$1,365 - $2,252 per month
Westmount at Winter Park
Studio - 3 Beds
1701 Lee Rd, Winter Park, FL 32789
59
Homes for Rent in ZIP Code 32789
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1701 Lee Rd, Winter Park, FL 32789
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$1,550 - $3,136 per month
741 Clay St, Winter Park, FL 32789Seven41 Winter Park
Studio - 2 Beds
741 Clay St, Winter Park, FL 32789
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$1,504 - $5,436 per month
1874 Harmon Ave, Winter Park, FL 32789Berkshire Winter Park
Studio - 3 Beds
1874 Harmon Ave, Winter Park, FL 32789
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$1,635 - $9,294 per month
1305 Morgan Stanley Ave, Winter Park, FL 32789Juno Winter Park
Studio - 3 Beds
1305 Morgan Stanley Ave, Winter Park, FL 32789
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$1,695 - $1,825 per month
520 N Orlando Ave, Winter Park, FL 32789The Lofts of Winter Park Village
1 Bed
520 N Orlando Ave, Winter Park, FL 32789
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$1,581 - $3,341 per month
1400 Morgan Stanley Ave, Winter Park, FL 32789Bainbridge Winter Park
1 - 3 Beds
1400 Morgan Stanley Ave, Winter Park, FL 32789
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$1,649 per month
712 Nicolet Ave, Winter Park, FL 32789Elon Winter Park
1 Bed
712 Nicolet Ave, Winter Park, FL 32789
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$1,807 - $6,390 per month
940 W Canton Ave, Winter Park, FL 32789Paseo at Winter Park Village
1 - 3 Beds
940 W Canton Ave, Winter Park, FL 32789
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$1,330 - $1,750 per month
311 N Knowles Ave, Winter Park, FL 32789Park East - Park Knowles Apartments
Studio - 2 Beds
311 N Knowles Ave, Winter Park, FL 32789
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$2,500 per month
- 3 Beds
- 1.5 Baths
- 1,279 Sq Ft
- House for Rent
2846 Euston Rd, Winter Park, FL 32789
2846 Euston Rd, Winter Park, FL 32789Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and
Vanessa Laboy 365 REALTY, INC.
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$1,750 per month
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Condo for Rent
1500 Gay Rd Unit 18A, Winter Park, FL 32789
1500 Gay Rd Unit 18A, Winter Park, FL 32789Winter Park Lakefront Community. Lakefront Deck, Dock, Grill, Community Building, Heated Pool and Sauna. Immaculate 2 Bedroom 2 Bath First Floor Unit. Upgraded Kitchen with Raised Ceiling, Maple Cabinets and Granite Counters. Cabinets (matching Kitchen Cabinets) and Counters built in Dining Room for extra Storage. Recently Painted. New Carpets in Bedrooms. Bathroom Vanities and Commodes have been
Janice Erickson REALCOM REAL ESTATE SERVICES INC
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$1,799 per month
- 2 Beds
- 1 Bath
- 804 Sq Ft
- Condo for Rent
151 N Orlando Ave Unit 101, Winter Park, FL 32789
151 N Orlando Ave Unit 101, Winter Park, FL 32789 -
$1,895 per month
- 2 Beds
- 2.5 Baths
- 959 Sq Ft
- Townhouse for Rent
295 Sandlewood Trail, Winter Park, FL 32789
295 Sandlewood Trail, Winter Park, FL 32789This 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
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$3,300 per month
- 2 Beds
- 2 Baths
- 1,209 Sq Ft
- House for Rent
870 Carver St Unit A, Winter Park, FL 32789
870 Carver St Unit A, Winter Park, FL 32789Welcome to 870 Carver Street, a thoughtfully designed two-bedroom, two-bath residence in the core of Winter Park. Offering more than 1,200 square feet, the newly constructed home features vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork that define its architectural character. The primary suite includes a floating wall closet system, a laundry
Drew Henner PREMIER SOTHEBY'S INTL. REALTY
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$4,500 per month
- 4 Beds
- 3 Baths
- 1,808 Sq Ft
- House for Rent
1802 Arbor Park Dr, Winter Park, FL 32789
1802 Arbor Park Dr, Winter Park, FL 32789Welcome home to this beautifully maintained 4-bedroom, 3-bath pool home located in Winter Park’s highly desirable Tree Streets neighborhood—an area known for its charming, tree-lined roads and peaceful atmosphere. Situated on an oversized .27-acre lot, one of the largest in the community, this property offers rare space and privacy while still being close to everything Winter Park has to offer.
Jorge Perez Gonzalez TBRO REALTY LLC
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$5,900 per month
- 4 Beds
- 3 Baths
- 2,741 Sq Ft
- House for Rent
220 W Reading Way, Winter Park, FL 32789
220 W Reading Way, Winter Park, FL 32789Welcome to your dream home! This recently renovated gem in the highly coveted Forrest Hills area of Winter Park is now available for rent. Surrounded by enchanting brick streets and majestic trees, this charming residence has been thoughtfully upgraded by the new owner, offering a perfect blend of modern amenities and classic charm. As you step onto the inviting front covered porch, you'll be
Thomas Hewitt HEWITT RESIDENTIAL, LLC
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$13,500 per month
- 8 Beds
- 6 Baths
- 7,000 Sq Ft
- House for Rent
1860 Via Contessa, Winter Park, FL 32789
1860 Via Contessa, Winter Park, FL 32789Exceptional Lease Opportunity | The Vias, Winter Park$13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available NowRarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched
Kelly Price KELLY PRICE & COMPANY LLC
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$5,895 per month
- 4 Beds
- 3 Baths
- 2,207 Sq Ft
- House for Rent
1235 Via Estrella, Winter Park, FL 32789
1235 Via Estrella, Winter Park, FL 32789Rare opportunity to lease a fully renovated 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence has been thoughtfully updated throughout and sits just a short stroll from the prestigious Winter Park Racquet Club.Step outside to your private backyard oasis, where a sparkling pool and heated spa are framed by lush,
Kelly Price KELLY PRICE & COMPANY LLC
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$2,500 per month
- 3 Beds
- 2 Baths
- 1,226 Sq Ft
- House for Rent
2743 Sanbina St, Winter Park, FL 32789
2743 Sanbina St, Winter Park, FL 32789Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights:-Primary suite featuring a walk-in closet and private ensuite bathroom-Classic terrazzo flooring-Recently remodeled
Summer Hornburg BELMONT REALTY
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$4,500 per month
- 2 Beds
- 2 Baths
- 1,143 Sq Ft
- Condo for Rent
104 S Interlachen Ave Unit 114, Winter Park, FL 32789
104 S Interlachen Ave Unit 114, Winter Park, FL 32789First-floor 2-bedroom, 2-bath condo for lease in The Cloisters on Lake Osceola, part of the Winter Park Chain of Lakes. This light-filled residence features an open living and dining area plus an enclosed sunroom ideal for a home office or additional sitting space. The split-bedroom floor plan offers privacy, with a spacious primary suite and private en-suite bath. Enjoy true Florida living with
Audra Wilks PREMIER SOTHEBY'S INTL. REALTY
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$6,750 per month
- 4 Beds
- 3.5 Baths
- 3,276 Sq Ft
- House for Rent
527 Langholm Dr, Winter Park, FL 32789
527 Langholm Dr, Winter Park, FL 32789Beautiful custom home with an open floor plan featuring 4 bedrooms, 3.5 baths, downstairs office, 2 car garage, huge loft for gaming and an additional private Bonus Room that can be utilized as a gym or flex room. Master Bedroom and office are conveniently located on the first floor. Additional features of this home include a gourmet kitchen with island, stainless steel appliances, granite
Nancy Woodruff WOODRUFF REALTY, INC.
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$1,895 per month
- 2 Beds
- 2.5 Baths
- 960 Sq Ft
- Townhouse for Rent
307 Sandlewood Trail, Winter Park, FL 32789
307 Sandlewood Trail, Winter Park, FL 32789This 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
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$6,995 per month
- 5 Beds
- 4 Baths
- 2,918 Sq Ft
- House for Rent
2075 Jewell Ave, Winter Park, FL 32789
2075 Jewell Ave, Winter Park, FL 32789 -
$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
151 N Orlando Ave Unit 118, Winter Park, FL 32789Investment 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
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$4,000 per month
- 4 Beds
- 2 Baths
- 1,548 Sq Ft
- House for Rent
1815 Barker Dr, Winter Park, FL 32789
1815 Barker Dr, Winter Park, FL 32789Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals,
Benjamin Cole, IV SOTERA LIVING
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$6,000 per month
- 2 Beds
- 2.5 Baths
- 1,500 Sq Ft
- Apartment for Rent
301 W Comstock Ave, Winter Park, FL 32789
301 W Comstock Ave, Winter Park, FL 32789Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.
Sydney Brownlee THE SYDGAN CORP
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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
1850 Whitehall Dr, Winter Park, FL 32789This 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
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$5,995 per month
- 3 Beds
- 2.5 Baths
- 2,069 Sq Ft
- Condo for Rent
1130 Washington Ave Unit 11C, Winter Park, FL 32789
1130 Washington Ave Unit 11C, Winter Park, FL 32789Unbeatable Location! Don't miss this very rare and exquisite 3 bedroom, 2.5 bath, two-story Executive-Style condo in Winter Park-ideally located just around the corner from N. Orange Avenue, Park Avenue and Rollins College. Nestled in a prime, tucked-away setting, this home has been extensively remodeled with all new plumbing, electrical, duct work, flooring, appliances, and a natural gas line.
Keith Race FUSILIER MANAGEMENT GROUP
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$3,750 per month
- 3 Beds
- 3 Baths
- 1,750 Sq Ft
- Apartment for Rent
421 W Fairbanks Ave, Winter Park, FL 32789
421 W Fairbanks Ave, Winter Park, FL 32789Occupying the entire second floor of a landmark 1925 brick building in the heart of Winter Park, this fully reimagined residence offers a rare opportunity to lease a true designer 3 bedroom, 3 bathroom loft just two blocks from Park Avenue. The open concept interior features high ceilings, abundant natural light from skylights and brand new windows, and a refined industrial aesthetic anchored by
Nicholas Cadwallader REALTY ONE GROUP MVP
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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
1695 Lee Rd Unit C110, Winter Park, FL 32789Spacious 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
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$5,490 per month
- 3 Beds
- 2.5 Baths
- 2,354 Sq Ft
- Condo for Rent
782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the
Steven Koleno BEYCOME OF FLORIDA LLC
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$1,425 per month
- 2 Beds
- 1 Bath
- 920 Sq Ft
- Condo for Rent
1380 Indiana Ave Unit 3, Winter Park, FL 32789
1380 Indiana Ave Unit 3, Winter Park, FL 32789Winter Park at your door step! This is a second floor 2 bedroom unit, in secured building. Large open backyard with rear balcony and patio space and plenty of parking. Unit has full kitchen, and washer/dryer in unit! Two full bedrooms both with walk-in closets and a full bath. Living room is large open/bright. Only a few blocks walk to Orlando Ave with all its shopping, Publix and restaurants.
Scott Butts KIMBRIDGE REALTY, LLC
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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
1742 Temple Dr, Winter Park, FL 32789An 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
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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
311 E Morse Blvd Unit 1-5, Winter Park, FL 32789Enjoy 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
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$2,650 per month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- House for Rent
865 S Pennsylvania Ave, Winter Park, FL 32789
865 S Pennsylvania Ave, Winter Park, FL 32789Historic 2-bedroom home walking distance to Park Avenue and Rollins College. This well-maintained rental features a living room fireplace, fresh interior paint, and new cordless blinds throughout. The kitchen includes stainless steel appliances and a gas stove. Enjoy a screened front porch, fully fenced yard, and ample rear parking. Prime Winter Park location with classic charm and modern updates.
Catherine Mitchell SANDRONI HOLDINGS REAL ESTATE LLC
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$3,150 per month
- 3 Beds
- 2 Baths
- 1,436 Sq Ft
- House for Rent
1835 Edwin Blvd, Winter Park, FL 32789
1835 Edwin Blvd, Winter Park, FL 32789Charming bungalow on a brick street in beautiful Winter Park, available March 1, 2026. This 3-bedroom, 2-bathhome offers a great split floorplan and newer finishes. The kitchen and both primary en-suite and secondary bathroomshave been completely remodeled with premium finishes. The home boasts a newer roof, hardwood and stone floorsthroughout, with granite counters, white cabinetry,
Vincent Scarlatos CORCORAN PREMIER REALTY
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$3,995 per month
- 3 Beds
- 2.5 Baths
- 2,317 Sq Ft
- Townhouse for Rent
438 W Swoope Ave, Winter Park, FL 32789
438 W Swoope Ave, Winter Park, FL 32789$4495.00 for a 15 MO LEASE$4695.00 12 MO LEASE Nestled within the exclusive 400 West enclave intimate community of just nine residences, just moments from Park Avenue this 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
Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT
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$3,850 per month
- 3 Beds
- 2.5 Baths
- 1,880 Sq Ft
- House for Rent
1302 Michigan Ave, Winter Park, FL 32789
1302 Michigan Ave, Winter Park, FL 32789This is a unique opportunity to live in this glamorous, impeccably maintained 3 bedrooms, 2.5 baths in the heart of Winter Park (Unfurnished). This beautiful home features formal living and dining rooms that open to the impressive gourmet kitchen fitted with wood cabinetry, stainless steel appliances, granite countertops, a breakfast bar, there is also room for a breakfast nook. Through the
Mo Jabr RE/MAX 200 REALTY
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$1,650 per month
- 1 Bed
- 1 Bath
- 502 Sq Ft
- House for Rent
1550 Michigan Ave, Winter Park, FL 32789
1550 Michigan Ave, Winter Park, FL 32789Welcome 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
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$3,995 per month
- 4 Beds
- 3.5 Baths
- 2,604 Sq Ft
- Townhouse for Rent
438 W Swoope Ave, Winter Park, FL 32789
438 W Swoope Ave, Winter Park, FL 32789SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!!$4395.00 for a 15 MO LEASE$4595.00 12 MO LEASENestled 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
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