Winter Park, FL Homes for Rent under $3,000

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  /35

  Starting at $1,638 Per Month

  • Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  Berkshire Winter Park

  

  1874 Harmon Ave, Winter Park, FL 32789
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  /11

  Starting at $1,559

  Total Monthly Price

  • 1 - 2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  Solis at Winter Park

  

  7502 Sun Key Blvd, Winter Park, FL 32792
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  /21

  $2,100

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Condo for Rent

  2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792

  Welcome to this charming and beautifully updated home in the serene Cedarwood Village community! Tucked away in a peaceful location, this unit offers a quiet retreat from traffic noise and features a private backyard with no rear neighbors perfect for enjoying the spacious, enclosed lanai. The modern kitchen features sleek granite countertops and matching cabinets, with the bathrooms and dining

  2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792
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  /20

  Starting at $1,328 Per Month

  • 1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  ARIUM Winter Park

  

  3250 Bishop Park Dr, Winter Park, FL 32792
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  /20

  $1,895 Per Month

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft
  • Townhouse for Rent

  162 Moyses Rd, Winter Park, FL 32792

  Property Id: 2563758 Be the first to live in this beautifully renovated home that has been completely remodeled from top to bottom! Everything is brand new, giving you the feel of moving into a new home with modern finishes throughout. This home features 2 spacious bedrooms and 1 full bathroom upstairs, creating a private and comfortable living space. The first floor offers an open

  162 Moyses Rd, Winter Park, FL 32792
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  /16

  $2,300 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,277 Sq Ft
  • House for Rent

  2866 Euston Rd, Winter Park, FL 32789

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

  2866 Euston Rd, Winter Park, FL 32789
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  /19

  $2,245 Per Month

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft
  • House for Rent

  7418 Antietam Ct E, 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 $2389.90. That covers your base rent, $2245.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7418 Antietam Ct E, Winter Park, FL 32792
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  /20

  $2,300 Per Month

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 207, Winter Park, FL 32789

  Welcome to your future home in the heart of Winter Park, located in the desirable Maitland district! This charming property offers a comfortable and convenient lifestyle, with easy access to an array of amenities and attractions.Experience the ease of living with central heating and cooling, complemented by air conditioning and ceiling fans for your comfort throughout the year. This

  151 N Orlando Ave Unit 207, Winter Park, FL 32789
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  /19

  $1,800 Per Month

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft
  • House for Rent

  2772 Prism Point, Winter Park, FL 32792

  Property Id: 2809706 Townhouse duplex for rent, very private culdesac. Two bedroom, 1 1/2 bath. All tiled except carpet on stairs… galley kitchen, stainless appliances, huge laundry room. Balcony off master bedroom Beautifully maintained all lawn care included. Sprinkler system…fence yard… cats ok Dogs ok must be under 25 pounds. Carport

  2772 Prism Point, Winter Park, FL 32792
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  /13

  $2,715

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft
  • Condo for Rent

  662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789

  The advertised rate of $2,716/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789
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  /20

  $2,435 Per Month

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • House for Rent

  4040 Waterview Loop, 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 $2579.90. That covers your base rent, $2435.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  4040 Waterview Loop, Winter Park, FL 32792
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  $1,730 Per Month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Condo for Rent

  659 Montego Bay Ct, Winter Park, FL 32792

  WINTER PARK VILLAS — 2-BEDROOM CONDO | $1,000 MOVE-IN CREDIT + WATER INCLUDED!$1,730/month • 2 Bedrooms • 2 Full Bathrooms • 1,037 Sq. Ft. LIMITED-TIME MOVE-IN SPECIALReceive a $1,000 MOVE-IN CREDIT with an approved 12-month lease! WATER INCLUDED IN RENT!No separate monthly water bill — water is included in your rent.Welcome to this charming

  659 Montego Bay Ct, Winter Park, FL 32792
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  /13

  $2,715

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft
  • Condo for Rent

  662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789

  The advertised rate of $2,716/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789
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  /20

  $2,300 Per Month

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 207, Winter Park, FL 32789

  Welcome to your future home in the heart of Winter Park, located in the desirable Maitland district! This charming property offers a comfortable and convenient lifestyle, with easy access to an array of amenities and attractions.Experience the ease of living with central heating and cooling, complemented by air conditioning and ceiling fans for your comfort throughout the year. This

  151 N Orlando Ave Unit 207, Winter Park, FL 32789
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  $2,360 Per Month

  • 3 Beds
  • 2 Baths
  • 1,384 Sq Ft
  • House for Rent

  3016 Village Hill Place, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

  3016 Village Hill Place, Winter Park, FL 32792
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  $2,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Condo for Rent

  1250 S Denning Dr, Winter Park, FL 32789

  Property Id: 346094 Spacious living area, large master bedroom w/ private bathroom & linen closet. Wide Closets in each bedroom. Quiet neighborhood. Lots of sunlight enters the apartment. Shaded and screened patio faces a courtyard/garden w/ seating. Brand new sliding glass patio door. Incredible location short distance to Park Avenue, Trader Joes/Whole Foods/Publix, I4 exit, & shopping

  1250 S Denning Dr, Winter Park, FL 32789
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  /20

  $2,395 Per Month

  • 5 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  3628 Datura Ct, 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 $2539.90. That covers your base rent, $2395.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3628 Datura Ct, Winter Park, FL 32792
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  $2,210 Per Month

  • 3 Beds
  • 2 Baths
  • 1,285 Sq Ft
  • House for Rent

  1710 Puritan Ave, 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 $2354.90. That covers your base rent, $2210.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1710 Puritan Ave, Winter Park, FL 32792
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  $1,675 Per Month

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

  200 St Andrews Blvd Unit 316, Winter Park, FL 32792

  Property Id: 2751801 Beautiful 1-Bedroom Condo for Rent in Winter Park Available Now! Enjoy comfortable living in this beautiful 1-bedroom, 1-bathroom condo located in the highly desirable Four Seasons Condominium Community in Winter Park. Conveniently situated at 200 St. Andrews Blvd, Winter Park, FL 32792, this condo offers an unbeatable location just minutes from

  200 St Andrews Blvd Unit 316, Winter Park, FL 32792
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  $2,390 Per Month

  • 3 Beds
  • 2 Baths
  • 1,992 Sq Ft
  • House for Rent

  7423 Antietam Ct E, 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 $2534.90. That covers your base rent, $2390.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7423 Antietam Ct E, Winter Park, FL 32792
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  $2,083 Per Month

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • House for Rent

  3321 Royal St, Winter Park, FL 32792

  Property Id: 2821609 Welcome to 3321 Royal Street in Winter Park! This beautifully updated 3-bedroom, 2-bathroom home offers approximately 1,197 sq. ft. of comfortable living space. Features include a spacious family room, durable tile and luxury vinyl flooring, central air conditioning, a 1-car attached garage with laundry area, and a large fully fenced backyard with a screened-in patio.

  3321 Royal St, Winter Park, FL 32792
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  /13

  $1,675 Per Month

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

  200 St Andrews Blvd Unit 316, Winter Park, FL 32792

  Property Id: 2751801 Beautiful 1-Bedroom Condo for Rent in Winter Park Available Now! Enjoy comfortable living in this beautiful 1-bedroom, 1-bathroom condo located in the highly desirable Four Seasons Condominium Community in Winter Park. Conveniently situated at 200 St. Andrews Blvd, Winter Park, FL 32792, this condo offers an unbeatable location just minutes from

  200 St Andrews Blvd Unit 316, Winter Park, FL 32792
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  $2,400

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • House for Rent

  530 Byron Rd, Winter Park, FL 32792

  Charming 3 bedroom, 2 bath, quiet neighborhood with nearby Wintee Park schools, Rollins college, Publix, Winter Park Hospital, YMCA. Freshly painted inside, new blinds, bathroom upgraded, fenced backyard, brand new washer and dryer

  530 Byron Rd, Winter Park, FL 32792
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  $1,950

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 989 Sq Ft
  • Townhouse for Rent

  2399 Antilles Dr, Winter Park, FL 32792

  Beautifully updated 2 bedroom / 1 bath townhome in Casselberry.? Updated kitchen? Freshly painted? Washer/Dryer? Large fenced backyard? 2 community pools? Pet friendly (under 50lbs)Minutes to Full Sail, AdventHealth Winter Park, UCF, shopping & restaurants.

  2399 Antilles Dr, Winter Park, FL 32792
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  $1,245

  Total Monthly Price

  • Studio - 1 Bed
  • 1 Bath
  • 615 Sq Ft
  • Condo for Rent

  2037 Linden Rd, Winter Park, FL 32792

  Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door

  2037 Linden Rd, Winter Park, FL 32792
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  $1,000

  Total Monthly Price

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

  5312 Poinsetta Ave Unit 2, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the three rooms has its own electronic keypad lock for your privacy and security. The large common areas provide the perfect space for dining and living. A spacious laundry and kitchen provide you with plenty of space

  5312 Poinsetta Ave Unit 2, Winter Park, FL 32792
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  $1,800

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Condo for Rent

  1920 Woodcrest Dr Unit 13, Winter Park, FL 32792

  Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath

  1920 Woodcrest Dr Unit 13, Winter Park, FL 32792
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  /24

  $1,800

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Condo for Rent

  1920 Woodcrest Dr Unit 13, Winter Park, FL 32792

  Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath

  1920 Woodcrest Dr Unit 13, Winter Park, FL 32792
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  $1,850

  Total Monthly Price

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

  2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792

  Close to Park Avenue Winter Park Restaurants and shopping near UCF and Full sail University also Rollins Colllege, Great Public schools. Close to the Orlando Airport and 30 minutes from Disney World and Universal Studios.

  2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792
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  $1,900

  Total Monthly Price

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

  1250 S Denning Dr Unit 127, Winter Park, FL 32789

  Updated 2BR/2BA Condo in Fabulous Winter Park – Water Included and Trash!1250 S. Denning Drive – Winter Park, FLEnjoy comfortable, low-maintenance living in this beautifully updated 2-bedroom, 2-bathroom condo located in one of Winter Park's most convenient neighborhoods.This 910-square-foot, first-floor unit features luxury vinyl plank flooring throughout, a modern

  1250 S Denning Dr Unit 127, Winter Park, FL 32789
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  /10

  $1,245

  Total Monthly Price

  • Studio - 1 Bed
  • 1 Bath
  • 615 Sq Ft
  • Condo for Rent

  2037 Linden Rd, Winter Park, FL 32792

  Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door

  2037 Linden Rd, Winter Park, FL 32792
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  $1,900

  Total Monthly Price

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

  1250 S Denning Dr Unit 127, Winter Park, FL 32789

  Updated 2BR/2BA Condo in Fabulous Winter Park – Water Included and Trash!1250 S. Denning Drive – Winter Park, FLEnjoy comfortable, low-maintenance living in this beautifully updated 2-bedroom, 2-bathroom condo located in one of Winter Park's most convenient neighborhoods.This 910-square-foot, first-floor unit features luxury vinyl plank flooring throughout, a modern

  1250 S Denning Dr Unit 127, Winter Park, FL 32789
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  $2,300

  Total Monthly Price

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

  151 N Orlando Ave Unit 262, Winter Park, FL 32789

  Modern furnished waterfront 1bdrm/1bath condo rental, move-in ready. Fully renovated, equipped kitchen with smooth stone countertops, stainless steel-appliances (Fridge/Stove/Dishwasher), a sleek under-mount sink, and minimalist cabinetry. In unit full-size stacked washer & dryer, walk-in closet. Remote control blinds throughout, including blackout one in the bedroom.Fresh, modern interior

  151 N Orlando Ave Unit 262, Winter Park, FL 32789
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  $1,000

  Total Monthly Price

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

  5312 Poinsetta Ave Unit 2, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the three rooms has its own electronic keypad lock for your privacy and security. The large common areas provide the perfect space for dining and living. A spacious laundry and kitchen provide you with plenty of space

  5312 Poinsetta Ave Unit 2, Winter Park, FL 32792
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  $1,900

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,158 Sq Ft
  • Townhouse for Rent

  622 St Johns Ct, Winter Park, FL 32792

  BRAND NEW LAMINATE FLOORING, FIREPLACE, ACROSS TENNIS COURT, COMMUNITY POOL, PARKING IN FRONT, RANGE, DISPOSAL, REFRIGERATOR, DISHWASHER, MICROWAVE, NEW CENTRAL AC UNIT, WALK IN CLOSETS, DEN, WASHER/DRYER HOOKUPS

  622 St Johns Ct, Winter Park, FL 32792
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  $2,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Condo for Rent

  2526 Tahoe Cir Unit 2526, Winter Park, FL 32792

  Must-See WINTER PARK CONDO, beautifully remodeled 2BR / 2BA + LOFT / potential office / 3rd BR or office. Formal Living Room w / wood-burning fireplace & Dining Room w/ wet-bar, beautiful open kitchen w/ island and stainless-steel appliances, laundry closet w/ washer & dryer, enclosed patio, bamboo & porcelain tile floors. Centrally located near SR 417 and 20 minutes from airport, zoned for great

  Elizabeth Beaudoin PR REAL ESTATE SERVICES

  2526 Tahoe Cir Unit 2526, Winter Park, FL 32792
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  $1,250 Per Month

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

  2500 Lee Rd, Winter Park, FL 32789

  Serene scenes surround the Lakeside Manor, absolutely beautiful through all the seasons. Waterfront Complex on Lake Killarney. Found on the ground floor, the unit opens up to the living room and dining room. Tile is laid all throughout the property, easy to clean and maintain! The bedroom and bathroom are toward the back of the unit. The bedroom features two closets! The community amenities

  2500 Lee Rd, Winter Park, FL 32789
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  $1,995 Per Month

  • 2 Beds
  • 1 Bath
  • 1,604 Sq Ft
  • Townhouse for Rent

  1618 Indiana Ave, Winter Park, FL 32789

  et on a friendly street in the heart of Winter Park, this freshly remodeled duplex delivers easy, low-maintenance living in one of Central Florida's most sought-after zip codes. Inside, 805 square feet of thoughtfully refreshed space welcomes you with brand-new appliances, a crisp new A/C system, and a casual breakfast bar top perfect for quick meals or morning coffee. Two comfortable bedrooms

  Brock Stocksett HOMEVEST REALTY

  1618 Indiana Ave, Winter Park, FL 32789
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  /20

  $2,275 Per Month

  • 4 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • House for Rent

  3362 Bougainvillea 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 $2419.90. That covers your base rent, $2275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3362 Bougainvillea Dr, Winter Park, FL 32792
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  /14

  $1,995 Per Month

  • 2 Beds
  • 1 Bath
  • 802 Sq Ft
  • Townhouse for Rent

  1618 Indiana Ave Unit 1616, Winter Park, FL 32789

  Freshly reimagined and ready for its next resident, this newly remodeled duplex in the heart of Winter Park pairs modern updates with an unbeatable central location. Offering two bedrooms, one bathroom, and 805 square feet of thoughtfully arranged living space, this half of a charming duplex feels both smart and welcoming from the moment you step inside. This duplex has been recently updated from

  Brock Stocksett HOMEVEST REALTY

  1618 Indiana Ave Unit 1616, Winter Park, FL 32789

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