Location: Winter Haven
Do Not Show Listings
2040 SAN MARCOS DR SE #202, WINTER HAVEN, FL 33880
$109,90014 Days on yellowkey MLS ID: P4938474
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 666 Built: 1985Monthly Fee: $237 Tax: $1,488 (2025)Community: Park Lake 03 02 AmdCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,488
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Cute as a Button! Charming 1-Bedroom, 1-Bath Condo in the desirable Park Lake community. This bright and inviting home features easy-care laminate flooring throughout, a cozy wood-burning fireplace, and a functional dinette area with a breakfast bar that flows into the dining space. Enjoy lots of Hot Water with the Natural Gas Tankless Hot Water Heater. The convenient stackable washer and dryer are included, making move-in a breeze. Step outside to enjoy your private screened-in porch — perfect for relaxing with your morning coffee or unwinding in the evening. Ideally suited for first-time homebuyers, investors, or anyone seeking low-maintenance living in a prime location, this condo is situated right in the heart of Winter Haven. The Park Lake community offers an abundance of amenities, including a sparkling community pool, direct lake access, clubhouse, fishing pier, exercise room, and more. Located on the shores of beautiful Lake Lulu, Park Lake is conveniently positioned next to the new AdventHealth Field House. You’re also just minutes from LEGOLAND, with quick access to the Disney and Universal entertainment areas. Excellent medical facilities and shopping are nearby as well. All measurements are approximate. Buyers and Buyers’ Agents to verify all listing information. Call today to schedule your private showing!
Listing is courtesy of: LAMOND REALTY INC. (863-875-8910)
Listing Agent: Robert Lamond (863-604-5400)
413 WINTER RIDGE BLVD #413, WINTER HAVEN, FL 33881
$144,500196 Days on yellowkey MLS ID: P4936697
REDUCED by $5,000 (3.3%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1995 Tax: $1,959 (2024)Community: Winter Ridge CondoCondo
Taxes:$1,959
Elementary School: Lake Alfred Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: PRICE REDUCED on this wonderful opportunity! Welcome to Winter Ridge Condominiums — Lakeside Living on the Winter Haven Chain of Lakes. Discover the charm of Winter Ridge, a desirable waterfront condominium community offering direct access to Lake Smart, part of the renowned Winter Haven Chain of Lakes. This inviting 2-bedroom, 2-bath home features an open floor plan with ceramic tile throughout, a galley-style kitchen equipped with a refrigerator, range, microwave, and dishwasher, plus a walk-in pantry/utility room with in-unit laundry hookups. Relax and unwind on the oversized screened lanai while taking in peaceful views of Lake Conine, perfect for morning coffee or evening unwinding. The home also includes two assigned parking spaces directly in front of the unit, with additional guest parking conveniently located near the clubhouse. Community amenities include a heated swimming pool, clubhouse, shuffleboard courts, and a fishing and boat dock—perfect for enjoying the waterfront lifestyle. The HOA takes care of exterior maintenance, roof upkeep, lawn care, common area landscaping, road maintenance, and pool and dock care, offering truly low-maintenance living. Outdoor enthusiasts will appreciate the public boat ramp across the street providing access to Lake Conine, and the nearby Lake Conine Nature Park (just 0.5 miles away), featuring walking trails, picnic areas, and scenic lake views. Centrally located near shopping, dining, and medical facilities, this property is also just minutes from Legoland and Highway 27, with easy access to Tampa and Orlando. Enjoy comfort, convenience, and lakeside living in one of Winter Haven’s most sought-after condo communities—Winter Ridge.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Michelle Heath (863-528-3123)
2040 SAN MARCOS DR SE #206, WINTER HAVEN, FL 33880
$166,00059 Days on yellowkey MLS ID: L4959883
2 Days Off yellowkey (back on 4/23/2026)
REDUCED by $5,000 (2.9%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 1985 Tax: $478 (2025)Community: Park Lake 03 02 AmdCondo
Taxes:$478
Remarks: Under contract-accepting backup offers. This move-in-ready home features fresh interior paint, updated countertops, brand-new cabinets, and renovated bathrooms, offering a clean, modern feel throughout. The open-concept floor plan creates a bright and inviting living space, perfect for entertaining or relaxing. Upstairs, a versatile loft provides the ideal spot for a home office, guest area, or flex space to fit your lifestyle. Enjoy low-maintenance living with fantastic community amenities, including a sparkling pool and lake access — perfect for soaking up the Florida sunshine. Ideal for first-time homebuyers, investors or anyone looking for comfort, convenience, and location all in one, this condo offers the perfect blend of style and lifestyle in the heart of Winter Haven. Some photos have been virtually staged to illustrate the property’s potential. Furnishings, décor, and enhancements shown in staged images are for marketing purposes only.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Marquita Smith (863-289-3343)
2085 ISLE ROYALE CT SE #284, WINTER HAVEN, FL 33880
$124,99982 Days on yellowkey MLS ID: O6380383
REDUCED by $1 (0.0%) on 04/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 648 Built: 2004Monthly Fee: $270 Tax: $213 (2025)Community: Park LakeCondo
Taxes:$213
Elementary School: John Snively Elem
Remarks: CORNER UNIT WITH VAULTED CEILINGS AND PRIVATE BALCONY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. This home also features a 2026 hot water heater, 2021 roof, and 2017 AC- offering peace of mind for years to come. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle. Listing agent is owner. Seller Financing Available.
Listing is courtesy of: LIONHEART BROKERS (321-214-4640)
Listing Agent: Claudia Centesimo (407-383-8882)
5850 CYPRESS GARDENS BLVD #405, WINTER HAVEN, FL 33884
$138,900147 Days on yellowkey MLS ID: G5104966
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1332 Built: 1975Monthly Fee: $436 Tax: $1,943 (2024)Community: Royal Crescent CondoCondo
Taxes:$1,943
Remarks: This two bedroom one and a half bath condo offers comfortable living. The kitchen features stainless steel appliances and an eat-in space. Bedrooms are upstairs with a full bath for privacy. A fenced patio provides outdoor relaxation and the community pool is just steps away. Convenient location near shopping dining and Legoland.
Listing is courtesy of: ORLANDO HOMES & INVESTMENTS (407-467-6515)
Listing Agent: Noel Moenssens (407-467-6515)
323 ORANGE BLOSSOM DR #323, WINTER HAVEN, FL 33880
$209,90010 Days on yellowkey MLS ID: P4938498
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1280 Built: 2001Monthly Fee: $408 Tax: $530 (2025)Community: Waters Edge Unit 1 ReplatCondo
Taxes:$530
Remarks: WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location!. Primary bedroom with ensuite and screened-in balcony, one car garage and open concrete patio. The screened patio is perfect for enjoying views of boaters and paddle boarders passing between the lakes. Focusing on recreation, this home is in the perfect spot for a multitude of outdoor activities. Community features include a sparkling pool . Fish from your backyard at the bank of Lake Lulu! This residence is convenient to Great restaurants, medical, shopping, entertainment, and LEGOLAND! Check us out today to see what Florida waterfront living is all about!
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Rick Hemenway (863-289-5657)
700 MIRROR TER NW #303, WINTER HAVEN, FL 33881
$99,900360 Days on yellowkey MLS ID: P4934745
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1029 Built: 1970Monthly Fee: $650 Tax: $180 (2024)Community: Spring Lake TowersCondo
Taxes:$180
Remarks: Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Kevin Tison (863-206-5755)
333 LAKE HOWARD DR NW #204C, WINTER HAVEN, FL 33880
$65,000645 Days on yellowkey MLS ID: U8249519
0 Days Off yellowkey (back on 4/21/2026)
REDUCED by $5,000 (7.1%) on 04/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1330 Built: 1973Monthly Fee: $485 Tax: $2,099 (2023)Community: Imperial Harboursphases 01 & 02Condo
Taxes:$2,099
Tax Year: 2023
Remarks: Short Sale. Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious 3-bedroom, 2-bath condo also features a bonus room. With three comfortable bedrooms, there’s ample space for guests, a home office, or crafting area. Enjoy an active lifestyle with shuffleboard courts, a well-equipped gym, and a billiard room. The heated pool ensures year-round relaxation, and a private community dock on Lake Howard is ideal for boating and fishing enthusiasts. Association dues cover water, basic cable, and internet, and also include access to dock your own boat. Located in the heart of Winter Haven, Imperial Harbor offers a serene and friendly community atmosphere, close to shopping, dining, recreational activities, and medical facilities. Act quickly because a property like this will not last long.
Listing is courtesy of: REALTY COOPERATIVE (800-704-6411)
Listing Agent: Tony Giglio (513-505-5222)
333 LAKE HOWARD DR NW #211A, WINTER HAVEN, FL 33880
$89,995112 Days on yellowkey MLS ID: TB8461846
0 Days Off yellowkey (back on 4/15/2026)
REDUCED by $10,000 (10.0%) on 04/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1218 Built: 1974Monthly Fee: $529 Tax: $1,931 (2025)Community: Imperial Harboursphases 01 & 02Condo
Taxes:$1,931
Remarks: Under contract-accepting backup offers. 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 amenities, including a heated pool, fitness center, shuffleboard, and billiards, all designed to support an active and relaxed lifestyle. Ideally situated just 45 minutes from both Tampa and Orlando, this central location offers the perfect balance of tranquility and accessibility. Inside, the open and airy floor plan feels inviting and relaxing. Refinished cabinets, fresh paint throughout and new double pane insulated windows make this home move-in ready! The primary suite is bright and spacious and two additional bedrooms provide flexibility for guests, hobbies, or a home office. HOA fees also include water, basic cable, and internet—making this an exceptional opportunity for low-maintenance, carefree living. Schedule a private tour today !
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: William Kilpatrick (863-669-8090)
381 WINTER RIDGE BLVD, WINTER HAVEN, FL 33881
$145,500114 Days on yellowkey MLS ID: S5140657
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1996Monthly Fee: $253 Tax: $2,125 (2025)Community: Winter Ridge CondoCondo
Taxes:$2,125
Elementary School: Fred G. Garnier Elem
Middle School: Lake Alfred-Addair Middle
Remarks: One or more photo(s) has been virtually staged. Waterfront view from your porch. Affordability, low-maintenance comfort, & strong rental income potential. Waterfront view from your porch. Discover serene living at this charming 2-bedroom, 2-bathroom condo offering stunning sunset water views from its screened lanai. The home has a functional layout, it includes a combination of living & dining area, a large master suite with a walk-in closet, & a sliding glass door towards your comfortable back porch overlooking the canal water view; the kitchen has sufficient space; & there is a large storage room. Enjoy your Florida lifestyle, this welcoming community with built-in amenities, has direct lakefront access via a community dock for boating, fishing, and water sports on the connected Chain of Lakes. For only $253 a month, HOA covers your home's exterior maintenance. Location is accessible to nearby shopping, hospitals, medical offices, schools, and about an hour drive Tampa or Orlando. To schedule a showing, provide your realtor your pre-approval letter or proof of cash funds. At this price range, this move-in ready condo is your best choice.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Lienyvette Grimaldo (863-399-0226)
207 WINTER RIDGE BLVD #4, WINTER HAVEN, FL 33881
$148,900177 Days on yellowkey MLS ID: P4936941
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1992Monthly Fee: $250 Tax: $2,035 (2024)Community: Winter Rdg CondoSpa: NoCondo
Taxes:$2,035
Remarks: Welcome to 207 Winter Ridge Blvd – A Serene Lakeside Retreat! This charming end-unit condo is a peaceful lakeview haven. Features; 2 spacious bedrooms, 2 bathrooms, and an open-concept living and dining area that flows effortlessly into an enclosed Florida room—ideal for soaking in breathtaking sunsets over Lake Conine. The kitchen features a built-in desk and a convenient closet pantry, while the master suite boasts a generous walk-in closet. Additional highlights include: Two dedicated parking spaces (one covered), brick paved front patio for outdoor enjoyment, high-end windows and doors, Hurricane shutters for peace of mind, new roof installed in 2024. Located within city limits, this quiet and well-maintained community offers resort-style amenities including a clubhouse, sparkling pool, shuffleboard courts, and access to a community dock and boat slip on Lake Smart. Whether you're fishing off the pier or strolling to nearby shops and restaurants in downtown Winter Haven, you'll love the blend of convenience & charm.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
2500 21ST ST NW #23, WINTER HAVEN, FL 33881
$178,00057 Days on yellowkey MLS ID: L4959772
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1334 Built: 1976 Tax: $636 (2025)Community: Casa Del Sol Condo Village Ph 02Condo
Taxes:$636
Middle School: Westwood Middle
Remarks: Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to the Winter Haven Chain of Lakes. This spacious 2bd/2.5 bath condo offers 1,334 sq. ft. of comfortable living with a smart two-story layout—main living areas downstairs and both bedrooms upstairs. The home incorporates rustic farmhouse design elements throughout, including decorative farmhouse wall paneling that adds warmth, texture, and character to the living spaces. Natural wood furnishings and neutral tones complement the farmhouse aesthetic, blending comfort with timeless style. This bedroom features a relaxed coastal design with soothing blue tones and nautical accents that create a bright, airy retreat. A bold navy accent wall highlights the space, complemented by decorative fishing net wall art and seaside décor. Large windows dressed in sheer navy curtains allow natural light to fill the room, enhancing the breezy coastal vibe. A second bedroom showcases a soft coastal palette with tranquil turquoise walls and light, breezy window treatments. The rustic whitewashed headboard adds a beach-cottage feel while coordinating with the natural textures and pastel bedding. The room’s calming color scheme and light-filled atmosphere create a peaceful, seaside-inspired retreat perfect for guests or family. The bathroom is enhanced with a sliding barn door, a popular farmhouse feature that combines charm with functionality. The door’s rustic wood finish and exposed hardware create a stylish focal point while maximizing space and adding a touch of modern farmhouse appeal. Enjoy low-maintenance living with HOA fees covering city water, sewer/garbage, exterior building maintenance, grounds care, and pool service. Community amenities include a clubhouse, two pools, tennis courts, shuffleboard, and a community dock with direct Lake Hartridge access. A rare bonus in condo living—an attached 2-car garage. Centrally located near major roadways for easy commuting to Lakeland, Auburndale, and the I-4 corridor, yet tucked into a peaceful residential setting close to downtown events, waterfront paths, and local dining. Ideal as a primary residence, seasonal home, or investment property. Opportunities like this don’t last—schedule your private showing today.
Listing Agent: Tomi Miller-Troupe (863-287-0231)
700 MIRROR TER NW #505, WINTER HAVEN, FL 33881
$129,900176 Days on yellowkey MLS ID: TB8445379
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1190 Built: 1970 Tax: $2,292 (2023)Community: Spring Lake TowersCondo
Taxes:$2,292
Remarks: Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The large primary bedroom has a walk-in closet leading to a sunroom, creating a versatile space for relaxation or hobbies. Newer oversized windows throughout the unit bathe the living area in natural light, further enhancing the spectacular lake views... Live an active lifestyle with sparkling swimming pool directly on the lake well-equipped fitness center, shuffleboard court, recreation room and library. On-site laundry facilities are available for residents. This condo is perfect for full-time residents seeking a tranquil lakeside retreat or snowbirds desiring an affordable winter getaway. Those seeking a low-maintenance lifestyle with condo fees covering water, sewer, trash, cable, internet, and all exterior maintenance. Additional highlights include a single covered parking spot, a dock for fishing or viewing the water, boat slips available on a first-come, first-served basis. Enjoy planned social events and activities for residents. No pets or smoking allowed. Winter Haven's central location provides easy access to theme parks like Orlando and Tampa Downtown area Grocery stores, shopping, movie theaters, restaurants and medical facilities, making this a prime location. Don't miss this extraordinary opportunity to own a piece of paradise. Escape to the tranquility, luxury, and with expansive water views where every day feels like a vacation.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Victoria Bollea (813-230-4529)
1776 6TH STREET NW #305, WINTER HAVEN, FL 33881
$155,00047 Days on yellowkey MLS ID: P4938080
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1549 Built: 1974Monthly Fee: $650 Tax: $576 (2025)Community: Lakeridge CondoCondo
Taxes:$576
Remarks: Under contract-accepting backup offers. RARELY AVAILABLE 3 BEDROOM 2 BATH (LAKERIDGE) CONDOMINIUM WITH 1,549 SQ.FEET & BEAUTIFUL LAKEVIEWS! The complex has all brand new dual pane, low E windows through out! Unit updates include: AC replaced in 2025; Water Heater replaced 2015; and, installation of new expensive remote controlled window shades in Florida room. Easy living is what you will find at this 55+ gated Winter Haven, Florida condominium with HEATED POOL. Make this your full time residence or winter home. As you enter the condo, note the LARGE kitchen that is open to the living/dining area allowing for easy entertaining. The kitchen includes wood cabinetry, convenient pull out shelves in lower cabinets, lot of counter top space and pantry closet. All appliances and washer/dryer are included. The primary bedroom is large and easily accommodates a king size bed and features a walk-in closet and an en-suite bathroom with up-dated comfort height vanity and walk in shower w/glass doors. Bedrooms #2 & #3 are large in size & and are accessed by hallway door that can be closed for additional privacy. The second bathroom has a tub shower combination and comfort height vanity. There are lots of closet and storage space throughout this condo. Extra assigned storage is located on the same floor! This condo is move in ready and can accommodate a quick close. Association amenities include gated entry/exits, covered assigned parking, heated pool, electric car charger, shuffleboard & tennis. MONTHLY ASSOCIATION FEE INCLUDES WATER,SEWER,TRASH REMOVAL,FIBER OPTIC CABLE PKG (CHOICE HD, A DIGITAL VIDEO RECORDER & FIBER OPTIC INTERNET with 1 GIG. SPEED), BUILDING INSURANCE, GROUND MAINTENANCE & RESERVE FUNDS. YOU ONLY HAVE TO PAY FOR YOUR ELECTRICITY HERE, AS EVERYTHING ELSE IS INCLUDED IN THE MONTHLY FEE. ONE SMALL PET MAY BE APPROVED. NON SMOKING PROPERTY. Lakeridge is a well managed, well maintained complex and is close to shopping, places of worship, groceries, restaurants, medical offices & hospital. Call today for your private showing! All information believed to be accurate but not guaranteed. Measurements are approximate. Buyer to verify any and all association questions and documents.
Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)
Listing Agent: Chris Goode (863-287-5454)
404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881
$120,00029 Days on yellowkey MLS ID: L4960788
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1252 Built: 1985Monthly Fee: $325 Tax: $1,415 (2025)Community: Country Lake CondoSpa: NoCondo
Taxes:$1,415
Elementary School: Elbert Elem
Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
307 EAGLE POND DR #307, WINTER HAVEN, FL 33884
$182,000273 Days on yellowkey MLS ID: P4935676
2 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1017 Built: 2009Monthly Fee: $355 Tax: $2,199 (2024)Community: Eagle Pond CondoCondo
Taxes:$2,199
Remarks: Under contract-accepting backup offers. PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings. Inside, you'll love the bright, open layout with 10' ceilings, rich wood cabinetry, and a breakfast-bar kitchen—ideal for casual meals, morning coffee, or entertaining. Both bedrooms feature spacious walk-in closets, plus you'll appreciate the extra outdoor storage for bikes, golf gear, and more. Enjoy the benefits of a low HOA that covers exterior maintenance, landscaping, pest control, and trash, along with access to the community pool and tennis courts. Cypresswood residents also enjoy resort-style amenities, including an 18-hole Ron Garl-designed golf course, clubhouse, restaurant, and junior Olympic pool. Ideal for first-time buyers, families, professionals, golf enthusiasts, seasonal residents, or investors seeking a turnkey rental in a premier gated community. Prime location: Minutes to I-4 and Hwy 27 for easy commuting. Close to LEGOLAND, Bok Tower Gardens, shopping, dining, medical facilities, and entertainment. Centrally located between Tampa and Orlando—the best of Central Florida at your doorstep. Don't miss this opportunity! Pond-view units in Cypresswood are highly desirable and move quickly. Schedule your private showing today and see why Cypresswood is such a wonderful place to call home.
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Mabel Vassallo (863-604-0499)
1700 6TH ST NW #B24, WINTER HAVEN, FL 33881
$105,000112 Days on yellowkey MLS ID: O6371915
REDUCED by $11,000 (9.5%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 960 Built: 1964Monthly Fee: $437 Tax: $1,425 (2025)Community: Winter Haven Harbour Apts CondoCondo
Taxes:$1,425
Remarks: 55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, and wood laminate floors throughout the living room, dining area, and hallway. Interior utility area includes washer and dryer for extra convenience. The primary bedroom opens to a screened-in balcony. This amenity-rich community offers a large heated pool, pickleball and shuffleboard courts, a grilling area, and a clubhouse with a fitness center, perfect for staying active or socializing with neighbors. Additional conveniences include a common laundry room, a secure storage area, reserved covered parking, and elevator access. Ideally located in central Winter Haven, this condo is just minutes from downtown, shopping, dining, hospitals, and medical facilities, with easy access to I-4, placing you perfectly between Orlando and Tampa. Enjoy a vibrant lifestyle in a prime location.
Listing Agent: Rosa Suarez (954-682-2633)
400 EL CAMINO DR #210, WINTER HAVEN, FL 33884
$130,00095 Days on yellowkey MLS ID: S5142500
REDUCED by $5,000 (3.7%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1666 Built: 1974Monthly Fee: $448 Tax: $1,368 (2025)Community: Orchid Spgs Vill 400 San MiguelSpa: NoCondo
Taxes:$1,368
Remarks: Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy and a peaceful feel while enjoying the security and convenience of community living. Inside you will find updated luxury vinyl flooring, windows, stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer and AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
100 EL CAMINO DR #101, WINTER HAVEN, FL 33884
$109,99029 Days on yellowkey MLS ID: S5147114
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1971 Tax: $393 (2025)Community: Orchid SpringsSpa: NoCondo
Taxes:$393
Elementary School: Garden Grove Elem
Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond 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 flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.
Listing Agent: Sharon Gastelbondo (863-800-4655)
100 EL CAMINO DR #111, WINTER HAVEN, FL 33884
$71,000116 Days on yellowkey MLS ID: S5141094
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 931 Built: 1971 Tax: $1,178 (2025)Community: GranadaSpa: NoCondo
Taxes:$1,178
Remarks: 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 flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.
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