1027 MAIN STREET, Windermere, FL 34786
OFF MARKET

$725,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,596 sqft (on 0.29 acres)

1027 MAIN STREET, Windermere, FL 34786

Est. Refi. Payment $5,065/mo*
Refinance Your Home
Currently Off Market - Sold Mar 22, 2024 for $690,000

Home Value

Trulia Estimate
$725K
Since last month
Increased$700 (+0.1%)
Since last year
Increased$46K (+6.8%)
Since last sale
Increased$34K (+4.9%)
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 +120% in the last 10 years
MonthEstimated value
2026
August 2026$724K
July 2026$723K
June 2026$724K
May 2026$728K
April 2026$720K
March 2026$721K
February 2026$721K
January 2026$707K
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
825 OAKDALE STREET, Windermere, FL
0.19
Single-Family Home
$770,000
06/11/26
3
2
1,664
4 CHASE ROAD, Windermere, FL
0.15
Single-Family Home
$900,000
06/02/26
3
2
2,386
1209 MAIN STREET, Windermere, FL
0.16
Single-Family Home
$925,000
01/05/26
3
2
2,095
1002 OAKDALE STREET, Windermere, FL
0.05
Single-Family Home
$890,000
08/11/26
4
3
3,516
720 MAIN STREET, Windermere, FL
0.26
Single-Family Home
$850,000
10/21/25
3
2
2,778
735 OAKDALE STREET, Windermere, FL
0.26
Single-Family Home
$910,000
05/09/26
3
2.5
2,475
616 MAGNOLIA STREET, Windermere, FL
0.39
Single-Family Home
$830,000
10/27/25
4
2
2,582
635 BUTLER STREET, Windermere, FL
0.37
Single-Family Home
$975,000
10/20/25
3
3
2,353
416 MAGNOLIA STREET, Windermere, FL
0.56
Single-Family Home
$820,000
03/06/26
2
1.5
2,115
414 E 5TH AVENUE, Windermere, FL
0.52
Single-Family Home
$1,050,000
05/14/26
3
2
2,521

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
1020 OAKDALE STREET, Windermere, FL 34786
0.03
$2,171,470
5
4.5
3,994
Recently Sold
1020 OAKDALE STREET LOT 57, Windermere, FL 34786
0.03
-
-
-
-
Off Market
98 E 10TH AVE, Windermere, FL 34786
0.04
$1,824,700
4
3.5
3,650
Off Market
1003 MAIN STREET, Orlando, FL 34786
0.04
$774,000
3
3
2,005
Off Market
1002 OAKDALE STREET, Windermere, FL 34786
0.05
$890,000
4
3
3,516
Recently Sold
1106 OAKDALE STREET, Windermere, FL 34786
0.06
$834,400
3
2
1,965
Off Market
925 MAIN STREET, Windermere, FL 34786
0.11
$1,042,400
5
2.5
2,971
Off Market
1003 OAKDALE STREET, Windermere, FL 34786
0.14
$2,347,400
6
5.5
4,599
Off Market
2 CHASE ROAD LOT 19, Windermere, FL 34786
0.14
$520,000
-
-
-
Recently Sold
4 CHASE ROAD, Windermere, FL 34786
0.15
$900,000
3
2
2,386
Recently Sold
836 OAKDALE STREET, Windermere, FL 34786
0.16
$2,046,500
4
4.5
3,917
Off Market

Local Information

  • Map ViewExplore the area around 1027 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
1988
Lot Size
0.29 acres
Living Area
1,596 sqft
Price/Sqft
$455
Parking
2 Car Garage
HOA
None

About this House

HIGHEST and BEST by 2/8/2024 4PM... Do not miss this opportunity! Nestled in a neighborhood of million-dollar homes, do not miss the UNIQUE OPPORTUNITY to purchase this RARE GEM at a REASONABLE PRICE. This MOVE-IN READY home combines uniqueness and affordability in the charming downtown of Windermere. Enjoy the charm of this GOLF CART COMMUNITY and WALKING DISTANCE to BOAT RAMPS, PARKS. TENNIS COURTS and exclusive RESIDENT-ONLY ACCESS to the Butler Chain of Lakes. METICULOUSLY CARED FOR, this residence was recently updated with a NEW ROOF and NEW HYBRID HOT WATER HEATER. The DOUBLE PANE WINDOWS enhance IMPROVED ENERGY EFFICIENCY and tranquility with reduced outdoor noise. This home features the DESIRED SPLIT FLOOR PLAN, offering optimal privacy and functionality. Enjoy the LUSH, MATURE and MANICURED LANDSCAPING that surrounds the property, offering a PRIVATE OASIS in the FENCED BACKYARD. With a well and septic system, say GOODBYE to water and sewer bills. This property offers FINANCIAL EFFICIENCY, NO HOA and MINIMAL UTILITY COST. This is an upscale community with natural beauty, making this home an idyllic retreat for those who appreciate both opulence and the charm of the great outdoors. Enjoy the CONVENIENCE of easy commuting, situated with its strategic proximity to major highways, excellent dining, shopping and entertainment. This residence is in a sought-after area with EXCELLENT SCHOOLS. YOUR AFFORDABLE DREAM HOME AWAITS in a HIGHLY DESIRED location. Call us for your private showing today and make this beautiful home yours, before it's gone! Exclusively for approved buyers only. Transferrable TERMITE BOND and transferrable WARRANTY for new roof ( 3month old)is available. This home also has SECURITY SYSTEM and VIDEO DOOR BELL For an immerse view, DONT MISS our engaging LISTING VIDEO for a captivating experience!!!
1027 MAIN STREET, Windermere, FL 34786 is a 3 bedroom, 2 bathroom, 1,596 sqft single-family home built in 1988. It last sold for $690,000 on Mar 22, 2024 (1% above the $685,000 asking price). More recently, it was listed as a rental in July 2012 with an asking price of $1,750 per month. That rental listing was removed on July 17, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $725,400, with a rent estimate of $2,874/month.
Last check for updates: about 7 hours ago
Listed by Petra Bukalo PA, (407) 484-0685
FLORIDA REALTY INVESTMENTS, (407) 207-2220
Bought with: Julie Pickren, UPSIDE REAL ESTATE INC, (407) 308-5750
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6175273
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 1027 MAIN STREET

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Bathroom 2, Balcony Porch Lanai, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1596 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity AvailableAppliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, WasherDishwasherDisposalDryerLaundry: In GarageRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Wood BurningHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Carpet, Ceramic Tile, Engineered Hardwood
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Carpet, Ceramic Tile, Engineered Hardwood
View
No View
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Irrigation System, LightingFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 7

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 172328933600611

Price & Status

Price
List Price: $685,000
Status Change & Dates
Off Market Date: Thu Feb 08 2024

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: 2394 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.29 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6175273Showing Advance Notice: 24Showing AttendedShowing Considerations: Security SystemShowing Requirements: 24 Hour Notice, Appointment Only, Call Before Showing, Call Listing Agent, Listing Agent Must Accompany, See RemarksUniversal Property Id: US-12095-N-172328933600611-R-N

Price and Tax history

DateEventPrice
Mar 22, 2024
Source: Stellar MLS #O6175273
Sold
$690,000
Feb 10, 2024
Source: Stellar MLS #O6175273
Pending
$685,000
Feb 1, 2024
Source: Stellar MLS #O6175273
Listed For Sale
$685,000
Aug 10, 2012
Source: Stellar MLS #O5109884
Sold
$325,000
Jul 17, 2012
Source: Agent Provided
ListingRemoved
$1,750

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
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  • 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."
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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
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  • 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
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  • 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
    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 1027 MAIN STREET

  • What is 1027 MAIN STREET estimated to be worth?
    Trulia's estimated value for 1027 MAIN STREET in Windermere, FL is $725,400.
  • What is the price history for 1027 MAIN STREET?
    1027 MAIN STREET in Windermere, FL last sold for $690,000 in March 2024.
  • 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 1027 MAIN STREET have air conditioning?
    Yes, 1027 MAIN STREET in Windermere, FL has air conditioning.
  • Does 1027 MAIN STREET have laundry facilities?
    Yes, 1027 MAIN STREET in Windermere, FL has in-unit laundry.

Explore by feature - Pet Friendly

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Apartments for Rent

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Off Market Homes Near 1027 MAIN STREET

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