2740 Midsummer Dr, Windermere, FL 34786
Property image
Property image
OFF MARKET

$3,506,700

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

2740 Midsummer Dr, Windermere, FL 34786

Est. Refi. Payment $25,513/mo*
Refinance Your Home
Currently Off Market - Sold Nov 1, 2018 for $1,425,000

Home Value

Trulia Estimate
$3.51M
Since last month
Decreased$135K (-3.7%)
Since last year
Increased$118K (+3.5%)
Since last sale
Increased$2M (+143.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +191% in the last 10 years
MonthEstimated value
2026
October 2026$3.47M
September 2026$3.51M
August 2026$3.61M
July 2026$3.53M
June 2026$3.59M
May 2026$3.53M
April 2026$3.44M
March 2026$3.51M
February 2026$3.57M
January 2026$3.58M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2722 INGEBORG COURT, Windermere, FL
0.20
Single-Family Home
$850,000
08/10/26
4
2.5
2,619
2828 INGEBORG COURT, Windermere, FL
0.23
Single-Family Home
$1,220,000
01/23/26
5
4.5
3,190
2641 HEMPEL AVENUE, Windermere, FL
0.29
Single-Family Home
$812,000
04/20/26
4
2
2,404
Address Not Disclosed, Windermere, FL
0.54
Single-Family Home
$2,750,000
07/27/26
4
4
4,194
2722 PARK ROYAL DRIVE, Windermere, FL
0.47
Single-Family Home
$950,000
04/20/26
4
3
2,967
2014 DOWN WOODS LANE, Windermere, FL
0.65
Single-Family Home
$1,390,000
07/28/26
4
3.5
3,344
10506 DOWN LAKEVIEW CIRCLE, Windermere, FL
0.64
Single-Family Home
$1,150,000
11/13/25
4
3
3,888
9631 HOLLYGLEN PLACE, Windermere, FL
0.41
Single-Family Home
$710,000
11/25/25
4
2.5
2,854
2806 WINDSOR HILL DRIVE, Windermere, FL
0.60
Single-Family Home
$1,040,000
06/12/26
4
3
3,181
325 MAGNOLIA STREET, Windermere, FL
0.92
Single-Family Home
$2,249,000
07/06/26
4
3
3,975

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
2730 Midsummer Dr, Windermere, FL 34786
0.03
$2,784,100
4
3.5
3,452
Off Market
2730 Midsummer Dr #14, Windermere, FL 34786
0.03
-
-
-
-
Off Market
2804 MIDSUMMER DRIVE LOT 12, Windermere, FL 34786
0.03
-
-
-
-
Off Market
2804 MIDSUMMER DRIVE, Windermere, FL 34786
0.03
$2,555,900
-
-
-
Off Market
2720 Midsummer Dr, Windermere, FL 34786
0.05
$4,305,900
4
2
2,614
Off Market
2814 Midsummer Dr, Windermere, FL 34786
0.05
$2,206,700
4
3
2,582
Off Market
2710 Midsummer Dr, Windermere, FL 34786
0.07
-
4
5
4,139
Off Market
2824 Midsummer Dr, Windermere, FL 34786
0.08
$2,480,400
4
3
2,639
Off Market
2834 Midsummer Dr, Windermere, FL 34786
0.10
$4,309,300
3
2
2,773
Off Market
2803 Midsummer Dr, Windermere, FL 34786
0.12
$1,044,400
4
3
3,100
Off Market
2700 Midsummer Dr, Windermere, FL 34786
0.12
$4,378,500
4
4
4,000
Off Market
2844 Midsummer Dr, Windermere, FL 34786
0.13
$2,829,600
4
4
3,328
Off Market
2813 Midsummer Dr, Windermere, FL 34786
0.13
$1,159,500
4
3
3,623
Off Market
2739 Midsummer Dr, Windermere, FL 34786
0.13
$972,000
4
3
3,080
Off Market
2823 Midsummer Dr, Windermere, FL 34786
0.13
$1,265,000
4
4
3,506
Off Market
2729 Midsummer Dr, Windermere, FL 34786
0.14
$1,044,000
3
3
3,044
Off Market
2719 Midsummer Dr, Windermere, FL 34786
0.14
$1,005,900
3
3
2,810
Off Market
2624 MIDSUMMER DRIVE, Windermere, FL 34786
0.15
$2,498,900
4
2.5
4,667
Off Market
2624 MIDSUMMER DRIVE LOT 19, Windermere, FL 34786
0.15
$2,500,000
-
-
-
Recently Sold
2833 Midsummer Dr, Windermere, FL 34786
0.15
$1,561,100
4
3.5
3,349
Off Market

Local Information

  • Map ViewExplore the area around 2740 Midsummer Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1984
2.63 acre lot
2,550 sqft
$1,375/sqft
Garage

About this House

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!
2740 Midsummer Dr, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,550 sqft single-family home built in 1984. It last sold for $1,425,000 on Nov 1, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,506,700.

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 and Tax history

DateEventPrice
Nov 1, 2018
Source: N/A
Sold
$1,425,000
Aug 31, 2018
Source: Agent Provided
Listed For Sale
$1,495,000

Market trends in Windermere

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$856K
$41.5KMoM
Sale-to-List Price
96.8%
0.4%MoM
Price per sq ft
$297
$5MoM
Available listings
274
22MoM

Around this home

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
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2740 Midsummer Dr

  • What is 2740 Midsummer Dr estimated to be worth?
    Trulia's estimated value for 2740 Midsummer Dr in Windermere, FL is $3,506,700.
  • What is the price history for 2740 Midsummer Dr?
    2740 Midsummer Dr in Windermere, FL last sold for $1,425,000 in November 2018.
  • 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 $856K. That is up $41.5K from the prior month.
  • Does 2740 Midsummer Dr have air conditioning?
    Yes, 2740 Midsummer Dr in Windermere, FL has air conditioning.
  • How big is the lot at 2740 Midsummer Dr?
    The lot at 2740 Midsummer Dr in Windermere, FL is about 2.6 acres.

Explore by feature - Pet Friendly

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Off Market Homes Near 2740 Midsummer Dr

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