Hollowbrook
Homes for Sale in Winter Springs, FL
All 159 homes for sale in Winter Springs, FL · median $420,000 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Homes listed or recently sold were built 1986–1989; 5 of 5 report an HOA (median $34/mo); none of the 5 geocoded homes sit in a FEMA special flood hazard zone (median elevation 66 ft). As of October 2026, the MLS records 44 closed sales in Hollowbrook in Winter Springs, FL since 2004, the most recent in October 2025. Recorded prices since 2024 ran from $377,000 to $490,000 (median $435,000), on homes of 1,734 to 2,223 sq ft. Across Winter Springs as a whole, 267 homes closed in the last 12 months at a median of $444,997, 33 median days on market, with 125 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $6,600 ($6,000 with the full homestead exemption).
Last 30 days in Hollowbrook: 1 new listing (median asking $449,000), 1 under contract right now. As of October 24, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Hollowbrook is a built-out pocket of about 220 homes in Winter Springs, with construction concentrated in the late 1980s and a median year built of 1987. At a median of roughly 1,959 living square feet, these are mostly comparable-footprint houses, so price here is driven far less by size than by condition, updates, and lot. Two homes on the same street can trade very differently depending on whether the kitchen, roof, and systems have been touched since original construction.
This is a low-turnover, owner-heavy neighborhood: homestead exemption covers roughly 77% of homes, which tends to hold inventory tight and keep the resale pool small. For sellers, that scarcity is leverage if your home is genuinely updated. For buyers, expect to compete when a well-kept house lists, and to underwrite renovation cost carefully on the ones that haven't been modernized.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Hollowbrook right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Hollowbrook is a stable, largely owner-occupied enclave of late-1980s homes on a consistent footprint, where the story is condition and upkeep rather than square footage.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
The setting & the homes.
Aerial and on-site photos of Hollowbrook. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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HollowbrookPhotos from Stellar MLS listings in Hollowbrook; content deemed reliable but not guaranteed.
Who Hollowbrook is best for.
Best for
- Buyers targeting a mid-size single-family home who value stability over churn
- Renovation-comfortable buyers who can add value through updates on an original house
- Long-hold owners who plan to stay and use the homestead exemption
Probably not for
- Buyers who want newer construction or modern floor plans
- Shoppers who need a wide, fast-moving selection of active listings
- Buyers with no budget or appetite for updating aging roofs and systems
The market around Hollowbrook
Hollowbrook is a small community — 55 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.
Across Seminole County, 1,538 homes are active and 629 pending (29% under contract).
Homes here are single family residence.
ZIP and county figures describe the wider market, not Hollowbrook specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Hollowbrook
Live MLS inventory for Hollowbrook. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Hollowbrook listings as of 2026-10-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Tap any home to ask about it.
Hollowbrook on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap contributors.
Schools
- Seminole County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Red Bug Elementary · Elementary
- Tuskawilla Middle · Middle
- Lake Howell High · High
Zoned schools reflect the assignments reported on recent Hollowbrook listings and can change; always confirm with Seminole County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Hollowbrook address.
The Hollowbrook buying strategy.
If we were buying in Hollowbrook 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 Hollowbrook.
A condition-driven resale market
With homes built between 1985 and 1990 and a median footprint near 1,959 square feet, Hollowbrook offers a fairly uniform product. That uniformity makes it easier to read value: once you've walked a few, you can quickly tell an updated house from an original one. The spread between the two can be wide, and it's almost entirely about what's been renovated and maintained.
The high homestead share, roughly 77%, signals people stay put. That keeps listing counts thin and rewards buyers who are ready to move when the right home appears. Homes near the end of their original roof, HVAC, and system life should be priced and negotiated with those replacement costs in view.
The location and the amenities are priced into every listing in Hollowbrook. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a tight, condition-sensitive market like Hollowbrook, the value is in reading each home honestly against the neighborhood's uniform footprint. We help sellers document what's been updated so it earns its price, and we help buyers separate cosmetic freshness from the systems that actually cost money, then negotiate accordingly.
Hollowbrook in 15 seconds.
Tools for a Hollowbrook 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 Hollowbrook sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Hollowbrook, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Hollowbrook home worth?
Get a no-obligation home value based on real comparable sales in Hollowbrook, 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 all homes for sale in Winter Springs →
| Location | Winter Springs, Seminole County, FL |
|---|---|
| Homes in the community | 220 (FL DOR 2025 assessment roll) |
| Years built | 1985–1990 (median 1987.0) |
| Typical living area | 1,959 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Owner-occupied (homestead) share | 77% |
Data as of July 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Hollowbrook key facts,” movewithmomentum.com/neighborhoods/hollowbrook, data as of July 13, 2026.
Housing distress & ownership in Hollowbrook, Winter Springs
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.
Every Home for Sale in Hollowbrook Right Now (2)
All 2 active and pending Hollowbrook listings with a detail page, newest first, refreshed twice a day from the MLS.
- 3600 Biscayne Drive · $449,000 · 4 bd / 2 ba · listed Oct 10, 2026 · listed by Lpt Realty, Llc
- 4038 Biscayne Drive · $525,000 · 4 bd / 2.5 ba · pending · listed Sep 30, 2026 · listed by Van Den Berg Real Estate Group
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Winter Springs guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Seminole County)
- Homestead exemption (Seminole County)
- Home insurance cost
- New construction (Seminole County)
Florida buyer guides
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Biscayne Drive (46 homes on record)
- Biscayne Drive (13 homes on record)
What it really costs to own in Hollowbrook
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $412/year (about $34/month) across 5 MLS listings (most billed annually; 2026-10-24). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Seminole County is $1,572/yr (1,203 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 1988 across 5 listings. An original roof here would be about 38 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Hollowbrook
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Hollowbrook
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Hollowbrook will answer, and the answer is published on this page for the next buyer.
28% of homes for sale in ZIP 32708 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 (2026-10-25).
Frequently Asked Questions
How many homes are in Hollowbrook?
What share of Hollowbrook is owner-occupied?
When were the homes in Hollowbrook built?
Do cash buyers compete in Hollowbrook?
Who is the best real estate agent for Hollowbrook?
How do I find a top Winter Springs real estate agent who knows Hollowbrook?
Can Momentum Realty connect me with an agent for Hollowbrook?
Where is Hollowbrook, and what county is it in?
Should you buy in Hollowbrook?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 23, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 32707/32708)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2004 (44 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 local comps.
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