729 MAIN STREET, Windermere, FL 34786
OFF MARKET

729 MAIN STREET
Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,950 sqft (on 0.37 acres)

$2,052,700

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $14,131/mo*
Refinance Your Home

$2,052,700

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $14,131/mo*
Refinance Your Home
5 Beds
4 Baths
3,950 sqft
(on 0.37 acres)

Home Value

Trulia Estimate
$2.05M
Since last month
Decreased$9K (-0.4%)
Since last year
Decreased$13K (-0.7%)
Since last sale
Decreased$18K (-0.9%)
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 +33% in the last 10 years
MonthEstimated value
2026
August 2026$2.05M
July 2026$2.06M
June 2026$2.07M
May 2026$2.05M
April 2026$2.04M
March 2026$2.01M
February 2026$2.03M
January 2026$2.03M
2025
2024
2023
2022
2021
2020

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
830 OAKDALE STREET, Windermere, FL
0.08
Single-Family Home
$1,700,000
10/10/25
4
4.5
3,670
1020 OAKDALE STREET, Windermere, FL
0.24
Single-Family Home
$2,171,470
04/29/26
5
4.5
3,994
735 OAKDALE STREET, Windermere, FL
0.07
Single-Family Home
$910,000
05/09/26
3
2.5
2,475
1002 OAKDALE STREET, Windermere, FL
0.21
Single-Family Home
$890,000
08/11/26
4
3
3,516
81 OAKDALE STREET, Windermere, FL
0.62
Single-Family Home
$2,200,000
07/31/26
5
4.5
4,284
720 MAIN STREET, Windermere, FL
0.05
Single-Family Home
$850,000
10/21/25
3
2
2,778
635 BUTLER STREET, Windermere, FL
0.18
Single-Family Home
$975,000
10/20/25
3
3
2,353
316 E 5TH AVENUE, Windermere, FL
0.27
Single-Family Home
$1,050,000
05/21/26
4
3
2,412
409 W 2ND AVENUE, Windermere, FL
0.59
Single-Family Home
$2,250,000
03/09/26
5
4.5
4,688
616 MAGNOLIA STREET, Windermere, FL
0.16
Single-Family Home
$830,000
10/27/25
4
2
2,582

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
826 OAKDALE STREET, Windermere, FL 34786
0.07
$1,378,500
4
6
3,753
Off Market
830 OAKDALE STREET, Windermere, FL 34786
0.08
$1,697,600
4
4.5
3,670
Off Market
836 OAKDALE STREET, Windermere, FL 34786
0.09
$2,067,000
4
4.5
3,917
Off Market
735 OAKDALE STREET, Windermere, FL 34786
0.07
$910,000
3
2.5
2,475
Recently Sold
825 OAKDALE STREET, Windermere, FL 34786
0.10
$770,000
3
2
1,664
Recently Sold
713 MAIN STREET, Windermere, FL 34786
0.04
$2,170,000
6
5
5,031
For Sale
720 MAIN STREET, Windermere, FL 34786
0.05
$850,000
3
2
2,778
Recently Sold
925 MAIN STREET, Windermere, FL 34786
0.14
$1,045,800
5
2.5
2,971
Off Market
116 W 7TH AVENUE, Windermere, FL 34786
0.09
$1,014,700
3
3
2,412
Off Market
120 W 7TH AVENUE, Windermere, FL 34786
0.11
$1,446,800
4
5
3,191
Off Market
721 MAGNOLIA STREET, Windermere, FL 34786
0.15
$712,200
4
2
1,737
Off Market

Local Information

  • Map ViewExplore the area around 729 MAIN STREET.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2015
Lot Size
0.37 acres
Living Area
3,950 sqft
Price/Sqft
$520
Parking
4 Car Garage
HOA
None

About this House

This custom home is truly a gem, blending luxury, craftsmanship, and the charm of small-town Windermere living. The attention to detail in every feature—from the stunning architectural design to the thoughtfully designed interiors—is remarkable. With its premium corner lot location, this home is not only a private oasis but also perfectly situated to take advantage of the vibrant and community-oriented lifestyle in Downtown Windermere. Key highlights that stand out are, 1. PRIME LOCATION: Nestled on a spacious 0.37-acre corner lot in the heart of Downtown Windermere, providing easy access to local amenities, tennis courts, events and lake activities.2.EXQUISITE CRAFTSMANSHIP: Rich wood finishes, solid wood beams, spray foam insulation, energy efficient doors and windows, recently added temperature controlled 1,000+ bottle wine cellar and unique details throughout create a warm yet sophisticated ambiance.3. GOURMET CHEF'S KITCHEN: High-end Wolf appliances, large walk-in pantry, and farmhouse-inspired design—perfect for entertaining or family gatherings.4. INDOOR-OUTDOOR LIVING: Heated saltwater pool, the summer kitchen including hibachi cooktop and inviting lanai seamlessly integrate with the interior living spaces for year-round enjoyment.5. MASTERFUL LAYOUT: Spacious bedrooms, versatile lofts, luxurious master suite with vaulted ceilings and two walk in closets, relaxing outdoor spaces on the front porch and backyard oasis and expansive driveway.6. MODERN CONVENIENCES: Energy-efficient features, remote controlled window shades, smart home lighting, natural gas generator, security cameras, gas fireplace, dual ovens, dual dishwashers, dual kitchen sinks and a climate-controlled 4-car garage ideal for car enthusiasts.7. CHARMING COMMUNITY: Enjoy golf-cart-friendly streets, farmer’s markets, food trucks, parks, enchanting boutiques, boating on the Butler Chain of Lakes and the new village center opening soon. This property offers a rare blend of luxury, functionality, and a welcoming community vibe. It’s a dream home for anyone seeking an elegant yet relaxed lifestyle in one of Central Florida’s most desirable locations. This home is move in ready and perfect for you!
729 MAIN STREET, Windermere, FL 34786 is a 5 bedroom, 4 bathroom, 3,950 sqft single-family home built in 2015. It last sold for $2,065,000 on Jul 14, 2025 (2% below the $2,100,000 asking price). It is currently off market. The Trulia Estimate is $2,052,700, with a rent estimate of $5,808/month.
Last check for updates: about 13 hours ago
Listed by Billinda Boldt, (321) 436-6059
COLDWELL BANKER RESIDENTIAL RE, (407) 647-1211
Bought with: Non-Member Agent, STELLAR NON-MEMBER OFFICE, (000) 000-0000
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#S5116063
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 729 MAIN STREET

Interior Features

Interior Details
Number of Rooms: 12Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Den, Dining Room, Family Room, Kitchen, Living Room, Loft, Media Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 3950 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Natural Gas ConnectedAppliances: Bar Fridge, Dishwasher, Disposal, Dryer, Exhaust Fan, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water SoftenerDishwasherDisposalDryerLaundry: Inside,Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Family Room, GasHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window TreatmentsFlooring: Carpet, Ceramic Tile, Concrete, Travertine, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Ceramic Tile, Concrete, Travertine, Hardwood
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Irrigation SystemFoundation: Stem WallHas a Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageParking Spaces: 4Parking: Garage Door Opener
Pool
Pool: Gunite, Heated, In Ground, Salt Water, Self CleaningPool
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 193

Property Information

Year Built
Year Built: 2015
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: HardiPlank Type, Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 172328933601470

Price & Status

Price
List Price: $2,100,000
Status Change & Dates
Off Market Date: Sat Jun 28 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINDERMERECommunity: WINDERMERE TOWN
School Information
Elementary School: Windermere ElemJr High / Middle School: Gotha MiddleHigh School: Olympia High

Building

Building Area
Building Area: 7358 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.37 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: S5116063Back On Market Date: Tue May 27 2025Showing Advance Notice: 24Showing AttendedShowing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent, Listing Agent Must AccompanyUniversal Property Id: US-12095-N-172328933601470-R-N

Price and Tax history

DateEventPrice
Jul 14, 2025
Source: Stellar MLS #S5116063
Sold
$2,065,000
Jun 30, 2025
Source: Stellar MLS #S5116063
Pending
$2,100,000
May 27, 2025
Source: Stellar MLS #S5116063
Listed For Sale
$2,100,000
May 13, 2025
Source: Stellar MLS #S5116063
ListingRemoved
$2,150,000
Apr 28, 2025
Source: Stellar MLS #S5116063
PriceChange
$2,150,000
Price decreased by 6%

Market trends in Windermere

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
296
11MoM

Around this home

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
    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
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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
    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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LGBTQ Local Legal Protections

Frequently asked questions about 729 MAIN STREET

  • What is 729 MAIN STREET estimated to be worth?
    Trulia's estimated value for 729 MAIN STREET in Windermere, FL is $2,052,700.
  • What is the price history for 729 MAIN STREET?
    729 MAIN STREET in Windermere, FL last sold for $2,065,000 in July 2025.
  • 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 $814K. That is up $92.5K from the prior month.
  • Does 729 MAIN STREET have air conditioning?
    Yes, 729 MAIN STREET in Windermere, FL has air conditioning.
  • Does 729 MAIN STREET have a pool?
    Yes, 729 MAIN STREET in Windermere, FL has a pool.

Explore by feature - Pet Friendly

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