Front elevation101 Lee Street, Windermere, FL 34786
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of September 16, 2026, 101 Lee Street in Town Of Windermere, Windermere is listed at $1,395,000 (4,186 sq ft, about $333 per sq ft). That is 56% above Town Of Windermere's median closed sale of $895,000 over the last 12 months (20 recorded sales). Per square foot it is below the community's recent $400/sq ft by about 17%. It came to market within the past week. Listing facts: built in 1978, a private pool, no HOA. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 1978 · 48 yrs
- 4,186 sq ft of living area
- 2-car garage
- Active listing
- HOA ~$50/mo (estimate; confirm)
Pricing & the Windermere Town market
How this home is priced against recent nearby sales, and where Windermere Town has been over 25 years. Momentum Research analysis of Stellar MLS records; closed sales, deemed reliable but not guaranteed. Estimates only; see data notes.
Price vs. size in Windermere Town
Each dot is a closed sale since 2014 (126 total). This home is the gold marker.
Sale price (y) by living area in sq ft (x). Stellar MLS closed sales.
Median $/sq ft by year
Community sold $/sq ft, 2015–2026. This home lists at $333/sq ft.
Median sale price by year
12-month median closed price, 2015–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2016–2026. Now 35 (cold).
This home’s history
- 1978BuiltPer public record
- NowActiveCurrently for sale
Build year is from public record. Listing milestones reflect movewithmomentum.com’s own observations since we began tracking this listing and are not the MLS listing history; dates and prices are deemed reliable but not guaranteed.
Estimated monthly payment
- Principal & interest $7,246/mo 78%
- Taxes $1,221/mo 13%
- Insurance $757/mo 8%
- HOA $50/mo 1%
$9,273/mo at 20% down, 30-yr @ 6.76% · edit any field to update.
Editable estimate — not a loan offer. Estimates only; see data & estimate notes.
Property taxes
✓ Based on certified county tax rollMany first-time Florida buyers are surprised when property taxes jump after closing. This estimate helps you budget before you make an offer.
Most of this comes from Florida’s Save Our Homes assessment cap resetting when the home sells — the current owner’s protected assessment doesn’t transfer to a new buyer.
Adjust for your exemptions, portability, and down payment
A market / assessed / taxable trend chart appears here once the prior-year rolls are ingested.
Sources: Florida DOR certified tax roll (2025), Stellar MLS. County public record, not MLS data — matched to this home by parcel ID. Estimates are not a tax bill.
Momentum Property Score
62/100 is solid, mid-pack across the objective indicators below. It reflects only those measures — not the home’s quality, condition, or desirability.
A 0-100 score built from objective property and market data: flood risk, insurance, pricing, supply, affordability, and recent sales. Higher means more measures line up in a buyer’s favor. It reflects only the factors below.
Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent nearby sales. They are not appraisals, valuations, investment advice, or judgments about a neighborhood or who should live there. Verify independently.
The Momentum read
🟡 Asking $333 per square foot, about 17% below the community’s $400 median. Windermere Town’s 12-month median sold price per square foot is $400. Median sold price per square foot is down 28.7% year over year. Confidence: High · 20 closed sales in 12 monthsMLS facts: Stellar MLS closed sales. A per-square-foot gap is context, not an appraisal; condition, lot, and view set the final number here.
66% of homes in Windermere Town are owner-occupied. An estimated 34% are non-owner-occupied, including 17% held in a company or trust and 100% out-of-state owners.Why it matters: a high owner-occupied share typically means fewer rentals nearby and steadier resale demand.Source: Florida Department of Revenue 2025 assessment roll (public records), 234 homes matched. Community-level context.
Recent Windermere Town sales closed near 93.6% of original asking.Why it matters: the community’s own record shows how far opening prices typically move, and how often buyers compete without financing.Momentum Research analysis of Stellar MLS records, community-level, 12 months ending September 12, 2026. Aggregates only; deemed reliable but not guaranteed.
What’s unique here: one of only 6 active listings in Windermere Town, no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Updated September 16, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
About this home
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.
Description provided by STOCKWORTH REALTY GROUP and reproduced from the MLS; not independently verified.
Every fact, sourced
Listing data, public records, our calculations, and what to verify — each fact shown once. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.
Listing facts MLS
Public records & third-party data
Calculated estimates
Buyer should verify Buyer verify
Provided via the Stellar MLS Internet Data Exchange, as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID. · deemed reliable but not guaranteedIDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed by the MLS to be accurate.The Messtimate
This is a deliberately dumb estimate — living area times a range of recent neighborhood $/sq ft, and nothing else. It is not an appraisal, not market value, and not a valuation of this home. Even a tight range from comparable sales can’t price a specific home — here’s why.
Actual list price: $1,395,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 27% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a 1978 home may have had its roof, kitchen, or HVAC replaced since, or not; sq ft can't see either.
- The lot & views — a premium golf, water, or preserve lot vs. a road-facing one: same sq ft, very different price.
- Outliers skew it — one flip or distressed sale in the comps drags the whole $/sq ft up or down.
- Carrying costs & concessions — CDD, HOA, insurance, and seller-paid buydowns change what a buyer actually pays.
- The pool — a private pool carries cost and value that living area doesn't capture.
And here's what the live market is doing — which the number above ignores entirely:
- 6 active listings competing, 1 under contract
- ≈3.3 months of supply
- 22 closed here in the last 12 months
For reference, this home is listed at $1,395,000 ($333/sq ft) — a number set with analysis a Messtimate can't do.
Selling your own home? Try the Messtimate on your address →
Methodology: 4,186 sq ft × $352–$448/sq ft from recent nearby closed sales (public records). Estimate for general information only; not an appraisal, valuation, or offer. Updated September 16, 2026.
Similar homes for sale near TOWN OF WINDERMERE
Active listings nearby at a comparable size and price. Listings held by brokerages other than Momentum Realty are marked with the listing broker. Deemed reliable but not guaranteed.
Recently off market in TOWN OF WINDERMERE
- 728 Forest Street · last listed $10,200,000 · 2026-09-15
- 725 Oakdale Street · 2026-09-10
- 109 E 12th Avenue · 2026-09-10
Price & listing history
Building permits
Flood zone & elevation
Sourced environmental data for the parcel. Confirm with FEMA and your insurer.
Not yet verified for this address. Look up the parcel at msc.fema.gov before relying on any flood assumption.
Approximate parcel elevation from USGS; confirm exact elevation with a survey.
This is a coastal Florida county. Premiums and coverage vary by home; obtain a quote from a licensed insurer.
Internet & broadband
AT&T Fiber covers much of NE Florida; confirm availability at the address.
Xfinity/Spectrum cable broadband is widely available.
T-Mobile / Verizon fixed-wireless as a backup option.
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Listed by STOCKWORTH REALTY GROUP · MLS # O6437573
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Recent sales activity in TOWN OF WINDERMERE
Recent comparable closed sales near this home, from public records. Summary figures are for general reference only and are not a valuation of this property. See the TOWN OF WINDERMERE neighborhood guide for more.
Recent nearby closings in the data set.
Canonical 12-month median closed price. Reference only.
Canonical 12-month median $/sq ft. Reference only.
Go deeper on TOWN OF WINDERMERE
See schools, amenities, builders, HOA/CDD detail, and every active & sold home in the community — the single biggest advantage of buying here over a portal.
Assigned schools
Schools currently assigned to this address in Orange County, provided as neutral factual data. Assignments can change — confirm current zoning with the school district. This is not a statement about the home's suitability for any person or family.
Assigned schools per the MLS listing — assignments can change; confirm current zoning with the district. Browse school-zone pages →
Comparable recent sales
Recent closed sales nearby, with photos, so you can compare. Sold prices are public record, deemed reliable but not guaranteed.
No closely comparable recent sales were found in this data set.
Investment snapshot
Objective rental and cash-flow estimates for a buyer weighing this as an investment. Rough figures for general information only — not a guarantee of rent, an appraisal, or investment advice. Verify independently.
Buyer research checklist
Items worth confirming for 101 Lee Street, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 1978 (48 years): ask for the roof and HVAC replacement dates — insurers commonly ask for roof age on homes this old, and it changes the premium.
- The listing reports no HOA: confirm with the county record that no deed restrictions or mandatory association apply to this parcel.
- Look up the parcel on FEMA's Flood Map Service Center and confirm with your insurer whether flood insurance is required.
- Get a homeowners insurance quote for this specific address in Orange County; a wind-mitigation inspection and, on older homes, a four-point inspection can change the premium.
- Private pool: confirm the barrier or alarm meets the state residential pool safety code and ask for pump, heater, and resurfacing records.
- Listed living area is 4,186 sq ft: verify it against the property appraiser's record and measure before relying on it.
- Order a survey to confirm lot boundaries and easements.
- Review permit history with the county.
- Property taxes: the estimate on this page (about $14,648/yr) assumes reassessment at the list price; the seller's homestead cap does not transfer, so their current bill is not a guide.
- School zoning shown here comes from district data and changes; confirm the assigned schools directly with the district before relying on them.
Approximate distances
Approximate drive times for general reference only.
Data sources & freshness
| Listing record | Stellar MLS, refreshed twice daily (last: September 16, 2026) |
| Community market stats | Stellar MLS closed sales, as of September 12, 2026 |
| Flood zone & elevation | Not verified for this address — look it up at msc.fema.gov |
| Taxes & monthly cost | Estimated from county rates; not a quote |
| Insurance figure | Modeled estimate; obtain a real quote before offering |
| Schools | 2025-26 district assignments; verify with the district |
Momentum Research lines are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Estimates are informational, not appraisals or advice. Methodology: how Momentum scores are computed.
Frequently asked questions
How big is 101 Lee Street and when was it built?
Per the listing record, 101 Lee Street was built in 1978 and has 4,186 sq ft of living area, 5 bedrooms and 4.0 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 101 Lee Street in?
101 Lee Street is in Town Of Windermere in Windermere, Orange County. The community section on this page shows recent closed sales, days on market, and active inventory for Town Of Windermere from the same MLS data.
Does 101 Lee Street have an HOA?
The listing reports no HOA. Confirm with the county record that no deed restrictions or mandatory association apply to the parcel.
Why might property taxes on 101 Lee Street differ from the current owner's?
The estimate on this page (about $14,648 per year) assumes reassessment at the list price. Florida's Save Our Homes rule caps annual assessment increases for homesteaded owners, and the assessment resets after a sale, so a new owner's bill may differ from the seller's. Any tax figure shown here is an estimate, not the actual bill — confirm with the county property appraiser and tax collector.
Is 101 Lee Street in a flood zone?
A flood designation has not been verified for this address. Look up the parcel on FEMA's Flood Map Service Center (msc.fema.gov) and confirm with your insurer.
Can I rely on the figures on this page?
No. Estimated taxes, insurance, payments, and any market or comparable-sales summary are opinions and estimates for general information only and should not be relied upon. Verify all information independently before making any decision.
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Opinion & estimate — do not rely on this page. Any figure on this page that is not a verbatim fact from the listing or a public record — including estimated property taxes, insurance, CDD/HOA amounts, mortgage payments, comparable-sales summaries, and market statistics — is an opinion and estimate provided for general informational purposes only. These figures may be inaccurate or out of date, are not appraisals, valuations, or financial, legal, tax, or investment advice, and should not be relied upon. Do not make any purchase, offer, financing, or other decision based on this page. Independently verify everything — price, square footage, lot size, year built, taxes, CDD/HOA, flood status, school assignments, permits, and community rules — with the listing broker, the county, your lender, a licensed inspector, an insurer, and your own advisors before acting.
Estimate methodology. Tax estimates apply a typical county millage rate to the list price and will differ from the actual assessed bill. Cost and market figures are derived from available data and simple calculations, not a professional appraisal. We make no representation that any estimate reflects fair market value.
Equal Housing Opportunity. Content on this page is compiled from public records, MLS data, and automated sources and may contain errors or be out of date. It is general information only, not a representation about any specific property, community, builder, or association. Verify information independently before relying on it. Momentum Realty supports the Fair Housing Act and does not discriminate on the basis of race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity. Information about schools, distances, and amenities is provided as neutral factual data to help you research the property and is not a statement about who should or should not live here or the suitability of the home or neighborhood for any person or group. School data may change — confirm current assignments with the school district.
Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email and we will review and correct or remove it promptly.
Automated content. Some summaries, distances, and estimates on this page are generated automatically from public and proprietary data sources and may contain errors or omissions. We strive for accuracy but cannot guarantee the completeness or accuracy of any information. Verify anything important independently.
No warranty; measurements & photos. No guarantee, warranty, or representation of any kind is made regarding the completeness or accuracy of any information, descriptions, or measurements on this page — including square-footage measurements and property condition — all of which should be independently verified through appropriate means, including in-person inspection and public records. Photographs may be virtually staged or digitally enhanced and may not reflect actual property conditions. Momentum Realty and its agents expressly disclaim any liability in connection with the information provided.
MLS / IDX. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Stellar MLS Internet Data Exchange, as distributed by MLS GRID. Real estate listings held by brokerage firms other than Momentum Realty are marked with the listing broker's name and include the name of the listing agent. Data provided is deemed reliable but is not guaranteed by the MLS to be accurate. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Source: Stellar MLS, as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. All rights reserved.
Listing data is deemed reliable but is not guaranteed and is subject to change or withdrawal without notice. Square footage and lot size are approximate. Real estate brokerage services provided by Momentum Realty, licensed in Florida and Georgia. © 2026 Move With Momentum LLC.