Winter Haven, FL Homes for Sale in a Senior Community under $100,000

/38
$99,995
- 3 Beds
- 2 Baths
- 1,218 Sq Ft
333 Lake Howard Dr NW Unit 211A, Winter Haven, FL 33880

Welcome to this beautifully maintained 3-bedroom, 2-bath condominium. It's located in the highly sought-after 55+ Imperial Harbor community of Winter Haven. Convenient elevator access makes daily living effortless in this serene lakefront retreat. Start your mornings with a walk to the private community dock on Lake Howard, where fishing and boating await. Enjoy an array of resort-style

Bill Kilpatrick KELLER WILLIAMS TAMPA CENTRAL

333 Lake Howard Dr NW Unit 211A, Winter Haven, FL 33880
/45
$34,999
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
138 Jay Dr, Winter Haven, FL 33880

Discover modern comfort in this meticulously updated 3-bedroom, 2-bathroom home located at 138 Jay Dr., Winter Haven, FL. Spanning a generous 1248 sq ft, this residence boasts a comprehensive uplift to enhance both its aesthetics and functionality. Step inside to find double-pane windows, updated siding, gutters, and exterior insulation that improve energy efficiency. The floors have been

Chrissy Walter Sunset Home Sales

138 Jay Dr, Winter Haven, FL 33880
/32
$75,000
- 2 Beds
- 2 Baths
- 1,366 Sq Ft
400 El Camino Dr Unit 202, Winter Haven, FL 33884

The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of Polk County. This is a second-floor unit with 2 bedrooms, 2 bathrooms, and is ready to move into. This is a 55+ community and has a nice square footage for this lifestyle. Many amenities are included in the HOA fee structure - lawn, water, sewer, natural gas, grounds, clubroom. The dishwasher is in

Renee Butler BROKERS REALTY OF CENTRAL FLOR

400 El Camino Dr Unit 202, Winter Haven, FL 33884
/16
$71,000
- 1 Bed
- 1 Bath
- 931 Sq Ft
100 El Camino Dr Unit 111, Winter Haven, FL 33884

Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room

Sharon Gastelbondo LPT REALTY, LLC

100 El Camino Dr Unit 111, Winter Haven, FL 33884
/67
$69,900
- 2 Beds
- 2 Baths
- 1,488 Sq Ft
4319 Cherrywood St, Winter Haven, FL 33880

This home is a blank slate with lots of room. Over 1400 sf of living space plus the lanai with over 300 sf. Much of the flooring is removed showing the sturdy plywood floors. The kitchen is very functional with lots of storage space. The laundry is conveniently located just off the kitchen. The split bedroom floor plan offers lots of privacy for guests. The guest bedroom is a large area that

Kathy Devor COLDWELL BANKER REALTY

4319 Cherrywood St, Winter Haven, FL 33880
/45
$45,000
- 2 Beds
- 2 Baths
- 840 Sq Ft
564 Chickasaw Loop Unit 34, Winter Haven, FL 33881

Hidden Cove East / Lot #34 / 2 Bedroom/2 Bath / 840 Sq. Ft. / $45,000.00 PRICE REDUCED ALMOST 3K!!! This home is located in the beautiful Hidden Cove East community, and is unusually hard to find a home as gorgeous as this one! Once residents purchase, they stay, so homes do not come on the market very often. Jump on this gorgeous home that has: New A/C Compressor Roof (2 years old) Sprinkler

Jennifer Torres CRF Communities

564 Chickasaw Loop Unit 34, Winter Haven, FL 33881
/35
$28,000
- 2 Beds
- 2 Baths
- 840 Sq Ft
58 Woodside Ln, Winter Haven, FL 33881

Hidden Cove / Lot #58 / 2 Bedroom/2 Bath / 840 Sq. Ft. / $28,000.00 Location! Location! Location! This large home is on an amazing lot that provides privacy and plenty of room! Nestled up against the woods, this home has a lot to offer: PRICE REDUCTION OF 7K! Large Screen Room with a View, Large Kitchen, Split Floor Plan, Two FULL Baths, Metal Roof, LOW LOT RENT! With a little bit of love, this

Jennifer Torres CRF Communities

58 Woodside Ln, Winter Haven, FL 33881
/19
$90,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
4165 Rolling Oaks Dr, Winter Haven, FL 33880

Priced to sell, Home has a new metal roof, CHA is approximately five years old, and you will feel right at home from the moment you walk in. Come enjoy the beautiful Florida sunsets in this 55+ gated, five-star park.

Rita Stead SOUTHERN BELLE REALTY

4165 Rolling Oaks Dr, Winter Haven, FL 33880
/51
$49,900
- 2 Beds
- 2 Baths
- 1,320 Sq Ft
263 Alpine Dr, Winter Haven, FL 33881

Swiss Village/ Lot #263 / 2 Bedroom/2 Bath / 1,320 Sq. Ft. / $49,900.00 Spring Savings! PRICE REDUCTION OF 6K ON THIS INCREDIBLE HOME! This home is absolutely amazing, and the pictures do not do it justice. It is stylishly & exquisitely decorated in beautiful, warm blues & sage, and comes fully furnished with updated furniture! There isn't room to list ALL of the updates & upgrades, but here are

Jennifer Torres CRF Communities

263 Alpine Dr, Winter Haven, FL 33881
/29
$68,500
- 2 Beds
- 2 Baths
- 864 Sq Ft
1400 Wild Dunes Ct Unit 48, Winter Haven, FL 33881

2 Bedroom | 2 Bath | 864 Sq Ft | $68,500 1400 Four Lakes Golf Club Lot 48 Price reduced $11K! Now $68,500 (was $79,900)! Discover lots of home in a compact, efficient floor plan with this beautifully maintained 2-bedroom, 2-bath retreat on a desirable corner lot in the Four Lakes Golf Club community. Thoughtfully designed and furnished, this home offers comfort, convenience and undeniable charm.

Cheryl Dobbs CRF Communities

1400 Wild Dunes Ct Unit 48, Winter Haven, FL 33881
/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
/35
$55,000
- 2 Beds
- 2 Baths
- 1,544 Sq Ft
125 Rigi Slope Dr, Winter Haven, FL 33881

HIGHLY MOTIVATED SELLERS! Located in the highly sought-after Swiss Village, this spacious 2-bedroom, 2-bathroom mobile home offers over 1,500 square feet of comfortable living space and comes fully furnished for an easy move-in. The home features all new duct work, updated double-pane windows, and a brand-new kitchen sink, adding both efficiency and peace of mind. The open living area is bright

Whitney Campbell-Conkey Pelican's Nest Mobile Home Sales, LLC.

125 Rigi Slope Dr, Winter Haven, FL 33881
/50
$49,900
- 2 Beds
- 2 Baths
- 840 Sq Ft
794 Sandtrap Cir, Winter Haven, FL 33881

2 Beds | 2 Baths | 840 Sqft | $49,900 | Lot 794 Spring Savings! $9,000 price reduction! Welcome to this beautifully maintained, furnished home! Enjoy being on a quiet street with no rear neighbors. Lots of room in this home to stretch out. Home offers spacious lanai 11x16 with AC adding approx. 200 sf of additional living space to the home for an office, craft space, or guests. Plus, 2 roomy

Brandi Sappington CRF Communities

794 Sandtrap Cir, Winter Haven, FL 33881
/51
$59,900
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
22 Alpine Dr, Winter Haven, FL 33881

Swiss Village / Lot #22 / 2 Bedroom/2 Bath / 1,260 Sq. Ft. / $59,900.00 HOME REDUCED 5K!! This home has the WOW FACTOR!! It has so many upgrades, that you may have to ask me what hasn't been either updated or replaced. It has been meticulously maintained and offers: NEW A/C, NEW ROOF/CARPORT, 4" WOOD BLINDS, CUSTOM BLINDS IN FLORIDA ROOM, NEW WINDOWS, UPDATED IN BOTH BATHROOMS, FRESHLY

Jennifer Torres CRF Communities

22 Alpine Dr, Winter Haven, FL 33881
/62
$79,900
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
1008 Eagle Dr, Winter Haven, FL 33881

2 Bed | 2 Bath | 1144 square foot | $79,900 (Swiss Golf and Tennis- Lot 1008) PRICE REDUCED! Located in highly sought after 55+ community! This gorgeous fully furnished, move-in-ready home offers a bright, comfortable layout with numerous recent upgrades. Enjoy peace of mind with updated interior and thoughtful custom touches throughout. Highlights include-New appliances and an additional upright

Brandi Sappington CRF Communities

1008 Eagle Dr, Winter Haven, FL 33881
/38
$65,000
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
757 Century Ln, Winter Haven, FL 33881

2 Bed | 2 Bath | 1008 square foot | $65,000 (Swiss Golf and Tennis- Lot 757) Fully furnished, move-in-ready home in a great location in highly sought after 55+ community. This cozy home is close to clubhouse, lake and restaurant! Highlights include -Newer AC -No rear neighbors -Spacious open layout with dedicated dining space -Walk in closets in bedrooms -Large storage shed. This home gives you

Brandi Sappington CRF Communities

757 Century Ln, Winter Haven, FL 33881
/29
$99,000
- 3 Beds
- 2 Baths
- 1,736 Sq Ft
1717 Woodmount Ln Unit 530, Winter Haven, FL 33881

3 Bedrooms | 2 Bathrooms | 1,736 Sq Ft | $99,900 Four Lakes Golf Club Lot 530 Discover a home where the kitchen truly steals the show! This beautifully designed 3-bedroom, 2-bath home in Four Lakes Golf Club is perfect for anyone who loves to cook, entertain and gather with friends and family. The standout feature of this home is the expansive, entertainer's kitchen offering counter space galore

Cheryl Dobbs CRF Communities

1717 Woodmount Ln Unit 530, Winter Haven, FL 33881
/26
$19,000
- 2 Beds
- 1.5 Baths
- 800 Sq Ft
424 Mockingbird Ave, Winter Haven, FL 33881

Motivated Seller! Welcome to this charming 2-bedroom, 1.5-bath home nestled on a desirable corner lot in the beautiful 55+ community of Lake Deer Hamlet Mobile Home Park. Offering great value and comfort, this home features a spacious Florida room addition, perfect for relaxing, entertaining, or enjoying your morning coffee. A large storage shed provides plenty of space for tools, hobbies, or

Lillian Lunsford TEAM SHERROD MOBILE HOME SALES, LLC.

424 Mockingbird Ave, Winter Haven, FL 33881
/11
$49,500
- 2 Beds
- 1 Bath
- 768 Sq Ft
47 Azalea Dr Unit AZ-47, Winter Haven, FL 33881

This Beautiful new home features 768 sq. ft. of well-designed living space, 2 bedrooms, and 1 bathroom. Open Floor plan, entertain while cooking. Floors are grey vinyl planked with light tones throughout the home. All new appliances and double stainless-steel sinks. Nice size lot with concrete sidewalk and driveway, off street parking. With restaurants, and shopping all nearby, this community

Sherri Streight Four Star Homes, Inc.

47 Azalea Dr Unit AZ-47, Winter Haven, FL 33881
/41
$30,000
- 2 Beds
- 1 Bath
81 Cape Horn Ave, Winter Haven, FL 33880

Welcome to this charming 2-bedroom, 1-bath home located on the southern Chain of Lakes in central Florida. Shipp-Reck Harbor is a waterfront community with access to Lake Shipp, ideal for water enthusiasts who love boating, fishing, skiing, and enjoying the outdoors. On top of all the surrounding lakes, a variety of famous Florida attractions are accessible in all directions. The vibrant cities

Linda Wilson Sunset Home Sales

81 Cape Horn Ave, Winter Haven, FL 33880
/33
$29,000
- 2 Beds
- 1.5 Baths
- 560 Sq Ft
24 Hideaway Ln, Winter Haven, FL 33881

Welcome to your serene retreat at 24 Hideaway Ln, nestled in the heart of Winter Haven's welcoming Hidden Cove community, an idyllic setting dedicated to those 55 and better. This charming two-bedroom, one & half bathroom home boasts a suite of upgrades over the last few years. From the moment you step inside, you'll be greeted by fresh, modern interiors. Step outside and experience the

Chrissy Walter Sunset Home Sales

24 Hideaway Ln, Winter Haven, FL 33881
/18
$16,900
- 2 Beds
- 1 Bath
- 616 Sq Ft
868 Sandtrap Cir, Winter Haven, FL 33881

2 Bed | 1 Bath | 616 square foot | $16,900 (Hidden Golf Club- Lot 868) Charming fixer-upper in a friendly 55+ community, offering a wonderful opportunity for the right buyer to bring out its full potential. This 2-bedroom, 1-bath home features a bright, open layout with plenty of natural light. Spacious Florida room. The home does need some updating and is priced with that in mind. Roof and AC

Brandi Sappington CRF Communities

868 Sandtrap Cir, Winter Haven, FL 33881
/23
$48,000
- 2 Beds
- 2 Baths
- 1,340 Sq Ft
21 Kinsmen Dr, Winter Haven, FL 33884

SELLER IS MOTIVATED AND IS OFFERING TO PAY SIX MONTH'S LOT RENT FOR NEW BUYER. Must see this lovely 2 bedroom, 2 bath double wide mobile home in sought after Orange Manor West community. Owners have left some furnishings, leaving space for you to purchase and furnish you new home just the way you like it. Perfect home for those cold winters up north or make it your year round residence. This home

Emily Muscarella

21 Kinsmen Dr, Winter Haven, FL 33884
/45
$9,999
- 2 Beds
- 1 Bath
54 Dale Dr, Winter Haven, FL 33880

Discover your new home at 54 Dale Dr in Winter Haven, FL! This 2-bedroom, 1-bathroom house is now on the market and ready for its next owner. Nestled in a peaceful, wooded neighborhood, this property offers the perfect blend of small-town living with big-city convenience. Recently updated with brand new flooring, this home will be move-in ready when you arrive. It's part of the Winter Haven MHC,

Chrissy Walter Sunset Home Sales

54 Dale Dr, Winter Haven, FL 33880
/69
$48,990
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
35 Dale Dr, Winter Haven, FL 33880

Welcome to Winter Haven! This charming 3-bedroom, 2-bathroom home offers the ideal blend of comfort and convenience you've been searching for. The spacious primary bedroom provides a peaceful sanctuary, while the impressive 12x24 Florida room becomes your personal oasis - perfect for morning coffee, evening relaxation, or entertaining friends year-round. Positioned on the edge of the community

Chrissy Walter Sunset Home Sales

35 Dale Dr, Winter Haven, FL 33880
/58
$99,000
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
148 Greenview Dr, Winter Haven, FL 33881

2 Bed | 2 Bath | 1568 square foot | $99,000 (Swiss Golf and Tennis- Lot 148) Enjoy resort-style living in this completely remodeled home with large bedrooms and walk in closets. Located in highly sought after 55+ Community! This home is like brand new- a must see! Dedicated dining space and breakfast nook. Home Features -New roof and A/C - only 2 years old -Modern kitchen with new cabinets,

Brandi Sappington CRF Communities

148 Greenview Dr, Winter Haven, FL 33881
/57
$17,900
- 2 Beds
- 1.5 Baths
43 Charles Dr, Winter Haven, FL 33880

Welcome to your renovation opportunity at 43 Charles Drive in Winter Haven! This charming 2-bedroom, 1.5-bathroom home is perfect for buyers seeking a project with excellent investment potential in a vibrant community setting. **Monthly lot rent is just $850, which includes water, sewer, and trash services** This handyman special comes equipped with essential appliances including washer, dryer,

Chrissy Walter Sunset Home Sales

43 Charles Dr, Winter Haven, FL 33880
/49
$62,500
- 2 Beds
- 2 Baths
- 1,440 Sq Ft
158 Sago Palm Way Unit 364, Winter Haven, FL 33880

2bd/2bath/1,440sf/$62,500/Winter Haven Oaks/#364 1991 Double-wide located in gated 55+ active retirement community. Located on a corner lot with a large double carport. This home has a 3.5 ton carrier A/C unit installed in 2017. Partially furnished. Lanai in back with an additional room with glass windows. Lots of closets and storage. Kitchen has a breakfast eating area and a separate formal

Donna Lattin CRF Communities

158 Sago Palm Way Unit 364, Winter Haven, FL 33880
/48
$59,900
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
184 Oak Tree Blvd Unit 39, Winter Haven, FL 33880

2bd/2bath/1,152sf/$55,900/Winter Haven Oaks/#39 This 1991 Double-wide is located in gated active 55 plus community. It is close to community clubhouse, swimming pool, and mail area. Enjoy the four-season lanai with new glass windows. Open kitchen living room with eating area and formal dining room. Large master bedroom with full length closet. Walk-in shower. Large guest bedroom with walk-in

Donna Lattin CRF Communities

184 Oak Tree Blvd Unit 39, Winter Haven, FL 33880
/24
$63,500
- 2 Beds
- 2 Baths
- 960 Sq Ft
5 Alpine Dr, Winter Haven, FL 33881

Located within walking distance of the clubhouse, two pools, shuffleboard, hot tubs, putt-putt, etc. U-shaped kitchen with eat-in bar and adjacent dining room. Living room opens up to screened room facing the street for morning coffee and visiting with neighbors. Spacious master bedroom suite with private bath. Extra screened room off the carport and utility room with washer and dryer. Roof is

Joanne Gauthier Four Star Homes, Inc.

5 Alpine Dr, Winter Haven, FL 33881
/27
$16,000
- 1 Bed
- 1 Bath
5601 Cypress Gardens Rd Unit 126, Winter Haven, FL 33884

**PRICED TO SELL** This Quaint and Cozy 1-bedroom 1-bath adorable home is located in Winter Haven, Florida, among the Chain of Lakes and close to all shopping, medical, and businesses, as well as major attractions such as DISNEY, LEGOLAND, and BOK TOWER. Hammondell RV Park is a 55+, pet-friendly community surrounded by an endless list of outdoor recreation opportunities, including nearly 50

Linda Wilson Sunset Home Sales

5601 Cypress Gardens Rd Unit 126, Winter Haven, FL 33884
/74
$18,000
- 2 Beds
- 2 Baths
- 896 Sq Ft
62 Dale Dr, Winter Haven, FL 33880

Seller is open to all offers. Make your own deal on this turnkey home! Whether you're looking to downsize, retire, or simply embrace the best of Florida's lifestyle, this 2 bedroom|2 bathroom in Winter Haven is the perfect place to make your dreams a reality. Winter Haven MHC is a 55+ pet-friendly community for active seniors. There is plenty of additional living space to entertain family/friends

Patti Alvin Sunset Home Sales

62 Dale Dr, Winter Haven, FL 33880
/45
$55,900
- 2 Beds
- 2 Baths
- 840 Sq Ft
602 Century Dr, Winter Haven, FL 33881

2 Bed | 2 Bath | 840 square foot | $55,900 (Hidden Golf Club- Lot 602) Welcome to this beautifully maintained, fully furnished turnkey home in active 55+ community! Enjoy an adorable, fenced courtyard perfect for relaxing and enhancing curb appeal. Inside, you'll find unique Spanish tile and charming accents throughout, complemented by beautiful newer flooring. The spacious bedrooms offer

Brandi Sappington CRF Communities

602 Century Dr, Winter Haven, FL 33881
/11
$59,900
- 1 Bed
- 1 Bath
- 850 Sq Ft
400 El Camino Dr Unit 223, Winter Haven, FL 33884

Welcome Home to Orchid Springs Village! Step into comfort with this inviting 1-bedroom, 1.5-bath condo located on the second floor of the peaceful Orchid Springs 55+ community. Surrounded by mature landscaping, this residence offers a quiet and comfortable setting, ideal for those looking to enjoy a relaxed Florida lifestyle. You’ll appreciate being conveniently close to shopping, dining, medical

Scott Cohara KELLER WILLIAMS CLASSIC

400 El Camino Dr Unit 223, Winter Haven, FL 33884
/26
$67,000
- 2 Beds
- 2 Baths
218 Green Meadow Dr, Winter Haven, FL 33884

If you are looking for the perfect retirement home that is fully furnished, this is the one for you. Located in gated Orange Manor West, a very popular 55+ community located in Southeast Winter Haven. This home is on leased land with a monthly fee of $513, which includes cable, internet and trash pickup. Park Lane Mobile Home 2 bedroom/2 bath with approximately 1,152 sf , king sized master

Emily Muscarella

218 Green Meadow Dr, Winter Haven, FL 33884
/45
$75,900
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
53 Greenview Dr, Winter Haven, FL 33881

Spring Savings! Price Reduced and seller will offer 2 months FREE lot rent if closed in March 2026! Beautifully maintained and mostly furnished home in a desirable 55+ active golf community. Features great curb appeal and an open, inviting layout. Enjoy peace of mind with a new roof (2024), updated plumbing, and newer flooring. Inside, you'll find a dedicated dining area and a spacious,

Brandi Sappington CRF Communities

53 Greenview Dr, Winter Haven, FL 33881
/57
$52,900
- 3 Beds
- 2 Baths
269 Hummingbird Ln, Winter Haven, FL 33884

***JUST REDUCED*** Welcome to this lovely 3-bedroom/2-bath manufactured home, just waiting for you in beautiful Central Florida. Located in the vibrant community of Winterset Shores Estates in Winter Haven, Florida, just southwest of Orlando. This peaceful waterfront community is located on Lake Winterset with a private beach, fishing dock, and boat slips. Perfect for the avid fisherman looking

Cynthia Cole Sunset Home Sales

269 Hummingbird Ln, Winter Haven, FL 33884
/57
$74,900
- 2 Beds
- 2 Baths
- 1,620 Sq Ft
281 Putter Cir, Winter Haven, FL 33881

2 Bed | 2 Bath | 1620 square foot | $74,900 (Swiss Golf and Tennis- Lot 281) 5K PRICE DROP! Seller Motivated and offering one-month FREE lot rent if closed by 4/1/2026. Beautifully updated and move-in ready home in a highly sought-after 55+ active golf community! This spacious open-layout home offers comfort, style, and plenty of room to relax or entertain. Partially furnished and loaded with

Brandi Sappington CRF Communities

281 Putter Cir, Winter Haven, FL 33881
/20
$59,900
- 2 Beds
- 2 Baths
- 1,153 Sq Ft
5 Temple Cir SE, Winter Haven, FL 33884

FREE GIFT! That's right...owners are offering to pay your first 3 months lot rent. What a gift! Call today to view this well cared for fully furnished 2 bedroom 2 bath home is located in Orange Manor East 55+ community. Home has living room with separate den which leads to the well appointed galley kitchen with built in breakfast table. Right off of the kitchen is dining room with built in

Emily Muscarella

5 Temple Cir SE, Winter Haven, FL 33884
/24
$32,000
- 2 Beds
- 1 Bath
- 988 Sq Ft
91 Orange Manor Dr, Winter Haven, FL 33884

ImmaculateHome with Cottage-Style Located in a 55+ Active Community in Winter Haven Homes in the Orange Manor East, a 55+ lake community, are on lot leased land in Winter Haven, Florida. Owning the home, but not the land, you pay a monthly lot rent of $ 700 which gives you and your guest access to the amenities of the community. Welcome to a beautifully maintained 2-bedroom, 1-bath

Bette Johnson Renee's Resales

91 Orange Manor Dr, Winter Haven, FL 33884

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