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.
166 homes with four or more bedrooms are for sale or pending in Winter Park, FL today across 102 communities. The median asking price is $1,562,450, from $299,900 to $6,995,000. Listings in Winter Park without that feature have a median of $429,900. Most listings right now: The Enclave Winter Park (7), Winter Park Village (6), Lawndale (5). Updated October 2, 2026 from the MLS.
Live 4-bedroom homes in Winter Park: the listings
123 active listings match today (42% of Winter Park inventory), median asking $1,598,000, $545/sq ft, median 41 days on market. Photo cards link to the listing; refreshed nightly.
Newest 4-bedroom homes in Winter Park
The most expensive 4-bedroom homes in Winter Park
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 901 Golfview Terrace | $6,995,000 | 5,479 | — |
| 1260 Alabama Drive | $6,900,000 | 6,396 | J Kronenberger |
| 698 N New York Avenue | $6,195,000 | 5,096 | — |
| 1571 Woodland Avenue | $6,000,000 | 7,397 | Comstock Park |
| 2661 Via Tuscany | $5,999,990 | 3,880 | Maitland Shores |
| 2228 Azalea Place | $5,600,000 | 5,152 | Maitland Shores |
| 313 Sylvan Drive | $5,500,000 | 4,775 | Sylvan Park |
| 1166 Palmer Avenue | $5,500,000 | 5,181 | Palmer Ave Lakeside Prop |
| 825 Palmer Avenue | $5,195,900 | 5,122 | J Kronenberger |
| 231 Chelton Circle | $4,700,000 | 5,550 | Forest Hills |
4-Bedroom Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 9 | 7% |
| $500K–$750K | 16 | 13% |
| $750K–$1M | 15 | 12% |
| $1M+ | 83 | 67% |
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 | 6 | 5 | $1,673,500 | $1,075,000 |
| Lawndale | 5 | 4 | $1,399,900 | $1,095,000 |
| Winter Park Pines | 5 | 0 | $775,000 | $695,000 |
| Charmont | 4 | 2 | $2,194,000 | $1,525,000 |
| Lake Knowles Terrace Add 02 | 4 | 2 | $2,119,500 | $1,425,000 |
| Maitland Shores First Add | 3 | 1 | $5,600,000 | $1,319,950 |
| J Kronenberger Sub | 3 | 1 | $5,195,900 | $2,195,000 |
| Forest Hills | 3 | 1 | $3,395,000 | $3,075,000 |
| Kenilworth Shores Sec 06 | 3 | 3 | $2,800,000 | $2,700,000 |
| Winter Park | 3 | 1 | $2,495,000 | $950,000 |
| 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 |
| Killarney Estates | 3 | 0 | $1,250,000 | $1,095,000 |
| Glencoe Sub | 3 | 0 | $630,000 | $605,000 |
| Palmer Ave Lakeside Prop | 2 | 1 | $4,950,000 | $4,400,000 |
| Park Grove | 2 | 1 | $4,072,500 | $3,495,000 |
| Comstock Park | 2 | 0 | $3,797,500 | $1,595,000 |
| Kenilworth Shores Sec 01 | 2 | 2 | $2,494,995 | $1,999,990 |
| Northwood Terrace | 2 | 1 | $1,710,000 | $925,000 |
| Fontainebleau | 2 | 0 | $1,687,500 | $1,625,000 |
| Eastgate Sub | 2 | 2 | $1,647,000 | $1,299,000 |
| Waters Edge At Hawks Crest | 2 | 0 | $1,462,500 | $1,325,000 |
| Karolina On Killarney | 2 | 2 | $1,084,000 | $918,000 |
| Kenilworth Shores Sec 07 | 2 | 0 | $930,750 | $599,000 |
| Lake Waunatta Woods | 2 | 0 | $654,388 | $569,000 |
| Winter Park Estates | 2 | 0 | $562,500 | $550,000 |
| Tanglewood Sec 3 Rep | 2 | 0 | $458,500 | $355,000 |
| Garden Lake Estates Unit 3 | 2 | 0 | $434,949 | $399,999 |
| Winter Woods Unit 01 | 2 | 0 | $430,000 | $375,000 |
| Eastbrook Sub | 2 | 0 | $333,950 | $299,900 |
| Golfview Terrace | 1 | 0 | $6,995,000 | $6,995,000 |
| Greens/Pk | 1 | 1 | $6,195,000 | $6,195,000 |
| Alabama Oaks | 1 | 0 | $5,900,000 | $5,900,000 |
| Sylvan Park | 1 | 1 | $5,500,000 | $5,500,000 |
| Lake Maitland | 1 | 0 | $4,750,000 | $4,750,000 |
| Alexander Place | 1 | 0 | $4,250,000 | $4,250,000 |
| Winflor Court Pt Rep | 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 |
| Detmar Terrace Winter Park | 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 |
| South Lakemont Shores | 1 | 0 | $2,190,000 | $2,190,000 |
| Lake Virgina Shores | 1 | 0 | $2,095,000 | $2,095,000 |
| Kenilworth Shores Sec 03 | 1 | 0 | $1,950,000 | $1,950,000 |
| Parklando 03 | 1 | 0 | $1,890,000 | $1,890,000 |
| Tantum Add | 1 | 0 | $1,875,000 | $1,875,000 |
| Lake Knowles Terrace 2Nd Add | 1 | 1 | $1,829,000 | $1,829,000 |
| Temple Estates | 1 | 0 | $1,795,000 | $1,795,000 |
| Sharon Place | 1 | 0 | $1,749,000 | $1,749,000 |
| Lakeview Terrace | 1 | 0 | $1,725,000 | $1,725,000 |
| Horton Aaron | 1 | 0 | $1,700,000 | $1,700,000 |
| Twin Acres | 1 | 0 | $1,649,000 | $1,649,000 |
Also with 4-bedroom homes for sale
- Lake Killarney Shores (1)
- Fremar (1)
- Virginia Heights Rep (1)
- Park Manor First Add (1)
- Bear Gully Pointe (1)
- Windsong Elizabeths Walk 43/81 (1)
- Orwin Manor Westminster Sec (1)
- Elizabeth Heights Sub (1)
- Quail Hollow (1)
- Parklando (1)
- Kenilworth Shores Sec 04 (1)
- Park Pointe Rep (1)
- Brookshire Heights 2Nd Add (1)
- Brookshire Heights 4Th Add (1)
- Lake Ann Estates Unit 3 (1)
- Osceola Or Lakeview Deed (1)
- Carver Town First Add (1)
- Lake Bell Terrace (1)
- Sherbrooke (1)
- Lake Ann Estates Unit 2 (1)
- Capens Add (1)
- Conwill Ests (1)
- Landings At Hawks Crest (1)
- Swoope Park (1)
- Kenilworth Estates 1St Add (1)
- Brookshire Heights (1)
- Winter Park Pines Rep (1)
- Seville Park (1)
- Orangewood Park (1)
- Golfside Sec 03 (1)
- Kings Cove (1)
- Attilio G Panacciones Sub (1)
- Enclave At Aloma (1)
- Arrowhead Cove (1)
- Winter Woods Unit 03 (1)
- Wrenwood Unit 3 3Rd Add (1)
- Cedar Ridge (1)
- Bel Aire Pines (1)
- Bel Aire (1)
- Ridge High 1St Add (1)
- Eastbrook Sub Unit 06 2Nd Rep (1)
- Ridge High Sub (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
- All homes for sale in Winter Park
- Winter Park ZIP codes with prices
- Winter Park pool homes
- Winter Park waterfront homes
- Winter Park gated community homes
- Winter Park homes under $300K
- Winter Park homes $300K–$500K
- 4-Bedroom Homes in every city
4-Bedroom Homes in nearby Orange County cities
- Orlando 4-bedroom homes (1645 for sale)
- Winter Garden 4-bedroom homes (499 for sale)
- Apopka 4-bedroom homes (341 for sale)
- Windermere 4-bedroom homes (225 for sale)
- Ocoee 4-bedroom homes (100 for sale)
- Maitland 4-bedroom homes (39 for sale)
- Oakland 4-bedroom homes (33 for sale)
- Belle Isle 4-bedroom homes (13 for sale)
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.