EasyStreet

Call to Schedule a Showing

(407) 444-0331

(407) 444-0331

View 18 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.

Viewing Homes 1 to 15 of 18

Winterset | House For Sale $398,000

3420 Lakeview Dr, Winter Haven, Florida 33884

Reduced By $1,900

Results Photo 2
Results Photo 3
Results Photo 4
3420 Lakeview Dr. Listed | 139 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2389

  • Year Built

    1957

  • $/SqFt

    $166

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 viewsfrom 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-suitefull 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*** 4629704

Winterset | House For Sale $1,269,000

130 Wyndham Dr, Winter Haven, Florida 33884

Reduced By $30,000

Results Photo 2
Results Photo 3
Results Photo 4
130 Wyndham Dr. Listed | 157 Days Ago
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5620

  • Year Built

    1997

  • $/SqFt

    $225

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*** 4629418

Winterset | House For Sale $99,750

606 Sweet Bay Cir # 606, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
606 Sweet Bay Cir # 606. Listed | July 1, 2014
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1096

  • Year Built

    1985

  • $/SqFt

    $91

Ground floor, corner unit at Winterset! Enclosed screened porch overlooks Lake Winterset and offers the perfect setting for Florida summer nights. This 2BR/2BA condo offers a gas fireplace, ceramic tile floors in living areas, and plenty of room to roam. Master bedroom features wood laminate flooring and a walk-in closet. Master bathroom features dual sinks and shower stall. Community offers an in-ground swimming pool, spacious club house, tennis court, and a boat ramp. 4700301

Winterset | House For Sale $259,900

0 Shoreline Ln, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
0 Shoreline Ln. Listed | July 12, 2014
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1800

  • Year Built

    2015

  • $/SqFt

    $144

This price includes lot and brand new home with floor plan shown with over sized two car garage. Spectacular sunsets over Lake Winterset are yours to enjoy from this patio home lot in the gated community of Winterset. Take a dip in the community pool or spa. Play tennis or volleyball next to the lake. There is a boat ramp for your use. This is the last available waterfront lot on Shoreline Lane, a private cul-de-sac. Monthly dues include complete lawn maintenance and irrigation, along with use of all recreational facilities. Build your dream home in this gated resort-style community and the ever changing sunsets are yours. The lot is also available for sale separately at MLS#P4598604. 4700452

Winterset | House For Sale $595,000

2679 Wyndsor Oaks Pl, Winter Haven, Florida 33884

Results Photo 2
2679 Wyndsor Oaks Pl. Listed | July 19, 2014
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3901

  • Year Built

    2004

  • $/SqFt

    $152

Executive Waterfront Pool Home. Absolutely stunning, this amazing residence is designed for the ultimate in entertaining. Situated in Wyndsor at Lake Winterset on .55 acre lot, this 4 bedroom, 4 bathroom home provides 3901sf and boasts the finest appointments and craftsmanship throughout. No expense has been spared or detail overlooked, enjoy the casual elegance with unique features in each room. Formal living and dining rooms feature: Custom inlaid tile flooring, stunning 12ft ceilings, extensive moldings & trim, majestic interior columns, hardwood flooring, elegant chandeliers. Gourmet island kitchen has; granite counter tops, stainless appliances, built-in oven, microwave & TV, walk-in pantry. Tropical pool area has automatic pool and spa. Large screen enclosure is perfect for entertaining including brick paved lanai and pool deck, pool bath and private porch. Complimented by artistically designed landscaping, brick paved drive and walkways. Gas generator to run entire home. 4700577

Winterset | House For Sale $79,900

105 Laurel Cove Way # 105, Winter Haven, Florida 33884

Reduced By $3,000

Results Photo 2
Results Photo 3
Results Photo 4
105 Laurel Cove Way # 105. Listed | 58 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1090

  • Year Built

    1985

  • $/SqFt

    $73

Beautiful condo in Guard gated community. Relax on the porch with these amazing water and sunset views of Lake Winterset! Granite kitchen, new fans throughout, this home has been taken care of beautifully and it shows. Community pool and tennis courts are a few of the many features this community has to offer. 4630912

Winterset | House For Sale $675,000

2683 Wyndsor Oaks Way, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
2683 Wyndsor Oaks Way. Listed | 89 Days Ago
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3648

  • Year Built

    2002

  • $/SqFt

    $185

ARTHUR RUTENBERG DESIGNED POND FRONTAGE POOL HOME IN GUARDED WYNDSOR AT LAKE WINTERSET...This beautiful Jacaranda model offers 4 huge bedrooms, 4 full bathrooms, bonus room / game room, an executive office, dramatic ceilings heights and a level of finishes that are sure to impress. Exterior is enhanced by rich barrel tile roofing, custom designed brick pavered driveway and a 1/2 acre corner lot of tropical plantings and mature palms. The entry is dramatic with 20' foyer and living area ceilings heights illuminated with elegant crystal chandeliers. Granite floors add to the one of a kind feel of this home along with extensive wood trim work, plantation shutters, gas fireplace and more. Master suite is located downstairs and offers his and her's walk-in closets, bay window sitting area overlooking the pool and a spa-like master bath with two vanities, walk-in shower and relaxing soaking tub. Family room is huge with 20' ceilings, handcrafted wood entertainment console and wood grain plantation shutters. Open kitchen is very large and offers granite counters, granite backsplash, stainless appliances and center prep island. All upstairs guest bedrooms have Jack & Jill bathrooms, lots of closet space and great views of the grounds and surrounding waterfront. Amazing waterfront pool area complete with pavered covered lanai and pool deck, 30' x 14' pool with vibrant blue colored finish and plenty of room for lounging and sunning. Great value and tons of potential to make this home an absolute show place!!! 4630431

Winterset | House For Sale $104,000

709 Magnolia Pl # 709, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
709 Magnolia Pl # 709. Listed | July 11, 2014
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1308

  • Year Built

    1987

  • $/SqFt

    $79

Wonderful 2 story condo, end unit with a view of Lake Winterset from the screened in balcony. Hassel free living....Community offers many amenities, 24hr manned security. You'll also have access to the clubhouse, racket ball and community pool. 4700437

* Potential Great Value

Winterset | House For Sale $560,000

109 Wyndham Dr, Winter Haven, Florida 33884

Reduced By $29,000

Results Photo 2
Results Photo 3
Results Photo 4
109 Wyndham Dr. Listed | 130 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3397

  • Year Built

    2004

  • $/SqFt

    $164

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 sink. The master suite is unparalleled in design & quality. Exquisite luxury master bathroom, elegant light fixtures, Kohler dual sink/vanities, Jacuzzi tub and separate over-sized 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. 4629848

Winterset | House For Sale $73,000

2003 Garden Lake Dr # 2003, Winter Haven, Florida 33884

Reduced By $4,000

Results Photo 2
Results Photo 3
Results Photo 4
2003 Garden Lake Dr # 2003. Listed | 306 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1018

  • Year Built

    1988

  • $/SqFt

    $71

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. 4627332

Winterset | House For Sale $589,000

2686 Wyndsor Oaks Pl, Winter Haven, Florida 33884

Reduced By $40,000

Results Photo 2
Results Photo 3
Results Photo 4
2686 Wyndsor Oaks Pl. Listed | 249 Days Ago
  • 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. 4628225

Winterset | House For Sale $250,000

7 Winterset Dr, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
7 Winterset Dr. Listed | 193 Days Ago
  • 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. 4628874

Winterset | House For Sale $538,000

2685 Wyndsor Oaks Pl, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
2685 Wyndsor Oaks Pl. Listed | 188 Days Ago
  • 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' ceilingheights, 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 areafor 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. 4628937

Winterset | House For Sale $335,000

2603 Wyndsor Oaks Ct, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
2603 Wyndsor Oaks Ct. Listed | 404 Days Ago
  • 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. 4625975

Winterset | House For Sale $89,900

303 Laurel Cove Way # 303, Winter Haven, Florida 33884

Results Photo 2
Results Photo 3
Results Photo 4
303 Laurel Cove Way # 303. Listed | 74 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1090

  • Year Built

    1985

  • $/SqFt

    $82

The property you are calling on is located in the gated, guarded community of Winteset located in the SE area of Winter Haven,FL. This newly renovated 2Bdr, 2Ba first floor condo is a fabulous waterfront unit. This is a lifestyle that you wont want to miss! 4630695

Viewing Homes 1 to 15 of 18