Winter Park, FL | Luxury Homes for Rent & Real Estate

$226,700

/ Month

2228 Winter Woods Blvd Blvd, Winter Park, FL

88,268 sf

Listing Courtesy of RS EQUITY SERVICE LLC, RADHA RAMBILAS - 347-557-4113, Office Contact - 347-557-4113

$158,700

/ Month

1740 STATE ROAD 436, Winter Park, FL

15,042 sf

virtual tour

Listing Courtesy of THE OUTLIER GROUP, JOYCE TEIXEIRA - 813-312-4231, Office Contact - 888-966-4820, mautrey@outliergroup.us

Empty room, Interior, Wood Texture Flooring

Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Interior, Wood Texture Flooring

$42,140

/ Month

1976 W FAIRBANKS Ave, Winter Park, FL

1,925 sf

virtual tour

Listing Courtesy of DIDOMENICO REALTY GROUP, MICHAEL DIDOMENICO, JR - 407-922-3277, Office Contact - 407-922-3277, mike@didomenicorealtygroup.com

price reduced

Attached, Exterior, Facade, French Provincial

Backyard, Exterior, Facade, French Provincial

Attached, Backyard, Exterior, Facade, Queen Anne Victorian

Glass Ceilings, Interior, Pool, Sun Room

Fireplace, Interior, Living room, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Dining room, Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Dining room, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances

Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Chandelier, Dining room, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Walk-in Closets, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Marble Walls, Recessed Lighting

Bedroom, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Recessed Lighting, Walk-in Closets, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Free Standing Baths, Glass Shower, Interior, Marble, Marble Walls, Recessed Lighting

Bathroom, Free Standing Baths, Interior, Marble, Marble Walls, Pendant Lights

Bathroom, Glass Shower, Interior, Marble Walls

Bathroom, Glass Shower, Interior, Marble, Marble Walls, Recessed Lighting

Bathroom, Free Standing Baths, Interior, Marble, Marble Walls

Bathroom, Bedroom, Glass Shower, Interior, Marble Walls, Recessed Lighting, Wood Texture Flooring

Bathroom, Bedroom, Dual Sink Vanities, Glass Shower, Interior, Marble, Marble Walls, Wood Texture Flooring

Bedroom, Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Interior, Marble, Marble Walls, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Marble, Marble Walls

Interior, Living room, Marble, Pendant Lights, Recessed Lighting

Dining room, Interior, Living room, Marble, Pendant Lights, Recessed Lighting

Dining room, Interior, Kitchen, Living room, Marble, Pendant Lights, Recessed Lighting

Interior, Living room, Marble, Recessed Lighting

Dining room, Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting

Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting

Empty room, Interior, Marble, Recessed Lighting

Bathroom, Glass Shower, Interior, Recessed Lighting

Bedroom, Interior, Marble, Recessed Lighting

Billiard Table, Game Room, Interior, Marble, Pendant Lights, Recessed Lighting

$16,550

/ Month

1860 VIA CONTESSA, Winter Park, FL

8 br6 BA7,000 sf

virtual tour

Listing Courtesy of SIERRA REALTY GROUP LLC, SYLVESTER HARDING - 407-557-3119, Office Contact - 407-557-3119, sylhardingjr@gmail.com

Attached, Exterior, Facade, Mediterranean

Empty room, Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Chandelier, Empty room, Interior, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances

Empty room, Interior, Marble, Pendant Lights, Recessed Lighting

Empty room, Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Bathroom, Interior, Marble Walls, Recessed Lighting

Empty room, Fireplace, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Free Standing Baths, Interior, Marble, Marble Walls, Recessed Lighting

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting

Attached, Backyard, Exterior, Facade, Mediterranean

$10,500

/ Month

1530 VIA TUSCANY, Winter Park, FL

4 br3 BA, 1 HALF BA3,341 sf

virtual tour

Listing Courtesy of CORCORAN PREMIER REALTY, DAN HABER - 321-624-0966, Office Contact - 407-965-1155, chocky@premierrealtyorlando.com

Interior, Pendant Lights, Recessed Lighting

Interior, Living room, Pendant Lights, Recessed Lighting

Bathroom, Empty room, Glass Shower, Interior, Recessed Lighting

Dining room, Interior, Pendant Lights, Recessed Lighting

Dining room, Interior, Kitchen, Pendant Lights

Chandelier, Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting

Interior, Kitchen, Pendant Lights, Recessed Lighting

Interior, Pendant Lights, Wood Texture Flooring

Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Empty room, Interior, Wood Texture Flooring

Bathroom, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Living room, Wood Texture Flooring

Interior, Kitchen, Wood Texture Flooring

Interior, Kitchen, Living room, Wood Texture Flooring

Bedroom, Interior, Wood Texture Flooring

$9,900

/ Month

1442 PALM Ave, Winter Park, FL

4 br5 BA3,611 sf

Listing Courtesy of RE/MAX ASSURED, BIANCA BOTELHO, PA - 407-709-4975, Office Contact - 800-393-8600, remaxassured@yahoo.com

price reduced

Fireplace, Interior, Stone Walls, Wooden Ceilings

Fireplace, Interior, Living room, Recessed Lighting, Stone Walls

Fireplace, Interior, Living room, Recessed Lighting, Stone Walls, Wooden Walls

Fireplace, Interior, Pendant Lights, Recessed Lighting, Stone Walls

Empty room, Interior, Pendant Lights, Recessed Lighting

Empty room, Interior, Water, Wooden Ceilings, Wooden Walls

Empty room, Interior, Sun Room, Wooden Ceilings, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Wood Texture Flooring

$8,990

/ Month

2020 VENETIAN Way, Winter Park, FL

4 br3 BA, 1 HALF BA4,188 sf

virtual tour

Listing Courtesy of PALMANO GROUP RE BROKERAGE LLC, NADIA MOAYERI - 310-877-2839, Office Contact - 321-214-1211, rich@palmanogroup.com

contract signed

Empty room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Stainless Steel Appliances, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Marble, Marble Walls, Recessed Lighting

$6,450

/ Month

501 W CANTON Ave, Winter Park, FL

3 br2 BA, 1 HALF BA2,165 sf

virtual tour

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES, NICOLE HOWELL - 321-217-7918, Office Contact - 407-644-1234, scott@fanniehillman.com

price reduced

Chandelier, Empty room, Interior, Pendant Lights, Wood Texture Flooring

Chandelier, Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances

Empty room, Interior, Pendant Lights, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Recessed Lighting, Wood Texture Flooring

$6,245

/ Month

1205 MAYFIELD Ave, Winter Park, FL

4 br5 BA3,948 sf

virtual tour

Listing Courtesy of RE/MAX 200 REALTY, MO JABR - 407-571-1441, Office Contact - 407-629-6330, barbarat@rmxmail.com

Dining room, Interior, Pendant Lights, Wood Texture Flooring

Dining room, Interior, Wood Texture Flooring

Chandelier, Home Office, Interior, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Wood Texture Flooring

$5,400

/ Month

1701 PALMER Ave, Winter Park, FL

4 br3 BA2,841 sf

virtual tour

Listing Courtesy of TRUST EQUITY GROUP LLC, RHONDA FISHER - 407-463-9163, Office Contact - 321-296-9355, rfisher@trustequitygroup.com

price reduced

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting, Tile Countertops

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

$5,350

/ Month

960 GEORGIA Ave, Winter Park, FL

4 br4 BA3,654 sf

Listing Courtesy of CORCORAN PREMIER REALTY, ALISON ASHBY - 407-310-8209, Office Contact - 407-965-1155, chocky@premierrealtyorlando.com

Attached, Backyard, Detached Garage, Exterior, Facade, Ranch

$4,695

/ Month

1166 PALMER Ave, Winter Park, FL

3 br3 BA, 2 HALF BA2,659 sf

Listing Courtesy of HOMEVEST REALTY, BROCK STOCKSETT - 321-507-7604, Office Contact - 407-897-5400, broker@homevest.com

new

Attached, Backyard, Exterior, Facade, Ranch

Dining room, Interior, Kitchen, Stainless Steel Appliances

Fireplace, Interior, Living room, Recessed Lighting, Stone Walls, Wood Texture Flooring

Interior, Living room, Recessed Lighting, Wood Texture Flooring

Dining room, Fireplace, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior

Bathroom, Glass Shower, Interior, Marble, Marble Walls

Bedroom, Home Office, Interior, Wood Texture Flooring

$4,500

/ Month

731 NORTHWOOD Cir, Winter Park, FL

4 br2 BA, 1 HALF BA2,990 sf

virtual tour

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY, JJ MACKLE - 321-217-9553, Office Contact - 407-644-3295, danny.williams@premiersir.com

Attached, Backyard, Exterior, Facade, Brick Facade, Cape Cod

Attached, Exterior, Facade, Brick Facade, Cape Cod

Fireplace, Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Stone Walls, Wood Texture Flooring

Interior, Recessed Lighting, Washer, Wood Texture Flooring

$4,400

/ Month

2627 VERONA Trl, Winter Park, FL

4 br3 BA2,422 sf

virtual tour

Listing Courtesy of EMPIRE NETWORK REALTY, WAYNE MYERS - 407-256-3226, Office Contact - 407-440-3798, empirenetworkrealty@gmail.com

Interior, Kitchen, Marble Walls, Stainless Steel Appliances

Empty room, Interior, Kitchen, Recessed Lighting, Wooden Ceilings, Wood Texture Flooring

$4,200

/ Month

1381 CANTERBURY Rd, Winter Park, FL

3 br2 BA1,819 sf

virtual tour

Listing Courtesy of MIAMI BEACH REAL ESTATE GROUP, MAXIMILIANO GARCIA - 305-915-4178, Office Contact - 786-202-3847, admin@miamibeachgroup.com

price reduced

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wooden Beams, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances, Wooden Beams

Interior, Kitchen, Pendant Lights, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Fireplace, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Fireplace, Interior, Living room, Recessed Lighting, Stone Walls, Wooden Beams, Wood Texture Flooring

Dining room, Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stone Walls, Wooden Beams, Wood Texture Flooring

Interior, Living room, Pendant Lights, Recessed Lighting, Stone Walls, Wood Texture Flooring

Fireplace, Interior, Recessed Lighting, Stone Walls, Wooden Beams, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Pendant Lights

Bathroom, Glass Shower, Interior, Marble Walls, Wood Texture Flooring

Bedroom, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

$4,000

/ Month

236 RIPPLING Ln, Winter Park, FL

3 br2 BA2,113 sf

virtual tour

Listing Courtesy of CORCORAN PREMIER REALTY, JENNIFER KING - 407-595-3272, Office Contact - 407-965-1155, chocky@premierrealtyorlando.com

$3,850

/ Month

2372 KESTREL PERCH Pl, Winter Park, FL

4 br4 BA, 1 HALF BA2,553 sf

virtual tour

Listing Courtesy of EAST PEARL REALTY, DAN LI - 407-808-1859, Office Contact - 407-802-6859, eastpearlfl@gmail.com

price reduced

Home Office, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Washer, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Fireplace, Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, Pendant Lights, Wood Texture Flooring

Interior, Utility Closets, Washer, Wood Texture Flooring

$3,750

/ Month

1681 WALNUT Ave, Winter Park, FL

3 br2 BA1,499 sf

virtual tour

Listing Courtesy of CITARELLI REALTY GROUP LLC, NATALIE CITARELLI - 321-607-3586, Office Contact - 321-607-3586, natalie@citarellirealtygroup.com

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Luxury listings for rent in Winter Park

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2228 Winter Woods Blvd Blvd, Winter Park, FL

1740 STATE ROAD 436, Winter Park, FL

1976 W FAIRBANKS Ave, Winter Park, FL

1860 VIA CONTESSA, Winter Park, FL

1530 VIA TUSCANY, Winter Park, FL

1442 PALM Ave, Winter Park, FL

2020 VENETIAN Way, Winter Park, FL

501 W CANTON Ave, Winter Park, FL

1205 MAYFIELD Ave, Winter Park, FL

1701 PALMER Ave, Winter Park, FL

960 GEORGIA Ave, Winter Park, FL

1166 PALMER Ave, Winter Park, FL

731 NORTHWOOD Cir, Winter Park, FL

2627 VERONA Trl, Winter Park, FL

1381 CANTERBURY Rd, Winter Park, FL

236 RIPPLING Ln, Winter Park, FL

2372 KESTREL PERCH Pl, Winter Park, FL

1681 WALNUT Ave, Winter Park, FL