Is Windermere, FL dog-friendly?

As of early 2026, 93% of users say it's dog friendly

Does Windermere, FL have sidewalks?

As of early 2026, 92% of users say there are sidewalks

Is a car needed in Windermere, FL?

As of early 2026, 87% of users say car is needed

Is parking easy in Windermere, FL?

As of early 2026, 87% of users say parking is easy

Would people walk alone at night in Windermere, FL?

As of early 2026, 81% of users say people would walk alone at night

Is Windermere, FL quiet?

As of early 2026, 80% of users say it's quiet

Does Windermere, FL show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

Do kids play outside in Windermere, FL?

As of early 2026, 78% of users say kids play outside

Are the streets well-lit in Windermere, FL?

As of early 2026, 75% of users say streets are well-lit

Are yards well-kept in Windermere, FL?

As of early 2026, 64% of users say yards are well-kept

Do residents of Windermere, FL plan to stay at least 5 years?

As of early 2026, 60% of users say they plan to stay for at least 5 years

Is Windermere, FL walkable to grocery stores?

As of early 2026, 59% of users say it's walkable to grocery stores

Is there wildlife in Windermere, FL?

As of early 2026, 56% of users say there's wildlife

Is Windermere, FL walkable to restaurants?

As of early 2026, 55% of users say it's walkable to restaurants

Are neighbors friendly in Windermere, FL?

As of early 2026, 54% of users say neighbors are friendly

Are there community events in Windermere, FL?

As of early 2026, 40% of users say there are community events

What is the estimated monthly payment for 101 LEE STREET?

Based on a $1,300,000 list price with 20% down at today's rates, the estimated monthly payment for 101 LEE STREET in Windermere, FL is approximately $9,473 (about $7,090 principal & interest, $2,308 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.

How does the list price for 101 LEE STREET compare to homes in Windermere?

101 LEE STREET in Windermere, FL is listed at $1,300,000, about 51% above the $860K median sale price in Windermere .

What do residents say about Windermere?

Residents describe Windermere, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Windermere, FL .

What are the closest schools to 101 LEE STREET?

The closest schools to 101 LEE STREET in Windermere, FL are Gotha Middle School (rated 6/10), Olympia High School (rated 5/10), Windermere Elementary School (Pre-K, rated 10/10).

Does 101 LEE STREET have air conditioning?

Yes, 101 LEE STREET in Windermere, FL has air conditioning.

Does 101 LEE STREET have a pool?

Yes, 101 LEE STREET in Windermere, FL has a pool.

FOR SALE

OPEN SUN, 12-2PM

3D VIEW

0.42 ACRES

$1,300,000

$1,395,000

5 Beds
4 Baths
4,186 sqft (on 0.42 acres)

101 LEE STREET, Windermere, FL 34786

Est. Mortgage $9,421/mo*

Get Pre-Qualified

Home Highlights

Single-Family Home

Built in 1978

0.42 acre lot

$311/sqft

2 Car Garage

Local Information

Map ViewExplore the area around 101 LEE STREET.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

What's unique:Cozy gas fireplaceStylish home gymEn-suite bedroomPool deckGranite countertopsPrivate master suite

Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere’s weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.

Last check for updates: about 5 hours ago

Listing Provided by: Julie Bettosini, PA, (321) 689-9594

STOCKWORTH REALTY GROUP, (407) 909-5900

Jenny Dunn, (407) 580-7964

STOCKWORTH REALTY GROUP, (407) 909-5900

Originating MLS: Orlando Regional

Source: Stellar MLS, MLS#O6437573

Also Listed on Stellar MLS.

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

Open House

Sunday, November 01

12:00 PM to 2:00 PM

Home Details for 101 LEE STREET

Interior Features
Interior Details Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 5, Bathroom 4, Great Room, KitchenWet Bar
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout Living Area: 4186 Square Feet
Appliances & Utilities Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Water ConnectedAppliances: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa Fireplace: Family Room, GasHas a Fireplace
Gas & Electric Has Electric on Property
Windows, Doors, Floors & Walls Door: French Doors, Sliding DoorsFlooring: Tile, Hardwood
Levels, Entrance, & Accessibility Stories: 3Levels: Three Or MoreFloors: Tile, Hardwood
View No View
Security Security: Smoke Detector(s)

Exterior Features
Exterior Home Features Roof: ShinglePatio / Porch: Covered, Patio, ScreenedVegetation: Mature Landscaping, Trees/LandscapedExterior: Balcony, Irrigation System, Lighting, Private Entrance, Private Mailbox, Rain GuttersFoundation: SlabHas a Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,Garage Faces Side
Pool Pool: Gunite, In Ground, Lighting, Screen EnclosurePool
Frontage Waterfront: Lake Privileges, Boat Ramp - PrivateRoad Surface Type: DirtNot on Waterfront
Water & Sewer Sewer: Septic Tank

Days on Market
Cumulative Days on Market: 42Days on Market: 58

Property Information
Year Built Year Built: 1978
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence
Building Construction Materials: Stucco, Wood FrameNot a New ConstructionNo Additional Parcels
Property Information Parcel Number: 072328933201760

Price & Status
Price List Price: $1,300,000Price Per Sqft: $311

Active Status
MLS Status: Active

Media
See Virtual Tour

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

Agent Information
Listing Agent Listing ID: O6437573

Building
Building Area Building Area: 5791 Square Feet

Community
Community Features: Private Boat Ramp, Golf Carts OK, Park, Tennis Court(s)Not Senior Community

HOA
Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information
Lot Area: 0.42 acres

Listing Info
Special Conditions: None

Offer
Listing Terms: Cash, Conventional, VA Loan

Business
Business Information Ownership: Fee Simple

Miscellaneous
Mls Number: O6437573Back On Market Date: Wed Sep 16 2026Showing AttendedShowing Requirements: Appointment Only, Call Agent 2, Call Listing Agent, Listing Agent Must Accompany, See RemarksUniversal Property Id: US-12095-N-072328933201760-R-N

Additional Information
Private Boat RampGolf Carts OKParkTennis Court(s)

Price and Tax history

Date	Event	Price
Oct 28, 2026 Source: Stellar MLS #O6437573	PriceChange	$1,300,000 Price decreased by 7%
Sep 16, 2026 Source: Stellar MLS #O6437573	Listed For Sale	$1,395,000
Jan 27, 2026 Source: Stellar MLS #O6344558	ListingRemoved	$1,485,000
Dec 7, 2025 Source: Stellar MLS #O6344558	PriceChange	$1,485,000 Price decreased by 4%
Nov 4, 2025 Source: Stellar MLS #O6344558	PriceChange	$1,550,000 Price decreased by 6%
Sep 23, 2025 Source: Stellar MLS #O6344558	Listed For Sale	$1,650,000
Aug 19, 2019 Source: N/A	Sold	$765,000
May 22, 2019 Source: Agent Provided	Listed For Sale	$825,000
Oct 14, 2014 Source: N/A	Sold	$647,000
Sep 10, 2014 Source: Agent Provided	Pending	$699,000
Aug 4, 2014 Source: N/A	Sold	$727,175
Jul 10, 2014 Source: Agent Provided	PriceChange	$699,000 Price decreased by 7%
Jun 14, 2014 Source: Agent Provided	PriceChange	$749,000 Price decreased by 2%
May 6, 2014 Source: Agent Provided	Listed For Sale	$764,900
Sep 25, 2013 Source: N/A	Sold	$407,000
Aug 18, 2013 Source: N/A	PriceChange	$399,900 Price decreased by 2%
Aug 7, 2013 Source: Agent Provided	PriceChange	$407,900 Price decreased by 5%
Jul 6, 2013 Source: Agent Provided	Listed For Sale	$428,900
May 15, 2013 Source: N/A	Sold	$99,100
May 17, 2002 Source: N/A	Sold	$325,000
Mar 8, 2002 Source: N/A	Sold	$233,800
Nov 5, 1993 Source: N/A	Sold	$220,000

Year	Property tax	Tax assessment
2024	$11,349	$918,376

Around this home

Windermere Elementary School
PK-5
Public
510 Students
Orange County Public Schools
10/10
GreatSchools Rating
Parent Rating Average
I wanted to write this review in hopes that it helps other families—especially those relocating from out of state—who are searching for the right school for their child.When we moved to Florida, we initially enrolled our daughter in a well-known private school for kindergarten and first grade. Coming from a state where public schools were underfunded, overcrowded, and filled with overwhelmed teachers, we assumed a private school would provide a better experience. Unfortunately, that wasn’t the case. Despite the big promises, the reality was underwhelming and fell short in many ways.This year, our daughter attended Windermere Elementary School, and the experience has completely restored our faith in public education.From the very first day, we felt the difference. WES has an incredibly supportive and tight-knit community of parents, an exceptional PTO, and dedicated teachers—many of whom have been at the school for over a decade. Her 2nd-grade teacher has been at WES for 12+ years and brings not just experience, but true passion and care. She saw and nurtured our daughter’s unique strengths, made learning fun and engaging, and created a classroom environment that my child couldn’t wait to return to each day. She literally cried on the last day of school because she will miss her teacher so much.Leadership at WES is also something special. The principal and assistant principal know the students by name—and by heart. My daughter gives them a hug every morning at drop-off, which speaks volumes about the kind of culture they've built.Academically, the transformation has been incredible. After two years in private school and nearly $50,000 in tuition, our daughter entered WES below grade level. Thanks to her teacher’s support, she not only caught up—she grew two levels on state testing and made honor roll.If you're looking for a school that will nurture your child—not just academically, but emotionally and socially—look no further. Windermere Elementary School is everything we hoped for and more.
Parent Review
1y ago
9 Reviews

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

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.

92% say there are sidewalks
80% say there's holiday spirit
54% say neighbors are friendly

Trulia Trick or TreatStart Ghost Hunt

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
Resident
1y ago
"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
Resident
1y ago
"Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
0
Flag
Valentina
Resident
2y ago
"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
Resident
2y ago
"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
Resident
2y ago
"Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
0
Flag
Snkdrwbwms
Resident
2y ago
"Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
0
Flag
Juliana Daurio
Resident
2y ago
"Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
0
Flag
Datylberman
Resident
2y ago
"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
Resident
2y ago
"Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
0
Flag
Garrett Hendrickson
Resident
2y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"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
Resident
6y ago
"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
Resident
6y ago
"Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
3
Flag
Shariel A.
Resident
6y ago
"tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
1
Flag
Msldancer
Resident
6y ago
"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
Resident
6y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
2
Flag
Fabiana B.
Resident
6y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"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.
Resident
6y ago
"People are very family oriented. Neighbors came about the appearance and condition of their property."
0
Flag
Jessica
Resident
6y ago
"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.
Resident
6y ago
"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.
Resident
6y ago
"Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
0
Flag
Jessica M.
Visitor
6y ago
"Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
1
Flag
Jamesgkoshy
Resident
6y ago
"Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
0
Flag
Loypippin
Resident
7y ago
"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.
Resident
7y ago
"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.
Resident
7y ago
"Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
1
Flag
Princess J.
Resident
7y ago
"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
Resident
7y ago
"Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
0
Flag

Market trends in Windermere

Last updated September 2026

Avg. sale price

$860K

$4.17KMoM

Sale-to-List Price

96.7%

0.1%MoM

Price per sq ft

$301

$4MoM

Available listings

267

8MoM

Sourced by Trulia Market Trends

Home Value

Trulia Estimate

$1.24M

Since last month

$117K (-8.6%)

Since last year

$315K (-20.3%)

Since last sale

$472K (+61.7%)

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 +68% in the last 10 years

Month	Estimated value
2026
October 2026	$1.24M
September 2026	$1.35M
August 2026	$1.34M
July 2026	$1.35M
June 2026	$1.4M
May 2026	$1.4M
April 2026	$1.4M
March 2026	$1.4M
February 2026	$1.39M
January 2026	$1.39M
2025
December 2025	$1.39M
November 2025	$1.45M
October 2025	$1.55M
September 2025	$1.61M
August 2025	$1.39M
July 2025	$1.4M
June 2025	$1.42M
May 2025	$1.41M
April 2025	$1.41M
March 2025	$1.41M
February 2025	$1.39M
January 2025	$1.4M
2024
December 2024	$1.36M
November 2024	$1.37M
October 2024	$1.4M
September 2024	$1.37M
August 2024	$1.4M
July 2024	$1.43M
June 2024	$1.42M
May 2024	$1.46M
April 2024	$1.44M
March 2024	$1.43M
February 2024	$1.41M
January 2024	$1.36M
2023
December 2023	$1.38M
November 2023	$1.35M
October 2023	$1.37M
September 2023	$1.35M
August 2023	$1.32M
July 2023	$1.34M
June 2023	$1.33M
May 2023	$1.32M
April 2023	$1.31M
March 2023	$1.3M
February 2023	$1.24M
January 2023	$1.18M
2022
December 2022	$1.18M
November 2022	$1.18M
October 2022	$1.18M
September 2022	$1.18M
August 2022	$1.2M
July 2022	$1.22M
June 2022	$1.24M
May 2022	$1.22M
April 2022	$1.17M
March 2022	$1.17M
February 2022	$1.1M
January 2022	$1.07M
2021
December 2021	$1.05M
November 2021	$1.03M
October 2021	$1.02M
September 2021	$1.01M
August 2021	$991K
July 2021	$984K
June 2021	$937K
May 2021	$874K
April 2021	$860K
March 2021	$848K
February 2021	$840K
January 2021	$840K
2020
December 2020	$828K
November 2020	$824K
October 2020	$817K
September 2020	$801K
August 2020	$807K
July 2020	$796K
June 2020	$800K
May 2020	$800K
April 2020	$790K
March 2020	$782K
February 2020	$784K
January 2020	$778K
2019
December 2019	$780K
November 2019	$772K
October 2019	$771K
September 2019	$769K
August 2019	$766K
July 2019	$803K
June 2019	$807K
May 2019	$789K
April 2019	$809K
March 2019	$794K
February 2019	$800K
January 2019	$797K
2018
December 2018	$778K
November 2018	$758K
October 2018	$750K
September 2018	$776K
August 2018	$774K
July 2018	$785K
June 2018	$770K
May 2018	$786K
April 2018	$789K
March 2018	$783K
February 2018	$792K
January 2018	$791K
2017
December 2017	$811K
November 2017	$782K
October 2017	$790K
September 2017	$794K
August 2017	$783K
July 2017	$783K
June 2017	$777K
May 2017	$774K
April 2017	$772K
March 2017	$757K
February 2017	$765K
January 2017	$755K
2016
December 2016	$733K
November 2016	$734K
October 2016	$734K

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
316 E 5TH AVENUE, Windermere, FL	0.24	Single-Family Home	$1,050,000	05/21/26	4	3	2,412
725 OAKDALE STREET, Windermere, FL	0.27	Single-Family Home	$1,000,000	08/28/26	3	2.5	2,795
735 OAKDALE STREET, Windermere, FL	0.28	Single-Family Home	$910,000	05/09/26	3	2.5	2,475
412 FOREST STREET, Windermere, FL	0.52	Single-Family Home	$765,000	07/30/26	5	2.5	2,539
1002 OAKDALE STREET, Windermere, FL	0.42	Single-Family Home	$890,000	08/11/26	4	3	3,516
706 OAKDALE STREET, Windermere, FL	0.31	Single-Family Home	$850,000	10/14/26	3	3	2,048
415 E 6TH AVENUE, Windermere, FL	0.16	Single-Family Home	$710,000	02/19/26	3	2	1,784
606 E 6TH AVENUE, Windermere, FL	0.08	Single-Family Home	$2,175,000	06/18/26	4	4.5	4,471
1020 OAKDALE STREET, Windermere, FL	0.44	Single-Family Home	$2,171,470	04/29/26	5	4.5	3,994
414 E 5TH AVENUE, Windermere, FL	0.18	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
517 E 6th Ave, Windermere, FL 34786	0.02	$1,620,100	5	5	5,376	Off Market
517 E 6th Ave, Windermere, FL 34786	0.02	-	-	-	-	Off Market
605 E 6th Ave, Windermere, FL 34786	0.03	$801,400	3	3	1,995	Off Market
105 Lee St, Windermere, FL 34786	0.03	$1,101,800	5	3	3,472	Off Market
509 E 6th Ave, Windermere, FL 34786	0.04	$683,300	3	2	1,811	Off Market
580 Ridgewood Dr, Windermere, FL 34786	0.04	$1,469,100	5	6	3,947	Off Market
610 Ridgewood Dr, Windermere, FL 34786	0.05	$1,355,600	5	3	4,151	Off Market
540 Ridgewood Dr, Windermere, FL 34786	0.05	$1,027,000	4	4	2,474	Off Market
515 E 6th Ave, Windermere, FL 34786	0.06	$838,700	4	4	2,591	Off Market
446 E 7th Ave, Windermere, FL 34786	0.06	-	-	-	-	Off Market
530 Ridgewood Dr, Windermere, FL 34786	0.06	$928,200	4	3	2,569	Off Market
611 E 6TH AVENUE LOT E21, Windermere, FL 34786	0.07	$650,000	-	-	-	Recently Sold
520 Ridgewood Dr, Windermere, FL 34786	0.07	$811,100	4	3	2,165	Off Market
510 Ridgewood Dr, Windermere, FL 34786	0.08	$834,500	4	3	2,744	Off Market
606 E 6TH AVENUE, Windermere, FL 34786	0.08	$2,175,000	4	4.5	4,471	Recently Sold
436 E 7TH AVENUE, Windermere, FL 34786	0.08	$2,175,000	4	5	3,136	For Sale
436 E 7th Ave #171, Windermere, FL 34786	0.08	-	-	-	-	Off Market
616 RIDGEWOOD DRIVE LOT E29, Windermere, FL 34786	0.08	$790,000	-	-	-	Recently Sold
618 RIDGEWOOD DRIVE LOT E30, Windermere, FL 34786	0.08	$810,000	-	-	-	Recently Sold
622 RIDGEWOOD DRIVE LOT E18, Windermere, FL 34786	0.08	$700,000	-	-	-	Recently Sold

LGBTQ Local Legal Protections

Additional Cost

Julie Bettosini, PA, STOCKWORTH REALTY GROUP, (407) 909-5900

Agent Phone: (321) 689-9594

Similar Homes You May Like

Skip to last item

0.55 ACRES
$1,369,000
5 bd
3.5 ba
3,274 sqft
9019 SPENCE COURT,
Gotha, FL 34734
LAKEFIELD REALTY GROUP LLC
1.2 ACRES
$1,750,000
3 bd
4 ba
3,287 sqft
9958 KILGORE ROAD,
Orlando, FL 32836
THE REAL ESTATE COLLECTION LLC
0.39 ACRES
$1,200,000
4 bd
3 ba
2,813 sqft
3625 WATERS EDGE DRIVE,
Belle Isle, FL 32812
KELLER WILLIAMS REALTY AT THE LAKES
0.38 ACRES
$1,879,000
4 bd
3.5 ba
3,005 sqft
220 ADAMS DRIVE,
Maitland, FL 32751
KELLY PRICE & COMPANY LLC
1.02 ACRES
$1,425,000
4 bd
3 ba
3,955 sqft
2214 EARLEAF COURT,
Longwood, FL 32779
LA ROSA REALTY KISSIMMEE
0.93 ACRES
$1,100,000
4 bd
3.5 ba
3,967 sqft
9642 BEAR LAKE ROAD,
Apopka, FL 32703
KELLER WILLIAMS HERITAGE REALTY
1.71 ACRES
$759,000
4 bd
2 ba
2,300 sqft
114 WAYLAND CIRCLE,
Longwood, FL 32779
GALLERY PROPERTIES INTERNATIONAL
0.5 ACRES
$1,200,000
4 bd
3 ba
3,145 sqft
10370 TROUT ROAD,
Orlando, FL 32836
SERHANT
$849,500
4 bd
4 ba
2,688 sqft
442 BRIERCLIFF DRIVE,
Orlando, FL 32806
HOPKEY REALTY
0.48 ACRES
$1,395,000
4 bd
4 ba
3,997 sqft
9548 CROWN PRINCE LANE,
Windermere, FL 34786
DOUGLAS ELLIMAN
OPEN SUN, 2-4PM
$848,000
4 bd
3.5 ba
2,399 sqft
2501 NANCY STREET,
Orlando, FL 32806
FLORIDA REALTY INVESTMENTS
0.47 ACRES
$1,899,999
4 bd
3 ba
3,789 sqft
15210 E OAKLAND AVENUE,
Winter Garden, FL 34787
EXP REALTY LLC
0.26 ACRES
$725,000
4 bd
2 ba
2,326 sqft
4123 FALLWOOD CIRCLE,
Orlando, FL 32812
ALVES AND HOWELL REALTY
1.01 ACRES
$1,299,000
5 bd
3 ba
3,356 sqft
2540 HEMPEL COVE CT,
Windermere, FL 34786
ALIGN REAL ESTATE LLC
$1,499,000
5 bd
5.5 ba
4,266 sqft
1229 GRAND TRAVERSE PARKWAY,
Kissimmee, FL 34747
REAL BROKER, LLC
OPEN SAT, 11-2PM
0.35 ACRES
$949,000
4 bd
3 ba
2,931 sqft
1281 WELLINGTON TERRACE,
Maitland, FL 32751
NOELKE REALTY
$929,000
5 bd
4 ba
3,012 sqft
26 BACKSPIN LANE,
Orlando, FL 32804
LPT REALTY, LLC
OPEN SAT, 11-2PM
1.11 ACRES
$969,000
3 bd
3 ba
2,346 sqft
14140 COUNTRY ESTATE DRIVE,
Winter Garden, FL 34787
CHARLES RUTENBERG REALTY ORLANDO
0.44 ACRES
$1,250,000
5 bd
3.5 ba
3,815 sqft
4509 PATRICIA ANN COURT,
Orlando, FL 32839
KELLER WILLIAMS ADVANTAGE 2 REALTY
OPEN SUN, 1-3PM
$1,099,000
3 bd
3.5 ba
2,273 sqft
1707 ASHER LANE,
Orlando, FL 32803
FANNIE HILLMAN & ASSOCIATES
OPEN SUN, 1-3PM
0.34 ACRES
$985,000
5 bd
3 ba
3,296 sqft
2330 WESTMINSTER CT.,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
1.23 ACRES
$1,699,999
5 bd
6 ba
6,250 sqft
334 VISTA OAK DRIVE,
Longwood, FL 32779
MARGAUX REALTY INC
7.39 ACRES
$1,400,000
5 bd
3 ba
3,300 sqft
12305 HOWEY CROSS ROAD,
Clermont, FL 34715
CHARLES RUTENBERG REALTY ORLANDO
0.54 ACRES
$899,000
5 bd
4 ba
5,194 sqft
12634 VALENCIA DRIVE,
Clermont, FL 34711
ALL REAL ESTATE & INVESTMENTS
0.38 ACRES
$1,498,000
3 bd
4 ba
2,467 sqft
1841 LAKE SPIER DRIVE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
0.26 ACRES
$1,699,000
4 bd
3.5 ba
3,307 sqft
2343 VERSAILLES AVENUE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
NEW CONSTRUCTION
$1,549,900
4 bd
3.5 ba
3,183 sqft
2630 HARRISON AVENUE,
Orlando, FL 32804
RE/MAX EXCLUSIVE COLLECTION
1.51 ACRES
$1,388,000
5 bd
5 ba
4,975 sqft
305 SWEETWATER CLUB CIRCLE,
Longwood, FL 32779
LPT REALTY, LLC
0.49 ACRES
$945,000
5 bd
4.5 ba
4,482 sqft
5240 ALLEMAN DRIVE,
Orlando, FL 32809
MAINFRAME REAL ESTATE
1.42 ACRES
$885,000
3 bd
2.5 ba
2,360 sqft
1825 DEMASTUS LANE,
Ocoee, FL 34761
BHHS FLORIDA REALTY
$900,000
4 bd
2.5 ba
3,684 sqft
637 LAKE HARBOR CIRCLE,
Orlando, FL 32809
DERENTHAL REALTY
0.28 ACRES
$1,800,000
5 bd
4.5 ba
4,029 sqft
281 BREWER AVENUE,
Winter Park, FL 32789
HENTHORN REAL ESTATE
0.77 ACRES
$1,499,000
4 bd
3.5 ba
3,277 sqft
16930 WINTER ROAD,
Montverde, FL 34756
SERHANT
$720,000
4 bd
3 ba
2,319 sqft
7698 MOUNT CARMEL DRIVE,
Orlando, FL 32835
WRA BUSINESS & REAL ESTATE
$1,495,000
5 bd
4.5 ba
3,122 sqft
1206 W HARVARD STREET,
Orlando, FL 32804
PREMIER SOTHEBY'S INTL. REALTY
$1,625,000
5 bd
4.5 ba
3,133 sqft
2407 LAFAYETTE AVENUE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
0.36 ACRES
$1,750,000
5 bd
4.5 ba
4,342 sqft
8826 SOUTHERN BREEZE DRIVE,
Orlando, FL 32836
CHARLES RUTENBERG REALTY ORLANDO
$1,090,000
6 bd
4 ba
3,834 sqft
6921 ARNOLDSON STREET,
Orlando, FL 32827
MCO REALTY GROUP LLC
0.48 ACRES
$1,649,999
6 bd
6 ba
5,096 sqft
9102 S BAY DRIVE,
Orlando, FL 32836
IAD REAL ESTATE
$1,250,000
5 bd
3 ba
3,415 sqft
2107 HARGILL DRIVE,
Orlando, FL 32806
CHARLES RUTENBERG REALTY ORLANDO
See more homes for sale in
Windermere
Take a look

Skip to first item

New Listings near 101 LEE STREET

Skip to last item

COMING SOON
1.08 ACRES
$1,100,000
4 bd
4 ba
3,348 sqft
14038 BLUEBIRD PARK ROAD,
Windermere, FL 34786
RE/MAX TOWN & COUNTRY REALTY
NEW
COMING SOON
0.41 ACRES
$1,250,000
4 bd
3.5 ba
4,175 sqft
1521 LAKE WHITNEY DRIVE,
Windermere, FL 34786
EXP REALTY LLC
OPEN SAT, 11-3PM
0.32 ACRES
$799,000
4 bd
2 ba
2,081 sqft
7606 ORANGE TREE LANE,
Orlando, FL 32819
KELLER WILLIAMS CLASSIC
NEW - 1 DAY AGO
$699,000
3 bd
2 ba
1,896 sqft
6339 COOPERS GREEN COURT,
Orlando, FL 32819
KAZA REAL ESTATE LLC
$1,595,000
5 bd
4.5 ba
3,652 sqft
7002 PHILLIPS COVE COURT,
Orlando, FL 32819
TONYDAVIDSHOMES.COM, LLC
0.28 ACRES
$825,000
4 bd
4 ba
3,078 sqft
2139 TILLMAN AVENUE,
Winter Garden, FL 34787
LA ROSA REALTY LLC
0.28 ACRES
$710,000
4 bd
3 ba
2,643 sqft
2039 HARBOR COVE WAY,
Winter Garden, FL 34787
KELLER WILLIAMS REALTY AT THE LAKES
1.15 ACRES
$1,845,000
6 bd
6 ba
5,869 sqft
4282 MCKINNON ROAD,
Windermere, FL 34786
COMPASS FLORIDA LLC
$699,000
5 bd
4 ba
3,078 sqft
2027 RICKOVER PLACE,
Winter Garden, FL 34787
CREEGAN GROUP
0.45 ACRES
$1,280,000
4 bd
2.5 ba
2,441 sqft
104 E 1ST AVENUE,
Windermere, FL 34786
NOVA REAL ESTATE SERVICES INC
0.36 ACRES
$799,000
4 bd
2.5 ba
2,729 sqft
7903 PALMDALE DRIVE,
Orlando, FL 32819
FLORIDA CONNEXION PROPERTIES
1.01 ACRES
$1,299,000
5 bd
3 ba
3,356 sqft
2540 HEMPEL COVE CT,
Windermere, FL 34786
ALIGN REAL ESTATE LLC
OPEN SAT, 12-3PM
$1,200,000
6 bd
4 ba
4,247 sqft
1812 LAKE ROBERTS LANDING DRIVE,
Winter Garden, FL 34787
EXP REALTY LLC
0.36 ACRES
$1,325,000
5 bd
4 ba
4,859 sqft
2204 CAIRNS COURT,
Orlando, FL 32835
EPIC REAL ESTATE ADVISORS LLC
NEW - 8 HRS AGO
NEW CONSTRUCTION
1.53 ACRES
$1,550,000
5 bd
4.5 ba
3,612 sqft
5638 NECTARINE DRIVE,
Windermere, FL 34786
LA ROSA REALTY LLC
See more homes for sale in
Windermere
Take a look

Skip to first item

Frequently asked questions about 101 LEE STREET

What is the estimated monthly payment for 101 LEE STREET?
Based on a $1,300,000 list price with 20% down at today's rates, the estimated monthly payment for 101 LEE STREET in Windermere, FL is approximately $9,473 (about $7,090 principal & interest, $2,308 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
How does the list price for 101 LEE STREET compare to homes in Windermere?
101 LEE STREET in Windermere, FL is listed at $1,300,000, about 51% above the $860K median sale price in Windermere.
What do residents say about Windermere?
Residents describe Windermere, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Windermere, FL.
What are the closest schools to 101 LEE STREET?
The closest schools to 101 LEE STREET in Windermere, FL are Gotha Middle School (rated 6/10), Olympia High School (rated 5/10), Windermere Elementary School (Pre-K, rated 10/10).
Does 101 LEE STREET have air conditioning?
Yes, 101 LEE STREET in Windermere, FL has air conditioning.
Does 101 LEE STREET have a pool?
Yes, 101 LEE STREET in Windermere, FL has a pool.

101 LEE STREET, Windermere, FL 34786 is a 5 bedroom, 4 bathroom, 4,186 sqft single-family home built in 1978. This property is currently available for sale and was listed by Stellar MLS on Sep 1, 2026. The MLS # for this home is MLS# O6437573.

$1,300,000

101 LEE STREET, Windermere, FL 34786

Home Highlights

Local Information

About this House

Open House

Home Details for 101 LEE STREET

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Media

Location

Agent Information

Building

Community

HOA

Lot Information

Listing Info

Offer

Business

Miscellaneous

Additional Information

Price and Tax history

Around this home

What Locals Say about Windermere

Trick-or-Treat Score

Market trends in Windermere

Home Value

Trulia Estimate

Comparable sales

Nearby home prices

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

Additional Cost

Similar Homes You May Like

New Listings near 101 LEE STREET

Frequently asked questions about 101 LEE STREET