Winter Park, FL Homes for Rent with Community Pool

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  $2,675 Per Month

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

  2760 Bright Bird Ln, Winter Park, FL 32792

  Stunning 3 beds/2.5 bath/1car garage townhome ready to move-in June at Grayson Square, Winter park. RENT INCLUDES high-speed 1GB fiber optic internet & 75 streaming cable and music channels. The first floor is efficiently laid out with the kitchen, powder room, and spacious gathering room perfect for entertaining with a sliding glass door that opens to the covered lanai and patio that overlooks a

  Fabian Berastegui P & C PROPERTIES

  2760 Bright Bird Ln, Winter Park, FL 32792
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  $1,750 Per Month

  • 2 Beds
  • 1 Bath
  • 854 Sq Ft
  • House for Rent

  2304 Inagua Way, Winter Park, FL 32792

  Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the

  2304 Inagua Way, Winter Park, FL 32792
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  $2,550 Per Month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Condo for Rent

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789

  **MOVE IN SPECIAL $500 off first months rent** Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
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  $1,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft
  • Condo for Rent

  3050 Autumn Ct, Winter Park, FL 32792

  ?? Price Reduced! 3BR Condo in Winter Park – Now $1,950Don’t miss this charming 3-bedroom, 2-bath condo—now available at a reduced price! Conveniently located just off 436 in Winter Park, this home offers the perfect mix of comfort, convenience, and community living.Step inside to find tile and laminate flooring throughout, making for easy maintenance and a modern feel. Enjoy the

  3050 Autumn Ct, Winter Park, FL 32792
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  $1,300 Per Month

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

  1695 Lee Rd Unit D213, Winter Park, FL 32789

  Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

  Rachel DeCamp RLL Real Estate Group

  1695 Lee Rd Unit D213, Winter Park, FL 32789
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  $1,725 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Townhouse for Rent

  3283 Oak Lake Place Unit 127, Winter Park, FL 32792

  Beautiful freshly painted and cleaned property in Winter park. This is a townhouse style condo (no neighbors above and only on one side)- end unit with rear patio and storage closet. The first floor is a large living space, kitchen, a half bath and laundry with a dining nook. While there are 3 bedrooms upstairs with 2 full baths. The first floor is fully tiled and the upstairs bedrooms have

  Kyle Petteway EXIT REAL ESTATE RESULTS

  3283 Oak Lake Place Unit 127, Winter Park, FL 32792
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  $3,895 Per Month

  • 4 Beds
  • 4.5 Baths
  • 2,553 Sq Ft
  • House for Rent

  1409 Lone Feather Trail, Winter Park, FL 32792

  Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter

  Yan Zuo EAST PEARL REALTY

  1409 Lone Feather Trail, 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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  $1,500 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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  $2,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Townhouse for Rent

  2379 Flamingo Way, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom townhome in the highly desirable area of Winter Park—perfect for renters seeking comfort, convenience, and a vibrant community lifestyle. Step inside to an open-concept layout designed for modern living, featuring stylish tile flooring and a spacious kitchen with granite countertops that flows effortlessly into the living and dining

  Samuel Kingsford STOCKWORTH REALTY GROUP

  2379 Flamingo Way, Winter Park, FL 32792
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  $2,800 Per Month

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

  1951 Canny Cove, Winter Park, FL 32792

  Enjoy comfortable Winter Park living in this freshly painted 3-bedroom, 2.5-bath townhome located in the gated community of Grayson Square. Thoughtfully designed for everyday living, this home features a spacious open-concept living and dining area, perfect for entertaining, with direct access to a covered lanai for relaxing outdoors. The kitchen offers stainless steel appliances, quartz

  Denise Del Castillo LPT REALTY, LLC

  1951 Canny Cove, 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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  $5,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,940 Sq Ft
  • Townhouse for Rent

  784 S Pennsylvania Ave, Winter Park, FL 32789

  Discover modern living in this beautifully designed townhome located in the heart of Winter Park. This residence has a spacious layout with contemporary finishes, high ceilings, modern light fixtures and shades, and abundant natural light. Enjoy the convenience of a well-appointed kitchen, an inviting living area, and a private patio for relaxing, and private access to the community pool! The

  Steven Koleno BEYCOME OF FLORIDA LLC

  784 S Pennsylvania Ave, Winter Park, FL 32789
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  $1,650 Per Month

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

  625 Trinidad Ct Unit 625, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Move right into this CLEAN & WELL-MAINTAINED 2 BEDROOM / 2 BATH ONE-STORY CONDO offering 1,037 SF OF COMFORTABLE LIVING SPACE in the heart of WINTER PARK! This MOVE-IN READY home features a SPACIOUS LAYOUT, NATURAL LIGHT, and a functional floor plan perfect for comfortable everyday living. Enjoy a SMALL & COZY BACKYARD PATIO AREA, perfect for

  Nydia Marrero ZEN LIVING HOMES LLC

  625 Trinidad Ct Unit 625, Winter Park, FL 32792
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  $9,700 Per Month

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft
  • House for Rent

  1760 Legion Dr, Winter Park, FL 32789

  Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
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  $1,350 Per Month

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

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet

  Torey Eisenman BENCHMARK REAL ESTATE GRP INC

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792
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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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  $2,500 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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  $1,800 Per Month

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

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  Welcome Home to Waterfall Cove in Winter Park! This spacious 3-bedroom, 2-bath ground floor corner unit is move-in ready with fresh paint and brand new carpet throughout. Corner placement means extra natural light and a layout that lives even larger than its generous footprint. Community Perks include a sparkling pool just in time for summer, secured building access, and a peaceful, park-like

  Ryan Hoppe ZEAL REALTY

  1695 Lee Rd Unit D116, Winter Park, FL 32789
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  $1,650 Per Month

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 815, Winter Park, FL 32792

  This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 815, 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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  $1,350 Per Month

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

  296 Lewfield Cir, Winter Park, FL 32792

  Experience effortless Winter Park living in this stylish, top-floor condo in the charming Stratford community. This move-in-ready gem features modern wood-look tile, a private balcony with serene landscape views, and the convenience of an in-unit washer/dryer. Enjoy resort-style perks like a sparkling pool, fitness center, and tennis courts—with water, trash, and maintenance all included.

  Steve Simpson 407 PROPERTIES

  296 Lewfield Cir, Winter Park, FL 32792
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  $1,350 Per Month

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

  3032 Antique Oaks Cir Unit 145, Winter Park, FL 32792

  1 Bedroom/1 Bath condo in Winter Park's Parkview Village! Situated just off of 436/South Semoran Blvd & so convenient to UCF, Full Sail University, 417 & more! The living room, dining & kitchen layout flows easily with sliding doors that lead to the screened patio! Fresh interior paint, washer & dryer. Parkview Village offers a pool, clubhouse. Take a look today!

  Barry Stephens MAINFRAME REAL ESTATE

  3032 Antique Oaks Cir Unit 145, Winter Park, FL 32792
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  $4,100 Per Month

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • House for Rent

  1026 S Lakemont Ave, Winter Park, FL 32792

  Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The

  Lianna D'Angelo SOTERA LIVING

  1026 S Lakemont Ave, Winter Park, FL 32792
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  $10,000 Per Month

  • 5 Beds
  • 4 Baths
  • 4,200 Sq Ft
  • House for Rent

  1814 Barker Dr, Winter Park, FL 32789

  Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a

  Tab Bish LLC REAL BROKER, LLC

  1814 Barker Dr, Winter Park, FL 32789
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  $1,360 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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  $3,150 Per Month

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

  1351 Merrydale Way, Winter Park, FL 32792

  Fantastic, Modern townhome WITH 3 beds & 2.5 baths. Hawk's Crest is a gated community in Winter Park. This home is has a very spacious open floor plan with a water view! The kitchen has granite countertops and is fully equipped with stainless steel Whirlpool appliances; oven, stove, microwave, refrigerator, dishwasher, and garbage disposal. The kitchen area also has a large pantry! This energy

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1351 Merrydale Way, 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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  $1,740 Per Month

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Condo for Rent

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792

  Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792
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  $1,595 Per Month

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

  1695 Lee Rd Unit C206, Winter Park, FL 32789

  Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community. This unit offers the perfect combination of comfort, space, and convenience — ideal for families or professionals looking for a clean and functional home ready for immediate move-in. PROPERTY HIGHLIGHTS:2 Bedrooms / 1 Full Bathroom - Second-floor unit (added privacy) -

  Yein Ross ROSS RENTALS LLC

  1695 Lee Rd Unit C206, Winter Park, FL 32789
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  $12,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,064 Sq Ft
  • House for Rent

  1041 Tuscany Place, Winter Park, FL 32789

  Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted

  Brad Barnett COMPASS FLORIDA LLC

  1041 Tuscany Place, Winter Park, FL 32789
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  $1,500 Per Month

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

  7340 Swallow Run Unit 7340, Winter Park, FL 32792

  Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

  Bobby Mills METRO CITY REALTY

  7340 Swallow Run Unit 7340, Winter Park, FL 32792
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  $3,300 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,891 Sq Ft
  • House for Rent

  1843 Shadyhill Terrace, Winter Park, FL 32792

  Available for lease in the desirable Autumn Glen community of Winter Park. This spacious and well-maintained 4-bedroom, 2-bathroom single-family home offers comfort, space, and serenity in a peaceful neighborhood setting. Thoughtfully landscaped with lush greenery and tranquil water views, the home features an oversized kitchen with stainless steel appliances, ample storage, and a pass-through

  Beatrice Miranda METRO CITY REALTY

  1843 Shadyhill Terrace, Winter Park, FL 32792
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  $5,200 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft
  • House for Rent

  5338 Ardsdale Ln, Orlando, FL 32814

  Rare opportunity to rent a beautiful single-family home in Baldwin Park. This stunning two-story Craftsman-style residence features a charming front porch overlooking a private mews and is just steps from the community pool. The home offers three bedrooms plus a spacious media or playroom, two and a half bathrooms, and a desirable first-floor primary suite. Interior highlights include gorgeous

  Carolina Brum WRA BUSINESS & REAL ESTATE

  5338 Ardsdale Ln, Orlando, FL 32814

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