Winter Park, FL Homes for Rent with Community Pool

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  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Townhouse for Rent

  609 Montego Bay Ct Unit 609, Winter Park, FL 32792

  2-bedroom, 2-bathroom townhome. Near to shopping malls and Sail University

  Jose Rodriguez JOSE ORLANDO RODRIGUEZ

  609 Montego Bay Ct Unit 609, Winter Park, FL 32792
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  $1,332 - $1,918 total monthly price

  Atlas at Winter Park

  1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  $1,875 per month

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Townhouse for Rent

  307 Sandlewood Trail, Winter Park, FL 32789

  This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  307 Sandlewood Trail, Winter Park, FL 32789
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  $1,474 - $1,761 per month

  POSTE Winter Park

  1 - 2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, Winter Park, FL 32792
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  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
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  $1,300 - $1,855 per month

  La Aloma

  1 - 3 Beds

  3040 Aloma Ave, Winter Park, FL 32792

  La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

  3040 Aloma Ave, Winter Park, FL 32792
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  $3,475 per month

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • House for Rent

  1850 Whitehall Dr, Winter Park, FL 32789

  This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1850 Whitehall Dr, Winter Park, FL 32789
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  $1,052 - $1,721 per month

  Carlton Arms of Winter Park

  Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  Carlton Arms of Winter Park is a well established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff. We offer an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, Winter Park, FL 32792
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  $2,695 per month

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

  1611 Little Wren Ln, 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

  1611 Little Wren Ln, Winter Park, FL 32792
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  $1,378 - $2,138 per month

  Westmount at Winter Park

  Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  1701 Lee Rd, Winter Park, FL 32789
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  $1,850 per month

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

  612 Trinidad Ct Unit 612, Winter Park, FL 32792

  Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area

  Carolina Barriento JEXOR LLC

  612 Trinidad Ct Unit 612, Winter Park, FL 32792
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  $1,320 - $2,745 per month

  Signal Pointe

  1 - 3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, Winter Park, FL 32792
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  $1,400 per month

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

  1695 Lee Rd Unit C110, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C110, Winter Park, FL 32789
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  $1,236 - $2,425 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, Winter Park, FL 32789
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  $17,000 per month

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft
  • House for Rent

  1742 Temple Dr, Winter Park, FL 32789

  An Enduring Work of Art: Winter Park’s Modern MasterpieceThis is more than just a property; it is an iconic masterpiece. Tucked within one of Winter Park’s most exclusive enclaves, this stunning four-bedroom, five-bathroom ground-up renovation offers a refined lifestyle where modern luxury and intelligent functionality converge.From the moment you enter it’s clear this home was designed

  Mark Anthony Buot ROI AVE LLC

  1742 Temple Dr, Winter Park, FL 32789
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  $956 - $1,356 per month

  Golden Oaks

  2 - 3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
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  $8,950 per month

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Condo for Rent

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

  Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
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  $1,314 - $2,763 per month

  Alvista Winter Park

  1 - 2 Beds

  3935 Sutton Place Blvd, Winter Park, FL 32792

  Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

  3935 Sutton Place Blvd, Winter Park, FL 32792
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  $1,800 per month

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

  205 Lewfield Cir Unit 205, Winter Park, FL 32792

  Wonderful! Owners pays Water & Internet. Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a barbeque with family and friends at the community

  Eimi Moreno Carrera LPT REALTY, LLC

  205 Lewfield Cir Unit 205, Winter Park, FL 32792
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  $1,458 - $2,620 per month

  Stonecastle Apartment Homes

  1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  $1,575 per month

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

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  2 Bedroom/2 Bathroom 2nd Floor Unit at Lancelot. Location, Location, Location... with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping. This 2nd floor end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar.

  Kelly Carr CFRP REALTY LLC

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
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  $1,375 total monthly price

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

  2500 Lee Rd Unit 212, Winter Park, FL 32789

  Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

  2500 Lee Rd Unit 212, Winter Park, FL 32789
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  $1,499 per month

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

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

  2-bedroom, 1.5-bathroom, two-story townhouse in Four Seasons Condos of Winter Park. This well maintained townhouse 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

  Amy Spano WILSON MANAGEMENT GROUP

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792
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  $1,502 - $2,784 per month

  ARIUM Winter Park

  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

  3250 Bishop Park Dr, Winter Park, FL 32792
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  $2,650 per month

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

  1986 Canny Cove, Winter Park, FL 32792

  FOR RENT in Winter Park! Experience comfortable living in this beautiful 3-bedroom, 2.5-bathroom townhome located in the gated community of Grayson Square. Rent includes high-speed internet and cable, offering great value and convenience. The home features a bright open floor plan with abundant natural light, a modern kitchen with quartz countertops and stainless steel appliances, and sliding

  Vildan Nigro RIVA REALTY GROUP LLC

  1986 Canny Cove, Winter Park, FL 32792
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  $1,550 total monthly price

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

  1695 Lee Rd Unit B106, Winter Park, FL 32789

  Ground Floor condo - Hardwood and Tile floors throughout! Available TODAYHardwood and Tile throughout! Ceiling fans ! lots of natural light! condo offers a peaceful setting with courtyard and pool views. no carpeted interiors. a galley-style kitchen with all appliances included. Stackable Washer and dryer are included . Great patio area for relaxing. Located in desirable Winter Park, you'll

  1695 Lee Rd Unit B106, Winter Park, FL 32789
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  $2,600 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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  $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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  $1,650 per month

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

  1695 Lee Rd Unit C216, Winter Park, FL 32789

  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

  1695 Lee Rd Unit C216, Winter Park, FL 32789
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  $1,000 - $1,700 per month

  District On Baldwin Park

  Studio - 3 Beds

  5590 Baldwin Park St, Orlando, FL 32807

  Join us at District on Baldwin Park in Orlando, where you'll revel in luxurious apartment living and resort-style amenities minutes from shopping, entertainment, restaurants and recreation. Lounge by one of our three sparkling pools, sip a cup of coffee and surf the net in our Internet cafe?? or chat with neighbors over cards in our clubhouse. At District on Baldwin Park, you get the resort

  5590 Baldwin Park St, Orlando, FL 32807
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  $1,395 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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  $19,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft
  • House for Rent

  1221 Richmond Rd, Winter Park, FL 32789

  Owner/Builder/Agent - An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park—offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024

  Christopher Salhab LA ROSA REALTY HORIZONS LLC

  1221 Richmond Rd, Winter Park, FL 32789
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  $1,250 per month

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

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

  Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

  SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
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  $2,950 per month

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • House for Rent

  1807 N Park Ave, Winter Park, FL 32789

  Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

  Jason Hamilton THE REALTY MEDICS

  1807 N Park Ave, Winter Park, FL 32789
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  /23

  $1,500 per month

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

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
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  $2,000 per month

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

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
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  $6,800 per month

  • 4 Beds
  • 2.5 Baths
  • 2,470 Sq Ft
  • House for Rent

  1420 Lyndale Blvd, Maitland, FL 32751

  LOOK NO FURTHER! This completely remodeled POOL home boast a spacious 4 bedroom's and 2.5 bathroom's that are situated on an oversized corner lot. From the moment you enter the front door, you can notice the large new tile floors, complimented by all custom cabinetry, high end light fixtures and a spacious floor plan. A gourmet kitchen with beautiful, light quartz counters to compliment the navy

  Jason Zinno RE/MAX ASSURED

  1420 Lyndale Blvd, Maitland, FL 32751

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