Villas Of Casselberry Ph 2
Homes for Sale in Winter Park, FL

Community in Winter Park · Seminole County
110 homesBuilt 1981–1989Median sale $270K
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Built fromLive Stellar MLS data15 years of closingsFL DOR public recordsUpdated twice daily
Live · Villas Of Casselberry Ph 2 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Price
$270K
Median sold · 12 mo
$230/sf
Sold $/sqft · 12 mo
peak $277 in 2024
94.5%
Sale vs ask
Seminole median: 96.2%
Tempo
33days
Median DOM · closed
5 days at the 2024 low
3
Sold · last 12 mo
10-yr average: about 2 a year
Ownership and context
59%
Owner-occupied · Villas Of Casselberry Ph 2
65 of 110 parcels homesteaded (FL DOR 2025)
41%
Non-owner-occupied · Villas Of Casselberry Ph 2
incl. 10% trust or LLC-held · 8% out-of-state
0%
Cash buyers · Villas Of Casselberry Ph 2
0 of 4 sales, 12 mo ending June 2024
110
Homes in the community
110 residential parcels (FL DOR 2025)
Track record · 15 years of records
Est. 1981
Community established
homes built 1981-1989, median 1984 (FL DOR 2025)
1
Failed listings · 2026
peaked at 3 in 2010
1,241sqft
Median sold home size
12-mo windows, closed sales
2.7%/yr
Turnover rate
about 3 of 110 homes trade a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Price here is driven by a specific product: compact villas built in the 1980s, with a median around 1,215 square feet and a median price of $270,000. At roughly $230 per square foot, what moves a number up or down is condition and updates, not square footage — these homes are close in size, so the spread you see comes down to how much work has been done inside.

The market posture is steady rather than frantic. A median of 33 days on market means well-priced, move-in-ready villas trade in about a month, while dated units sit longer and negotiate. Sellers should price to condition and resist stretching; buyers have enough time to inspect and think, but not enough to sit on a sharp listing.

The 60-Second Overview

Villas Of Casselberry Ph 2 market snapshot (as of July 13, 2026): the median sale price is about $270K ($230 per sq ft over the trailing 12 months of closed sales), and a median 33 days on market for closed sales.

Villas Of Casselberry Ph 2 is a community of 110 homes in Winter Park, Seminole County, built between 1981 and 1989 (median 1984.0), with a median living area of about 1,214 square feet. 59% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

Villas Of Casselberry Ph 2 is a small, uniform community of about 110 villas in Winter Park (Seminole County), built between 1981 and 1989. Because the homes are so similar in vintage and size, this is a market where condition — not floor plan — is the main variable.

Best for

  • Right-sizers wanting a compact, single-story-scale villa around 1,200 square feet near a $270,000 budget
  • Buyers prioritizing a Winter Park location in Seminole County over maximum size
  • Value-minded buyers willing to update an 1980s villa and build equity through condition

Probably not for

  • Buyers who need substantially more than the roughly 1,215-square-foot median footprint
  • Anyone wanting newer construction than the 1981-1989 build era
  • Buyers unwilling to budget for aging systems in an older home

Windows contain 0 to 7 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Deemed reliable but not guaranteed.

Median sale price · trailing 12 mo
$100K$200K$300K20122014201620182020202220242026
Every sale since 2011 · price vs size
$0$100K$200K$300K1k1k2k
31 closed sales; green = recent. Size sets the floor, condition and lot set the rest.
Sold $ per sq ft · trailing 12 mo
$100$200$30020122014201620182020202220242026
Up from $85 in 2012 to a $277 peak in 2024; $230 now.
Median days on market · closed sales
10203020122014201620182020202220242026
5 days at the 2024 low; 33 now.
Sale price vs original ask · median
94%96%98%100%20122014201620182020202220242026
94.5% now vs Seminole 96.2%.
Homes sold per 12-mo window
024620122014201620182020202220242026
0 to 7 a year; 3 in the current window.
Sellers who gave up · failed listings per year
012320062010201220202026
Canceled, expired, or withdrawn. 3 quit in 2010; 1 so far in 2026. The clearest stress gauge a community has.

If we were buying in Villas Of Casselberry Ph 2 today, this is the order of operations we would run for our clients.

1

Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Villas Of Casselberry Ph 2.

Best Buy
Buyers who want a low-maintenance villa in a Winter Park, Seminole County address at a moderate price.
Biggest Risk
Older 1980s systems mean roof, HVAC and plumbing age deserve close scrutiny.
Sweet Spot
An updated villa priced near the $270,000 median that shows move-in ready.
Avoid If
You need large square footage or new construction.

A condition-driven villa market

With 110 homes and a tight build window of 1981 to 1989, this is a predictable pool of inventory. The median living area sits around 1,215 square feet, so most listings compete on the same footprint. That makes updates — kitchens, baths, flooring, HVAC and roof age — the deciding factor between a quick sale and a slow one. A median of $229.65 per square foot is the benchmark to measure any given villa against.

Roughly 59% of homes carry a homestead exemption, which points to a meaningful share of owner-occupants rather than a purely investor-held complex. For a buyer, that mix tends to mean stable ownership; for a seller, it means your comparables are real, lived-in units, and pricing to the median with credit for genuine upgrades is the honest path.

The location and the amenities are priced into every listing in Villas Of Casselberry Ph 2. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a community this uniform, the money is made or lost on reading condition against the $270,000 median and the roughly 33-day pace. We know which updates the local buyer pool actually pays for versus the ones that don't return, and we price and stage accordingly instead of guessing.

Villas Of Casselberry Ph 2 in 15 seconds.

Best forBuyers who want a low-maintenance villa in a Winter Park, Seminole County address at a moderate price.
Biggest advantageA uniform, easy-to-comp community where value is straightforward to read.
Biggest riskOlder 1980s systems mean roof, HVAC and plumbing age deserve close scrutiny.
Sweet spotAn updated villa priced near the $270,000 median that shows move-in ready.
Avoid ifYou need large square footage or new construction.

HOA, CDD & Fees

In short
  • Mandatory HOA — confirm current dues
  • Any club/amenity membership is billed separately

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Villas Of Casselberry Ph 2 sales matched to your home.

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Frequently Asked Questions

What is the median home price in Villas Of Casselberry Ph 2?
The median sale price in Villas Of Casselberry Ph 2 was $270K over the 12 months ending July 13, 2026 (3 closed sales, Stellar MLS).
How long do homes in Villas Of Casselberry Ph 2 take to sell?
Homes that closed in the 12 months ending July 13, 2026 took a median 33 days on market (3 sales, Stellar MLS).
How many homes are in Villas Of Casselberry Ph 2?
The Florida DOR 2025 assessment roll shows 110 homes in Villas Of Casselberry Ph 2 (public records).
What share of Villas Of Casselberry Ph 2 is owner-occupied?
59% of Villas Of Casselberry Ph 2 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Villas Of Casselberry Ph 2 built?
Homes in Villas Of Casselberry Ph 2 were built between 1981 and 1989, with a median year built of 1984.0 (FL DOR 2025 roll).
Do cash buyers compete in Villas Of Casselberry Ph 2?
Cash buyers took 0% of Villas Of Casselberry Ph 2 sales in the 12 months ending June 2024 (0 of 4 closings, Stellar MLS).
Who is the best real estate agent for Villas Of Casselberry Ph 2?
The best agent for Villas Of Casselberry Ph 2 is one who actively works Winter Park and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Villas Of Casselberry Ph 2.
How do I find a top Winter Park real estate agent who knows Villas Of Casselberry Ph 2?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Villas Of Casselberry Ph 2 and the wider Winter Park area.
Can Momentum Realty connect me with an agent for Villas Of Casselberry Ph 2?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Villas Of Casselberry Ph 2 purchase or sale - no call center and no pressure.
Right-sizers wanting a compact, single-story-scale villa around 1,200 square feet near a $270,000 budgetExcellent fit
Buyers prioritizing a Winter Park location in Seminole County over maximum sizeExcellent fit
Value-minded buyers willing to update an 1980s villa and build equity through conditionExcellent fit
Buyers who need substantially more than the roughly 1,215-square-foot median footprintProbably not
Anyone wanting newer construction than the 1981-1989 build eraProbably not
Buyers unwilling to budget for aging systems in an older homeProbably not

Data sources & freshness

Community market statsStellar MLS closed sales, 12-month windows ending July 13, 2026
Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (5 streets, ZIP 32707/32792))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2011 (31 transactions analyzed)

Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.

Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.

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