View 19 Winterset Homes for Sale

Below you can view all the homes for sale in the Winterset subdivision located in Winter Haven Florida. Listings in Winterset are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Winterset, give us a call at (407) 444-0331.

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Viewing Homes 1 to 19 of 19

Winterset $399,900

3420 Lakeview Dr Winter Haven Florida 33884

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  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2389

  • Year Built

    1957

  • $/SqFt

    $167

AMAZING CHAIN OF LAKES RESIDENCE ON S.E. WINTER HAVEN'S LAKE WINTERSET...This 3 bedroom, 2.5 bath water-lover's dream offers some of the most amazing views and lakefront-living you will ever find at this price. Walking through the front door you are immediately greeted by jaw dropping panoramic scenes of the postcard perfect lakefront. Layout consists of a large great room, formal dining space, game room/family room and a split-bedroom plan for the perfect blend of privacy and comfort while offering views from almost every room. Kitchen is finished with granite counters, handcrafted custom cabinetry, oversized range and a double oven. Relaxing master suite has beautiful bedside water views and a crisp clean master bath. Second bedroom provides an en-suite full bathroom and dimensions worth of a junior suite. The cypress screened lanai is the perfect spot for waterfront evening dining or watching the morning's sunrise while sipping coffee. Making your way lakeside you will find a pristine white sand beachfront, dock with covered boathouse, boat lift, jet ski lift and crystal clear waters begging you to jump in. This is the ideal home for all watersport enthusiasts and Lake Winterset has long been one of the most desirable lakes on the chain for it's superior water quality and waterski-friendly conditions. Spend the weekend cruising all 17 lakes on the Southern Chain or boat just one lake over to watch the Legoland waterski show. Living the lakefront-lifestyle at it's finest!!! ***SEE VIRTUAL TOUR***

Winterset $82,000

1808 Garden Lake Dr # 1808 Winter Haven Florida 33884

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  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1103

  • Year Built

    1986

  • $/SqFt

    $74

Lovely ground floor condo in Winterset. Gated Chain of Lakes access makes this SE Winter Haven community very sought after. This condo has a screen porch that overlooks a quiet lagoon and private boardwalk is available for residents. The addition of a Gas fireplace is perfect for crispy winter evenings. Newer CH/A & carpet. Lots of amenities with community pool, tennis courts, clubhouse, & access to Lake Winterset. Near Legoland and other attractions. Don't miss seeing this one...

Winterset $1,299,000

130 Wyndham Dr Winter Haven Florida 33884

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  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5620

  • Year Built

    1997

  • $/SqFt

    $231

One Plus Acre Chain of Lakes Luxury Estate...5,620 sqft stately residence offering 4 bedrooms, 4 full baths, 2 half baths, executive office, game room and a 4 car garage. This exquisite property showcases refined architectural detail and a level of amenities one expects to find in this price category. Impressive travertine columned entry opens to a grand foyer and a massive formal living room with panoramic views of pristine Lake Winterset. Formal dining room and walk-thru wet bar are located just off the chef's kitchen which offers granite counters, double oven, walk-in pantry, prep island and breakfast nook. Elegant family room boasts an impressive chandelier, travertine gas fireplace and astonishing views of the pool and lakefront. Master suite is highlighted by amazing bedside lake views, sitting room, mirrored dressing area, his/hers walk-in closets with built-ins and a luxurious master bath with soaking tub & walk-in shower. Three guest bedrooms located downstairs, all with full en-suite bathrooms. Executive office features rich hardwood flooring and custom built-in desks. Large leisure area, powder room and game room located on the upper level. Premium outdoor living with covered poolside kitchen, expansive travertine pool deck and envious poolside scenery. Covered dock with boat lift and two jet ski lifts sits on 157' of prime Lake Winterset frontage, the most sought after and desirable lake on the chain for it's clean bottom, crystal clear waters and light boat traffic. ***SEE VIRTUAL TOUR***

Winterset $429,000

6771 Winterset Gardens Rd Winter Haven Florida 33884

Reduced By $140,000

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  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2478

  • Year Built

    1976

  • $/SqFt

    $173

Gorgeous Pool Home on Winter Haven's Chain of Lakes. Open split plan offers; 3 bedrooms, 2 bathrooms plus a dining room and bonus room (2478sf). Living room features a brick gas fireplace and new carpet. Island kitchen has wood cabinets, closet pantry, tray ceiling, updated appliances and a breakfast bar plus pass thru window to bonus room. Bonus room has laminate flooring, and a wet bar. Master suite has a double sink vanity, double head heated shower and walk in closet. Second bedroom is lake view and has a walk-in closet. Other features include; Double paned windows, blinds, pocket doors, recess lights, chair railing and lots of storage. Screened pool/spa with waterfall and brick paved lanai. Seawall and dock with boat lift. Oversized 2 car garage with shower. Stunning home is located on almost a ? acre lot on Lake Winterset.

Winterset $60,000

1712 Garden Lake Dr Winter Haven Florida 33884

Reduced By $9,000

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  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    828

  • Year Built

    1986

  • $/SqFt

    $72

Chain of Lakes Community - 2nd Floor condo located in Winterset. Offers; 1 bedroom and 1 bathroom with living/dining combo and eat-in kitchen with breakfast bar. Living/dining has volume ceilings and sliding glass doors to screened balcony overlooking interior pond. Master bedroom has walk-in closet and large windows and also has sliding doors to balcony. Bathroom has tub with shower and laminate flooring. Located in a guard gated community with community pool, tennis, volleyball, clubhouse and access to Lake Winterset.

* Potential Great Value

Winterset $538,000

2685 Wyndsor Oaks Pl Winter Haven Florida 33884

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  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3481

  • Year Built

    2006

  • $/SqFt

    $154

Immaculate 4 bedroom, 4 bathroom pond frontage pool home with 28x13 bonus room in S.E. Winter Haven's prestigious gated & guarded Wyndsor at Lake Winterset. Spacious floor plan featuring a grand foyer, formal dining & living rooms, family room, open kitchen with breakfast nook, inside laundry, triple split bedroom layout with all 4 bedrooms downstairs and a large 28x13 upstairs bonus room/second master suite with a full bathroom. Kitchen features rich granite counters, a center island, stainless steel appliances, under & over cabinet lighting, built-in wine rack & large pantry. The master suite is highlighted by a gorgeous tray ceiling & French doors to the pool. With his & her walk-in closets, dual vanities, a jetted soaking tub & tiled walk-in shower with dual heads, this suite has it all! The triple split bedroom layout offers a 4th bedroom & 4th bath (access to the pool) with a pocket door & complete privacy for visiting guests. Other interior features include extensive crown molding, 12'-14' ceiling heights, hardwood floors, tile in wet areas, recessed lighting, surround sound throughout, security system & more. Outdoors you will find amazing views of the pond from the natural gas heated pool equipped with a salt-filtered system, shallow wading area for lounging and a planter with 3 fountains. Brick pavered lanai offers 2 covered areas, surround sound speakers & TV hookups. Other features include a 3 car garage, extended brick paver driveway, irrigation well with timer & over a 1/2 acre corner lot.

Winterset $169,000

5 Winterset Dr Winter Haven Florida 33884

Reduced By $10,900

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  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2110

  • Year Built

    1987

  • $/SqFt

    $80

Bring Offers! Great LOCATION for this 3 bedroom 2 bath POOL home with a FIREPLACE is located close to LEGOLAND the property offers a 1/2 acre FENCED lot. Property needs a little updating but can't you just can't beat the location. Close to the park, local shopping , and restaurants. It also has easy access to get to Disney or Universal.

Winterset $589,000

109 Wyndham Dr Winter Haven Florida 33884

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  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3397

  • Year Built

    2004

  • $/SqFt

    $173

Elegance in The Prestigious Chain of Lakes Gated Community 'Wyndham at Lake Winterset'. Designed for the ultimate in entertaining, custom built with exceptional features & craftsmanship this 3 bedroom 3 bathroom home is a must see. Tastefully decorated; Specialty ceilings & recess lighting. Extensive molding & trim, interior columns, plantation shutters, niches &archways. Split plan with separate living and formal areas. The flowing floor plan encompasses 3397 sf of luxury living area, providing; Living room with a traditional fireplace, formal dining room with faux painting, & elegant chandelier. Versatile office/4th bedroom. Family/Game room has a beautiful stone wood-burning fireplace and plank wood flooring. Gourmet kitchen; Granite counter tops, ice maker, top of the line appliances, built-in microwave & double convection ovens, 5 burner gas cook top, Wine cellar with iron door detailing. Breakfast room has seamless glass window enjoying the view of the pool. Laundry room, complete with cabinets and sink. The master suite is unparalleled in design & quality. Exquisite luxury master bathroom, elegant light fixtures, Kohler dual sink/vanities, Jacuzzi tub and separate oversized Rain head shower with seating. Separate his/her closets with wood shelving. Screen enclosed heated pool/spa, with lush tropical planters, 2 covered areas. Brick paved lanai, open patio, driveway & walkway. Situated on an interior pond, professionally landscaped with outdoor lighting. Former 'Parade of Homes' Winner in 2004

Winterset $103,500

606 Sweet Bay Cir # 606 Winter Haven Florida 33884

Reduced By $6,500

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  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1096

  • Year Built

    1985

  • $/SqFt

    $94

Come and enjoy beautiful lake views from this Ground floor condo. Sit in the screen enclosed back patio while watching the sunset over Lake Winterset. This 2 bdrm. 2bath condo. has a Gas Fireplace to help keep you warm on those chilly winter nights.The Master Bedroom has wood laminate flooring and a spacious walk in closet. Kitchen and living area have tile floors. There are lots of amenities to enjoy including a spacious club house, community pool, tennis court, and boat ramp for launching your boat to go fishing, skiing, or just a leisurely boat ride

Winterset $250,000

7 Winterset Dr Winter Haven Florida 33884

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  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2701

  • Year Built

    1973

  • $/SqFt

    $92

Unique family home within walking distance of Legoland. This home has exceptional features inside and outside, including fireplace with heatalator, outdoor grilling pit, workshop, oversized garage, two bonus rooms inside for office, exercise room and updates to kitchen and bath.

Winterset $75,000

2003 Garden Lake Dr # 2003 Winter Haven Florida 33884

Reduced By $2,000

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  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    828

  • Year Built

    1988

  • $/SqFt

    $90

Lovely 2 bedroom & 2 bath ground floor condo in Winterset. Living Room & Dining Room combination has a full mirrored wall. Sliding doors open to a screen porch that overlooks the pond/lagoon. The large Balcony/Deck area is used by all the residents of this building. The Master bedroom has a mirrored wall and also has a slider that opens to the porch area. The monthly condo maintenance fee covers all ground maintenance, exterior building maintenance, clubhouse, community pool, tennis courts, and all common areas. Furnishings stay for the convenience of the Seller and have no value toward a sale or mortgage. Come see this affordable condo today. Owner is very motivated.

Winterset $77,000

601 Sweet Bay Cir # 601 Winter Haven Florida 33884

Reduced By $28,000

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  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1096

  • Year Built

    1985

  • $/SqFt

    $70

Beautiful lakefront sunset views from this 2/2 end unit condo. First floor condo with beautiful panoramic views of Lake Winterset. This well maintained, fully tiled condo features include a living room with gas fireplace, dining room. Fully equipped kitchen with refrigerator, stove and microwave, breakfast bar. Large master with walk-in closet. Master has beautiful view of the lake. Master bath has dual sinks, large shower. 2nd bedroom and 2nd bath separated from master for privacy. Inside laundry hook up. Gas appliances. Large lanai to enjoy the lake views. This resort-style living community on the famous Winter Haven Chain of Lakes is gated with 24 hour gated and guard security, heated community pool and spa, lake access with boat ramp, lakeside tennis courts, volleyball, and shuffleboard. Also features a clubhouse, fitness center, and beautiful landscaping. Conveniently located to Legoland, Hwy 27, shopping, schools, and medical. Call today for a private showing.

Winterset $589,000

2686 Wyndsor Oaks Pl Winter Haven Florida 33884

Reduced By $40,000

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  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3455

  • Year Built

    2002

  • $/SqFt

    $170

Custom built home located in Guard Gated Wyndsor @ Lake Winterset. Canal front home with private dock with boat lift. This 2 story home features a kitchen every woman loves with granite, stainless steel appliances, double oven & island with breakfast bar. Master bedroom downstairs with huge designer bath which has a door that leads to the pool. Office room with closet & huge laundry room also located downstairs. Upstairs there are 2 bedrooms & bonus/theater room with closet. This home has hardwood flooring, tile, marble & upgraded carpeting throughout. There has not been one detailed over looked from crown molding, designer painting, custom flooring & more. The salt system pool has brick coping with a water feature. Irrigation system is run by a well to save on water cost. Three car garage with pull down storage attic space. A truly amazing home you won't want to miss. Call agent for details.

Winterset $549,900

2694 Wyndsor Oaks Pl Winter Haven Florida 33884

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  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4208

  • Year Built

    2006

  • $/SqFt

    $130

This property was a previous parade of homes entry with no details overlooked- spectacular pool and spa with computerized features- builder touches like custom woodwork, crown molding, tray ceilings, beautiful wood floors and entertainment movie room with wet bar- state of the art kitchen, master suite with built in caf? and jetted tub. 3 Car garage- One of Winter Haven's exclusive gated neighborhoods

Winterset $550,000

148 Wyndham Dr Winter Haven Florida 33884

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  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3137

  • Year Built

    1999

  • $/SqFt

    $175

Wonderful Wyndham Guard gated community. This executive 5 bed 3.5 bath 3 car garage with play pool home sits on just over a half acre with pond views/frontage to the right of the home for extra privacy. Built in entertainment center with separate formal living & dining rooms with tray ceilings, crown molding, &

Winterset $335,000

2603 Wyndsor Oaks Ct Winter Haven Florida 33884

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  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2611

  • Year Built

    2006

  • $/SqFt

    $128

Executive pool home located near all the growth in a gated community. This property is located in the SE area of Winter Haven in Wyndsor Oaks. This is a very well maintained home in a beautiful area located on a 1/2 acre lot.

Winterset $399,900

2602 Wyndsor Oaks Ct Winter Haven Florida 33884

Reduced By $20,000

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  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2959

  • Year Built

    2005

  • $/SqFt

    $135

.Absolutely stunning custom-built one owner home in sought after gated SE community. This 4 bedroom 2.5 bath split plan home has terrific flowing floor plan. As you enter the home, you are welcomed into a large open great room which looks out over the private backyard complete with pool and rock waterfall. Just off the great room is the beautiful chef's kitchen with granite, upgraded stainless appliances and custom wood cabinetry. For outdoor entertainment, the pavered lanai and pool area make for the perfect venue. Or for those cooler evenings, take a walk down the pavered path in the backyard to the custom-built firepit for a cozy evening of relaxing by the fire.

Winterset $92,500

406 Laurel Cove Way # 1 Winter Haven Florida 33884

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  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1250

  • Year Built

    1986

  • $/SqFt

    $74

Beautiful water front condo on Winter Haven Chain of Lakes. 2 bedroom, 2 bathroom with several amenities. Clubhouse, pool, volleyball courts, 24/7 security. Must see! Call to schedule a showing.

Winterset $435,000

105 Wyndham Dr Winter Haven Florida 33884

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  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2638

  • Year Built

    1998

  • $/SqFt

    $164

Exquisite home located in a prestigious guard gated community. Spacious plan offers 3 bedrooms and 3 bathroom plus office, family and formal rooms, breakfast nook and utility room (2638sf). Features: 10 ft Tray ceilings, recess lighting, crown molding, arched doorways and art niches. Window treatments, plantation shutters home theatre and security systems. Hardwood flooring throughout with ceramic tile in bathrooms and carpet in bedrooms. Family room has wood burning fireplace and built in bar. Kitchen has stainless GE Monogram built-in appliances and granite countertops with breakfast bar and built-in desk. Breakfast nook overlooks interior pond. Home office has French doors and built-in desk and bookshelves. Master bedroom has sliding doors to lanai, double walk-in closets, garden tub and walk-in shower. Secondary bedrooms share adjoining bathroom and second also has walk-in closet. Utility room has cabinets, countertop and wash tub. Screen enclosed salt water pool and spa is heated and features brick paved lanai with built in planters and exterior columns. Landscaped with mature Oak and palm trees, tiled roof, side entry 2 car garage. Home is overlooking an interior pond in Wyndham.

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Viewing Homes 1 to 19 of 19