Grayson Square Homes for Sale in Winter Park, FL

Townhome community · Winter Park · Seminole County

A townhome community in Winter Park, Seminole County.

Seminole CountyLow maintenanceNear everyday destinations

Live Market Pulse

50/100
Momentum

Buyer-Leaning Market (limited data)

Home styles and condition vary here; confirm the fee, reserves, any CDD, and rental rules for the specific home.

Free · No obligation

Unlock Off-Market Grayson Square

Listings before the portals, true comps, and the renovation and carrying-cost math, before you tour.

Built fromLive Stellar MLS data14 years of closingsLocal renovation analysisUpdated twice daily

LiveMarket PulseStellar MLS

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Median Price

0mo

Supply

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Avg DOM

Soft

Seller Leverage

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Median $/Sqft

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1-Yr Price Change

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Distress

Jon's Current Read

"Grayson Square reads as much on the association as the home: the HOA dues, the reserve picture, the insurance line, and any CDD drive both your carrying cost and your financing. Condition and the comparable sales separate the leaders from the sitters, so we read the budget and the comps before anything else."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Grayson Square is a townhome community in the Winter Park and Casselberry area of Seminole County, in Winter Park, Seminole County. Homes here are townhomes and villas; floor plans, lot positions, and condition vary, so confirm the specifics of any individual home with the listing.

What sets your true monthly cost is not only the price but the carrying costs: HOA dues, property taxes, Florida insurance, and any assessment. Confirm any community development district (CDD) assessment on the tax bill during due diligence. Read the association documents and the budget before you offer.

The honest read here is condition, location within the community, and the association's financial health. We pull the comparable sales on similar homes, not a community average, and we represent you, not the seller.

Quick Match

Who Grayson Square is best for.

Best for

Buyers who want a home in the Winter Park area of Seminole County
Buyers who value low-maintenance, lock-and-leave living
Buyers who will read the association budget and reserves before offering
Buyers weighing the all-in carrying cost, not just the list price

Probably not for

Buyers who want no association rules or monthly fee
Buyers who want large acreage or a fully rural setting
Buyers who want a predictable fee with no assessment risk
Buyers unwilling to verify the budget, reserves, and any CDD

Market Pulse

How Grayson Square is performing right now

50/100
momentum

Buyer-Leaning Market (limited data)

Seller's marketBalancedBuyer's market

0Months of supplytight

72Median days on marketdays

0 : 0Under contract vs for salestrong demand

0Sold in last 12 monthsliquidity

+127%Median price since 2012appreciation

+0%Asking vs recent sold $/sqftroom to negotiate

Tight supply and strong demand favor sellers here. Homes still take about two months to sell, though, and with asking prices running above recent sales per square foot, a prepared buyer has room on anything overpriced. Reading each home against the real comps, not the headline trend, is where the edge is.

Live from Stellar MLS, as of June 23, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Grayson Square listings and the trailing twelve months of closed sales.

Where prices are going$850K2026 YTD

Median sale price by year. Tap a label to compare Capistrano or Winter Park. The 1-year price change is the median sold price over the most recent year versus the prior year, the same measure most listing sites and local Realtor reports use. It reflects the mix of homes that sold, not the change in any single home's value, which is why median price per square foot is shown alongside it to adjust for home size. In thinly traded neighborhoods, where a sale or two can swing the median, we lead with the mix-resistant price-per-square-foot trend instead.

Price per square foot$3072026 YTD

Median $/sqft by year. 2026 is year to date.

Supply and demand now0 : 0active : pending

For sale0

Pending0

Sold 12mo0

Active and pending listings now vs homes sold in the last 12 months.

8.6A- score

Momentum intelligence

Momentum buy score

Our proprietary read on how a home in Grayson Square buys, holds, and resells. See the five factors.

Interactive Map

Grayson Square on the map.

Every active, pending, and recently sold home, plotted. Toggle the layers, color the dots by status or lot type, and tap a home for the details.

Listing locations from Stellar MLS; lot type inferred from listing descriptions. Destination pins are approximate. Map data © OpenStreetMap, tiles © CARTO. Flood, school, and commute overlays are on the roadmap.

Nearby & Commute

How far is everything?

The takeaway

Everyday destinations across the Winter Park area are a short drive; confirm your real commute at your real departure time.

Drive times from Grayson Square. Times are approximate and vary with traffic.

Cranes Roost / Altamonte~10 min · ~5 miles

Winter Park / Park Avenue~12 min · ~6 miles

Full Sail University~12 min · ~6 miles

University of Central Florida~20 min · ~12 miles

Downtown Orlando~25 min · ~13 miles

Drive times are approximate and vary with traffic and your exact departure point.

Nearby Communities

Explore more neighborhoods near Grayson Square Homes for Sale in Winter Park, FL with Momentum Realty’s local guides.

Winter Park PinesWinter Park, FL · 0.9 mi

ALBERT LEE RIDGE 1ST ADDWinter Park, FL · 1.9 mi

ALBERT LEE RIDGE ADD 02Winter Park, FL · 1.9 mi APALOMA PARK Homes for Sale in Winter Park, FLWinter Park, FL · 1.9 mi ATALOMA TRAILS Homes for Sale in Winter Park, FLWinter Park, FL · 1.9 mi

ALOMAWinter Park, FL · 1.9 mi

ARROWHEAD COVEWinter Park, FL · 1.9 mi ASART SYSTEMS CENTER Homes for Sale in Winter Park, FLWinter Park, FL · 1.9 mi

ATTILIO G PANACCIONES SUBWinter Park, FL · 1.9 mi

Browse all Florida neighborhood guides →

Carrying cost · the no-CDD edge

No CDD bond means thousands less per year than newer master plans.

Typical CDD community~$2,500/yr

Grayson Square (no CDD)$0/yr

Roughly $25,000 saved over 10 years in carrying cost, before resale.

Illustrative. NE Florida CDD assessments commonly run $1,500-$3,500+/yr and vary by community; verify per property.

Schools

15-Second Take

Seminole County Public Schools
Verify the zoned schools by address
Magnet and choice options may be available
Confirm current ratings before relying on them
Private and parochial options nearby

Grayson Square is served by Seminole County Public Schools. Assignment is by address and can change, so confirm the exact zoned elementary, middle, and high schools for any specific home, plus any magnet or choice options. Treat published ratings as a starting point, not the full story.

Buying with schools in mind? We can confirm the exact zoned schools for any Grayson Square address.

The takeaway

What is shaping value at Grayson Square: statewide insurance and reserve-funding pressure on fees, steady Greater Orlando growth, and the community's own assessments. Confirm each item for the specific home.

Recent Developments in Grayson Square

Development Intelligence

Our read on what is being built around Grayson Square, scored for direction, significance, and how close the effect lands. The full sourced timeline follows below.

Net OutlookBullishDemand for well-located homes in the Winter Park area holds, but statewide insurance and reserve pressure is the watch item on fees. Read the association's financials before you offer.

Florida insurance and reserve rules shaping fees

Ongoing

BearishNotable impact

SignificanceRadius: Statewide

Statewide insurance and reserve-funding pressure can push association fees up; confirm the community's current fee and reserve plan.

Greater Orlando growth supports area demand

Ongoing

BullishNotable impact

SignificanceRadius: Region

Steady population and job growth across the Orlando metro supports demand for well-located, well-kept homes.

Association budget shapes the true carry

Ongoing

NeutralNotable impact

SignificanceRadius: Community

The community's assessments and budget, not just the price, drive the true monthly cost; confirm them per parcel.

Direction, significance, and effect-radius ratings are Momentum's proprietary, qualitative read of the sourced items below, not investment advice or a prediction for any specific home.

Development, infrastructure, retail, and school activity affecting Grayson Square, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated June 2026.

Showing the latest, scroll for all updates ↓

January 2026
Market
Florida community fee and assessment pressure continues
Statewide insurance and reserve-funding requirements continue to pressure association budgets; confirm the specific community's current fee, reserve study, and any assessment. Why it matters: The fee and reserve picture, not just the price, drive the true carrying cost in any Florida community today. Source

Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.

The Strategy

The Grayson Square buying strategy.

If we were buying in Grayson Square, this is the order of operations we would run, and the one we run for our clients.

Get the HOA dues and what they cover in writing. The fee is a real part of the monthly carry.

Read the reserve study and recent minutes. They tell you whether an assessment may be coming.

Confirm any CDD or special assessment on the tax bill for the specific parcel.

Verify the Florida insurance picture, which moves both the budget and your own premium.

Comp the specific home against similar homes nearby, not a community average, with Capistrano as one cross-shop.

The Quick Decision

Best Buy

An updated home matched honestly to recent comparable sales

Biggest Risk

An assessment or a rising fee from reserves or insurance

Best Lot

Position within the community and what the home backs to

Smart Timing

Confirm the budget, reserves, and any CDD before you offer

Deep-Dive Intelligence

The full read, only if you want it.

The takeaway

On mobile, tap any heading below to open it. This is the home by home, lot by lot, club and renovation detail, organized so you can jump straight to what matters to you.

Community Details at a Glance

Grayson Square is a townhome community in the Winter Park and Casselberry area of Seminole County, in Winter Park, Seminole County, served by Seminole County Public Schools. Confirm the current HOA dues, reserve study, insurance, any CDD assessment, and the rental rules with the listing and the association, since these drive both carrying cost and financing. Home styles and condition vary, so the read that matters is the comparable-sales analysis on the specific home.

Grayson Square Homes For Sale

What your money buys in Grayson Square.

The takeaway

Three honest price bands. Condition and lot, not the square footage alone, decide where a home lands.

Here are the broad resale bands in Grayson Square today. The right home is the one matched to your budget and the renovation math, so seeing fitting listings early is the edge.

The Entry Home

Original-condition homes, the value door into the community. Budget the updates and read the association budget.

Lowest entry

The Updated Home

Renovated, well-kept homes in a well-run community, the heart of the resale market here.

Most inventory

The Best Position

The best-positioned or most-updated homes with a healthy association, the strongest hold-value story.

Strongest resale

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

See Off-Market & Private Listings

What Your Money Buys

What ~$900K buys here.

Three realistic price bands. Where a home lands comes down to condition and lot, not square footage alone.

The Entry Home

Original-condition homes, the value door into the community. Budget the updates and read the association budget.

The Updated Home

Renovated, well-kept homes in a well-run community, the heart of the resale market here.

The Best Position

The best-positioned or most-updated homes with a healthy association, the strongest hold-value story.

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

Operator Intelligence

Renovation & Resale Intelligence

The factors that actually move value in Grayson Square, condition, lot, and the renovation math, read from current listings and recent sales.

15-Second Take

Renovation math decides the deal
Better lots and views resell strongest
Roof and HVAC age drive the insurance quote
Interior lots are where buyers overpay

Proprietary Data

The renovation premium.

Renovated-listing inventory in Grayson Square is too thin right now to compute a reliable renovation premium. We read condition home by home against real comps before you offer.

Lot Value

The lot premium.

On a preferred homesite (water, preserve, corner, or a larger lot), the homesite is the part of your money the market gives back at resale. The house can be renovated; the lot cannot, so premium lots hold their value better than interior ones. How much more they command varies by frontage, view, and condition, which is why we read it home by home against real comparable sales rather than a single headline figure.

Operator Note

Most buyers overpay on interior lots in the back half of the community. A sharp renovation can distract you, but the weaker resale position follows the lot, not the finishes. We read the homesite before the kitchen.

Resale Strength Scorecard

How well Grayson Square holds value.

Our read on the factors that protect resale here, and the one to manage.

Location in the Winter Park areaStrong

Low-maintenance lifestyleStrong

Everyday destinations a short drive awayPositive

Fee moves with reserves and insuranceManage it

Verify reserves and any assessmentVerify it

Momentum analysis based on the community's structure, location, lot scarcity, and housing stock. Not a guarantee of future value.

Operator Note

The strongest value pocket is usually a renovated home on a good lot priced just under the next tier up. Buyers chasing the single biggest house often pay top prices for what is really a renovation project.

5 Mistakes Buyers Make in Grayson Square

15-Second Take

Calling the listing agent (who works for the seller)
Misjudging the renovation budget
Overpaying for an interior lot
Underbudgeting the carrying costs
Skipping the roof, HVAC, and systems check

The same five mistakes cost buyers the most in any market. Every one is avoidable with the right preparation before you tour.

Calling the listing agent

The agent on the sign works for the seller. In a market where condition swings price by hundreds of thousands, negotiating against that agent with no one in your corner is the costliest move of all.

Misjudging the renovation math

A dated home looks like a deal until you price the roof, HVAC, pool, and full modernization honestly. Underbudget the reno and the bargain becomes the expensive house.

Overpaying for an interior lot

A premium homesite (water, preserve, or a preferred position) carries a real, durable premium. Pay a top price for an interior lot and you are buying the weakest version of the value.

Underbudgeting the carrying costs

Two similar homes can cost very differently to own once the HOA, any CDD, insurance, and upkeep are priced in. Buyers who do not run the full monthly carrying cost misread the real number.

Skipping the systems check

An older home means older systems unless updated. Roof age, HVAC age, pool equipment, and prior renovations drive both price and insurability, and a thorough inspection matters more here than in a new build.

“

The deal is won or lost on condition, the comps, and the association's health, not the headline price.

Jon Brooks · Founder, Momentum Realty

Momentum Intelligence

Momentum Buy Score.

Our proprietary 0 to 10 read across the five factors that decide how a home here buys, holds, and resells.

6.9B- · Buy Score

Resale Strength6.8/10

Renovation Risk7.4/10

Location Efficiency7.6/10

Long-Term Defensibility6.4/10

Carrying Cost Advantage6.8/10

Momentum Intelligence Scores are our proprietary, qualitative assessment based on the analysis on this page, on a 0 to 10 scale. They are a framework for comparing communities, not a guarantee of future value or advice on a specific home.

Momentum Housing Intelligence

Why our read on Grayson Square is different.

Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live Stellar MLS feed, fourteen years of closed sales, and a renovation-by-renovation read of what actually moves value here, lot by lot. No Zestimate, no guesswork.

Live Stellar MLS feed14 years of closed salesRenovation-premium analysisLot-by-lot, no automated estimates

Jon Brooks, founder of Momentum Realty. A housing economist with a background in real estate investment banking at Deutsche Bank and consulting at Ernst & Young, who has built and analyzed Northeast Florida real estate from the ground up.

About the analyst · Our methodology

Which Lots & Views Hold Value Best

Proprietary Data · Lot Value Map

Where the value actually sits. Each home is shaded by its price per square foot (a value read, not just a price) and ringed by lot type, so you can see at a glance which pockets carry a real, durable premium and where a renovation play makes sense.

Value ($/sqft)

$261 value$401 premium

Lake / waterPreserveInterior

Fill = price per square foot; ring = lot type, inferred from listing descriptions. Sold homes are shown by realized $/sqft (lot type not always recorded). Asking and recent-sold figures from Stellar MLS; for orientation, not an appraisal.

15-Second Take

Position and condition drive value more than headline size
Verify what each home backs to before paying a premium
Updated homes command real premiums over original-condition twins
The location cannot be renovated, the home can
Read the comparable sales on the specific home, not an average

In Grayson Square, the variables that move value are the home's position within the community, its condition and updates, and the association's financial health. Read the budget, the reserves, and the comparable sales on similar homes before you pay a premium.

The 15-Second Verdict

Grayson Square in 15 seconds.

Best forBuyers who want a home in Winter Park with an honest read on the carrying costs.

Biggest advantageA townhome setting in the Seminole County area, with everyday destinations a short drive away.

Biggest riskA rising fee or assessment from reserves, insurance, or a CDD.

Sweet spotAn updated home in a community with a healthy, well-funded budget.

Avoid ifYou want no association, no fee, or a fully rural, large-acreage setting.

HOA, CDD & Fees

15-Second Take

The HOA dues is part of the monthly carry
Read the reserve study and minutes
Confirm any CDD on the tax bill
Florida insurance is a real line item
Comp similar homes, not an average

Dues vary; confirm the current amount, what they cover, the reserves, and any assessment for the specific home. Confirm any community development district (CDD) assessment on the tax bill during due diligence.

Typically common-area upkeep and shared amenities; confirm the exact inclusions for the specific home.

Amenities, where present, are association-maintained common areas; confirm what is included.

Run Your Numbers

Tools for a Grayson Square buy.

Free calculators to pressure-test the real cost before you tour.

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxSeminole County millage and the homestead picture.Rent vs buyThe breakeven on owning in Grayson Square.Save Our HomesProject your homestead tax cap over time.

The takeaway

Selling here is won on condition and view, not the Zestimate. The right number comes from closed comps matched to your renovation level and lot.

Selling in Grayson Square

Price it to condition and real comps, not an automated estimate.

If you are thinking about selling in Grayson Square, the right list price comes from recent comparable sales matched to your home's condition and position, not an online estimate.

Momentum listings (YTD)

97.98%

Sold-to-list ratio across our market for our agents, sellers keeping more of their price.

Market average (YTD)

96.73%

The broader metro average sold-to-list ratio over the same period.

Momentum days on market

64 days

Median days on market for our listings, faster sales mean less carrying cost and stronger leverage.

Market days on market

72 days

The broader metro median over the same period.

Sold-to-list and days-on-market figures reflect Momentum Realty listings versus our market average, year to date. Your home's result depends on pricing, condition, lot, view, and preparation.

In Grayson Square, condition and view decide your number

Because buyers here are weighing your home against renovated comps and cross-shopping Capistrano, a home priced to the community average instead of its true condition and view either leaves money on the table or sits. A renovated kitchen, newer roof and HVAC, and a golf or lake view all deserve to show up in your price, and a buyer pool reading renovation math needs to be shown why your home is worth it. We build that case with real comps and a pricing strategy for the current market.

What is your Grayson Square home worth?

Get a no-obligation home value based on real comparable sales in Grayson Square matched to your condition, lot, and view, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.

See homes for sale in Grayson Square on the map →
Or get your Grayson Square home value & selling guide →

Real comps, not a Zestimate.

Grayson Square Market Scorecard

Thin data

Grayson Square is currently a thin data. Limited supply, a median asking price of n/a.

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Months supply

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Median list

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Median sold

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Per sqft

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Days on mkt

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Active/Pend/Sold

Go deeper: true cost calculator · affordability calculator.

Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

What is Grayson Square?

Grayson Square is a townhome community in the Winter Park and Casselberry area of Seminole County, in Winter Park, Seminole County. Confirm the specifics of any individual home with the listing.

What does the HOA dues cover?

It typically covers common-area upkeep and shared amenities. Get the exact current amount and inclusions in writing, since fees move with reserves and insurance.

Is there a CDD?

Confirm any community development district (CDD) assessment on the tax bill during due diligence.

What schools serve the community?

Grayson Square is part of Seminole County Public Schools; school assignment is by address and changes periodically, so confirm the current zoning with the district.

Can I rent a home here?

Rental and leasing rules are set by the association and can change; some communities cap rentals. Get the current policy in writing before you offer, especially if you are an investor.

What about insurance?

Florida property and, for condominiums, master-policy insurance drive both the fee and your own premium. Confirm the current picture before you commit.

How far is it to the major destinations?

From Grayson Square, everyday destinations such as Cranes Roost / Altamonte and Winter Park / Park Avenue are a short drive; times are approximate and vary with traffic.

Are the homes updated?

Condition varies home to home. Updated homes command real premiums over original-condition comparables; pay for documented, permitted work.

Should I use the listing agent?

No. The listing agent works for the seller. Having your own representation is the higher-leverage choice when condition and the association can swing value.

What should I budget beyond the mortgage?

The HOA dues, property taxes, insurance, any CDD, and a reserve for a possible assessment. The fee, not just the price, sets the true monthly carry.

Is this a good place to invest?

Demand in the Winter Park area is supported by the location, but condition, the fee, and the rental rules drive the outcome; this is not a guarantee of future value.

How competitive is buying here?

Updated homes in well-run communities move faster; tired homes and communities with assessment risk linger, and that is where negotiation lives.

What is the biggest risk?

A rising fee or a pending assessment from reserves, a CDD, or Florida insurance. Reading the association's financials early is how we catch it before you offer.

Is Grayson Square a gated community?

Access and amenities vary; confirm whether the community is gated and what is included with the listing.

The Verdict

Should you buy in Grayson Square?

An honest fit check. We will tell you when it is not your community.

Buyers who want a home in the Winter Park area of Seminole CountyExcellent fit

Buyers who value low-maintenance, lock-and-leave livingExcellent fit

Buyers who will read the association budget and reserves before offeringExcellent fit

Buyers weighing the all-in carrying cost, not just the list priceExcellent fit

Buyers who want a manageable ownership footprint near everyday destinationsExcellent fit

Buyers who want no association rules or monthly feeProbably not

Buyers who want large acreage or a fully rural settingProbably not

Buyers who want a predictable fee with no assessment riskProbably not

Buyers unwilling to verify the budget, reserves, and any CDDProbably not

Buyers who want full control over exterior and landscapingProbably not

Get the inside read on Grayson Square

Whether you are buying a renovation project, comparing the lots and views, weighing the carrying costs, or selling your Grayson Square home, tell us what you need. Every inquiry comes straight to us. We represent you, not the seller, and what your agent is paid is negotiable and set in a written buyer agreement up front. No obligation, no spam, no high-pressure follow-up.

You are all set.

A Momentum Realty Grayson Square specialist will reach out personally, usually the same day.

Thinking about hiring an agent here? How to find the best real estate agent in Grayson Square — what to look for, questions to ask, and your local expert.

Photography on this page is sourced from active and recently sold MLS listings in this community and remains the property of the listing brokerage and/or photographer. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX 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; deemed reliable but not guaranteed by MLS GRID.

Grayson Square Homes for Sale in Winter Park, FL

The 60-Second Overview

Who Grayson Square is best for.

Best for

Probably not for

How Grayson Square is performing right now

Grayson Square on the map.

How far is everything?

Nearby Communities

Schools

Recent Developments in Grayson Square

Florida insurance and reserve rules shaping fees

Greater Orlando growth supports area demand

Association budget shapes the true carry

Florida community fee and assessment pressure continues

The Grayson Square buying strategy.

The full read, only if you want it.

What your money buys in Grayson Square.

What ~$900K buys here.

Renovation & Resale Intelligence

The renovation premium.

The lot premium.

How well Grayson Square holds value.

5 Mistakes Buyers Make in Grayson Square

Calling the listing agent

Misjudging the renovation math

Overpaying for an interior lot

Underbudgeting the carrying costs

Skipping the systems check

Momentum Buy Score.

Why our read on Grayson Square is different.

Which Lots & Views Hold Value Best

Grayson Square in 15 seconds.

HOA, CDD & Fees

Tools for a Grayson Square buy.

Price it to condition and real comps, not an automated estimate.

In Grayson Square, condition and view decide your number

What is your Grayson Square home worth?

Price History: What Homes Here Have Actually Sold For

Grayson Square Market Scorecard

Frequently Asked Questions

Should you buy in Grayson Square?

Get the inside read on Grayson Square

You are all set.

Need to sell fast in Seminole County?

You just read the data. Now see what your home is worth.