Front elevation266 N Ranger Boulevard, Winter Park, FL 32792
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of September 28, 2026, 266 N Ranger Boulevard in Winter Park Pines, Winter Park is listed at $724,900 (1,692 sq ft, about $428 per sq ft). That is 21% above Winter Park Pines's median closed sale of $600,000 over the last 12 months (23 recorded sales). Per square foot it is above the community's recent $324/sq ft by about 32%. It came to market within the past week. Listing facts: built in 1964, no HOA. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 1964 · 62 yrs
- 1,692 sq ft of living area
- 2-car garage
- Listed at $724,900 — recent neighborhood median sale price ~$600,000 (nearby sales; deemed reliable, not an appraisal)
- Active listing
- HOA ~$50/mo (estimate; confirm)
Pricing & the winter park pines market
How this home is priced against recent nearby sales, and where winter park pines has been over 25 years. Momentum Research analysis of Stellar MLS records; closed sales, deemed reliable but not guaranteed. Estimates only; see data notes.
This home’s $/sq ft vs. nearby sales
List $/sq ft against recent nearby closed sales; the community median is marked.
Price vs. size in winter park pines
Each dot is a closed sale since 2005 (350 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, 2012–2026. This home lists at $428/sq ft.
Median sale price by year
12-month median closed price, 2012–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2013–2026. Now 63 (hot).
This home’s history
- 1964BuiltPer public record
- Sep 28, 2026First trackedObserved at $724,900
- 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 $3,870/mo 78%
- Taxes $634/mo 13%
- Insurance $393/mo 8%
- HOA $50/mo 1%
$4,947/mo at 20% down, 30-yr @ 7.03% · 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
42/100 is below average 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 $428 per square foot, about 32% above the community’s $324 median. winter park pines’s 12-month median sold price per square foot is $324. Median sold price per square foot is up 13.2% year over year. Confidence: High · 23 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.
79% of homes in winter park pines are owner-occupied. An estimated 21% are non-owner-occupied, including 6% 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), 289 homes matched. Community-level context.
Recent winter park pines sales closed near 97.6% 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 20, 2026. Aggregates only; deemed reliable but not guaranteed.
What’s unique here: one of only 8 active listings in winter park pines, no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Updated September 28, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
About this home
FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for.
Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator.
The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror.
The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023.
Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance.
Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person.
Schedule your private showing today!
Description provided by ELITE PROPERTY REAL ESTATE LLC 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: $724,900 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 14% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a 1964 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 — the band above comes from 6 nearby sales; one flip or distressed sale moves the whole $/sq ft.
- Carrying costs & concessions — CDD, HOA, insurance, and seller-paid buydowns change what a buyer actually pays.
And here's what the live market is doing — which the number above ignores entirely:
- 9 active listings competing, 5 under contract
- ≈2.9 months of supply
- 32 closed here in the last 12 months
For reference, this home is listed at $724,900 ($428/sq ft) — a number set with analysis a Messtimate can't do.
Selling your own home? Try the Messtimate on your address →
Methodology: 1,692 sq ft × $324–$370/sq ft from recent nearby closed sales (public records). Estimate for general information only; not an appraisal, valuation, or offer. Updated September 28, 2026.
Similar homes for sale near WINTER PARK PINES
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.
Newest listings in WINTER PARK PINES
- 739 Roughbeard Road · $780,000 · 5 bd / 3.0 ba · listed September 24, 2026 (courtesy of SERHANT)
- 274 N Ranger Boulevard · $659,900 · 3 bd / 2.0 ba · listed September 10, 2026 (courtesy of EXPLORE FLORIDA REALTY SERVICES LLC)
Recently off market in WINTER PARK PINES
- 729 Monmouth Way · last listed $793,500 · 2026-09-26
- 528 Saint Dunstan Way · last listed $536,000 · 2026-09-26
- 505 Cornwall Road · last listed $670,000 · 2026-09-26
- 2803 Banchory Road · last listed $474,000 · 2026-09-25
- 333 Cornwall Road · 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 ELITE PROPERTY REAL ESTATE LLC · MLS # O6444727
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Recent sales activity in WINTER PARK PINES
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 WINTER PARK PINES 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 WINTER PARK PINES
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.
Community 12-month median: $324/sq ft. Shown for general reference only — this is not an appraisal or a statement of this home's value. Sold prices are public record and deemed reliable but not guaranteed.
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 266 N Ranger Boulevard, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 1964 (62 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.
- Listed living area is 1,692 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 $7,611/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 28, 2026) |
| Community market stats | Stellar MLS closed sales, as of September 20, 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 266 N Ranger Boulevard and when was it built?
Per the listing record, 266 N Ranger Boulevard was built in 1964 and has 1,692 sq ft of living area, 4 bedrooms and 3.0 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 266 N Ranger Boulevard in?
266 N Ranger Boulevard is in Winter Park Pines in Winter Park, Orange County. The community section on this page shows recent closed sales, days on market, and active inventory for Winter Park Pines from the same MLS data.
Does 266 N Ranger Boulevard 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 266 N Ranger Boulevard differ from the current owner's?
The estimate on this page (about $7,611 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 266 N Ranger Boulevard 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.
See 266 N RANGER BOULEVARD in person
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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.