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Windermere

Overview for Windermere, FL

3,034 people live in Windermere, where the median age is 52.7 and the average individual income is $101,291. Data provided by the U.S. Census Bureau.

3,034

Total Population

52.7 years

Median Age

High

Population Density Population Density This is the number of people per square mile in a neighborhood.

$101,291

Average individual Income

Welcome to Windermere, FL

A Serene Lakeside Oasis in the Heart of Central Florida

Windermere, located in Orange County, Florida, is a picturesque lakeside town known for its natural beauty, luxury living, and charming small-town atmosphere. Nestled among the stunning Butler Chain of Lakes, Windermere is a tranquil escape from the hustle and bustle of nearby Orlando, yet still close to world-class attractions, shopping, and entertainment. With its tree-lined streets, upscale homes, and focus on preserving the town’s natural beauty, Windermere offers residents a peaceful, elegant lifestyle.


Windermere Town Hall – a historic landmark in Windermere, Florida

 

Windermere, Florida – Community Overview & Real Estate Guide

Set on the pristine Butler Chain of Lakes in southwest Orange County, Windermere blends small-town charm with lakeside luxury. Residents prize boating, paddle sports, and sunset cruises across 13 interconnected lakes, plus quick access to Orlando’s dining, shopping, and attractions. Leafy streets, historic civic buildings, and premier private golf communities like Isleworth and Keene’s Pointe make Windermere a favorite for buyers seeking privacy, water access, and enduring value close to the city.

Overview of Windermere, FL

Within minutes of Walt Disney World and downtown Orlando, Windermere offers a refined outdoor lifestyle anchored by the Outstanding Florida Waters–designated Butler Chain. Weekend rhythms revolve around the water, miles of nearby nature trails at Tibet-Butler Preserve, and tee times at private clubs. Whether your vision is a lakefront estate with a private dock or a quiet in-town residence, Windermere pairs natural beauty with convenience and a tight-knit community feel.

Key Facts about Windermere, FL
Area ~1.93 sq mi land (town limits); ~2.69 sq mi total
County Orange County
Incorporated February 2, 1925
Population (2020 Census) 3,030 (town)
Signature Setting Butler Chain of Lakes (13 connected lakes; Outstanding Florida Waters designation)
Nature & Parks Tibet-Butler Preserve • R.D. Keene Park (public boat ramp to Butler Chain)
Golf & Private Clubs Isleworth Golf & Country Club • The Golden Bear Club at Keene’s Pointe (Jack Nicklaus Signature)
Main Roads Conroy-Windermere Rd • Winter Garden Vineland Rd (CR 535) • Apopka-Vineland Rd
ZIP / Area Codes 34786 • 407 / 689
Lifestyle Lakefront living, private docks, low-speed neighborhood streets, walkable town center.
Outdoors Boating, kayaking, paddleboarding, birding trails, sunset cruises across clear, spring-fed lakes.
Convenience Minutes to Orlando’s dining & shopping; quick access to theme parks and major corridors.
Real Estate Distinguished lakefront estates, gated golf communities, and charming in-town homes.

From serene lakefront estates to gated golf enclaves, Windermere delivers a rare balance of privacy, prestige, and natural beauty—backed by exceptional outdoor recreation and proximity to Orlando’s best amenities.

 

 

Location & Connectivity in Windermere

Windermere sits on the Butler Chain of Lakes in southwest Orange County, minutes from Orlando’s dining, shopping, and world-class attractions. Its tree-lined streets and village core are supported by nearby corridors such as Conroy-Windermere Road, Winter Garden Vineland Road (CR 535), and Apopka-Vineland Road. Day-to-day mobility is primarily by car, complemented by golf carts in some neighborhoods, cycling around lakeside lanes, and ride-share.

For regional and long-haul access, residents rely on Orlando International Airport (MCO), Orlando Executive (ORL) for private/business aviation, and Sanford (SFB) for select carriers. Major expressways including Florida’s Turnpike, SR 408, and SR 429 connect Windermere to the wider metro.

Connectivity & Transportation — Windermere, FL
Location Map & Area Overview in Windermere Southwest Orange County town surrounded by the Butler Chain of Lakes. Minutes to Orlando’s premier shopping/dining, golf clubs, and world-famous theme parks. Primary local spines include Conroy-Windermere Rd, Winter Garden Vineland Rd (CR 535), and Apopka-Vineland Rd.
Nearby Areas & Communities in Windermere
  • Dr. Phillips — upscale dining, shopping, performing arts
  • Winter Garden — historic downtown, bike trail, weekend markets
  • Horizon West — modern retail/dining hubs and master-planned villages
  • Bay Hill — Arnold Palmer’s Bay Hill Club & Lodge (nearby)
  • Lake Buena Vista — resort/attractions corridor
Attractions & Points of Interest in Windermere
  • Butler Chain of Lakes — boating, paddle sports, sunset cruises
  • Tibet-Butler Preserve & R.D. Keene Park — trails and public boat ramp access
  • Disney/Resort Area — ~15–25 min depending on gate/park
  • Private Golf — Isleworth, Keene’s Pointe (Golden Bear Club)
Public Transport in Windermere
  • Regional bus (LYNX) service on nearby corridors; most residents rely on car/ride-share.
  • Tour/Private Drivers — black-car, sprinter vans, and charter services for events & airport transfers.
Road Access & Main Highways in Windermere
  • Florida’s Turnpike & SR 408 — downtown Orlando access
  • SR 429 — Western Beltway to I-4, Apopka, and I-75 corridor
  • I-4 — regional east–west spine to Tampa/Daytona
Typical Drive Times* in Windermere
  • Windermere → Disney area: ~15–25 min
  • Windermere → Dr. Phillips: ~10–15 min
  • Windermere → Winter Garden: ~10–15 min
  • Windermere → Downtown Orlando: ~25–35 min
  • Windermere → MCO (Orlando Int’l): ~25–35 min
*Subject to traffic, season, and event schedules
Parking in Windermere Street parking around Windermere’s town center (time limits may apply). Ample on-site parking at parks, clubs, and retail centers; resort/attraction areas may require paid parking.
Walking & Cycling in Windermere Walkable village core; lakeside lanes popular for cycling and golf-cart use in select neighborhoods. Multi-use trails and preserves nearby for hiking/birding.
Taxi & Ride Apps in Windermere Uber and Lyft operate widely. Local black-car and chauffeured services are common for special events and airport runs.
Airport Access in Windermere
  • Orlando International (MCO) — ~25–35 min SE
  • Orlando Executive (ORL) — ~25–35 min E (business/private)
  • Sanford Int’l (SFB) — ~45–60 min NE
Private FBOs and charter options available across the metro.
Accessibility & EV Notes in Windermere Newer retail, hotels, and attractions are generally ADA-friendly; confirm specifics ahead. EV drivers will find Level 2 and DC fast chargers at area shopping centers, resorts, and public lots across the metro.

Windermere combines effortless regional access with lakeside serenity—scenic drives, golf-cart-friendly streets, preserved natural areas, and convenient air links make it an exceptional base for luxury living in Greater Orlando.

 

Windermere Real Estate Market Trends (2025)

Windermere’s real estate market reflects its reputation as one of Central Florida’s most desirable luxury enclaves. Known for lakefront estates, exclusive golf community homes, and family-friendly neighborhoods, the market remains competitive. As of mid–late 2025, the median sale price is around $1.05M, with a median price per sq. ft. near $360. Homes typically spend 45–60 days on market, while trophy estates on the Butler Chain of Lakes may take longer to sell due to their exclusivity. Rental demand is strong among relocating professionals and families, supported by proximity to Disney, downtown Orlando, and top-rated schools.

Property Type (Windermere) Median Price (USD) Price per Sq.Ft (USD) Average Rent (USD/month) Rental Yield
2BR Condo / Townhome (Windermere) $420,000 (est.) $275 $2,300 6.5% (est.)
3BR Single-Family Home (Windermere) $750,000 (est.) $325 $3,200 5.1% (est.)
4BR Golf Community Home (Windermere) $1,200,000 (est.) $360 $4,800 4.8% (est.)
Lakefront Luxury Estate (Windermere) $3,750,000 (est.) $520 $9,500 3.0% (est.)

Methodology & Notes: Median sale price ($1.05M) and $360/sq.ft. reflect mid-2025 Windermere market trackers. Segment medians were derived by applying price-per-foot to typical property sizes. Rental data represents late summer 2025 averages for Windermere, adjusted for luxury weighting and proximity to lakes/golf. Yield estimates vary significantly based on lake frontage, gated community amenities, and property updates.

Windermere, FL — Real Estate Market Snapshot

 

Lifestyle in Windermere

Life in Windermere blends lakeside serenity with proximity to Orlando’s world-class amenities. The town is nestled among the Butler Chain of Lakes, offering boating, fishing, paddleboarding, and sunset cruises. Residents enjoy tree-lined streets, a charming walkable town center, and access to exclusive golf and country clubs. With major shopping, dining, and entertainment districts just minutes away, Windermere provides a rare mix of privacy, natural beauty, and convenience.

Location in Windermere

Situated in southwest Orange County, Windermere is surrounded by the Butler Chain of Lakes. Minutes to Orlando’s dining, shopping, and theme parks, while retaining a peaceful small-town feel.

Community in Windermere

Close-knit and family-oriented, with neighborhood events, farmers’ markets, and a historic downtown. Streets are lined with oaks and Spanish moss, creating an inviting village atmosphere.

Dining in Windermere

Local cafés, wine bars, and eateries anchor the town center. Upscale dining options expand into nearby Dr. Phillips’ Restaurant Row, and world-class cuisine is just a short drive into Orlando.

Education in Windermere

Served by Orange County Public Schools, with top-rated public and charter programs. Access to prestigious private schools nearby, plus enrichment in arts, STEM, and athletics.

Housing in Windermere

Includes townhomes, family neighborhoods, golf community residences, and luxury lakefront estates. Homes with private docks and lake views command premium pricing.

Transportation in Windermere

Primarily car-dependent, with golf carts common in certain neighborhoods. Quick access via Conroy-Windermere Rd, CR 535, and Apopka-Vineland Rd to Orlando’s expressways and downtown.

Climate in Windermere

Humid subtropical: hot summers, mild winters, and abundant sunshine. Afternoon storms in summer; hurricane-season precautions apply. Lakes provide natural cooling breezes.

Amenities in Windermere

Parks, playgrounds, and lake access throughout town. Exclusive amenities in gated communities include golf, tennis, and fitness centers. Nearby shopping districts add convenience.

Demographics in Windermere

A blend of professionals, executives, athletes, and families seeking privacy. Strong emphasis on quality of life, education, and community involvement.

Pros in Windermere

Lakeside living, prestigious golf communities, proximity to Orlando and Disney, top-rated schools, and a serene small-town atmosphere.

Cons in Windermere

Higher housing costs for lakefront properties, limited public transportation, and seasonal tourist traffic on nearby roads.

Outdoor Activities in Windermere

Boating, fishing, kayaking, paddleboarding, and golf. Nature trails at Tibet-Butler Preserve and family recreation at R.D. Keene Park.

Windermere’s lifestyle combines lakeside tranquility with urban convenience—offering outdoor recreation, family-friendly neighborhoods, and easy access to Greater Orlando’s premier amenities.

 

Amenities in Windermere, FL

Windermere offers a premier mix of amenities—from lakeside parks and fitness clubs to boutique shopping, dining, and pet-friendly services. Below are highlights that make Windermere one of Central Florida’s most desirable places to live.

  • Hospitals & Clinics in Windermere

    Windermere • Dr. Phillips • Orlando
    Residents benefit from proximity to leading healthcare systems, specialty practices, and urgent care centers.
    • Orlando Health Dr. P. Phillips Hospital — nearby, full-service hospital
    • AdventHealth Winter Garden — emergency & specialty services
    • Windermere Medical Center — family & urgent care
    • Nemours Children’s Hospital — accessible in Lake Nona
    Comprehensive care within 10–25 minutes
  • Shopping & Markets in Windermere

    Windermere Village • Winter Garden Village • Dr. Phillips
    Everyday essentials, boutique finds, and upscale shopping centers are minutes away.
    • Windermere Village — local shops, groceries, dining
    • Publix Super Market — neighborhood staple
    • Winter Garden Village — retail & lifestyle center
    • Dr. Phillips Restaurant Row — dining and specialty markets
    Retail & dining hubs within 5–15 minutes
  • Fitness & Recreation in Windermere

    Gyms • Parks • Country Clubs
    Residents enjoy active living through private clubs, community parks, and lakefront recreation.
    • RD Keene Park — boat ramp & sports fields
    • Tibet-Butler Preserve — nature trails & birding
    • Isleworth Golf & Country Club — championship golf
    • The Golden Bear Club at Keene’s Pointe — golf, tennis, fitness
    Outdoor and club amenities within 5–20 minutes
  • Pet Services in Windermere

    Veterinary • Grooming • Boarding
    A pet-friendly town with veterinary clinics, groomers, and nearby boarding facilities.
    • Windermere Veterinary Services — full-service veterinary care
    • Pet Paradise Winter Garden — daycare & boarding
    • Downtown Pet Grooming — local groomer
    • Lakefront dog-friendly parks — trails & play areas
    Convenient pet care across Windermere & surrounds

Schools & Preschools in Windermere

Families in Windermere are served by Orange County Public Schools (OCPS), including highly regarded elementary, middle, and high schools. In addition, there are top-ranked charter and private schools in the surrounding area. Many parents choose Windermere for its strong focus on education, small-town setting, and access to both public and private options.

Programs emphasize college-prep rigor, STEM enrichment, performing arts, athletics, and global learning. Always confirm current attendance zones, magnet programs, and admission requirements before enrolling.

School / Preschool Type Location Highlights
Windermere Elementary Public (K–5) — OCPS Downtown Windermere Historic neighborhood school with strong academics, arts, and community involvement.
Bay Lake Elementary Public (K–5) — OCPS Near Horizon West Modern campus with STEM initiatives, digital learning, and diverse enrichment programs.
Keenes Crossing Elementary Public (K–5) — OCPS Windermere area Popular with local families; strong parent engagement and academic support programs.
Bridgewater Middle School Public (6–8) — OCPS Windermere Large middle school with STEM electives, athletics, and arts; highly rated academics.
Windermere Preparatory Middle Private (6–8) Windermere International Baccalaureate curriculum with small class sizes, arts, and athletics.
Windermere High School Public (9–12) — OCPS Horizon West / Windermere area Comprehensive AP, athletics, and career pathways; serves a growing suburban population.
Olympia High School Public (9–12) — OCPS Dr. Phillips / MetroWest AP/Honors programs, athletics, and arts; serves students from nearby Windermere neighborhoods.
Windermere Preparatory School Private (K–12) Windermere IB World School; strong arts, athletics, and global learning emphasis; highly ranked private option.
Imagine Schools at South Lake Charter (K–8) Nearby Clermont Charter option with focus on character education, STEM, and individualized learning.
Foundation Academy Private (K–12) Winter Garden Christian college-prep; athletics and faith-based curriculum; multiple campuses near Windermere.
Windermere Union Preschool Private Preschool Windermere Play-based early learning with strong parent involvement and community roots.
Primrose School of Windermere Private Preschool / Kindergarten Windermere Accredited preschool offering balanced curriculum with focus on academics and social development.
Montessori World School Private Preschool / Elementary Dr. Phillips Montessori-based learning; independence, hands-on exploration, and bilingual programs.

District: Orange County Public Schools (OCPS). Tip: Attendance zones and program offerings can shift—verify current boundaries, magnet programs, and admissions details directly with OCPS or each private school before enrollment.

 

Investment Potential in Windermere, FL

Windermere is one of Greater Orlando’s most coveted luxury submarkets, centered on the Butler Chain of Lakes and premier golf communities. Scarcity of true lakefront parcels, gated-club amenities, and proximity to Orlando’s employment and entertainment hubs support long-term desirability and value.

Why Windermere? Lakeside living, top-tier schools, private-club lifestyle (Isleworth, Keene’s Pointe), and easy access to Disney and downtown Orlando. Limited lakefront inventory and strong executive relocation demand make Windermere compelling for both primary residences and investment properties. Note: Short-term rental (STR) regulations vary by municipality and HOA—verify before purchase.

Lakefront Estates
 
Highest demand & scarcity
Golf Community Homes
 
Club lifestyle premium
Long-Term Rentals
 
Relocation & executive demand
Capital Growth
 
Limited supply dynamics
  • Luxury Market: Trophy properties on the Butler Chain command significant premiums and attract national/global buyers.
  • Rental Strength: Executive and family demand fueled by schools, corporate relocations, and proximity to attractions.
  • Supply Constraints: Few buildable lakefront lots; quality inventory moves quickly when priced correctly.
  • Risk & Compliance: STR/HOA rules vary; confirm town/HOA restrictions, flood zones, docks/boat-lift permitting, and insurance.

Rental Snapshot in Windermere

Luxury Homes: $7,500–$15,000+/mo
4BR Golf Community: $4,500–$7,500/mo
3BR SFR: $3,200–$4,800/mo

Ranges vary by lake frontage, club membership, updates, and school zoning.

What Performs Well in Windermere

  • Lakefront estates with private docks and western sunset exposure.
  • Homes inside premier clubs (Isleworth, Keene’s Pointe) with modern upgrades.
  • Family floor plans (4–5BR), pool/spa, outdoor kitchens, guest suites.
  • Proximity to top schools and expressways (SR 429/408, Turnpike).

Compliance & Risk in Windermere

  • Confirm STR rules with the Town/County and your HOA.
  • Assess floodplain & lakeside setbacks; review dock/boat-lift permits.
  • Obtain quotes for wind/hail and flood insurance; verify seawall and shoreline condition.
  • Check title for easements and riparian rights.

Investor Playbook in Windermere

  • Luxury Buy & Hold: Renovate for outdoor living (dock, pool, summer kitchen).
  • Club-Lifestyle Focus: Target move-in-ready homes near tees/amenities.
  • Value-Add: Modernize kitchens/baths, add offices/flex suites, refresh landscaping & lighting.
  • Long-Term Rental: Quality finishes + school zones optimize occupancy and rents.

Windermere’s blend of lakes, clubs, and location advantages supports resilient demand across market cycles—especially for updated homes with outdoor living and water access.

 

Thinking About Moving to Windermere?

Nestled among the Butler Chain of Lakes, Windermere offers a lifestyle of lakeside luxury and small-town charm. Residents enjoy boating, fishing, paddleboarding, and sunset views, all while being minutes from Orlando’s world-class attractions and employment centers.

Housing options range from lakefront estates with private docks and golf course residences to family neighborhoods and modern townhomes. Properties in Isleworth, Keene’s Pointe, and other gated communities command premiums for privacy, amenities, and access to top schools.

Daily life in Windermere balances outdoor recreation with modern conveniences. Residents frequent R.D. Keene Park, Tibet-Butler Preserve, and nearby golf clubs, while also enjoying easy access to shopping, dining, and cultural destinations in Dr. Phillips and Winter Garden. Top-rated schools and excellent healthcare further enhance the appeal.

With its blend of prestige, lakeside beauty, and accessibility, Windermere is one of Central Florida’s most desirable locations for full-time living, vacation homes, and investment properties.

Explore Windermere Real Estate →

Informational FAQs about Windermere

What factors influence home prices in Windermere?
Location is the biggest driver: lakefront estates on the Butler Chain command the highest premiums, followed by golf community residences in Isleworth and Keene’s Pointe. School zoning, lot size, and modern upgrades also affect pricing.
How does the rental market in Windermere function?
Long-term rentals are in strong demand due to executive relocations and family moves. Luxury homes in gated communities often lease for $4,500–$7,500+, while standard single-family rentals range from $2,800–$4,000. Short-term rentals are regulated—HOA and municipal rules vary.
What types of properties are most common in Windermere?
Windermere offers a mix of family neighborhoods, lakefront estates with private docks, and golf course residences in gated clubs. Newer suburban-style homes are more common in nearby Horizon West.
What makes Windermere attractive compared to nearby communities?
Its unique blend of lakeside living, exclusive country clubs, and proximity to both Orlando’s entertainment corridor and downtown employment hubs. The town maintains a quiet, small-town charm despite being minutes from Disney and Dr. Phillips.
How do residents typically get around Windermere?
Daily life is car-dependent, with quick access to CR 535, Conroy-Windermere Road, and SR 429/408 for regional travel. Many neighborhoods allow golf cart use, and boating is common for lakefront homeowners.
Which schools serve families in Windermere?
Public schools are managed by Orange County Public Schools, including Windermere Elementary, Bridgewater Middle, and Windermere High. Private options like Windermere Preparatory School and Foundation Academy offer alternative pathways, including IB programs.
What is the local lifestyle like in Windermere?
A balance of outdoor recreation—boating, fishing, paddleboarding, and golf—with suburban conveniences like shopping and dining in Dr. Phillips and Winter Garden. The community is family-friendly, with a strong emphasis on schools and neighborhood events.

Windermere offers a rare combination of natural beauty, luxury amenities, and family-focused living, making it one of Central Florida’s most distinctive communities.


Demographics and Employment Data for Windermere, FL

Windermere has 1,217 households, with an average household size of 2.49. Data provided by the U.S. Census Bureau. Here’s what the people living in Windermere do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 3,034 people call Windermere home. The population density is 1,569.42 and the largest age group is Data provided by the U.S. Census Bureau.

3,034

Total Population

High

Population Density Population Density This is the number of people per square mile in a neighborhood.

52.7

Median Age

48.62 / 51.38%

Men vs Women

Population by Age Group

0-9:

0-9 Years

10-17:

10-17 Years

18-24:

18-24 Years

25-64:

25-64 Years

65-74:

65-74 Years

75+:

75+ Years

Education Level

  • Less Than 9th Grade
  • High School Degree
  • Associate Degree
  • Bachelor Degree
  • Graduate Degree
1,217

Total Households

2.49

Average Household Size

$101,291

Average individual Income

Households with Children

With Children:

Without Children:

Marital Status

Married
Single
Divorced
Separated

Blue vs White Collar Workers

Blue Collar:

White Collar:

Commute Time

0 to 14 Minutes
15 to 29 Minutes
30 to 59 Minutes
60+ Minutes

Schools in Windermere, FL

All ()
Primary Schools ()
Middle Schools ()
High Schools ()
Mixed Schools ()
The following schools are within or nearby Windermere. The rating and statistics can serve as a starting point to make baseline comparisons on the right schools for your family. Data provided by the U.S. Census Bureau.
Type
Name
Category
Grades
School rating

Around Windermere, FL

There's plenty to do around Windermere, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.

25
Car-Dependent
Walking Score
38
Somewhat Bikeable
Bike Score

Points of Interest

Explore popular things to do in the area, including Henko Cafe, CrossFit WaterSide Windermere, and Iron Shamrock.

Name Category Distance Reviews
Ratings by Yelp
Dining · $$ 3.69 miles 8 reviews 5/5 stars
Active 2.1 miles 6 reviews 5/5 stars
Active 3.89 miles 9 reviews 5/5 stars
Active 0.54 miles 23 reviews 5/5 stars
Beauty 4.33 miles 6 reviews 5/5 stars
Beauty 1.96 miles 12 reviews 5/5 stars
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