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34786 Homes For Sale & 34786 FL Real Estate

Home For Sale $1,999,900

Reduced By $18,000,000

Stunning yellow home featuring a brick driveway, mature landscaping, and a three-car garage at 11954 Provincial Way, Windermere, FL 34786
View Details 59 Photos
Attractive yellow home showcasing a red tile roof, lush landscaping, and a well-manicured lawn at 11954 Provincial Way, Windermere, FL 34786
Elegant entryway showcasing manicured landscaping, a brick path, and double doors at 11954 Provincial Way, Windermere, FL 34786
Inviting foyer boasting hardwood floors, an open floor plan, and ample natural light at 11954 Provincial Way, Windermere, FL 34786
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4800

  • Year Built

    2005

  • $/SqFt

    $417

The “Reserve at Belmere” is a conveniently located Windermere 24 hour guarded-gated community with clubhouse, fitness center, basketball, tennis, and sand volleyball courts, playground and community gazebo where you can enjoy breathtaking sunsets. COLDWELL BANKER REALTY.

Home For Sale $1,200,000

Charming two-story home featuring a brick driveway, stone accents and meticulously landscaped front yard at 12002 Angle Pond Ave, Windermere, FL 34786
View Details 44 Photos
Elegant home foyer featuring stylish flooring, a decorative rug, and views of the living and dining rooms at 12002 Angle Pond Ave, Windermere, FL 34786
Inviting living room featuring an ornamental chandelier and opening up to an adjacent dining room at 12002 Angle Pond Ave, Windermere, FL 34786
Refined dining room with stylish chandelier, view into the living room, and seating for eight at 12002 Angle Pond Ave, Windermere, FL 34786
On Market Today

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4457

  • Year Built

    2013

  • $/SqFt

    $269

This extraordinary home is not to be missed—a must-see opportunity! ORLANDO ADVANTAGE REALTY INC.

Home For Sale $799,000

Charming single-story home with a brick driveway, a well-manicured lawn, and a two-car garage at 6799 Helmsley Cir, Windermere, FL 34786
View Details 55 Photos
Inviting single-story home with brick driveway, well-kept lawn, and a convenient two-car garage at 6799 Helmsley Cir, Windermere, FL 34786
Cozy front porch featuring outdoor seating, a bench, and an inviting entrance with a red door at 6799 Helmsley Cir, Windermere, FL 34786
Bright foyer with wood floors and a modern white door with glass panes, offering a welcoming entrance at 6799 Helmsley Cir, Windermere, FL 34786
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2876

  • Year Built

    2011

  • $/SqFt

    $278

Don’t miss this opportunity—reach out today to make this dream home yours! KARDOSH REALTY.

Home For Sale $4,495,000

Stunning two-story home featuring manicured landscaping, stone accents, and a circular driveway at 801 W 2Nd Ave, Windermere, FL 34786
View Details 44 Photos
An entertainer's backyard featuring a covered patio with a built-in grill and a private swimming pool at 801 W 2Nd Ave, Windermere, FL 34786
Bright living room with modern fireplace, hardwood flooring and a decorative accent wall at 801 W 2Nd Ave, Windermere, FL 34786
Deluxe home theater with premium seating, a projector, and an illuminated bar top at 801 W 2Nd Ave, Windermere, FL 34786
On Market For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    5639

  • Year Built

    2008

  • $/SqFt

    $797

Aladar On Lake Butler - An exclusive respite, this home represents a refined, opulent lifestyle inside and out. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $3,150,000

Stunning two-story home with a gray exterior, a white metal roof and an expansive driveway at 5243 W Lake Butler Rd, Windermere, FL 34786
View Details 77 Photos
Aerial view of a beautiful waterfront home featuring a metal roof and well-manicured landscaping at 5243 W Lake Butler Rd, Windermere, FL 34786
Charming two-story home with a well-maintained lawn and mature landscaping at 5243 W Lake Butler Rd, Windermere, FL 34786
Aerial view of a beautiful waterfront home featuring a metal roof and manicured landscaping at 5243 W Lake Butler Rd, Windermere, FL 34786
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3255

  • Year Built

    1996

  • $/SqFt

    $968

Summerport - Opportunities like this are rare. Schedule your private showing today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,050,000

Charming home with a well-manicured lawn and stone accents beneath a large, shady tree at 9548 Crown Prince Ln, Windermere, FL 34786
View Details 50 Photos
Stunning home with a circular driveway, lush landscaping and stone accents at 9548 Crown Prince Ln, Windermere, FL 34786
Wide driveway leading to a house with beautiful landscaping and garage access at 9548 Crown Prince Ln, Windermere, FL 34786
A spacious three-car garage is featured alongside a patterned brick driveway and lush landscaping at 9548 Crown Prince Ln, Windermere, FL 34786
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3997

  • Year Built

    1999

  • $/SqFt

    $263

Located in the desirable Windsor Hill community, residents enjoy amenities such as tennis courts and a playground, enhancing the neighborhood’s appeal.Don’t miss your chance to create something truly special in this highly sought-after community. Schedule your private tour today! COLEDEV REAL ESTATE LLC.

Home For Sale $720,000

Charming two-story home featuring a small balcony, front garden with tropical plants, and brick-paved walkway at 8498 Powder Ridge Trl, Windermere, FL 34786
View Details 87 Photos
Charming two-story home featuring a small balcony, front garden with tropical plants, and brick-paved walkway at 8498 Powder Ridge Trl, Windermere, FL 34786
Brick and stone landscaping on the side yard with a white fence creating a quaint and private space at 8498 Powder Ridge Trl, Windermere, FL 34786
Inviting front porch features brick pavers, lush landscaping, and a decorative wreath on the gray front door at 8498 Powder Ridge Trl, Windermere, FL 34786
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2393

  • Year Built

    2015

  • $/SqFt

    $301

Schedule your private showing today. Video tour available. OLYMPUS EXECUTIVE REALTY INC.

Home For Sale $2,170,000

Stately two-story home with balconies, brick driveway, manicured landscaping, and fountain at 1984 Windermere Rd, Windermere, FL 34786
View Details 54 Photos
Aerial view showcasing the property's expansive lot and proximity to a large lake at 1984 Windermere Rd, Windermere, FL 34786
Wide aerial showcasing the property's layout, including pool, patio and proximity to the road at 1984 Windermere Rd, Windermere, FL 34786
Detailed view of front entrance with stately columns and wrought iron detailing on balconies at 1984 Windermere Rd, Windermere, FL 34786
*POTENTIAL GREAT VALUE
On Market For 6 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    6601

  • Year Built

    2014

  • $/SqFt

    $329

Schedule your private tour today and experience the luxury of this one-of-a-kind estate! KELLER WILLIAMS WINTER PARK.

Pended $1,027,583

Attractive, tan-colored single-story home with a well-manicured lawn, lush landscaping, and attached two-car garage at 14347 Crest Palm Ave, Windermere, FL 34786
View Details 3 Photos
Detailed floor plan showcasing the layout of the lower level of the home, including dimensions and room locations at 14347 Crest Palm Ave, Windermere, FL 34786
Upstairs floor plan showcases bonus and bedroom, including dimensions and room locations at 14347 Crest Palm Ave, Windermere, FL 34786
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3100

  • Year Built

    2025

  • $/SqFt

    $331

With soaring ceilings—up to 10 feet on the first floor and 9 feet on the second (as per plan)—and luxury ceramic tile flooring in key areas, this home exudes a sense of spaciousness and sophistication. OLYMPUS EXECUTIVE REALTY INC.

Home For Sale $770,000

An aerial view showcases this home's lush, green surroundings and charming exterior at 9272 Gotha Rd, Windermere, FL 34786
View Details 53 Photos
Aerial view highlighting the home, large yard, outbuilding and proximity to a lake at 9272 Gotha Rd, Windermere, FL 34786
Overhead angle of this home showing a large lot, two-car garage, and neutral exterior at 9272 Gotha Rd, Windermere, FL 34786
Aerial view showing the home, detached garage, circular driveway, and mature trees at 9272 Gotha Rd, Windermere, FL 34786
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1886

  • Year Built

    1988

  • $/SqFt

    $408

Gotha - Don’t miss this incredible opportunity—your dream estate awaits RE/MAX PRIME PROPERTIES.

Home For Sale $3,600,000

Stunning home featuring neutral tones, a three-car garage, and a well-manicured lawn at 6208 Winter Garden Vineland Rd, Windermere, FL 34786
View Details 17 Photos
A luxurious backyard featuring a swimming pool, lounge chairs, and outdoor seating and kitchen at 6208 Winter Garden Vineland Rd, Windermere, FL 34786
Detailed floor plan showcasing the layout, pool, and outdoor sport court at 6208 Winter Garden Vineland Rd, Windermere, FL 34786
Serene main bedroom featuring modern lighting, decor, and furniture at 6208 Winter Garden Vineland Rd, Windermere, FL 34786
On Market For 8 Days

  • Bedrooms

    6

  • Full Bath(s)

    7

  • Sq. Ft.

    5441

  • Year Built

    2025

  • $/SqFt

    $662

Schedule a visit and discover what makes this house truly special! WRA BUSINESS & REAL ESTATE.

Home For Sale $1,595,000

Stunning home featuring a blue tile roof and a meticulously landscaped front yard with an expansive brick driveway at 3326 Butler Bay N Dr, Windermere, FL 34786
View Details 45 Photos
Enclosed pool area featuring a pool and jacuzzi, with an impressive spiraling staircase that adds a striking visual element at 3326 Butler Bay N Dr, Windermere, FL 34786
Aerial perspective showcasing the estate's rear, featuring a pool, screened enclosure, and adjacent tennis court at 3326 Butler Bay N Dr, Windermere, FL 34786
Elevated shot inside the screened enclosure, overlooking the pool, hot tub, and tennis court in the backyard at 3326 Butler Bay N Dr, Windermere, FL 34786
On Market For 7 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3650

  • Year Built

    1987

  • $/SqFt

    $437

Butler Bay - Schedule your private tour today—before it’s gone yesterday! BOARDWALK REALTY, LLC.

Home For Sale $929,900

Stunning single-story home with mature palm trees and meticulous landscaping enhancing curb appeal at 2746 Park Royal Dr, Windermere, FL 34786
View Details 40 Photos
Expansive lawn leads up to an inviting single-story home with a well-maintained exterior at 2746 Park Royal Dr, Windermere, FL 34786
Exterior view of house showing driveway, landscaping, and attached garage at 2746 Park Royal Dr, Windermere, FL 34786
Bright living room features tile flooring, arched windows, and elegant furnishings at 2746 Park Royal Dr, Windermere, FL 34786
On Market For 7 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2878

  • Year Built

    1990

  • $/SqFt

    $323

This property's blend of spacious interiors, outdoor amenities, and prime location makes it a standout choice for those seeking a comfortable and convenient lifestyle in Windermere. Book your showing today! ERA GRIZZARD REAL ESTATE.

Home For Sale $2,650,000

Modern white home features a striking architectural design, beautiful landscaping, and a circular driveway at 409 W 2Nd Ave, Windermere, FL 34786
View Details 57 Photos
Expansive aerial view of a luxury home with a private pool surrounded by lush landscaping and mature trees at 409 W 2Nd Ave, Windermere, FL 34786
Resort style pool and backyard oasis with jacuzzi and floor-to-ceiling windows overlooking the outdoor space at 409 W 2Nd Ave, Windermere, FL 34786
Bright, spacious living room with tall windows, tile floors, and open staircase at 409 W 2Nd Ave, Windermere, FL 34786
On Market For 8 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4688

  • Year Built

    1995

  • $/SqFt

    $565

Don’t miss this rare opportunity to own a one-of-a-kind contemporary gem in one of Windermere’s most coveted locations! UPSIDE REAL ESTATE INC.

Home For Sale $1,495,000

Charming two-story home with black shutters, a front porch, and meticulously landscaped front yard at 11521 Camden Park Dr, Windermere, FL 34786
View Details 71 Photos
Inviting front porch with stone tile flooring, white columns, wood ceiling, and charming decor at 11521 Camden Park Dr, Windermere, FL 34786
Backyard pool features a rock waterfall, spa, and enclosed screened for ultimate privacy and relaxation at 11521 Camden Park Dr, Windermere, FL 34786
Enclosed pool area features a waterfall, connected spa, and comfortable poolside seating at 11521 Camden Park Dr, Windermere, FL 34786
On Market For 8 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3483

  • Year Built

    2005

  • $/SqFt

    $429

Keenes Pointe - KELLER WILLIAMS REALTY AT THE PARKS.

Pended $1,350,000

Elegant home featuring lush landscaping, a paver driveway, and a tile roof, showcasing curb appeal at 6424 Cartmel Ln, Windermere, FL 34786
View Details 69 Photos
A brick entrance sign welcomes you to Lake Butler Sound with colorful flowers and lush greenery at 6424 Cartmel Ln, Windermere, FL 34786
The entrance to Lake Butler Sound is beautifully landscaped and features a charming gatehouse at 6424 Cartmel Ln, Windermere, FL 34786
Elegant home with manicured front yard, tile roof, and paver driveway, presenting a luxurious curb appeal at 6424 Cartmel Ln, Windermere, FL 34786
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3211

  • Year Built

    2004

  • $/SqFt

    $420

This home is an absolute DO-NOT-MISS-MUST-SEE! WATSON REALTY CORP.

Home For Sale $3,248,000

Reduced By $2,000

Elegant home showcasing a beautifully landscaped front entrance with a tiled roof and ornate double doors at 6030 Greatwater Dr, Windermere, FL 34786
View Details 64 Photos
A spacious home features a well-manicured lawn and side-entry garage, surrounded by lush landscaping at 6030 Greatwater Dr, Windermere, FL 34786
Beautiful backyard pool and hot tub with lounge chairs and serene landscaping at 6030 Greatwater Dr, Windermere, FL 34786
A bright dining room features a glass table, seating for eight, dark wood floors, and an elegant chandelier at 6030 Greatwater Dr, Windermere, FL 34786
On Market For 9 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6683

  • Year Built

    1999

  • $/SqFt

    $486

With 24-hour security and a tight-knit community atmosphere, you'll feel safe and welcomed in this prestigious enclave. REAL BROKER, LLC.

Home For Sale $1,249,000

Charming single-story home with lush landscaping, stone accents, and a welcoming front yard at 2106 Ridgewind Way, Windermere, FL 34786
View Details 53 Photos
Beautiful exterior view of a single-story home with stone accents and a manicured lawn at 2106 Ridgewind Way, Windermere, FL 34786
Elegant front entrance with white columns, a black front door, and vibrant green landscaping at 2106 Ridgewind Way, Windermere, FL 34786
Close-up of the front door entrance featuring glass inserts and potted plants on a tiled porch at 2106 Ridgewind Way, Windermere, FL 34786
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    1999

  • $/SqFt

    $440

Call today for your private showing! SOUTHERN REALTY GROUP LLC.

Pended $950,000

An aerial view showcases a home with mature landscaping and a serene lake backdrop at 400 W 2Nd Ave, Windermere, FL 34786
View Details 37 Photos
Charming single-story home with a well-manicured lawn, lush landscaping and a tile roof at 400 W 2Nd Ave, Windermere, FL 34786
An aerial view that shows a beautiful neighborhood with mature trees and lake access at 400 W 2Nd Ave, Windermere, FL 34786
Spacious living room with wood floors, a large window, fireplace and traditional furnishings at 400 W 2Nd Ave, Windermere, FL 34786
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2346

  • Year Built

    1986

  • $/SqFt

    $405

Don’t miss out—schedule your showing today! UPSIDE REAL ESTATE INC.

Pended $782,000

Charming single-Gathering home featuring a well-manicured lawn, a red front door, and a brick driveway and walkway at 6232 Talaria Dr, Windermere, FL 34786
View Details 56 Photos
Beautiful two-story house with a three car garage, brick driveway, well kept lawn, and attractive landscaping at 6232 Talaria Dr, Windermere, FL 34786
An inviting screened-in pool with brick pavers, providing a private and refreshing outdoor space at 6232 Talaria Dr, Windermere, FL 34786
Spacious living room with tile flooring, a large sofa, and sliding doors to the outdoors at 6232 Talaria Dr, Windermere, FL 34786
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3387

  • Year Built

    2004

  • $/SqFt

    $231

Community offers a pool, playground, gazebo, and walking trails, all within minute from Walt Disney World, Hamlin Grove, and Fowlers Grove. CENTURY 21 CARIOTI.

Home For Sale $20,000,000

Stunning exterior view of a Mediterranean-style home with a brick driveway, lush landscaping, and palm trees at 11900 Lake Butler Blvd, Windermere, FL 34786
View Details 91 Photos
Elegant home features a circular driveway with a fountain, lush landscaping, and Mediterranean architecture at 11900 Lake Butler Blvd, Windermere, FL 34786
Expansive waterfront property with a luxurious home, boat house, lush lawns, and a private canal at 11900 Lake Butler Blvd, Windermere, FL 34786
Relaxing poolside view with palm trees and serene lake views during a colorful sunset at 11900 Lake Butler Blvd, Windermere, FL 34786
On Market For 10 Days

  • Bedrooms

    7

  • Full Bath(s)

    8

  • Sq. Ft.

    10649

  • Year Built

    2014

  • $/SqFt

    $1,878

Metcalf Park - Truly a picture-perfect unmistakable showplace offering the very best for the most discriminating buyer. STOCKWORTH REALTY GROUP.

Home For Sale $995,000

Beautiful home featuring a large garage, lush landscaping, and a well-maintained lawn at 10986 Ledgement Ln, Windermere, FL 34786
View Details 47 Photos
Aerial shot showcasing a beautiful home with a tile roof, a long driveway, and a well-manicured lawn at 10986 Ledgement Ln, Windermere, FL 34786
Inviting foyer featuring tiled floors, neutral paint, and a decorative light fixture at 10986 Ledgement Ln, Windermere, FL 34786
Foyer view showcasing the entrance and a glimpse of the living room with hardwood floors at 10986 Ledgement Ln, Windermere, FL 34786
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3080

  • Year Built

    2003

  • $/SqFt

    $323

Don’t miss this incredible opportunity, viewing by appointment only - schedule your showing today! TEAM DONOVAN.

Home For Sale $554,900

Charming single-story home featuring a well-maintained lawn, covered entry, and two-car garage at 4852 Blue Major Dr, Windermere, FL 34786
View Details 58 Photos
Large backyard featuring mature trees, a well-maintained lawn, and a white vinyl fence at 4852 Blue Major Dr, Windermere, FL 34786
View of the expansive backyard featuring white vinyl fence from covered patio at 4852 Blue Major Dr, Windermere, FL 34786
Spacious backyard featuring mature trees, a well-maintained lawn, and a white vinyl fence at 4852 Blue Major Dr, Windermere, FL 34786
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2083

  • Year Built

    2005

  • $/SqFt

    $266

Come see your new home today! PHYLLIS KENT REAL ESTATE LLC.

Home For Sale $1,399,999

Charming traditional-style home featuring a well-manicured lawn and a welcoming front entrance with decorative windows at 2515 Ridgewind Way, Windermere, FL 34786
View Details 64 Photos
Bright living room with hardwood floors and fireplace at 2515 Ridgewind Way, Windermere, FL 34786
Open-concept living room with hardwood floors and recessed lighting at 2515 Ridgewind Way, Windermere, FL 34786
Inviting living room with neutral decor and access to the pool at 2515 Ridgewind Way, Windermere, FL 34786
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3400

  • Year Built

    2000

  • $/SqFt

    $412

Don't miss this exceptional opportunity to enjoy the finest Windermere living. MAXIM REALTY ORLANDO.

Pended $895,000

Beautiful single-story home with a circular driveway and manicured landscaping under a partly cloudy blue sky at 2230 Lake Crescent Ct, Windermere, FL 34786
View Details 62 Photos
A bright and inviting single-story home with lush landscaping and a circular driveway on a sunny day at 2230 Lake Crescent Ct, Windermere, FL 34786
Well-maintained single-story home with a circular driveway and manicured landscaping, framed by a large tree at 2230 Lake Crescent Ct, Windermere, FL 34786
Charming single-story home with a circular driveway and beautifully landscaped front yard, framed by a mature shade tree at 2230 Lake Crescent Ct, Windermere, FL 34786
On Market For 7 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2761

  • Year Built

    1989

  • $/SqFt

    $324

Don’t miss your chance to experience this exceptional home—schedule your private showing today! JULIAN PROPERTIES, INC..

Pended $875,000

Charming one-story home featuring a beautifully landscaped yard, vibrant green lawn and a pristine white stucco exterior at 2544 Carter Grove Cir, Windermere, FL 34786
View Details 46 Photos
Charming single-story home with a well-manicured lawn, mature palm trees and manicured shrubs adding to its curb appeal at 2544 Carter Grove Cir, Windermere, FL 34786
This exterior view captures the home's side facade, showcasing its architectural style and meticulous landscaping at 2544 Carter Grove Cir, Windermere, FL 34786
Beautiful one-story home with a lush green lawn, mature trees, manicured shrubs and mulch beds framing the residence at 2544 Carter Grove Cir, Windermere, FL 34786
On Market For 10 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2802

  • Year Built

    1997

  • $/SqFt

    $312

Manors At Butler Bay - Don’t miss this rare opportunity to own a home of this caliber in the sought-after Manors at Lake Butler. RE/MAX PRIME PROPERTIES.

Home For Sale $653,000

Charming home with a well-maintained lawn, three-car garage, and attractive curb appeal on a sunny day at 13422 Exbury Ln, Windermere, FL 34786
View Details 46 Photos
Bright living room with high ceilings, decorative chandelier, and elegant wainscoting detail at 13422 Exbury Ln, Windermere, FL 34786
Bright foyer with high ceilings, decorative chandelier, staircase and elegant wainscoting detail at 13422 Exbury Ln, Windermere, FL 34786
Spacious room with high ceilings and multiple windows, featuring modern flooring and ample natural light at 13422 Exbury Ln, Windermere, FL 34786
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2745

  • Year Built

    2005

  • $/SqFt

    $238

Lakes Of Windermere - close to all major highways, highway I4, highway 528, and highway 429. REALTY TECH INC.

Home For Sale $535,999

Charming single-Gathering home with a two-car garage and well-maintained landscaping at 12863 Holdenbury Ln, Windermere, FL 34786
View Details 17 Photos
Close-up of the home's entrance, showcasing the front door, sidelight window, and manicured shrubbery at 12863 Holdenbury Ln, Windermere, FL 34786
Charming home exterior featuring a large arch window, trimmed bushes, and well-maintained lawn at 12863 Holdenbury Ln, Windermere, FL 34786
Bright living room showcasing large arch window allowing for ample natural light at 12863 Holdenbury Ln, Windermere, FL 34786
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2148

  • Year Built

    2006

  • $/SqFt

    $250

Lakes Of Windermere - Don’t miss your chance to own this exceptional property OLYMPUS EXECUTIVE REALTY INC.

Pended $4,200,000

Stunning Mediterranean-style home featuring a fountain, lush landscaping, and a circular driveway at 3402 Cocard Ct, Windermere, FL 34786
View Details 72 Photos
Elegant home featuring a prominent fountain, a grand entrance, and a circular brick driveway at 3402 Cocard Ct, Windermere, FL 34786
Expansive home with tiled roof, circular brick driveway, fountain, lush greenery, and swimming pool at 3402 Cocard Ct, Windermere, FL 34786
Beautifully landscaped Mediterranean-style home with a circular driveway and fountain at 3402 Cocard Ct, Windermere, FL 34786
*POTENTIAL GREAT VALUE
On Market For 13 Days

  • Bedrooms

    5

  • Full Bath(s)

    7

  • Sq. Ft.

    9909

  • Year Built

    2009

  • $/SqFt

    $424

Chaine Du Lac - The property offers a four-car garage (2+2 configuration) and a vast paver driveway, complete with a fountain illuminated by multi-colored lights, all located at the end of a serene cul-de-sac. CORCORAN PREMIER REALTY.

Home For Sale $3,250,000

Stunning home showcasing the spacious driveway and meticulous landscaping at 4205 Clarice Ct, Windermere, FL 34786
View Details 56 Photos
Grand foyer featuring a modern light fixture and marble floors at 4205 Clarice Ct, Windermere, FL 34786
Elegant entryway with modern doors and a glimpse of the dining area at 4205 Clarice Ct, Windermere, FL 34786
Foyer boasts a modern chandelier and views into adjacent rooms at 4205 Clarice Ct, Windermere, FL 34786
On Market For 12 Days

  • Bedrooms

    7

  • Full Bath(s)

    8

  • Sq. Ft.

    7042

  • Year Built

    2006

  • $/SqFt

    $462

This home truly offers a living experience like no other, combining luxury, sustainability, and smart technology in one perfect package! WEMERT GROUP REALTY LLC.

Home For Sale $1,450,000

Charming single-Gathering home featuring a well-manicured lawn, mature trees, and an attached two-car garage at 11537 Claymont Cir, Windermere, FL 34786
View Details 47 Photos
Inviting backyard pool and spa area, perfect for relaxation and entertaining with a fenced yard at 11537 Claymont Cir, Windermere, FL 34786
Modern kitchen featuring stainless steel appliances, gray cabinets, quartz countertops, and pendant lighting at 11537 Claymont Cir, Windermere, FL 34786
Bright and airy kitchen with gray cabinets, quartz countertops, stainless appliances, and breakfast bar seating at 11537 Claymont Cir, Windermere, FL 34786
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3164

  • Year Built

    2002

  • $/SqFt

    $458

Keenes Pointe - Don't miss this opportunity to live in one of Windermere’s most sought-after communities—schedule your showing today! STOCKWORTH REALTY GROUP.

Home For Sale $3,000,000

Stunning aerial view of a luxurious waterfront community with beautiful homes and lush greenery at 8336 Boyla Ct, Windermere, FL 34786
View Details 100 Photos
Beautiful home featuring a circular driveway, lush landscaping, and an attached three-car garage at 8336 Boyla Ct, Windermere, FL 34786
Beautiful home featuring a circular driveway, lush landscaping, and an attached three-car garage at 8336 Boyla Ct, Windermere, FL 34786
Beautiful home featuring a circular driveway, lush landscaping, and an attached three-car garage at 8336 Boyla Ct, Windermere, FL 34786
On Market For 13 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5905

  • Year Built

    2003

  • $/SqFt

    $508

Keenes Pointe - Be sure to click on the virtual tour links. THE SIMON SIMAAN GROUP.

Home For Sale $1,625,000

Charming single-story home with a well-manicured lawn and lush landscaping creating excellent curb appeal at 2931 Sunbittern Ct, Windermere, FL 34786
View Details 72 Photos
Beautifully landscaped single story house with a well maintained lawn and mature trees providing ample shade at 2931 Sunbittern Ct, Windermere, FL 34786
Charming exterior view of house at dusk with lush landscaping and a warm, inviting glow at 2931 Sunbittern Ct, Windermere, FL 34786
View of Windermere city government building with a patriotic horse statue at the entrance at 2931 Sunbittern Ct, Windermere, FL 34786
On Market For 13 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4018

  • Year Built

    1985

  • $/SqFt

    $404

Butler Bay - With extensive upgrades, a flexible layout, and a prime location, this home is truly a rare find in Windermere. KELLER WILLIAMS CLASSIC.

Home For Sale $1,299,000

Charming home with a well manicured lawn, a stone accent, and three car garage under a vibrant sky at 1403 Lake Whitney Dr, Windermere, FL 34786
View Details 47 Photos
Beautiful home with a lush front lawn, a stately stone facade, and a convenient three-car garage at 1403 Lake Whitney Dr, Windermere, FL 34786
Beautiful two-story home with a three-car garage, nice landscaping and driveway at 1403 Lake Whitney Dr, Windermere, FL 34786
Inviting front entrance with decorative stone pillars, tiled steps, and elegant door at 1403 Lake Whitney Dr, Windermere, FL 34786
On Market For 13 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4041

  • Year Built

    2004

  • $/SqFt

    $321

Reserve At Belmere - Move-in ready, this is an opportunity you won’t want to miss! Schedule your private tour today! ALLIANCE REAL ESTATE GROUP.

Pended $1,122,346

Charming one-story home with stone accents, well-manicured lawn, two-car garage, and covered front porch at 14378 Crest Palm Ave, Windermere, FL 34786
View Details 4 Photos
Detailed first floor plan showcasing the layout of the bedrooms, bathrooms, kitchen, living spaces, and garage at 14378 Crest Palm Ave, Windermere, FL 34786
Detailed second floor plan showcasing the layout of the bedrooms, bathrooms, bonus room, and kitchen at 14378 Crest Palm Ave, Windermere, FL 34786
Community map showcasing the layout of the lots, streets, ponds, and amenities within the neighborhood at 14378 Crest Palm Ave, Windermere, FL 34786
On Market For 12 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4222

  • Year Built

    2025

  • $/SqFt

    $266

With soaring ceilings—up to 10 feet on the first floor and 9 feet on the second (as per plan)—and luxury ceramic tile flooring in key areas, this home exudes a sense of spaciousness and sophistication. OLYMPUS EXECUTIVE REALTY INC.

Home For Sale $879,000

Charming two-story home with a black door, white columns, manicured lawn, and beautiful landscaping at 6244 Little Lake Sawyer Dr, Windermere, FL 34786
View Details 57 Photos
Charming home featuring a well-manicured lawn, mature trees, and beautiful landscaping at 6244 Little Lake Sawyer Dr, Windermere, FL 34786
Elegant home with a three-car garage, brick driveway, lush lawn, and meticulously maintained landscaping at 6244 Little Lake Sawyer Dr, Windermere, FL 34786
Inviting front porch with stylish decor, including potted plants and comfortable seating at 6244 Little Lake Sawyer Dr, Windermere, FL 34786
On Market For 13 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3300

  • Year Built

    2002

  • $/SqFt

    $266

This home is also ideally situated with immediate proximity to Windermere Prep and only minutes from downtown Windermere, downtown Winter Garden, Walt Disney World and other world-famous attractions of Orlando. INDEPENDENCE REALTY LLC.

Pended $683,000

Charming two-story home with a well-manicured lawn and a two-car garage at 11725 Sprawling Oak Dr, Windermere, FL 34786
View Details 37 Photos
Charming two-story home with a well-manicured lawn and a two-car garage at 11725 Sprawling Oak Dr, Windermere, FL 34786
Charming two-story home with a well-manicured lawn and a two-car garage at 11725 Sprawling Oak Dr, Windermere, FL 34786
Inviting hallway with stylish wood-look tile flooring and natural light at 11725 Sprawling Oak Dr, Windermere, FL 34786
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2591

  • Year Built

    2016

  • $/SqFt

    $264

Ashlin Park - Enjoy a gourmet kitchen equipped with high-end appliances, expansive living areas, and a thoughtfully designed floor plan perfect for family living and entertaining. BAHIA INTERNATIONAL REALTY.

Home For Sale $939,000

Charming two-story home with landscaped front yard and a classic white and black exterior at 315 E 6Th Ave, Windermere, FL 34786
View Details 56 Photos
Beautifully landscaped home featuring a circular driveway and a white and black exterior at 315 E 6Th Ave, Windermere, FL 34786
Inviting two-story home with landscaped front yard, classic white and black exterior, and paver driveway at 315 E 6Th Ave, Windermere, FL 34786
Stylish living room with wood beam ceiling, modern furniture, and black brick fireplace at 315 E 6Th Ave, Windermere, FL 34786
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2869

  • Year Built

    1964

  • $/SqFt

    $327

Don’t miss out on the opportunity to own this exceptional property! Schedule your private showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $675,000

Charming home with a welcoming front porch, dormer windows, and manicured landscaping at 6613 Duncaster St, Windermere, FL 34786
View Details 39 Photos
A close-up of the home's front door with columns, hedges, and symmetrical window placement at 6613 Duncaster St, Windermere, FL 34786
Inviting front porch with white railings and columns offering shade and curb appeal at 6613 Duncaster St, Windermere, FL 34786
Open-concept living room boasts hardwood floors, modern lighting, and an arched entryway at 6613 Duncaster St, Windermere, FL 34786
*POTENTIAL GREAT VALUE
On Market For 14 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3045

  • Year Built

    2005

  • $/SqFt

    $222

Hot Water Heater 2023. Downstairs AC 2022 UPSIDE REAL ESTATE INC.

Home For Sale $2,899,000

Beautiful single-story home featuring a red tile roof, well-manicured lawn and a brick driveway at 6120 Payne Stewart Dr, Windermere, FL 34786
View Details 35 Photos
Charming single-story home with a red tile roof, attached garage, and a brick driveway at 6120 Payne Stewart Dr, Windermere, FL 34786
Inviting entryway featuring hardwood floors, a decorative table, and elegant wall decor at 6120 Payne Stewart Dr, Windermere, FL 34786
Welcoming entryway with hardwood floors, stylish decor, and a view of the front porch at 6120 Payne Stewart Dr, Windermere, FL 34786
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3636

  • Year Built

    1987

  • $/SqFt

    $797

Also close to dining, shopping, top-rated public and private schools, expressways and tourist attractions making this the perfect choice to call home. SOUTHERN REALTY GROUP LLC.

Home For Sale $1,950,000

Breathtaking aerial view of a home with lush landscaping, long brick driveway, and sprawling green lawns at 3130 Butler Bay N Dr, Windermere, FL 34786
View Details 65 Photos
Stunning home features lush landscaping, a terracotta roof, and circular drive with a fountain on a sprawling lot at 3130 Butler Bay N Dr, Windermere, FL 34786
Beautiful single-story home with lush landscaping, a brick driveway, and a tile roof, exuding curb appeal at 3130 Butler Bay N Dr, Windermere, FL 34786
Inviting entryway with a double-door entrance, brick steps, and stone-tiled driveway, offering a grand welcome at 3130 Butler Bay N Dr, Windermere, FL 34786
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4490

  • Year Built

    1985

  • $/SqFt

    $434

Butler Bay - Please see embedded video link for complete walk-through tour. ADAIR REALTY INC.

Home For Sale $1,850,000

Charming Mediterranean-style home with lush landscaping, a tile roof, and a brick walkway at 8437 Lake Burden Cir, Windermere, FL 34786
View Details 49 Photos
Beautiful Mediterranean-style home with red tile roof, white stucco walls, and landscaped front yard at 8437 Lake Burden Cir, Windermere, FL 34786
An aerial view of a Mediterranean-style home with a red tile roof surrounded by lush greenery at 8437 Lake Burden Cir, Windermere, FL 34786
Elegant foyer with tile flooring, arched doorways, and a decorative medallion inlay at 8437 Lake Burden Cir, Windermere, FL 34786
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3797

  • Year Built

    2005

  • $/SqFt

    $487

Keenes Pointe - Keene's Pointe is more than a golf community. IT'S A LIFESTYLE. B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE.

Home For Sale $1,295,000

Elegant home exterior featuring a lush, landscaped front yard and a brick driveway leading to the main entrance at 1613 Glenwick Dr, Windermere, FL 34786
View Details 70 Photos
Open kitchen featuring stainless steel appliances, granite countertops, an island, and a cozy breakfast nook at 1613 Glenwick Dr, Windermere, FL 34786
Comfortable main bedroom with a dark blue accent wall, carpeted floor, a ceiling fan, and sliding doors to the yard at 1613 Glenwick Dr, Windermere, FL 34786
Modern bathroom featuring a soaking tub, a dark vanity with double sinks, tile floors, and a glass block window at 1613 Glenwick Dr, Windermere, FL 34786
On Market For 15 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3958

  • Year Built

    2002

  • $/SqFt

    $327

Reserve At Belmere - Don’t miss the opportunity to own this exquisite home in one of Windermere’s most sought-after communities. Schedule your private tour today! PREMIER SOTHEBYS INT'L REALTY.

Home For Sale $1,125,000

Reduced By $125,000

Beautiful single-story home with an orange roof, lush green lawn, and tall palm trees at 12820 Butler Bay Ct, Windermere, FL 34786
View Details 81 Photos
Aerial view of a house with a private pool and a red tile roof surrounded by lush landscaping at 12820 Butler Bay Ct, Windermere, FL 34786
A luxurious pool with a waterfall feature, surrounded by tropical landscaping, offering a private oasis at 12820 Butler Bay Ct, Windermere, FL 34786
Front entrance with an arched portico, gray door, manicured landscaping, and a red tile roof at 12820 Butler Bay Ct, Windermere, FL 34786
On Market For 18 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4127

  • Year Built

    1989

  • $/SqFt

    $273

Butler Bay - Don't miss this incredible opportunity—schedule your private showing today! RE/MAX 200 REALTY.

Pended $525,000

Charming two-story home with a manicured lawn and cozy front porch, complemented by lush landscaping at 8321 Bryce Canyon Ave, Windermere, FL 34786
View Details 39 Photos
A street view of modern homes showcasing well-maintained lawns, driveways, and basketball hoop at 8321 Bryce Canyon Ave, Windermere, FL 34786
Inviting front porch with white railing, offering a glimpse of the neighborhood and lush greenery at 8321 Bryce Canyon Ave, Windermere, FL 34786
A welcoming front porch featuring neutral tones, a decorative rug, and a view of the neighborhood at 8321 Bryce Canyon Ave, Windermere, FL 34786
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1891

  • Year Built

    2016

  • $/SqFt

    $278

Don’t miss out on this incredible opportunity—schedule your private showing today! FLORIDA CONNEXION PROPERTIES.

Home For Sale $1,949,900

Reduced By $148,100

Charming, single-story stucco home with manicured landscaping and a beautiful brick-paved walkway leading to the front door at 12860 Jacob Grace Ct, Windermere, FL 34786
View Details 50 Photos
A warm-toned home with a tile roof, lush landscaping, and a spacious front yard viewed from the sidewalk at 12860 Jacob Grace Ct, Windermere, FL 34786
Inviting front entrance featuring double doors, brick archway, and manicured bushes flanking the walkway at 12860 Jacob Grace Ct, Windermere, FL 34786
Elegant sitting room with a grand piano, large arched window, and stylish decor at 12860 Jacob Grace Ct, Windermere, FL 34786
On Market For 18 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5844

  • Year Built

    2004

  • $/SqFt

    $334

Tildens Grove - Nestled within the coveted Tilden’s Grove community, this property offers an unparalleled combination of luxury, privacy, and convenience in one of Windermere’s most desirable neighborhoods. CORCORAN PREMIER REALTY.

Pended $995,000

Stunning aerial view of a two-story home on a large lot near a beautiful lake at 9332 Windy Ridge Rd, Windermere, FL 34786
View Details 61 Photos
Charming two-story home with a spacious porch and a bright blue front door at 9332 Windy Ridge Rd, Windermere, FL 34786
Inviting two-story home with a large wraparound porch, perfect for relaxing outdoors at 9332 Windy Ridge Rd, Windermere, FL 34786
Traditional home featuring a wraparound porch and a detached garage with mature trees at 9332 Windy Ridge Rd, Windermere, FL 34786
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2892

  • Year Built

    1985

  • $/SqFt

    $344

Enjoy peace of mind with new HVAC units and a roof installed in 2023, ensuring comfort and energy efficiency for years to come. CORCORAN PREMIER REALTY.

Home For Sale $899,000

Reduced By $51,000

Beautiful two-story home featuring a three-car garage, landscaped yard, and a mix of stucco and stone accents at 6926 Trellis Vine Loop, Windermere, FL 34786
View Details 51 Photos
Inviting front porch with comfortable wicker seating area and a beautifully painted front door with a welcome mat at 6926 Trellis Vine Loop, Windermere, FL 34786
Stylish entryway showcasing wood-look flooring, decorative wallpaper, and a view into the home's open layout at 6926 Trellis Vine Loop, Windermere, FL 34786
Serene bedroom with patterned wallpaper, plush carpeting, and a stylish bed with tufted headboard and soft pink bedding at 6926 Trellis Vine Loop, Windermere, FL 34786
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3124

  • Year Built

    2018

  • $/SqFt

    $288

Don't miss your chance to enjoy everything this exceptional home has to offer—schedule your viewing today! TALENT REALTY SOLUTIONS.

Pended $539,000

Charming single-story home with a well-manicured lawn and inviting front porch and sidewalk at 12919 Freeman St, Windermere, FL 34786
View Details 72 Photos
Exterior view of home showcasing a beautiful lawn, sidewalk and front porch with columns at 12919 Freeman St, Windermere, FL 34786
Lush backyard featuring a screen enclosed lanai area for outdoor relaxation and enjoyment at 12919 Freeman St, Windermere, FL 34786
Screened lanai featuring an outdoor ceiling fan and patio furniture, with a view of the backyard at 12919 Freeman St, Windermere, FL 34786
On Market For 20 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2151

  • Year Built

    2004

  • $/SqFt

    $251

Lakes Of Windermere - Walking distance to a new Orange County park which includes a playground and a dog park. KELLER WILLIAMS ELITE PARTNERS III REALTY.

Home For Sale $3,999,999

Elegant home with lush landscaping and a paved driveway leading to the grand entrance at twilight at 11306 Bridge House Rd, Windermere, FL 34786
View Details 88 Photos
A luxurious home boasts a circular driveway and classic architectural design with warm inviting lights at 11306 Bridge House Rd, Windermere, FL 34786
Luxury home boasts manicured bushes, a circular driveway, and warm lighting accentuating the facade at 11306 Bridge House Rd, Windermere, FL 34786
Elegant home features mature trees, manicured lawns, and a paved driveway in a lush, daytime setting at 11306 Bridge House Rd, Windermere, FL 34786
On Market For 20 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    6742

  • Year Built

    2007

  • $/SqFt

    $593

Reserve At Lake Butler Sound - Additionally, residents enjoy exclusive access to a private back gate, providing a short walk to Windermere Preparatory School—ranked by Niche as the top private high school in Orlando and Orange County for 2025. LAKESIDE REALTY WINDERMERE INC.

Viewing HOMES 1 to 50 of 275

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407 718 3706 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$533,093
$434,500
128
1.6%
49.2%
84

Apopka
$532,887
$460,000
564
1.2%
51.1%
92

Belle Isle
$810,958
$649,993
25
0.0%
44.0%
64

Casselberry
$456,382
$439,900
91
2.2%
49.5%
67

Celebration
$1,383,137
$1,127,000
48
0.0%
50.0%
119

Champions Gate
$687,399
$699,990
21
0.0%
52.4%
255

Chuluota
$818,300
$684,900
25
0.0%
44.0%
43

Clermont
$570,750
$494,901
690
0.7%
50.9%
84

Gotha
$1,069,222
$692,495
12
0.0%
41.7%
61

Groveland
$477,490
$410,164
265
0.8%
51.3%
83

Harmony
$438,929
$419,900
75
0.0%
28.0%
89

Kissimmee
$512,404
$439,350
2382
1.6%
47.8%
104

Longwood
$770,712
$569,700
192
1.6%
49.5%
81

Maitland
$875,327
$629,000
75
2.7%
50.7%
91

Minneola
$556,145
$534,613
130
0.8%
36.9%
91

Montverde
$1,456,328
$1,106,322
56
0.0%
42.9%
125

Ocoee
$524,061
$465,000
179
1.7%
56.4%
81

Orlando
$687,841
$490,000
2827
1.6%
46.8%
80

Oviedo
$718,330
$648,750
184
1.1%
44.6%
80

Poinciana
$329,575
$314,990
266
0.8%
59.0%
127

Reunion
$1,878,152
$1,210,000
106
0.9%
48.1%
160

Saint Cloud
$561,764
$471,000
540
1.1%
72.8%
162

Sanford
$520,646
$415,990
379
1.1%
54.6%
99

Sorrento
$586,466
$457,995
112
1.8%
65.2%
87

Winter Garden
$850,916
$699,000
603
0.5%
50.2%
85

Winter Park
$1,269,937
$719,000
275
0.4%
47.3%
82

Winter Springs
$580,129
$475,000
124
0.0%
41.9%
74

EasyStreet

Call to Schedule a Showing

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