2729 Midsummer Dr, Windermere, FL 34786
Abundance of windows and natural light
Bedroom 3
OFF MARKET

2729 Midsummer Dr
Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 3,044 sqft (on 1.04 acres)

$1,039,600

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $7,199/mo*
Refinance Your Home

$1,039,600

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $7,199/mo*
Refinance Your Home
3 Beds
3 Baths
3,044 sqft
(on 1.04 acres)

Local Information

  • Map ViewExplore the area around 2729 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
1978
Lot Size
1.04 acres
Living Area
3,044 sqft
Price/Sqft
$342
Parking
Garage

About this House

Butler Chain of Lakes Access. Charming one story home located in a desirable lake community with spacious one + acre homesites. High elevation with lake views from the front and private fenced yard with tennis court in the back. Long drive is lined with mature azaleas and shaded by oaksâ¦room for boat and rv parking. Open plan features wood and beamed vaulted ceilings, stone fireplace, crown molding and tile floors throughout. Excellent condition with new roof, septic and a/c. Screened porch extends the kitchen family room. New 30' x 40' secondary detached CMU garage. HOA dues $100 per year covers nearby boat ramp. Convenient location with easy access to 408, golf, shopping and dining.
2729 Midsummer Dr, Windermere, FL 34786 is a 3 bedroom, 3 bathroom, 3,044 sqft single-family home built in 1978. It last sold for $542,500 on Mar 4, 2019. It is currently off market. The Trulia Estimate is $1,039,600, with a rent estimate of $5,631/month.

Home Details for 2729 Midsummer Dr

Interior Features

Heating & Cooling
Heating: Other, ElectricAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Interior Details
Additional StorageNumber of Rooms: 8Types of Rooms: Dining Room, Family Room, Laundry Room, Master Bath, WorkshopStorage
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: StonePatio
Parking & Garage
GarageParking Spaces: 10Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1978Year Updated: 1979
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 1.04 acres

Mobile R/V

RV Parking
Rv Parking

Building

Fitness & Sports
Tennis Court

Price History for 2729 Midsummer Dr

DatePriceEventSource
03/04/2019$542,500Sold
N/A
01/22/2019$569,900PendingAgent Provided
11/15/2018$569,900Listed For SaleAgent Provided
03/17/2005$375,000Sold
N/A
06/29/1994$173,000Sold
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$12,081
Assessment$760,555
Home facts updated by county records

Comparable Sales for 2729 Midsummer Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9538 LAVILL COURT, Windermere, FL
0.26
Single-Family Home
$799,000
08/22/25
4
3
2,748
2641 HEMPEL AVENUE, Windermere, FL
0.19
Single-Family Home
$812,000
04/20/26
4
2
2,404
2828 INGEBORG COURT, Windermere, FL
0.16
Single-Family Home
$1,220,000
01/23/26
5
4.5
3,190
2722 PARK ROYAL DRIVE, Windermere, FL
0.34
Single-Family Home
$950,000
04/20/26
4
3
2,967
9631 HOLLYGLEN PLACE, Windermere, FL
0.38
Single-Family Home
$710,000
11/25/25
4
2.5
2,854
9792 WILD OAK DRIVE, Windermere, FL
0.40
Single-Family Home
$700,000
02/13/26
3
3.5
3,102
9641 CROWN PRINCE LANE, Windermere, FL
0.37
Single-Family Home
$1,070,000
09/30/25
5
4
3,924
2806 WINDSOR HILL DRIVE, Windermere, FL
0.46
Single-Family Home
$1,040,000
06/12/26
4
3
3,181
9447 WESTOVER CLUB CIRCLE, Windermere, FL
0.44
Single-Family Home
$765,000
09/10/25
4
3
2,568
2624 MIDSUMMER DRIVE, Windermere, FL
0.19
Single-Family Home
$2,500,000
09/05/25
4
2.5
4,667

Nearby homes

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Assigned Schools

These are the assigned schools for 2729 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 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

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
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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
    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
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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
    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
    Flag
  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

43 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

67 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

79 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

21 rentals with an outdoor space in Windermere, FL

Homes for sale near 2729 Midsummer Dr

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Off Market Homes Near 2729 Midsummer Dr

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Frequently asked questions about 2729 Midsummer Dr

  • What is 2729 Midsummer Dr estimated to be worth?
    Trulia's estimated value for 2729 Midsummer Dr in Windermere, FL is $1,039,600.
  • What is the price history for 2729 Midsummer Dr?
    2729 Midsummer Dr in Windermere, FL last sold for $542,500 in March 2019.
  • 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 2729 Midsummer Dr have air conditioning?
    Yes, 2729 Midsummer Dr in Windermere, FL has air conditioning.
  • Does 2729 Midsummer Dr have laundry facilities?
    Yes, 2729 Midsummer Dr in Windermere, FL has laundry facilities.