Winter Haven, FL Homes under $300,000

• 

  

  

  /14

  $275,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  4981 Kaia Ave, Winter Haven, FL 33884

  Under Construction. Brand new, energy-efficient home available by May 2025! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter

  Tatiana Souza MERITAGE HOMES OF FL REALTY

  4981 Kaia Ave, Winter Haven, FL 33884
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  /26

  $284,990 Open Fri 10AM - 6PM

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  3495 Costello Cir, Winter Haven, FL 33884

  Under Construction. "Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort.Inside this 4-bedroom, 2-bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3495 Costello Cir, Winter Haven, FL 33884
• 

  

  

  /43

  $262,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  3880 Giorgio Dr, De Soto, FL 33884

  Brand new, energy-efficient home ready NOW! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have

  Tatiana Souza MERITAGE HOMES OF FL REALTY

  3880 Giorgio Dr, De Soto, FL 33884
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  /51

  $215,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2885 Attwater Loop, Winter Haven, FL 33884

  Prime LOCATION in Traditions – A Premier 55+ CommunityDiscover the perfect blend of comfort and convenience in this charming 2-bedroom, 2-bathroom villa with a versatile Flex Room, ideal for a home office, quiet retreat, or formal dining space. This smart home is designed for modern living, featuring a work-efficient kitchen with elegant white cabinets, crown molding, brushed nickel hardware,

  Michelle Urena REALTY OF AMERICA

  2885 Attwater Loop, Winter Haven, FL 33884
• 

  

  

  /16

  $299,999 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  1946 Sarah St, Winter Haven, FL 33884

  The first floor of this new two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom.

  Lennar

  Edison, Winter Haven, FL 33884
• 

  

  /19

  $284,999 New Construction

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft

  1954 Sarah St, Winter Haven, FL 33884

  This new single-story home is a modern take on a classic design. Down the foyer is a spacious and open-plan family room which has direct access to the cozy dining room, well-equipped kitchen and attached patio, perfect for everyday living. In a private corner is the owner’s suite with a convenient adjoining bathroom, while on the opposite side of the home are three secondary bedrooms to offer

  Lennar

  Celeste, Winter Haven, FL 33884
• 

  

  /17

  $269,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  1966 Sarah St, Winter Haven, FL 33884

  This new home is laid out on a single level for low maintenance living. Two secondary bedrooms share a bathroom in the hall at the front of the home, while the owner’s suite is tucked into the back corner with an attached bathroom and walk-in closet. Down the foyer is the open-concept living area, which includes a fully equipped kitchen, an intimate dining room and family room with patio access.

  Lennar

  Belmont, Winter Haven, FL 33884
• 

  

  /13

  $294,790 New Construction

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  Belmont, Winter Haven, FL 33884

  This new home is laid out on a single level for low maintenance living. Two secondary bedrooms share a bathroom in the hall at the front of the home, while the owner’s suite is tucked into the back corner with an attached bathroom and walk-in closet. Down the foyer is the open-concept living area, which includes a fully equipped kitchen, an intimate dining room and family room with patio access.

  Lennar

  Belmont, Winter Haven, FL 33884
• 

  

  /13

  $255,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,604 Sq Ft

  305 Wharf Way, Winter Haven, FL 33881

  2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are

  George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  305 Wharf Way, Winter Haven, FL 33881
• 

  

  /14

  $284,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  2767 San Marco Way, Winter Haven, FL 33884

  Pre-Construction. To be built. Villamar in Winter Haven, Florida, is a thoughtfully designed community offering modern homes in a prime location. Residents enjoy scenic surroundings, nearby lakes, and family-friendly amenities. With stylish home designs, energy-efficient features, and a welcoming neighborhood atmosphere, Villamar is the perfect place to call home. Among the available homes, The

  Charles Pennant NEW HOME STAR FLORIDA LLC

  2767 San Marco Way, Winter Haven, FL 33884
• 

  

  /14

  $284,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  2751 San Marco Way, Winter Haven, FL 33884

  Pre-Construction. To be built. This charming home maximizes every inch, starting with an inviting front porch and entryway that leads into a mudroom, offering easy access to the spacious garage. It seamlessly connects to the expansive family room, the heart of the home, where a large window fills the space with natural light. Positioned at the rear, the airy breakfast room features a large

  Charles Pennant NEW HOME STAR FLORIDA LLC

  2751 San Marco Way, Winter Haven, FL 33884
• 

  

  /29

  $298,000 New Construction

  • 4 Beds
  • 2 Baths
  • 1,819 Sq Ft

  2586 San Marco Way, Winter Haven, FL 33884

  Short Sale. bank has approved the listed priceStep into a realm of elegance and comfort with this beautifully designed home. Boasting vaulted ceilings and an expansive open concept floor plan, this 4 bedroom, 2 bathroom residence ensures a perfect setting for quiet family living or grand entertaining. Enjoy culinary freedom in the spacious kitchen featuring a large island, walk-in pantry, and

  John Mansker FOLIO REALTY LLC

  2586 San Marco Way, Winter Haven, FL 33884
• 

  /2

  $250,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  3916 Giorgio Dr, Winter Haven, FL 33884

  Under Construction. Brand new, energy-efficient home available by Jul 2025! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter

  Tatiana Souza MERITAGE HOMES OF FL REALTY

  3916 Giorgio Dr, Winter Haven, FL 33884
• 

  /2

  $300,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft

  3884 Giorgio Dr, Winter Haven, FL 33884

  Brand new, energy-efficient home available NOW! Configure the flex room in the front of the home to an at home office space or hobby space for the kids. Past the foyer, the open kitchen flows to the dining space, great room and outside patio. Private primary suite offers a spacious area to relax. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have

  Tatiana Souza MERITAGE HOMES OF FL REALTY

  3884 Giorgio Dr, Winter Haven, FL 33884
• 

  /2

  $298,670 New Construction

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  4993 Kaia Ave, Winter Haven, FL 33884

  Brand new, energy-efficient home available NOW! Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to

  Tatiana Souza MERITAGE HOMES OF FL REALTY

  4993 Kaia Ave, Winter Haven, FL 33884
• 

  /2

  $286,232 New Construction

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft

  985 Lunar Ln, Winter Haven, FL 33884

  Under Construction. Crescent Pointe is a brand new community located in Winter Haven, FL, conveniently situated off State Rd 653 and boasting easy access to a range of nearby attractions. For residents who enjoy outdoor activities, the Winter Haven Chain of Lakes is nearby. It offers opportunities for boating, fishing, and other recreational activities. The community is also close to the bustling

  Ed Laderer VANTAGE PROPERTY MANAGEMENT LLC

  985 Lunar Ln, Winter Haven, FL 33884
• 

  

  /34

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  307 Sterling Dr, Winter Haven, FL 33884

  Short Sale. Looking for a nice home with amazing potential and opportunity to gain equity? This one may be IT for you! Welcome to this 3-bedroom, 2-bath move-in ready home located in the peaceful and sought-after SE Winter Haven area! Situated on an OVERSIZED corner lot, this home features a fully fenced backyard, high ceilings, and ceramic tile flooring throughout the main living spaces. You’ll

  Krichely Gonzalez Rodriguez KELLER WILLIAMS ADVANTAGE III

  307 Sterling Dr, Winter Haven, FL 33884
• 

  

  /22

  $210,600

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft

  4747 Mandolin Loop, Winter Haven, FL 33884

  Auction Property. Welcome! Located in a desirable gated community in Southeast Winter Haven. This inviting property offers 3 spacious bedrooms and 2 full bathrooms, perfect for families, first-time buyers, or those looking to downsize without compromising comfort.Enjoy peaceful Florida living with a screened-in back porch—ideal for relaxing evenings, morning coffee, or entertaining guests.

  Don Jerue KELLER WILLIAMS REALTY SMART 1

  4747 Mandolin Loop, Winter Haven, FL 33884
• 

  

  /11

  $280,900

  • 4 Beds
  • 2.5 Baths
  • 2,928 Sq Ft

  312 Lake Smart Cir, Winter Haven, FL 33881

  Short Sale. Short Sale. "SHORT SALE" Sale third party approval-Short Sale is being professionally processed by Quick Homes, LLC. Buyer Responsible for Short Sale Processing Fee of $5,000. Property sold as-is do not send low ball offers, no assignable as will not be review.

  Ivy Gonzalez SWEET HOMES REALTY LLC

  312 Lake Smart Cir, Winter Haven, FL 33881
• 

  

  /19

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,849 Sq Ft

  920 Cambridge Dr, Winter Haven, FL 33881

  Please use showingtime to schedule showings. Call listing agent.

  Briana Willis Global Advantage Realty LLC

  920 Cambridge Dr, Winter Haven, FL 33881
• 

  

  /35

  $300,000

  • 5 Beds
  • 3 Baths
  • 2,527 Sq Ft

  235 Hibiscus St, Winter Haven, FL 33881

  Discover a rare opportunity for instant equity with this spacious 5-bedroom, 3-bathroom home in Winter Haven. Ideal for multi-generational living or growing households, the first floor features an open layout plus a bedroom and a full bathroom—perfect for guests or extended family. Upstairs, the generous master suite includes a walk-in closet and private bath, along with a large loft for flexible

  Jared Lippelgoos COLDWELL BANKER RESIDENTIAL RE

  235 Hibiscus St, Winter Haven, FL 33881
• 

  

  /17

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft

  1224 Vienna Square Dr, Winter Haven, FL 33884

  CAN'T BEAT THIS PRICE IN THIS COMMUNITY!!! This is a charming 2-bedroom, 2-bath home in a desirable adult living gated community. This well-kept residence features a spacious master suite with a walk-in shower, a bright and open living area, and a functional kitchen perfect for everyday living. Step outside to a screened-in back porch—ideal for relaxing or entertaining in comfort. Enjoy the many

  Don Jerue KELLER WILLIAMS REALTY SMART 1

  1224 Vienna Square Dr, Winter Haven, FL 33884
• 

  

  /5

  $270,000

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  1104 Star Ruby Ln, Winter Haven, FL 33880

  Short Sale. Spacious Cali model featuring 4 bedrooms and 2 baths. The home is located within the Squires Grove community of Winter Haven. The home features 4 spacious bedrooms. The open concept kitchen is great for entertaining with family and friends. The home also features an attached 2 car garage. The home is being sold in as is condition.This home is being sold through the short sale process.

  Jesse Carriedo REALTYCITY INC

  1104 Star Ruby Ln, Winter Haven, FL 33880
• 

  

  /7

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1540 Avenue C NE, Winter Haven, FL 33881

  Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

  Robert Miller MILLSHIRE REALTY

  1540 Avenue C NE, Winter Haven, FL 33881
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  /44

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft

  136 Krenson Bay Loop, Winter Haven, FL 33881

  Short Sale. PRICE REDUCED—MOTIVATED SELLER! Nestled in the desirable gated community of Krenson Bay, this well-maintained 3-bedroom, 2-bathroom home is move-in ready and waiting for you! Offering 1,720 sq. ft. of thoughtfully designed living space, this home blends comfort, style, and energy efficiency—built by Adams Homes to help keep utility costs low. Step inside to all-tile flooring, with

  Lori Edwards COLDWELL BANKER REALTY

  136 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /51

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  300 Lake Smart Cir, Winter Haven, FL 33881

  Short Sale. Price must be approved by the bank. Short Sale-Welcome to this beautiful 3-bedroom, 2-bathroom single-family home featuring a spacious two-car garage and a relaxing screened-in patio. Nestled in a desirable community with a private fishing pier, this home is perfect for outdoor enthusiasts. Plus, a public boat ramp is conveniently located just across the street, providing easy access

  Brandy Duncan COLDWELL BANKER REALTY

  300 Lake Smart Cir, Winter Haven, FL 33881
• 

  

  /9

  $279,000

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  100 High St, Winter Haven, FL 33880

  Great opportunity for an over 1/4-acre property in Winter Haven - with NO HOA or CDD! This home has 3 bedrooms, 2 bathrooms, 1732 square foot including a bonus room off the carport with private access, that is separated from the main home by an oversized 2 car carport. This creates great potential for an office or in law space. The main home of 1396 square feet feels very open when you step

  Trish Carter CARTER COMPANY REALTORS

  100 High St, Winter Haven, FL 33880
• 

  

  /23

  $275,000

  • 4 Beds
  • 2.5 Baths
  • 3,020 Sq Ft

  5018 Strada Dr, Winter Haven, FL 33880

  Short Sale. Packed with potential! This spacious two-story home, featuring 4 bedrooms, 2.5 baths, and a versatile bonus room needs some repairs, cleaning, and TLC, but that’s where the attractive price comes in! The main floor includes a large great room, white kitchen with granite countertops, front living room/den, laundry, enclosed bonus room and a 3-car garage. The lanai offers a great

  Tanja Cisliek FUTURE HOME REALTY INC

  5018 Strada Dr, Winter Haven, FL 33880
• 

  

  /12

  $295,500

  • 4 Beds
  • 3 Baths
  • 2,020 Sq Ft

  3077 Brenton Manor Loop, Winter Haven, FL 33881

  Short Sale. SHORT SALE. SHORT SALE, Calling Investors ,FIXER UPPER, 4 bedrooms, 3 bath home in Central Florida! Enjoy privacy with only one side neighbor and no back neighbor, come and see this Beautiful Home with an open-concept layout and spacious bedrooms & high vaulted ceilings Don't miss the chance to make this property your new home. SELLER WILL NOT MAKE ANY REPAIRS, PROPERTY IS AS IS.

  Amanda Linsey VYLLA HOME

  3077 Brenton Manor Loop, Winter Haven, FL 33881
• 

  

  /38

  $260,000

  • 4 Beds
  • 2 Baths
  • 1,748 Sq Ft

  5716 Lakeside Landings Blvd, Winter Haven, FL 33881

  Short Sale. MOTIVATED SELLER! TAKE ADVANTAGE OF THE SHORT SALE! Built in 2018, the HVAC, water heater, and roof are all in excellent condition, ensuring worry-free living. The property boasts an enclosed screened lanai perfect for relaxing evenings, with luxury vinyl fencing adding both privacy and style. Enjoy serene nature walks around the neighborhood, or unwind by the community pool and

  Liam Lugo KELLER WILLIAMS WINTER PARK

  5716 Lakeside Landings Blvd, Winter Haven, FL 33881
• 

  

  /61

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,597 Sq Ft

  103 13th St SE, Winter Haven, FL 33880

  Short Sale. PRICED TO SELL IMMEDIATELY! NO HOA! If you qualify, you could assume the VA loan on this home at just 5.625% interest, cutting your monthly payments up to 13%! Well-maintained and move-in ready, this three bedroom, two bathroom house has everything you need to call it "home". The roof was replaced in 2022 and the wiring was replaced within the last two years. Wood-look ceramic tile

  Kris Bender BENDER REALTY, LLC

  103 13th St SE, Winter Haven, FL 33880
• 

  

  /65

  $289,000

  • 3 Beds
  • 2 Baths
  • 2,029 Sq Ft

  4469 Turnberry Ln, Lake Wales, FL 33859

  MOTIVATED SELLER! CDD DEBT PAID IN FULL! ******PRICED TO SELL***** 4469 Turnberry Lane Lake Wales, Florida 33859 is a 3 Bedroom/2 Bath Provence floor plan located in Lake Ashton, a gated and guarded 55+ community with resort style amenities and activities. This spacious floor plan offers new interior paint, freshly painted garage floor, tray ceilings, crown molding, custom columns with

  Lori Raath LAKE ASHTON REALTY INC.

  4469 Turnberry Ln, Lake Wales, FL 33859
• 

  

  /49

  $225,000 Open Sat 10PM - 12PM

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

  4488 Turnberry Ln, Lake Wales, FL 33859

  Welcome Home! Come discover the charm of this cozy 2-bedroom, 2-bathroom home nestled within the beautiful 55+ community of Lake Ashton. Enjoy elegant touches like crown molding and stainless-steel appliances in the kitchen, a relaxing private screened lanai, and ALL the convenience of an active amenity rich golf community. Lake Ashton offers, two gated entrances with 24/7 guard services. The

  Candra Alston LAKE ASHTON REALTY INC.

  4488 Turnberry Ln, Lake Wales, FL 33859
• 

  

  /60

  $239,000

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

  4480 Turnberry Ln, Lake Wales, FL 33859

  *****PRICE REDUCED***** 4480 Turnberry Lane, Lake Wales, Florida is a Marbella floor plan home in Lake Ashton. This "Move-In Ready" 2 Bedroom / 2 Bath home has the CDD Debt FULLY PAID, SAVING YOU THOUSANDS $$$$$$. The curb appeal is enhanced by the quality landscaping, widened paver driveway, paver walk and screened entry. The screened lanai at the front of the home gives you an

  Lori Raath LAKE ASHTON REALTY INC.

  4480 Turnberry Ln, Lake Wales, FL 33859
• 

  

  /51

  $270,000

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

  4112 Aberdeen Ln, Lake Wales, FL 33859

  One or more photo(s) has been virtually staged. HUGE PRICE ADJUSTMENT-Welcome Home to Lake Ashton – 55+ Community Living at Its Finest! This beautifully UPDATED 3-bedroom, 2-bath home in the sought-after Lake Ashton community offers the perfect blend of comfort, style, and sustainability. CDD Bond is Paid in Full. Featuring a NEWER ROOF and fully paid-off SOLAR PANELS, (average electric bill is

  Jannette Joseph LPT REALTY, LLC

  4112 Aberdeen Ln, Lake Wales, FL 33859
• 

  

  /49

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,319 Sq Ft

  4152 Aberdeen Ln, Lake Wales, FL 33859

  MOTIVATED SELLER! BRING THE SELLER AN OFFER! This home is ready for a new owner. This South facing home offers 2 Bedrooms, 2 Baths and an enclosed lanai with transitional windows and awning. Located behind the secure gates of Lake Ashton, this Caribbean Floor Plan home offers a new roof (2021) and gutters and backs up to a pond. The new owner will enjoy the paver driveway and walk way that

  Lori Raath LAKE ASHTON REALTY INC.

  4152 Aberdeen Ln, Lake Wales, FL 33859
• 

  

  /56

  $284,900

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

  4432 Waterford Dr, Lake Wales, FL 33859

  The CDD DEBT IS PAID IN FULL, adding even more value to this incredible property! This wonderful 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

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  4432 Waterford Dr, Lake Wales, FL 33859
• 

  

  /35

  $250,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  8150 Cherokee Rd, Bartow, FL 33830

  One or more photo(s) has been virtually staged. Under Construction. This brand-new home is scheduled to be completed and affixed to the property by the end of August. The first photo is a rendering for visualization purposes, and the additional images showcase the model unit of the "Marvelous 3" by Clayton Homes. This stunning 3-bedroom, 2-bathroom home offers 1,450 square feet of thoughtfully

  Chad Lindsey KELLER WILLIAMS REALTY SMART 1

  8150 Cherokee Rd, Bartow, FL 33830
• 

  

  /13

  $279,990

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft

  546 Lorient Dr, Eagle Lake, FL 33839

  Short Sale. Come see this beautiful 4 bedroom 2 bathroom home located in the sought after community of Normandy Heights! Why wait nearly a year on a new construction home when you can move into this 2019 model ASAP and get tons of upgrades as well! This home is nearly 1800 living sq. ft., has an open floor plan great for entertaining, and offers the following upgrades: vinyl plank flooring

  Zaida Cordero LA ROSA REALTY LLC

  546 Lorient Dr, Eagle Lake, FL 33839

Showing Results 241 - 279, Page 7 of 7