2730 Midsummer Dr, Windermere, FL 34786
Property image
Property image
OFF MARKET

2730 Midsummer Dr
Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,452 sqft (on 2.78 acres)

$2,765,800

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $19,057/mo*
Refinance Your Home

$2,765,800

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $19,057/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,452 sqft
(on 2.78 acres)

Local Information

  • Map ViewExplore the area around 2730 Midsummer Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1984
Lot Size
2.78 acres
Living Area
3,452 sqft
Price/Sqft
$801
Parking
Garage

About this House

Welcome to 2730 Midsummer Drive in Windermere Florida on the Eastern shores of Lake Down 1 of 13 lakes in the famed Butler Chain of Lakes receiving the designation of Outstanding Florida Waters from the Florida Department of Environmental Protection in 1985 because of its water quality and wildlife habitat - Midsummer Drive is one of the most charming oak canopy covered roads you will find in Central Florida with only 20 magnificent lakefront estate sized properties that rarely become available - The property provides romantic sunsets with panoramic views overlooking the large 30x15 pool and impressive rear lawn with over 145 feet of depth and 130 feet of lakefront shoreline boasting crystal clear water and white sand beach - The property is over 350 feet deep on both sides providing more space and privacy than you will find in traditional neighborhoods and plenty of room to expand the home or add a guest cottage - There is a Party Pavillion entertainment center on the pool deck that is the perfect place to have family & friends enjoy the Florida lifestyle - The home is located about 30 minutes from Orlando International Airport and a few miles to numerous restaurants, stores, houses of worship, offices & hospitals making it a very convenient location - The 2 story traditional home has a Formal Living Room and Dining Room, large Kitchen and Breakfast Nook, Pool bath and 44 x 10 Covered Screen Room on the 1st floor overlooking the Pool & Lake - Upstairs there is 4 Bedrooms, 3 Baths, large theatre with full wet bar that could easily become a guest suite - There is access from the Master Suite and Guest Suite to a Balcony deck with views of the Pool & Lake - This property has not been for sale since 1997 and the opportunity to live on Midsummer Drive rarely comes along so don't miss this chance
2730 Midsummer Dr, Windermere, FL 34786 is a 4 bedroom, 4 bathroom, 3,452 sqft single-family home built in 1984. It last sold for $2,150,000 on May 10, 2022. It is currently off market. The Trulia Estimate is $2,765,800, with a rent estimate of $6,301/month.

Home Details for 2730 Midsummer Dr

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Brick
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

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: 2.78 acres

Price History for 2730 Midsummer Dr

DatePriceEventSource
01/29/2023$2,350,000PendingStellar MLS #O6085160
01/21/2023$2,350,000Listed For SaleStellar MLS #O6085160
05/10/2022$2,150,000Sold
N/A
02/10/2022$2,500,000PendingStellar MLS #O5888668
12/12/2021$2,500,000PriceChange
Stellar MLS #O5888668
08/31/2021$1,995,000PendingToActiveStellar MLS #O5888668
08/26/2021$1,995,000PendingStellar MLS #O5888668
08/22/2021$1,995,000PriceChange
Stellar MLS #O5888668
04/06/2021$2,100,000PendingToActiveStellar MLS #O5888668
12/19/2020$2,100,000PendingStellar MLS #O5888668
08/30/2020$2,100,000Listed For SaleAgent Provided
10/07/1997$650,000Sold
N/A

Market trends in Windermere

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$722K
$50KMoM
Sale-to-List Price
97.3%
0.2%MoM
Price per sq ft
$273
$11MoM
Available listings
285
6MoM
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Property Tax and Assessment

Year2024
Tax$25,152
Assessment$1,943,681
Home facts updated by county records

Comparable Sales for 2730 Midsummer Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2624 MIDSUMMER DRIVE, Windermere, FL
0.12
Single-Family Home
$2,500,000
09/05/25
4
2.5
4,667
10505 Down Lakeview Cir, Windermere, FL
0.53
Single-Family Home
$2,750,000
07/28/26
4
3.5
4,194
2722 INGEBORG COURT, Windermere, FL
0.19
Single-Family Home
$850,000
08/10/26
4
2.5
2,619
2828 INGEBORG COURT, Windermere, FL
0.24
Single-Family Home
$1,220,000
01/23/26
5
4.5
3,190
9538 LAVILL COURT, Windermere, FL
0.30
Single-Family Home
$799,000
08/22/25
4
3
2,748
325 MAGNOLIA STREET, Windermere, FL
0.94
Single-Family Home
$2,249,000
07/06/26
4
3
3,975
2014 DOWN WOODS LANE, Windermere, FL
0.63
Single-Family Home
$1,390,000
07/28/26
4
3.5
3,344
9641 CROWN PRINCE LANE, Windermere, FL
0.46
Single-Family Home
$1,070,000
09/30/25
5
4
3,924
2641 HEMPEL AVENUE, Windermere, FL
0.27
Single-Family Home
$812,000
04/20/26
4
2
2,404
10506 DOWN LAKEVIEW CIRCLE, Windermere, FL
0.63
Single-Family Home
$1,150,000
11/13/25
4
3
3,888

Nearby homes

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Assigned Schools

These are the assigned schools for 2730 Midsummer Dr.
View nearby schools on GreatSchools
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 271 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

  • 80 % 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

Sourced by Trulia users. 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
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  • 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
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  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
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  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
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  • 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
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  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
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  • 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
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  • 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
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  • 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
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  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
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  • 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
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  • 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
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

56 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

79 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

93 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

98 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

86 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

26 rentals with an outdoor space in Windermere, FL

Homes for sale near 2730 Midsummer Dr

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Off Market Homes Near 2730 Midsummer Dr

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Frequently asked questions about 2730 Midsummer Dr

  • What is 2730 Midsummer Dr estimated to be worth?
    Trulia's estimated value for 2730 Midsummer Dr in Windermere, FL is $2,765,800.
  • What is the price history for 2730 Midsummer Dr?
    2730 Midsummer Dr in Windermere, FL last sold for $2,150,000 in May 2022.
  • Is Windermere a buyer's or seller's market?
    Windermere is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windermere?
    The median sale price in Windermere is $722K. That is up $50K from the prior month.
  • Does 2730 Midsummer Dr have air conditioning?
    Yes, 2730 Midsummer Dr in Windermere, FL has air conditioning.
  • Does 2730 Midsummer Dr have a pool?
    Yes, 2730 Midsummer Dr in Windermere, FL has a pool.