Neighborhood · Winter Park, Florida
Orange Grove
Winter Park living with room to breathe
1
Homes for sale
$2,569,999
Median list price
$700
Avg price / sqft
1
Median days on market
Orange Grove sits inside one of Central Florida's most established residential pockets, surrounded by the tree-lined character that defines Winter Park homes for sale. It's a neighborhood of larger-lot single-family homes near landmarks like Lake Killarney and within reach of the walkable dining and shops around Hannibal Square. Families are drawn here for the assigned schools — Winter Park High, Maitland Middle, and Lakemont Elementary — and for the mix of quiet streets and easy access to everything Winter Park offers.
The market here is thin and premium: as of now there's a single active listing at $2,569,999, priced around $700 per square foot for a roughly 3,670-square-foot home. Over the last 12 months only two homes changed hands, at a median sold price of $1,575,000, and sellers averaged about 92% of their asking price. If you're comparing options nearby, communities like Winter Park Pines and Eastbrook round out the wider picture — but in Orange Grove itself, expect low inventory and to move quickly when the right home appears.
Orange Grove is a community in Winter Park, Florida.
Quick facts
$2,569,999 – $2.6M price range
3,670 sqft median home
2 sold in 12 months
On the market now
Homes for sale in Orange Grove
Every active listing inside the Orange Grove boundary
Open full map search →Find your fit
Browse Orange Grove
By feature — on the live map
The numbers that matter
The Orange Grove market
2
Sold, last 12 months
$1,575,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
19 days
Median time to sell
Orange Grove vs Winter Park
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Orange Grove boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Orange Grove is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Orange Grove home
≈ $14,068/mo
$2,569,999 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
136
Median age
49
Median income
$227,708
Median home value
$916,100
Beyond the listings
Living in Orange Grove
Relationships
Top 6% in the U.S.Connected Motherhood
Motherhood is a unique journey for every woman. There are highs, lows,and lots to celebrate. These moms seek to share their experiences and engage with a community of moms.
Emotional
Top 6% in the U.S.Memory Lane
Intentionally preserving memories of lost loved ones, joyful times, or reflecting on painful experiences in the past.
Lifestyles
Top 10% in the U.S.Student Life
There's more to student life than academics. It's about the experience - from classes and homecoming, to making lifetime friends and alumni events. These are students at school, taking classes online, or finding other ways to be students in their daily lives.
Beliefs
Top 13% in the U.S.Activism
This population seeks to advocate for a more just world. Common activities include protests, rallies, and spreading awareness to the public about social justice issues.
Lifestyles
Top 16% in the U.S.Nerd Culture
These people aren't afraid to nerd out. Common activities include comic books, video games, and often intellectual pursuits.
Emotional
Top 19% in the U.S.Happy Place
Expressing feelings of safety, comfort and happiness - especially with loved ones.
People who close here
Our Winter Park experts
Straight answers
Orange Grove FAQs
Is Orange Grove a good place to live?+
It's an established Winter Park neighborhood of larger single-family homes near Lake Killarney, with the walkable dining and shopping of Hannibal Square close by. Families value the assigned schools — Winter Park High, Maitland Middle, and Lakemont Elementary. The quiet streets and central location make it a strong fit for buyers who want space without leaving Winter Park.
Is Orange Grove expensive?+
Yes — it sits at the upper end of the Winter Park market. The single active listing is priced at $2,569,999, and homes here trade around $700 per square foot. Over the past year the median sold price was $1,575,000, so this is a premium neighborhood.
What do homes cost in Orange Grove?+
The current active listing is $2,569,999 for about 3,670 square feet, or roughly $700 per square foot. Actual closings tell a more grounded story: two homes sold in the last 12 months at a median of $1,575,000. Pricing varies widely with lot size and home condition, so expect a range.
How is the market in Orange Grove?+
Inventory is very tight — there's just one active listing right now, and only two homes sold over the past 12 months. When homes do come up they move fast; the current listing has been on the market a single day, and sellers averaged about 92% of asking. Because Winter Park homes for sale in this pocket are so limited, serious buyers should be ready to act.
What are the HOA and property taxes like?+
Median property tax in Orange Grove runs about $3,808 per year based on recent records. HOA data isn't available for the neighborhood, which is common for areas of independent single-family homes. Always confirm current tax and any association details on a specific property before you buy.
Keep exploring
More Winter Park neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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