4 Bedroom Homes for Sale in Winter Park, FL
Four bedrooms is the most-searched size in most Florida and Georgia markets. This page tracks every Winter Park listing whose MLS record reports four or more bedrooms, by community, with live counts and asking prices, and how the price compares with smaller homes in the same city.
153 homes with four or more bedrooms are for sale or pending in Winter Park, FL today across 95 communities. The median asking price is $1,574,900, from $249,900 to $7,250,000. Listings in Winter Park without that feature have a median of $415,000. Most listings right now: The Enclave Winter Park (7), Winter Park Village (5), Winter Park Pines (5). Updated September 11, 2026 from the MLS.
Winter Park 4-bedroom homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale. The 60 communities with the most 4-bedroom homes listed are tabled; the rest follow.
| Community | 4-Bedroom Homes | New build | Median list | From |
|---|---|---|---|---|
| The Enclave Winter Park | 7 | 7 | $2,275,000 | $1,550,000 |
| Winter Park Village | 5 | 4 | $1,749,000 | $1,075,000 |
| Winter Park Pines | 5 | 0 | $695,000 | $474,000 |
| Park Grove | 4 | 3 | $4,297,000 | $1,824,000 |
| Maitland Shores First Add | 4 | 1 | $4,175,000 | $1,319,950 |
| Kenilworth Shores Sec 06 | 4 | 3 | $2,750,000 | $1,590,000 |
| Charmont | 4 | 3 | $2,749,000 | $1,565,000 |
| Lawndale | 4 | 4 | $1,409,950 | $1,249,900 |
| Forest Hills | 3 | 1 | $3,395,000 | $3,075,000 |
| Comstock Park | 3 | 0 | $2,699,000 | $1,640,000 |
| Lake Forest Park | 3 | 3 | $1,925,000 | $1,699,000 |
| Conwill Estates | 3 | 2 | $1,900,000 | $775,000 |
| Sylvan Heights | 3 | 2 | $1,750,000 | $1,380,000 |
| Lake Knowles Terrace Add 02 | 3 | 1 | $1,690,000 | $1,425,000 |
| Temple Estates | 2 | 1 | $2,090,000 | $1,795,000 |
| Winter Park | 2 | 1 | $1,745,499 | $995,999 |
| Fontainebleau | 2 | 0 | $1,745,000 | $1,625,000 |
| Northwood Terrace | 2 | 1 | $1,735,000 | $975,000 |
| Waters Edge At Hawks Crest | 2 | 0 | $1,462,500 | $1,325,000 |
| Killarney Estates | 2 | 0 | $1,425,000 | $1,250,000 |
| Karolina On Killarney | 2 | 2 | $1,084,000 | $918,000 |
| Kenilworth Shores Sec 07 | 2 | 0 | $930,750 | $599,000 |
| Swoope Park | 2 | 0 | $697,000 | $695,000 |
| Lake Waunatta Woods | 2 | 0 | $654,388 | $569,000 |
| Glencoe Sub | 2 | 0 | $647,400 | $629,900 |
| Winter Park Estates | 2 | 0 | $562,500 | $550,000 |
| 2 | 0 | $458,500 | $355,000 | |
| 2 | 0 | $442,400 | $414,900 | |
| Robert Dhu Macdonald Park | 1 | 1 | $7,250,000 | $7,250,000 |
| J Kronenberger Sub | 1 | 0 | $6,900,000 | $6,900,000 |
| Sylvan Park | 1 | 1 | $5,500,000 | $5,500,000 |
| Woodmere Terrace Rep | 1 | 0 | $4,900,000 | $4,900,000 |
| 1 | 0 | $4,750,000 | $4,750,000 | |
| Alexander Place | 1 | 0 | $4,250,000 | $4,250,000 |
| 1 | 0 | $3,995,000 | $3,995,000 | |
| Timberlane Shores | 1 | 1 | $3,890,000 | $3,890,000 |
| Cloister Grove Sub | 1 | 1 | $3,750,000 | $3,750,000 |
| 1 | 0 | $3,600,000 | $3,600,000 | |
| Maitland Shores 1St Add | 1 | 0 | $3,500,000 | $3,500,000 |
| Sylvan Lake Shores | 1 | 1 | $3,300,000 | $3,300,000 |
| Ellno Willo | 1 | 0 | $3,275,000 | $3,275,000 |
| Green Oaks Rep 02 | 1 | 0 | $3,265,000 | $3,265,000 |
| Orange Grove Sub | 1 | 1 | $2,569,999 | $2,569,999 |
| Villa View Park | 1 | 0 | $2,390,000 | $2,390,000 |
| Lugano Terrace | 1 | 0 | $2,195,000 | $2,195,000 |
| Kenilworth Shores Sec 01 | 1 | 1 | $1,999,990 | $1,999,990 |
| 1 | 0 | $1,995,000 | $1,995,000 | |
| Parklando 03 | 1 | 0 | $1,899,000 | $1,899,000 |
| 1 | 1 | $1,829,000 | $1,829,000 | |
| Kenilworth Shores Sec 03 | 1 | 0 | $1,800,000 | $1,800,000 |
| Lakeview Terrace | 1 | 0 | $1,725,000 | $1,725,000 |
| Horton Aaron | 1 | 0 | $1,700,000 | $1,700,000 |
| Parklando #3 | 1 | 0 | $1,649,000 | $1,649,000 |
| Twin Acres | 1 | 0 | $1,649,000 | $1,649,000 |
| Fremar | 1 | 0 | $1,599,000 | $1,599,000 |
| Virginia Heights Rep | 1 | 0 | $1,595,000 | $1,595,000 |
| Park Manor First Add | 1 | 0 | $1,500,000 | $1,500,000 |
| Orwin Manor Westminster Sec | 1 | 1 | $1,399,000 | $1,399,000 |
| Bear Gully Pointe | 1 | 0 | $1,395,000 | $1,395,000 |
| Lake Killarney Shores | 1 | 1 | $1,389,500 | $1,389,500 |
Also with 4-bedroom homes for sale
- Windsong Elizabeths Walk 43/81 (1)
- Elizabeth Heights Sub (1)
- Eastgate Sub (1)
- Quail Hollow (1)
- Parklando (1)
- Kenilworth Shores Sec 04 (1)
- Lake Knowles Terrace (1)
- Park Pointe Rep (1)
- Temple Terrace (1)
- (1)
- Carver Town First Add (1)
- Lake Bell Terrace (1)
- (1)
- Capens Add (1)
- (1)
- Brookshire Heights (1)
- (1)
- Winter Park Pines Rep (1)
- Seville Park (1)
- Orangewood Park (1)
- Arrowhead Cove (1)
- Attilio G Panacciones Sub (1)
- (1)
- Wrenwood Unit 3 3Rd Add (1)
- (1)
- Winter Park Pines Merrie Oaks (1)
- Ridge High 1St Add (1)
- (1)
- (1)
- (1)
- (1)
- Suburban Homes First Add (1)
- Eastbrook Sub (1)
- (1)
- Whisperwood Condo (1)
What the fourth bedroom costs
The answer block above compares the median asking price of four-plus-bedroom homes with the median of everything else listed in the city; the gap is what the extra room, and usually the extra square footage and lot, is priced at today. Compare on price per square foot, not price alone: a four-bedroom home at 2,000 square feet and one at 2,800 are different purchases, and the MLS square footage on each listing page makes that comparison in seconds. Newer subdivisions tend to deliver four bedrooms in less square footage than older ones; the community pages show year-built ranges so you can see which is which.
Questions to ask about any four-bedroom listing
Is the fourth bedroom a true bedroom with a closet and window, or a converted den, garage bay or bonus room? Are the bedrooms split (owner’s suite away from the others) or all on one side? Is there a second full bath near the secondary bedrooms? What does the seller pay for insurance and, in an HOA community, what do the dues cover? A local agent who works the area will know which builders’ four-bedroom plans hold their value.
Common questions
How many homes with four or more bedrooms are for sale in Winter Park?
What do 4-bedroom homes cost in Winter Park?
Which Winter Park community has the most 4-bedroom homes for sale?
How much more does a 4-bedroom home cost?
Keep exploring Winter Park
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- Winter Park ZIP codes with prices
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- Winter Park gated community homes
- Winter Park homes under $300K
- Winter Park homes $300K–$500K
- 4-Bedroom Homes in every city
Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Winter Park, FL whose MLS record reports four or more bedrooms. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.