Winter Park, FL Homes for Rent

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  $4,700 per month

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Townhouse for Rent

  1802 Mondrian Cir, Winter Park, FL 32789

  Welcome to The Mondrian Winter Park Townhomes, an exclusive waterfront community featuring 30 stunning contemporary homes on the picturesque shores of Lake Killarney. This exceptional former model home is a true standout, boasting a wealth of high-end upgrades that set it apart from the competition. Step inside to discover a neutral painted interior adorned with modern light fixtures, stylish

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1802 Mondrian Cir, Winter Park, FL 32789
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  $1,795 per month

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792

  2-bedroom, 1.5-bathroom, two-story condo in Four Seasons Condos of Winter Park. This well maintained condo includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with

  Amy Spano WILSON MANAGEMENT GROUP

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792
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  $3,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  1302 Michigan Ave, Winter Park, FL 32789

  Please visit our website at www.ORLrent.com you will find photos of our homes, tenant application, pet application, sample lease and more information. If applying for any of our homes all adult applicants over the age of 18 must submit a fully completed Application online. Application fee is $95.00 for each adult. An application reservation fee must be paid in the amount of one month's rent (in

  Mo Jabr RE/MAX 200 REALTY

  1302 Michigan Ave, Winter Park, FL 32789
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  $2,800 per month

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Townhouse for Rent

  1957 Canny Cove, Winter Park, FL 32792

  Enjoy the Winter Park lifestyle in this 3-bedroom, 21⁄2-bath end-unit townhome located in the Grayson Square community. The open-concept layout benefits from abundant natural light and includes a covered lanai and a well-appointed kitchen with stainless steel appliances and quartz countertops. The home offers ample storage throughout, and the owner’s suite features a walk-in closet and an ensuite

  Denise Del Castillo LPT REALTY, LLC

  1957 Canny Cove, Winter Park, FL 32792
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  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  3212 Netherwood Dr, Winter Park, FL 32792

  This 400sqft QUICK MOVE in-law suite, with kitchen, bedroom and bathroom, along with living room space. Water and electricity are included with your rent. Laundry on-site. Suitable for 2-person occupancy.

  Sara Cruz FLORIDA HOMES REALTY & MORTGAGE

  3212 Netherwood Dr, Winter Park, FL 32792
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  /15

  $4,325 per month

  • 4 Beds
  • 2.5 Baths
  • 3,305 Sq Ft
  • House for Rent

  1441 Place Vendome, Winter Park, FL 32789

  With 4 bedrooms, 2.5 baths, and 3,305 square feet of living space, this thoughtfully designed home offers room for your family to spread out while still feeling connected in spaces meant for everyday living.Its main living area centers around a classic fireplace and built-in shelving, creating a cozy focal point for relaxing evenings or casual gatherings. Wide-plank flooring, soft neutral

  1441 Place Vendome, Winter Park, FL 32789
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  $3,250 per month

  • 4 Beds
  • 3 Baths
  • 2,804 Sq Ft
  • House for Rent

  521 Brookside Cir, Maitland, FL 32751

  WELCOME TO THIS AMAZING HOME! This newly updated and exceptionally spacious 4-bedroom, 3-bath single-family home is located in the highly sought-after Forest Brook community in beautiful Maitland. The home features a newly renovated kitchen with brand-new cabinetry, new countertops, and new stainless-steel appliances. Additional highlights include a cozy wood-burning fireplace and a large balcony

  Kevan Patel CENTRAL FLORIDA REALTY MANAGEMENT LLC

  521 Brookside Cir, Maitland, FL 32751
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  $2,650 per month

  • 4 Beds
  • 2 Baths
  • 1,714 Sq Ft
  • House for Rent

  950 Hedgewood Ct, Winter Park, FL 32792

  Great opportunity to rent this 4-bedroom, 2-bath single-family home located on a quiet cul-de-sac. The home features a 2-car garage and a spacious backyard ideal for outdoor entertaining. Zoned for top-rated schools and conveniently located near major roadways, shopping, dining, and everyday amenities (MORE PHOTOS TO FOLLOW).

  Esther Griller FLORIDA REALTY INVESTMENTS

  950 Hedgewood Ct, Winter Park, FL 32792
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  /20

  $2,900 per month

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft
  • Property for Rent

  1315 Westchester Ave, Winter Park, FL 32789

  Wow, expect to be impressed. This home has been lovingly updated and features handscraped wood floors and tile throughout...no carpeting! In addition, there is an expansive ceiling in the living room, updated kitchen with tumbled marble backsplash, sleek appliances, granite counters and lots of wood cabinetry for storage. This home has double pane windows, updated bathrooms with granite counters

  Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  1315 Westchester Ave, Winter Park, FL 32789
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  /17

  $2,900 per month

  • 3 Beds
  • 2 Baths
  • 1,201 Sq Ft
  • House for Rent

  3383 Hamlet Loop, Winter Park, FL 32792

  Beautiful house with a pool in Winter Park, with all new appliances, just minutes from downtown where you'll find excellent restaurants, museums, and entertainment to enjoy on foot.

  Daynell Rodriguez Cardenas LA ROSA REALTY ORLANDO LLC

  3383 Hamlet Loop, Winter Park, FL 32792
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  /20

  $1,750 per month

  • 1 Bed
  • 1 Bath
  • 502 Sq Ft
  • House for Rent

  1550 Michigan Ave, Winter Park, FL 32789

  Welcome to your future home in the charming district of Winter Park, FL! This inviting property offers a warm atmosphere perfect for relaxation and convenience, surrounded by a vibrant community.This residence boasts spacious living equipped with essential comforts. With ample bedrooms and bathrooms, it accommodates various lifestyles. You'll appreciate the central heating and cooling

  1550 Michigan Ave, Winter Park, FL 32789
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  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft
  • House for Rent

  1575 Lawndale Cir, Winter Park, FL 32792

  **WASHER AND DRYER INCLUDED** Welcome to your dream home at 1575 Lawndale Cir, Winter Park, FL 32792! Nestled in the heart of the highly coveted Winter Park, this 2-story gem offers the perfect blend of comfort and style. Step into a world of elegance with laminate wood and ceramic tile flooring gracing every corner of this home. The spacious living areas have great natural light for a warm and

  Dean Itani KELLER WILLIAMS ADVANTAGE REALTY

  1575 Lawndale Cir, Winter Park, FL 32792
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  /15

  $2,835 per month

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft
  • House for Rent

  2224 King Richards Ct, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  2224 King Richards Ct, Winter Park, FL 32792
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  $5,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,740 Sq Ft
  • House for Rent

  2823 Wilford Ave, Orlando, FL 32814

  Welcome to turn-key, fully furnished living in this charming Mediterranean bungalow with classic tile roof, nestled in the heart of Baldwin Park! This beautifully upgraded 3-bedroom, 2.5-bath home offers bright, professionally decorated & furnished interior, a fully equipped gourmet kitchen, renovated spa-like bathrooms, a downstairs study with French doors, and light oak flooring throughout the

  Benjamin Cole, IV SOTERA LIVING

  2823 Wilford Ave, Orlando, FL 32814
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  $3,599 per month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  1945 Gunn Rd, Winter Park, FL 32792

  Fantastic Winter Park renovation. This 3 bedroom, 2 bathroom, plus an office home has been turned into a showplace. Great location zoned for Brookshire, Glenridge and Winter Park High School. The home features upscale fixtures, open floor plan, huge laundry room, office nook, new windows, ample dining space, new appliances and large fenced in backyard. A must see! Not furnished.

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  1945 Gunn Rd, Winter Park, FL 32792
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  /14

  $2,300 per month

  • 3 Beds
  • 2.5 Baths
  • 1,397 Sq Ft
  • House for Rent

  3381 Hamlet Loop, Winter Park, FL 32792

  Welcome to this stunning 3 bed, 2.5 bath, two-story single-family home located in the heart of Winter Park. Just minutes from shopping, dining, and close to UCF. This home features a bright open floor plan with a dramatic double-height ceiling in the living room, creating an airy and elegant atmosphere perfect for everyday living and entertaining. The primary suite is conveniently located on the

  Amy Guo AAA GLOBAL VENTURES PA

  3381 Hamlet Loop, Winter Park, FL 32792
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  $2,675 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  1986 Canny Cove, Winter Park, FL 32792

  This beautiful 3-bedroom, 2.5-bathroom two-story townhome is located in Grayson Square, a gated community in Winter Park. High-speed Internet and cable are included. There are no rear neighbors, so you will enjoy relaxing on your back porch. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features stainless steel appliances, including a refrigerator,

  Vildan Nigro RIVA REALTY GROUP LLC

  1986 Canny Cove, Winter Park, FL 32792
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  /10

  $2,920 per month

  • 4 Beds
  • 3 Baths
  • 2,194 Sq Ft
  • House for Rent

  3061 Nicholson Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3064.90. That covers your base rent, $2920.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3061 Nicholson Dr, Winter Park, FL 32792
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  /18

  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 106, Winter Park, FL 32792

  Recently renovated first floor 2-bedroom, 2 bathroom, 840sqft condominium is located in Lancelot at Winter Park just off of University Blvd and Goldenrod Road. It's been beautifully updated with brand new 42" cabinets and new counter tops, vinyl plank floors throughout, new bathroom vanities, high efficiency AC system, window blinds and fresh paint. The newly renovated kitchen is expansive and

  Justin Recca INNOVATIVE REALTY, LLC

  3651 N Goldenrod Rd Unit 106, Winter Park, FL 32792
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  $1,700 per month

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Townhouse for Rent

  2523 Alexa Ct, Winter Park, FL 32792

  Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

  Jaleel Smith LA ROSA REALTY LLC

  2523 Alexa Ct, Winter Park, FL 32792
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  /16

  $1,950 per month

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  7765 Fernbrook Way, Winter Park, FL 32792

  Come and see your new home!! In a great area. There are lots of updates they make this rental beautiful!! Come see all new bathrooms, new ceramic floors and completely new paint. Large rear yard for entertaining. Call today to see your new home!!!

  Jodi Nielsen OVER THE TOP REALTY LLC

  7765 Fernbrook Way, Winter Park, FL 32792
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  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  1994 Canny Cove, Winter Park, FL 32792

  This beautiful three bedroom, two and a half bath townhome is located in the newly developed Grayson Square, a gated community in Winter Park. High-speed Internet and cable are included. There are no rear neighbors, so you will enjoy relaxing on your back porch with a beautiful water view. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features

  Vildan Nigro RIVA REALTY GROUP LLC

  1994 Canny Cove, Winter Park, FL 32792
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  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • House for Rent

  4044 Tenita Dr, Winter Park, FL 32792

  Welcome to this beautiful and cozy single-story home with a pool, designed to captivate your senses from the moment you step inside. This thoughtfully laid-out residence offers a spacious living area, dining space, and an open-concept kitchen—the true heart of the home. Featuring elegant cascading quartz countertops, modern white and blue cabinetry, and stainless steel appliances, the kitchen is

  4044 Tenita Dr, Winter Park, FL 32792
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  /10

  $2,540 per month

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • House for Rent

  191 Jergo Rd, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2684.90. That covers your base rent, $2540.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  191 Jergo Rd, Winter Park, FL 32792
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  /15

  $1,395 per month

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Condo for Rent

  3011 George Mason Ave Unit 3, Winter Park, FL 32792

  This 2 bedroom, 2 bathroom condo is located in the Colonies community near local shops, restaurants, and schools. Features include a spacious floor plan with a large main living room area, a lovely kitchen, a dining room, a wonderful primary suite, a laundry closet, a rear patio, and a community pool. Schedule a showing or submit an application online. All Real Property Management & Realty

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  3011 George Mason Ave Unit 3, Winter Park, FL 32792
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  /7

  $1,475 per month

  • 1 Bed
  • 1 Bath
  • 653 Sq Ft
  • Condo for Rent

  1250 S Denning Dr Unit 208, Winter Park, FL 32789

  A+++ Location in Winter Park. Remodeled 1 bedroom and bath apartment. Close to everything Advent Health, Park Avenue, Rollins College, Orange Avenue, Fairbanks, 17-92 and 1-4. No pets please.

  Ruth Harris COLDWELL BANKER RESIDENTIAL RE

  1250 S Denning Dr Unit 208, Winter Park, FL 32789
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  /15

  $3,150 per month

  • 4 Beds
  • 3 Baths
  • 1,856 Sq Ft
  • House for Rent

  2029 Taylor Ave, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  2029 Taylor Ave, Winter Park, FL 32792
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  $2,775 per month

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Townhouse for Rent

  2460 Firstlight Way, Winter Park, FL 32792

  This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2460 Firstlight Way, Winter Park, FL 32792
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  /16

  $2,665 per month

  • 5 Beds
  • 3 Baths
  • 2,047 Sq Ft
  • House for Rent

  3117 Raiders Run, Winter Park, FL 32792

  TWO MASTER SUITESThis spacious 5 bedroom 3 bathroom features a split floor plan with double master bedrooms, and a large bonus room with a private entrance. Updated kitchen, new flooring, screened back porch and fenced yard. Fantastic location with easy access to major highways and close to the Winter Park shopping and dining district. Zoned for Lakemont Elementary, Maitland Middle and Winter

  Chantel Gutierrez-Davis RISE 24 REAL ESTATE LLC

  3117 Raiders Run, Winter Park, FL 32792
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  /20

  $4,995 per month

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  Nestled within the exclusive 400 West enclavean intimate community of just nine residences just moments from Park Avenuethis modern townhome seamlessly combines superior craftsmanship, elegant interiors, and outstanding walkability. Entering through either the private garage or the charming garden-style front path, you're welcomed into a luminous, open-concept main level that emphasizes comfort,

  438 W Swoope Ave, Winter Park, FL 32789
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  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Apartment for Rent

  2918 Antique Oaks Cir Unit 31, Winter Park, FL 32792

  Property Description (For Lease – Fully Furnished) This beautifully updated, fully furnished two-bedroom, two-bathroom ground-floor condominium is available for lease in the highly desirable Parkview Village Community. Designed for comfort and convenience, this move-in-ready home offers a modern living experience in the heart of Winter Park. The open-concept floor plan features premium luxury

  Yahui Li FLORIDA REALTY INVESTMENTS

  2918 Antique Oaks Cir Unit 31, Winter Park, FL 32792
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  $1,695 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  Unlisted Address

  Available for immediate move-in, this comfortable second-floor corner condo offers a peaceful setting with playground and pool views. The home features a fully carpeted interior, a spacious kitchen with a pantry closet, and a newer refrigerator. Washer and dryer are included for added convenience. Great balcony for relaxing on the cooler Florida days! Located in desirable Winter Park, you'll

  Yarmmys Vargas ZEN LIVING HOMES LLC

  Unlisted Address
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  /20

  $4,399 per month

  • 4 Beds
  • 3 Baths
  • 2,252 Sq Ft
  • House for Rent

  1112 Chichester St, Orlando, FL 32803

  Discover this inviting four-bedroom, three-bathroom residence nestled in the highly sought-after Orwin Manor community of Orlando. Meticulously maintained, this home offers a thoughtful layout that seamlessly blends comfort and practicality. The main house features three spacious bedrooms and two full bathrooms, while a separate in-law suite or guest house includes an additional bedroom,

  1112 Chichester St, Orlando, FL 32803
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  /20

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 3B, Winter Park, FL 32789

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
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  $3,200 per month

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Townhouse for Rent

  2963 Upper Park Rd, Orlando, FL 32814

  Available for rent on 12-15-2025. Experience upscale living in this renovated Baldwin Park townhome. This 1,800 sq/ft townhome is minutes away from Blue Jacket Park and centrally located in the heart of Baldwin Park. This impressive townhome delivers both style and functionality in one of Orlando's most desirable neighborhoods. The well-appointed kitchen boasts warm wood cabinets, granite

  2963 Upper Park Rd, Orlando, FL 32814
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  $1,495 per month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792

  This is a 2 bedroom, 2 bathroom, second floor condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include a spacious main living area, a lovely kitchen, vaulted ceilings, spacious bedrooms, and a laundry closet. Community amenities include a pool, gym, and clubhouse. Schedule a showing or submit an application online. All Real Property Management &

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792
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  /15

  $1,975 per month

  • 4 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  275 N Capen Ave, Winter Park, FL 32789

  This unique, old Florida style 4 ba / 2 ba 1180 sqft home features a single car garage, two baths, three smaller bedrooms and a master bedroom with walk in closet. Less than a mile away from desirable Park Avenue, and Rollins Collage. Washer/dryer included. Application Fee: $50 each adult (18+)**Full Credit/Skip/Eviction/Background check is done on all applicants.**Please have the

  Kenneth Warren PREMIER MANAGEMENT GROUP INC

  275 N Capen Ave, Winter Park, FL 32789
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  $10,950 per month

  • 4 Beds
  • 3 Baths
  • 2,918 Sq Ft
  • House for Rent

  2220 Via Tuscany, Winter Park, FL 32789

  Now available fully furnished, this elegant single-story residence on Winter Park’s prestigious Via Tuscany offers an exceptional opportunity to lease in one of Central Florida’s most coveted neighborhoods. Just steps from the Winter Park Racquet Club, this thoughtfully updated home features four bedrooms, three bathrooms, and designer-appointed interiors curated for both comfort and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2220 Via Tuscany, Winter Park, FL 32789
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  /22

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Townhouse for Rent

  2552 Gold Ct, Winter Park, FL 32792

  Welcome to 2552 Gold Court – Your Perfect Winter Park Rental Home!Discover comfortable living in this beautifully renovated 3-bedroom, 2-bath duplex offering approximately 1,020 square feet of thoughtfully designed space. This move-in ready home combines modern updates with practical amenities to create the ideal rental experience.This charming residence features a bright, open floor plan

  Kelly Price KELLY PRICE & COMPANY LLC

  2552 Gold Ct, Winter Park, FL 32792
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  /25

  $3,800 per month

  • 2 Beds
  • 2 Baths
  • 949 Sq Ft
  • Condo for Rent

  101 S Interlachen Ave Unit 104, Winter Park, FL 32789

  FOR RENT! SUPER RARE, GROUND FLOOR, DOWNTOWN WINTER PARK CONDO AT LACHEN HOUSE! This gorgeous 2 bedroom, 2 bath condo has been completely remodeled and features new laminate flooring, bright recessed lighting, and a stunning gourmet kitchen. Each bedroom is oversized with ample closet space. A charming courtyard off the back bedrooms provides a relaxing outdoor space to enjoy year round. Enjoy

  Kelly Price KELLY PRICE & COMPANY LLC

  101 S Interlachen Ave Unit 104, Winter Park, FL 32789

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