2740 Midsummer Dr, Windermere, FL 34786
OFF MARKET

2740 Midsummer Dr
Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,550 sqft (on 2.63 acres)

$3,418,900

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $22,825/mo*
Refinance Your Home

$3,418,900

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $22,825/mo*
Refinance Your Home
4 Beds
3 Baths
2,550 sqft
(on 2.63 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

NEVER offered before...once in a lifetime opportunity to own something truly unique. Spectacular nightly picture perfect sunsets and Disney fireworks plus year-round outdoor Florida lakefront living and approximately 150' of crystal clear shoreline sitting on approximately 1 acre high and dry on Lake Down make this property the ideal location for building the custom home of your dreams! No need to look any further than at this hidden gem perfectly wrapped in mature landscaping nestled in the highly sought out storybook like streets of Lake Down Shores. The property boasts a retaining wall that emphasizes the sugar sand lake bottom that leads to your own private boat dock. Lake Down is one of 11 connected lakes of the famed Butler Chain of lakes in Windermere known for its great quality of life and community lifestyle. Like a scene from old time past, the town takes on more vibrancy during the weekly Farmer's Market and the various seasonal events. The community offers a boat ramp, is zoned in sought after "A" rated schools, and is conveniently located near golf, world-renowned shopping, fine dining, major roadways, and the local area attractions. Be the fortunate one to own this trophy property as it will not last. Call today to set up your private showing!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
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HOA
None
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Listed
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Home Details for 2740 Midsummer Dr

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: Composition
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1984Year Updated: 1984
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 2.63 acres

Price History for 2740 Midsummer Dr

DatePriceEventSource
11/01/2018$1,425,000Sold
N/A
08/31/2018$1,495,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$48,484
Assessment$3,418,187
Home facts updated by county records

Comparable Sales for 2740 Midsummer Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2624 Midsummer Dr, Windermere, FL
0.15
Single-Family Home
$2,500,000
09/05/25
4
2.5
4,667
9538 Lavill Ct, Windermere, FL
0.28
Single-Family Home
$799,000
08/22/25
4
3
2,748
9601 Ambleside Dr, Windermere, FL
0.26
Single-Family Home
$815,000
07/21/25
4
2.5
3,018
2828 Ingeborg Ct, Windermere, FL
0.23
Single-Family Home
$1,220,000
01/23/26
5
4.5
3,190
2532 Waterview Pl, Windermere, FL
0.26
Single-Family Home
$850,000
06/26/25
4
2.5
2,478
2641 Hempel Ave, Windermere, FL
0.29
Single-Family Home
$812,000
04/20/26
4
2
2,404
9501 Hempel Cove Blvd, Windermere, FL
0.42
Single-Family Home
$1,325,000
06/12/25
4
4
4,789
2722 Park Royal Dr, Windermere, FL
0.47
Single-Family Home
$950,000
04/20/26
4
3
2,967
9676 Wildoak Dr, Windermere, FL
0.43
Single-Family Home
$745,000
07/28/25
4
2.5
2,856
10506 Down Lakeview Cir, Windermere, FL
0.64
Single-Family Home
$1,150,000
11/13/25
4
3
3,888

Assigned Schools

These are the assigned schools for 2740 Midsummer Dr.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 270 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 79 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Learn more about our methodology.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
    0
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  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
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  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
    0
    Flag
  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
    0
    Flag
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
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  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
    0
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
    0
    Flag
  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
    5
    Flag
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
    3
    Flag
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
    0
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  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
    2
    Flag
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
    0
    Flag
  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
    2
    Flag
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
    Flag
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
    Flag
  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
    Flag
  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
    0
    Flag
  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
    0
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
    Flag
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
    Flag
  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
    1
    Flag
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
    Flag
  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
    Flag
  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
    1
    Flag
  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
    0
    Flag
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
    1
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
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Homes for sale near 2740 Midsummer Dr

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Off Market Homes Near 2740 Midsummer Dr

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2740 Midsummer Dr, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,550 sqft single-family home built in 1984. This property is not currently available for sale. 2740 Midsummer Dr was last sold on Nov 1, 2018 for $1,425,000. The current Trulia Estimate for 2740 Midsummer Dr is $3,418,900.