUTHERN BELLE REALTY

  4155 Rolling Oaks Dr, Winter Haven, FL 33880
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  /49

  $169,900

  • 2 Beds
  • 2 Baths
  • 1,044 Sq Ft

  39 Kimberly Ct, Winter Haven, FL 33880

  Welcome to Brandy Chase Village!! This well desired 55+ community located in Winter Haven Florida is centrally located between Tampa and Orlando. The beautiful 2 bedroom and 2 bathroom home is well maintained and ready for you! Enjoy your oversized sunroom that adds extra square footage of living space for you to enjoy. Updated appliances and a new AC was installed in 2021 , as well as it was

  Rosalia Abreu ALLSTATE REALTY SERVICES

  39 Kimberly Ct, Winter Haven, FL 33880
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  /20

  $109,000

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft

  2909 Shoal Creek Place Unit 798, Winter Haven, FL 33881

  3 Bedroom | 2 Bath | 1,286 sq ft | PRICE REDUCED FROM $116,000 TO $109,000! Welcome to your move-in-ready home: Four Lakes Lot 798! This 3 bedroom, 2 bath doublewide boasts a unique split floor plan complete with office, pass-through kitchen, and Florida Room. Step into the freshly painted main living area, which feels warm and inviting. The living room flows seamlessly into the master suite,

  Cheryl Dobbs CRF Communities

  2909 Shoal Creek Place Unit 798, Winter Haven, FL 33881
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  /20

  $119,900

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880

  Welcome to 333 Lake Howard Drive – a bright and spacious 2 bedroom, 2-bath unit condo in the desirable Imperial Harbours 55+ lakefront community in Winter Haven. This unit has ample natural light, This well-maintained condo offers an open living and dining area, charming kitchen, primary suite offers a walk-in closet, in-unit laundry, Imperial Harbours offers more than just a home – it’s a

  Kevin Tison LPT REALTY, LLC

  333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880
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  /21

  $22,900

  • 2 Beds
  • 1.5 Baths
  • 672 Sq Ft

  139 Jay Dr, Winter Haven, FL 33880

  Affordable living in Central Florida makes your dream life-style a reality! Welcome to this quaint and well-kept 2-bedroom 1.5-bath bungalow in a beautiful resort-style 55+ pet-friendly community in Winter Haven, Florida. This lovely home features several updates: New laminate flooring throughout, New kitchen and bathroom countertops, Fresh paint throughout, New washer and dryer, and a large

  Teresa Gago Sunset Home Sales

  139 Jay Dr, Winter Haven, FL 33880
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  /37

  $165,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  345 24th St NW Unit 25, Winter Haven, FL 33880

  Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ residential community, sitting within a short walking distance to beautiful Lake Howard. Inside, you’ll find updated flooring throughout and both bathrooms tastefully renovated, giving the home a fresh, move-in-ready feel. The open

  Michele Elchin DALTON WADE INC

  345 24th St NW Unit 25, Winter Haven, FL 33880
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  /43

  $166,000

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft

  6015 Grand Oaks Dr SE, Winter Haven, FL 33884

  Experience the Best of Florida Living!Immerse yourself in the vibrant Floridian lifestyle with this beautifully maintained 2-bedroom, 2-bath manufactured home located in the desirable 55+ Garden Grove Oaks community. Designed for comfort and accessibility, this home features a convenient handicap ramp for easy entry.Step inside to a bright and inviting open-concept living and dining area,

  Jason Stewart EXP REALTY LLC

  6015 Grand Oaks Dr SE, Winter Haven, FL 33884
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  /28

  $110,000

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  333 Lake Howard Dr NW Unit 213D, Winter Haven, FL 33880

  A 55+ Active community well maintained surrounded by gorgeous landscaping, dock access to the Winter Haven's Chain of Lakes (LAKE HOWARD). This second floor unit offers a range of amenities that includes a recreational room, heated community pool, shuffleboard, and grills to BBQ by the beautiful gazebo, community boat ramp nearby fishing allowed. Check out this 2 bedroom, 2 bath condo with an

  Lisa Simpson KELLER WILLIAMS REALTY SMART 1

  333 Lake Howard Dr NW Unit 213D, Winter Haven, FL 33880
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  /34

  $159,900

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  1728 Glen Abby Ln Unit 692, Winter Haven, FL 33881

  Triple the Space. Triple the Views. Triple the WOW! Purchase and get FREE lot rent for the rest of 2026! 1728 Glen Abby Lane - Lot 692 3 Bedrooms | 2 Bathrooms | 2,120 Sq. Ft. Welcome to a rare and truly spectacular triple-wide home offering breathtaking golf course, water and sunset views-all wrapped into one turnkey, fully furnished retreat in Four Lakes Golf Club. With windows galore framing

  Cheryl Dobbs CRF Communities

  1728 Glen Abby Ln Unit 692, Winter Haven, FL 33881
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  /23

  $125,000

  • 2 Beds
  • 2 Baths
  • 1,188 Sq Ft

  6027 Grand Oaks Dr SE, Winter Haven, FL 33884

  Welcome to Garden Grove Oaks – A Charming 55+ Community! This beautifully maintained 2-bedroom, 2-bathroom mobile home has been thoughtfully updated and is move-in ready. Step inside to find new carpet and padding and freshly painted living and dining areas, creating a bright and inviting space. The functional floor plan features a spacious living room, cozy dining area, and a well-equipped

  Brandy Duncan COLDWELL BANKER REALTY

  6027 Grand Oaks Dr SE, Winter Haven, FL 33884
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  /52

  $840,000

  • 3 Beds
  • 3.5 Baths
  • 2,968 Sq Ft

  4120 Limerick Dr, Lake Wales, FL 33859

  One or more photo(s) has been virtually staged. Welcome to this stunning, one-of-a-kind residence in one of Central Florida’s most exclusive 55-plus RV communities. From the moment you pass through the private gates, you’re transported into a world of relaxation, beauty and resort-style living. Arriving at the property, you’re greeted by lush landscaping that enhances its curb appeal and

  Alejandro Quiel, Jr PREMIER SOTHEBYS INT'L REALTY

  4120 Limerick Dr, Lake Wales, FL 33859
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  /44

  $200,000

  • 2 Beds
  • 2 Baths
  • 1,083 Sq Ft

  4440 Turnberry Ln, Lake Wales, FL 33859

  Welcome to your sunny Florida escape in the highly sought-after Lake Ashton Golf Club, a premier 55+ active community in Central Florida. This beautifully maintained 2-bedroom, 2-bath residence is being offered fully turnkey—just bring your suitcase! Even better, the sale includes a golf cart and a Cadillac, making it easy to start enjoying the Florida lifestyle from day one.Designed with

  Julie Seay COLDWELL BANKER REALTY

  4440 Turnberry Ln, Lake Wales, FL 33859
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  /51

  $295,000

  • 2 Beds
  • 2 Baths
  • 1,688 Sq Ft

  4115 Aberdeen Ln, Lake Wales, FL 33859

  $35,000 Price Reduction — Best Value in Lake Ashton. Well-maintained Hemingway style home located on a pond-front lot with a nature preserve view on a street ending in a cul-de-sac. This 2-bedroom, 2-bath home also includes an additional flexible room that can function as a guest room, den, office, or craft room. The kitchen and main living areas have recent interior paint. Luxury laminate

  Nellie Peralta KELLER WILLIAMS ADVANTAGE 2 REALTY

  4115 Aberdeen Ln, Lake Wales, FL 33859
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  /65

  $369,900

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  4016 Dunmore Dr, Lake Wales, FL 33859

  4016 Dunmore Drive Lake Wales, Florida 33859 is a beautiful home located near the 17th Green of the East Golf Course in Lake Ashton. CDD DEBT PAID IN FULL**** This OPEN and SPACIOUS home offers 3 Bedrooms/2 Baths, a double car garage and a single car garage entry. The oversized garage is ideal for 3 cars. This light and bright home shows exceptionally well and checks off a lot of the boxes. It

  Lori Raath LAKE ASHTON REALTY INC.

  4016 Dunmore Dr, Lake Wales, FL 33859
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  /82

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft

  4489 Strathmore Dr, Lake Wales, FL 33859

  Welcome to your personal haven in Lake Ashton—Central Florida’s premier 55+ active-adult community. This beautifully maintained 2-bedroom, 2-bath home offers 1,530 square feet of thoughtfully designed living space, along with a 10’ x 13’ golf cart garage. Freshly painted both out and in the living room and kitchen, it feels bright, crisp, and truly move-in ready. The home’s curb appeal shines

  Brad Kirwan GLOBAL LIFESTYLE LLC

  4489 Strathmore Dr, Lake Wales, FL 33859
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  /23

  $16,500

  • 1 Bed
  • 1 Bath
  • 620 Sq Ft

  1015 Dundee Rd Unit 34, Dundee, FL 33838

  Welcome to Greenfield Village, a quaint 55+ community in Dundee, Florida! This community has a LOW lot rent of just $450 per month, and has amenities including shuffleboard, swimming pool, clubhouse, and fishing! This home is super cute and compact, and is ready for immediate occupancy! Out front, there is a single car carport, and a lovely screen room. The main home has a kitchen with new

  Jennifer Maasdorp Integrity Mobile Homes

  1015 Dundee Rd Unit 34, Dundee, FL 33838
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  /41

  $69,000

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  143 Wright St, Cypress Gardens, FL 33884

  Discover a turnkey two-bedroom, two-bath mobile home in the Cypress Gardens 55+ community. This corner-lot residence features a large front yard, and the home was updated in 2023. The home boasts a modern A/C system, CPVC plumbing, fresh interior paint, laminate flooring, ceiling fans, and new windows throughout. The kitchen shines with new countertops, soft-close cabinets, and new appliances,

  Tanya Johnston American Mobile Home Sales of Tampa Bay, Inc.

  143 Wright St, Cypress Gardens, FL 33884
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  /64

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft

  4144 Aberdeen Ln, Lake Wales, FL 33859

  Welcome home! 4144 Aberdeen Lane Lake Wales, Florida is a 2 Bedroom, 2 Bath, Plus Den home located in Lake Ashton. This ESSEX Floor Plan home is move in ready and has the CDD BOND DEBT PAID IN FULL, a real MONEY SAVER! Open the Storm Door and Step inside this warm and inviting foyer. The transom window above the front entry door provides an abundance of natural light into the home. The foyer has

  Lori Raath LAKE ASHTON REALTY INC.

  4144 Aberdeen Ln, Lake Wales, FL 33859
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  /17

  $52,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  152 Winterdale Dr Unit LOT 190, Lake Alfred, FL 33850

  Discover Your Dream Home in Kings Pointe - A Premier Gated 55+ Community in Polk County Homes in Kings Pointe, a 55+ pet friendly community are on lot leased land in Lake Alfred, Florida. Owning the home, but not the land, you pay a monthly lot rent of $740.00 which gives you and your guest access to the amenities of the community. If you're searching for the perfect place to call home, look no

  Pam Pullen Renee's Resales

  152 Winterdale Dr Unit LOT 190, Lake Alfred, FL 33850
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  /27

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  4072 Stone Creek Loop, Lake Wales, FL 33859

  Beautiful Lake Ashton Home- 55+ Golf Community. This is an exceptionally well maintained 3Bed/2bath home w/ enclosed air conditioned lanai which creates expanded living space (St. Croix floorplan). This home has exceptional landscaping w/ beautifully cement curbed garden beds around whole exterior of house. Sealed brick pavers in driveway/front walkway/back exterior patio. Freshly painted

  Rob Blakely CHARLES RUTENBERG REALTY ORLANDO

  4072 Stone Creek Loop, Lake Wales, FL 33859
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  /15

  $24,999

  • 3 Beds
  • 2 Baths
  • 896 Sq Ft

  26 Lazy Ln, Lake Alfred, FL 33850

  LOWERED PRICE and QUICK CLOSE in 3-5 days!! This spacious 3-bedroom, 2-bathroom home is located on a desirable corner lot in the 55 community of Leisure Homes MHP. This well-lit home features an open floor plan, beautiful shade trees, and is partially furnished for added convenience. Each bedroom includes built-in dressers, and additional features include an inside laundry room, vinyl flooring,

  Todd Newby NEWBY REALTY INC

  26 Lazy Ln, Lake Alfred, FL 33850
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  /62

  $39,990

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  130 Winterdale Dr, Lake Alfred, FL 33850

  **ESTATE SALE OPPORTUNITY!** Discover this three-bedroom, two-bathroom residence nestled within 55 Plus gated community of Kings Pointe. The estate's heirs are motivated to secure a swift transaction, creating an unprecedented opportunity to embrace the sophisticated retirement lifestyle you deserve at an exceptional value, where every detail has been thoughtfully curated for discerning

  Chrissy Walter Sunset Home Sales

  130 Winterdale Dr, Lake Alfred, FL 33850
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  /50

  $217,500

  • 2 Beds
  • 2 Baths
  • 1,083 Sq Ft

  4488 Turnberry Ln, Lake Wales, FL 33859

  Welcome Home! Step into comfort in this cozy 2-bedroom, 2-bathroom retreat nestled in the heart of Lake Ashton’s 55+ community. The kitchen gleams with crown molding, Samsung stainless-steel appliances, and a sleek design that blends style with functionality. A true hidden gem awaits beyond the living room: a three-panel sliding glass door opens wide to a screened lanai, seamlessly merging indoor

  Candra Alston LAKE ASHTON REALTY INC.

  4488 Turnberry Ln, Lake Wales, FL 33859
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  /62

  $296,500

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft

  4480 Strathmore Dr, Lake Wales, FL 33859

  Don’t let this one slip by! This beautifully cared-for ESSEX floor plan home in Lake Ashton Golf Club is waiting for you. With 2 bedrooms, 2 baths, plus a den. Tucked into a peaceful corner of the community, yet just minutes from all the resort-style amenities this 55+ neighborhood is known for with the CDD BOND PAID IN FULL! From the moment you arrive, you’ll notice the pride of ownership: lush

  Candra Alston LAKE ASHTON REALTY INC.

  4480 Strathmore Dr, Lake Wales, FL 33859
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  /92

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,847 Sq Ft

  4568 Turnberry Ln, Lake Wales, FL 33859

  Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this beautifully updated and immaculately maintained 3-bedroom, 2-bath home awaits. From the moment you step inside, you’ll feel the home’s fresh, crisp, and welcoming atmosphere—a reflection of thoughtful care and more than $76,000 in upgrades since February 2024, when

  Brad Kirwan GLOBAL LIFESTYLE LLC

  4568 Turnberry Ln, Lake Wales, FL 33859
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  /19

  $99,999 New Construction

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  1 Leisure Ln, Lake Alfred, FL 33850

  Price Just Reduced! This stunning custom-built 2 bedroom, 2 bathroom home is move-in ready and can close in as little as 3-5 days!! Featuring numerous upgrades, including a large farmhouse-style kitchen sink, stainless steel Whirlpool appliances, walk-in closets, and an open floor plan perfect for entertaining. Enjoy a spacious, fenced lot in Leisure Homes MHP, a peaceful 55 lakeside community.

  Todd Newby NEWBY REALTY INC

  1 Leisure Ln, Lake Alfred, FL 33850
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  /33

  $405,000

  • 3 Beds
  • 2 Baths
  • 2,027 Sq Ft

  4081 Dunmore Dr, Lake Wales, FL 33859

  Discover exceptional value in the guard-gated 55+ community of Lake Ashton with this pristine waterfront residence, featuring the significant advantage of a fully paid CDD debt. Situated on a prime waterfront lot, this home is just steps away from the resort-style amenities. This 3-bedroom, 2-bath property with a separate office offers impressive energy savings through leased solar panels at

  Mary Sorrell MAZELG REALTY

  4081 Dunmore Dr, Lake Wales, FL 33859
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  /64

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,312 Sq Ft

  4496 Strathmore Dr, Lake Wales, FL 33859

  **Huge Price Reduction – Buyer Savings CDD BOND PAID IN FULL ** This beautiful spacious 3-bedroom, 2-bath home in Lake Ashton Golf Community is move-in ready! Nestled on a desirable corner lot, the home welcomes you with a screened front porch perfect for enjoying peaceful mornings and breezy Florida evenings. Inside, the thoughtfully designed split floor plan features soaring ceilings, crown

  Candra Alston LAKE ASHTON REALTY INC.

  4496 Strathmore Dr, Lake Wales, FL 33859
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  /57

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,847 Sq Ft

  4429 Turnberry Ln, Lake Wales, FL 33859

  New Price! The CDD debt portion is paid in full !Resort-Style Living in Lake Ashton's 55+ Community Golf, Pools & More! This move-in ready 3-bedroom, 2-bath home features a stunning decorative glass entry door with twin sidelights and an arched transom window that welcomes you into the grand foyer filled with natural light. The open floor plan features ceramic tile throughout the main living

  Julie Seay COLDWELL BANKER REALTY

  4429 Turnberry Ln, Lake Wales, FL 33859
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  /74

  $535,000

  • 3 Beds
  • 3 Baths
  • 2,371 Sq Ft

  4105 Limerick Dr, Lake Wales, FL 33859

  CDD DEBT PAID IN FULL! Stunning and sprawling lake, canal and golf course views will keep you transfixed on all the natural birds and wildlife calling Lake Ashton home. Keep the Binocular's close by!!! This beautiful 3 bedroom, 3 full bath RV HOME is located on the highly sought after Limerick Drive in Lake Ashton, a gated Florida Retirement, 55+ community with resort style amenities and

  Lori Raath LAKE ASHTON REALTY INC.

  4105 Limerick Dr, Lake Wales, FL 33859
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  /56

  $279,900

  • 2 Beds
  • 2 Baths
  • 1,605 Sq Ft

  4432 Waterford Dr, Lake Wales, FL 33859

  This stunning Caribbean model home, located in the prestigious golfing community of Lake Ashton, offers resort-style living at its finest. The spacious 2-bedroom, 2-bathroom floor plan is designed for both comfort and entertainment. As you step through the screened-in front porch, you’ll be welcomed into an open-concept living space with high ceilings and an abundance of natural light, thanks to

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  4432 Waterford Dr, Lake Wales, FL 33859
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  /78

  $300,000

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft

  4424 Waterford Dr, Lake Wales, FL 33859

  GREAT SNOWBIRD HOME! FURNITURE and WASHER/DRYER TO CONVEY WITH THE SALE OF 4424 WATERFORD DRIVE LAKE WALES, FLORIDA 33859. Well Maintained Bali Floor Plan Offers an Open and Spacious Entry, Living Room Area, Kitchen and Dinette area. There is an Enclosed Lanai with Acrylic Windows with Screen Option, too. This 2 Bedroom /2 Bath home is located in Lake Ashton, a gated 55+ community in Florida. NO

  Lori Raath LAKE ASHTON REALTY INC.

  4424 Waterford Dr, Lake Wales, FL 33859
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  /73

  $319,900

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

  4139 Aberdeen Ln, Lake Wales, FL 33859

  One or more photo(s) has been virtually staged. **** BEAUTIFUL, NEWLY UPDATED HOME with NO BACKYARD NEIGHBORS and CDD DEBT PAID IN FULL**** Retirement at its best in this Beautiful 2 Bedroom, PLUS Den, 2 Bath home located in Lake Ashton, an exclusive 55+ community in Florida. This Essex floor plan home with over 1,500 sq. ft. living area has been remodeled and it shows like a NEW HOME. The list

  Lori Raath LAKE ASHTON REALTY INC.

  4139 Aberdeen Ln, Lake Wales, FL 33859
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  /85

  $599,900

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  3834 Litchfield Loop, Lake Wales, FL 33859

  Welcome to your personal haven and next chapter in beautiful Lake Ashton—Central Florida’s premier 55+ active-adult community and home of the LA Travelers, the largest Family Motor Coach Association chapter in the southeastern United States. Designed as both a serene retreat and an ideal travel base, this immaculate home radiates timeless elegance, thoughtful design, and Florida charm. At the

  Brad Kirwan GLOBAL LIFESTYLE LLC

  3834 Litchfield Loop, Lake Wales, FL 33859

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