Galloway Place
Homes for Sale in Winter Park, FL

All 394 homes for sale in Winter Park, FL · median $636,250 · 169 homes for sale in 32789 · Orange County homes for sale

Community in Winter Park · Orange County · ZIP 32789
37 homesBuilt 1925–2023
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Built fromLive Stellar MLS data12 years of closingsFL DOR public recordsUpdated twice daily

As of November 2026, the MLS records 6 closed sales in Galloway Place Rep in Winter Park, FL since 2014, the most recent in January 2026. Across Winter Park as a whole, 887 homes closed in the last 12 months at a median of $499,000, 37 median days on market, with 326 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,320 ($7,650 with the full homestead exemption).

Live · Galloway Place Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Ownership and context
84%
Owner-occupied · Galloway Place
31 of 37 parcels homesteaded (FL DOR 2025)
16%
Non-owner-occupied · Galloway Place
incl. 14% trust or LLC-held · 100% out-of-state
37
Homes in the community
37 residential parcels (FL DOR 2025)
Track record · 12 years of records
1925–2023
Years homes were built
median 1968 · county roll (FL DOR 2025)
Jon Brooks, Co-Founder of Momentum Realty
Jon's Read · written July 21, 2026

Galloway Place Rep is a small pocket of Winter Park housing stock built mostly in the mid-20th century, with a median build year of 1951 stretching all the way to homes finished as recently as 2023. That spread tells the real story here: this is not a tract of uniform product, it is a mix of original construction and later infill or rebuilds sitting on the same streets. Pricing in a community like this is driven far more by what has been done to a given house — foundation, systems, additions, finish level — than by any single neighborhood-wide standard.

With only 76 homes in the dataset, this is a thin market where a handful of sales can shift the read from one quarter to the next. Homestead share sits at roughly 70 percent, which points to a base of owner-occupied households and generally less turnover than an investor-heavy pocket. For sellers, that means fewer comparable competing listings at any given time. For buyers, it means patience and a willingness to move when the right property surfaces, since inventory does not replenish quickly.

Figures in this note are as of July 21, 2026. The live market numbers elsewhere on this page update nightly and are newer.

Nearby homes for sale

No active listings inside Galloway Place 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.

1399 ALOMA AVENUE
$575K · 0.1 mi away
3 bd · 2 ba · 1,804 sqft
1399 ALOMA AVENUE
Listed by FANNIE HILLMAN & ASSOCIATES
281 BREWER AVENUE
$1.80M · 0.2 mi away
5 bd · 4.5 ba · 4,029 sqft
281 BREWER AVENUE
Listed by HENTHORN REAL ESTATE
450 LAKEWOOD DRIVE
$2.50M · 0.3 mi away
5 bd · 5 ba · 4,572 sqft
450 LAKEWOOD DRIVE
Listed by CHARLES RUTENBERG REALTY ORLANDO
276 DETMAR DRIVE
$3.60M · 0.3 mi away
4 bd · 5 ba · 4,202 sqft
276 DETMAR DRIVE
Listed by CALL IT CLOSED INTL REALTY
1441 GROVE TERRACE
$5.95M · 0.3 mi away
5 bd · 6 ba · 5,796 sqft
1441 GROVE TERRACE
Listed by ONE LUXURY INTERNATIONAL LLC
1398 GROVE TERRACE
$1.95M · 0.3 mi away
4 bd · 3.5 ba · 3,450 sqft
1398 GROVE TERRACE
Listed by COMPASS FLORIDA LLC

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

Galloway Place Rep sits in Winter Park, Orange County, with a housing stock that spans over a century of construction — from homes built at the turn of the 20th century to recent completions — and a median living area of 2,733 square feet, indicating homes here tend to run larger than a typical infill lot would suggest.

Stellar MLS sales records identify 10 homes in Galloway Place that have changed hands since 2010, built between 1928 and 2023 (median 1948), with a median living area of about 3,483 sq ft and a typical 4-bedroom, 4-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

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.

Best for

  • Buyers prioritizing larger living space in an established Winter Park location over amenity access.
  • Buyers comfortable doing property-specific diligence on a home built anywhere from the early 1900s to recent years.
  • Buyers planning to hold long-term in a market where owner-occupancy is the norm rather than the exception.

Probably not for

  • Buyers who want a clubhouse, pool, or other shared community amenities as part of the purchase.
  • Buyers who want a single, predictable architectural style or construction era across the neighborhood.
  • Buyers expecting a high-volume, fast-turnover market with abundant comparable listings at any given time.

The market around Galloway Place

Galloway Place is too small for its own price trend, so here is the market around it.

In ZIP 32789, 239 homes are on the market and 23% are under contract — a steady corner of Winter Park.

Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).

In ZIP 32789 (Winter Park), 111 homes closed in the last 12 months at a median of $627K ($396/sq ft), down 21.6% year over year, with a median 42 days on market. Right now 34 active and 4 pending listings put supply at about 3.7 months — a buyer's market. See the live ZIP 32789 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Galloway Place specifically. Momentum Research analysis of MLS records.

Galloway Place by the numbers

From county property records and closed MLS sales for the Galloway Place subdivision: 8 homes on record; built 1928–2023; typical size about 3,515 heated sq ft; 4 bedrooms is the median. Housing mix: single-family 100%.

YearRecorded salesMedian price
20181$558,000
20201$1,034,000
20211$1,800,000
20221$825,000
20252$3,237,500
20261$525,000

Newest recorded sale: $525,000 on 2026-01-20.

Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.

If we were buying in Galloway Place 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 Galloway Place.

Best Buy
Buyers looking for a Winter Park address with larger-than-typical living space and are comfortable evaluating homes on individual condition rather than a uniform community standard.
Biggest Risk
With only 76 homes and no listed amenities, this is a thin, condition-driven market where comps can be inconsistent.
Sweet Spot
Buyers who want a larger home footprint (median 2,733 sq ft) in an established Winter Park location and are willing to do diligence on individual property condition.
Avoid If
You are seeking a community with shared recreational amenities or a uniform, single-era housing product.

A Mixed-Vintage Pocket Without Amenity-Driven Pricing

The defining fact about Galloway Place Rep is its age range: a median build year of 1951 bracketed by a range running from 1901 to 2023. That is not a community with one architectural era or one construction standard. Some of what is on the market will be original mid-century construction, unrenovated or partially updated. Some will be recent builds or substantial rebuilds on older lots. Buyers need to evaluate each property on its own condition and systems rather than assuming anything about the block based on one listing.

No community amenities were identified from current MLS listings, which means whatever draws buyers here is the location and the homes themselves — not a shared pool, clubhouse, or recreational infrastructure. With a homestead share near 70 percent, the area reads as a place where owners tend to settle in rather than cycle through quickly, which is worth factoring into expectations around how often, and under what circumstances, homes here actually come to market.

“

The location and the amenities are priced into every listing in Galloway Place. 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 small, mixed-vintage market like Galloway Place Rep, the work is in the details: knowing which of the 76 homes have been substantially updated versus which are original, and pricing accordingly. We track this pocket closely enough to tell you what a given house's age and condition actually mean for value, rather than leaning on a single neighborhood average that does not fit anyone's specific property.

Galloway Place in 15 seconds.

Best forBuyers looking for a Winter Park address with larger-than-typical living space and are comfortable evaluating homes on individual condition rather than a uniform community standard.
Biggest advantageThe age range means there is real variety in what is available, from original mid-century homes to recent construction.
Biggest riskWith only 76 homes and no listed amenities, this is a thin, condition-driven market where comps can be inconsistent.
Sweet spotBuyers who want a larger home footprint (median 2,733 sq ft) in an established Winter Park location and are willing to do diligence on individual property condition.
Avoid ifYou are seeking a community with shared recreational amenities or a uniform, single-era housing product.
The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Galloway Place sales matched to your home.

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Real comps, not an automated estimate.
Galloway Place key facts
LocationWinter Park, Orange County, FL · ZIP 32789
Homes in the community37 (FL DOR 2025 assessment roll)
Years built1925–2023 (median 1968)
Typical living area3,404 sq ft (median)
Owner-occupied (homestead) share84%

Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Galloway Place key facts,” movewithmomentum.com/neighborhoods/galloway-place-rep, data as of September 20, 2026.

Streets in this community

Street-level pages: every home on record, what sold and what is for sale on each street.

Email me new listings in Galloway Place

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.

Equal Housing Opportunity. Every community is open to everyone; alerts are about homes, never about who lives here.

Ask an agent about Galloway Place

Have a question about the homes, fees, rules or commute here? A Momentum agent who works Galloway Place will answer, and the answer is published on this page for the next buyer.

Property facts only: homes, fees, rules, commute. Every community is open to everyone; agents do not answer questions about who lives here.

Frequently Asked Questions

How many homes are in Galloway Place?
The Florida DOR 2025 assessment roll shows 37 homes in Galloway Place (public records).
What share of Galloway Place is owner-occupied?
84% of Galloway Place parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Galloway Place built?
Homes in Galloway Place were built between 1925 and 2023, with a median year built of 1968 (FL DOR 2025 roll).
Who is the best real estate agent for Galloway Place?
The best agent for Galloway Place 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 Galloway Place.
How do I find a top Winter Park real estate agent who knows Galloway Place?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Galloway Place and the wider Winter Park area.
Can Momentum Realty connect me with an agent for Galloway Place?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Galloway Place purchase or sale - no call center and no pressure.
Where is Galloway Place, and what county is it in?
Galloway Place is in Winter Park, Orange County, FL, ZIP 32789.
Buyers prioritizing larger living space in an established Winter Park location over amenity access.Excellent fit
Buyers comfortable doing property-specific diligence on a home built anywhere from the early 1900s to recent years.Excellent fit
Buyers planning to hold long-term in a market where owner-occupancy is the norm rather than the exception.Excellent fit
Buyers who want a clubhouse, pool, or other shared community amenities as part of the purchase.Probably not
Buyers who want a single, predictable architectural style or construction era across the neighborhood.Probably not
Buyers expecting a high-volume, fast-turnover market with abundant comparable listings at any given time.Probably not

Data sources & freshness

Housing stock & ownershipFlorida DOR assessment roll (street-list match (2 streets, ZIP 32789))
Under-contract sharesStellar MLS records, as of 2026-09-20
Historical depthClosed-sale records back to 2014 (6 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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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. A Momentum agent can price yours against live local comps.

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Nearby Communities

Explore more neighborhoods near Galloway Place with Momentum Realty’s local guides.

SHSorensen Heights0.1 mi awayOSOsceola Summit0.1 mi awayCortland Park0.2 mi away · 46 homes, built 1925–22Stratford Winter Park0.2 mi awayLakemont Estates0.2 mi away · 1 for saleArt Systems Center0.2 mi awayWinter Park Comm0.2 mi away · 1 for saleSylvan Park0.3 mi away · 220 homes, built 1901–24, 1 for sale

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