Bear Gully Pointe
Homes for Sale in Winter Park, FL
True comps, carrying-cost math, and listings before the portals.
Price here is driven by size and condition, not by a hot market. At a median of $1,095,000 on roughly $278 per square foot, the number reflects large homes — a median of just over 4,000 living square feet — built across a span from the early 1970s into the late 1990s. That age spread means what you pay is really a bet on how much updating a given house has already absorbed. Two homes at similar asking prices can be very different underneath.
The current posture favors buyers who can be patient. Median days on market sit at 75, and year-over-year pricing is down 4.8 percent, so sellers should expect a longer runway and realistic pricing rather than a quick bidding contest. For buyers, that slower pace is leverage — time to inspect, to negotiate on condition, and to walk away. This is a small community, with only a handful of closings in the recent window, so any single sale moves the averages.
BEAR GULLY POINTE right now
🔴 Off the recent peak. The trailing-12-month median ($1.01M) is down 13.3% from the prior 12 months ($1.17M). With about 1 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Low (3 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Bear Gully Pointe right now
🟡 Off the recent peak. The trailing-12-month median ($1.10M) is down 4.8% from the prior 12 months ($1.15M). With about 1 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending July 15. Confidence: Low (4 and 3 sales in the two windows).
What's unique here: the median sale price is about 3x the typical Seminole County sale ($1.10M vs $410K, trailing 12 months, Stellar MLS records).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated July 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Bear Gully Pointe market snapshot (as of July 15, 2026): the median sale price is about $1.10M ($278 per sq ft over the trailing 12 months of closed sales), and a median 75 days on market for closed sales. The trailing-12-month median is down 5% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
Bear Gully Pointe is a community of 60 homes in Winter Park, Seminole County, built between 1972 and 1999 (median 1993.5), with a median living area of about 4,068 square feet. 93% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Bear Gully Pointe is a small, established enclave of about 60 larger homes in Winter Park's slice of Seminole County, where the median house is a substantial build from the mid-1990s vintage and price turns almost entirely on updating and layout.
Who Bear Gully Pointe is best for.
Best for
- Buyers seeking substantial square footage — around 4,000 feet — as a long-term hold
- Those with budget or appetite to renovate an older home to their standard
- Buyers who value a patient, low-pressure negotiation over a bidding war
Probably not for
- Buyers who need move-in-ready new construction with no deferred maintenance
- Anyone counting on a quick flip or short-term resale gain
- Buyers who want a broad selection on demand — inventory here is thin and slow
Median sale price over the trailing 12 months ending July 15 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.10M) IS the median in the snapshot above, and the move from 2025 ($1.15M) IS the -4.8% one-year change.
Windows contain 0 to 5 sales each (4 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.
The Bear Gully Pointe buying strategy.
If we were buying in Bear Gully Pointe today, this is the order of operations we would run for our clients.
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.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
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 Bear Gully Pointe.
A condition-driven market on a slow clock
With homes dating from 1972 to 1999 and a median build around 1993, the housing stock here is well past its original systems. Roofs, HVAC, kitchens, and baths are the real variables. The median price tells you the center of gravity — $1,095,000 — but the spread around it is about how much work a house still needs, not about tiers of new construction. Read every listing through that lens and budget for the difference.
A homestead share above 93 percent tells you these are overwhelmingly owner-occupied, long-held homes rather than a churn of rentals or flips. That tends to mean fewer listings and slower turnover, which lines up with a 75-day median on market. Inventory is thin, so timing matters more than in a larger neighborhood — the right house may not appear on your schedule.
The location and the amenities are priced into every listing in Bear Gully Pointe. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Bear Gully Pointe buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (6.3). Basis: Recent Direction -4.8% year-over-year; Owner Commitment 93% owner-occupied; Pricing Power 92.1% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a small, condition-driven market like this, the value is in reading houses accurately — what a given home's age, systems, and square footage actually justify against that $1,095,000 median. With turnover this thin and days on market this long, we help buyers use the slower clock as negotiating room and help sellers price to the current down-trend rather than to last year's hopes.
Bear Gully Pointe in 15 seconds.
HOA, CDD & Fees
- 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.
Tools for a Bear Gully Pointe buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Bear Gully Pointe sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Bear Gully Pointe, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Bear Gully Pointe home worth?
Get a no-obligation home value based on real comparable sales in Bear Gully Pointe, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Bear Gully Pointe?
How long do homes in Bear Gully Pointe take to sell?
How many homes are in Bear Gully Pointe?
What share of Bear Gully Pointe is owner-occupied?
When were the homes in Bear Gully Pointe built?
Do cash buyers compete in Bear Gully Pointe?
Who is the best real estate agent for Bear Gully Pointe?
How do I find a top Winter Park real estate agent who knows Bear Gully Pointe?
Can Momentum Realty connect me with an agent for Bear Gully Pointe?
Should you buy in Bear Gully Pointe?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (4 streets, ZIP 32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2004 (26 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.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.01M) IS the median in the snapshot above, and the move from 2025 ($1.17M) IS the -13.3% one-year change.
Windows contain 0 to 4 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 2004 through 2025. Deemed reliable but not guaranteed.
33% of homes for sale in ZIP 32792 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-08-01).
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (4 streets, ZIP 32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2004 (26 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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.
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See how BEAR GULLY POINTE fits the bigger picture — live prices, inventory, and Momentum Scores:
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