Winter Park, FL Homes for Rent with Community Pool

/26
$1,465 per month
- 1 Bed
- 1 Bath
- 645 Sq Ft
- Condo for Rent
2500 Lee Rd Unit 244, Winter Park, FL 32789

Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

Rustina Gibson

RE/MAX VANTAGE

(321) 336-5615

2500 Lee Rd Unit 244, Winter Park, FL 32789
Explore Winter Park
/21
$1,750 per month
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Condo for Rent
1500 Gay Rd Unit 18A, Winter Park, FL 32789

Winter 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

(689) 336-1800

1500 Gay Rd Unit 18A, Winter Park, FL 32789
/29
$1,799 per month
- 2 Beds
- 1 Bath
- 804 Sq Ft
- Condo for Rent
151 N Orlando Ave Unit 101, Winter Park, FL 32789

Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of theLake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & openlayout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining orcasual family meals. Granite

Elizabeth Fowler

THE FLORIDA PROPERTY SHOP SALE

(689) 588-1599

151 N Orlando Ave Unit 101, Winter Park, FL 32789
/131

$1,295 - $2,075 per month

Oak Reserve at Winter Park

1 - 3 Beds

541 Oak Reserve Ln, Winter Park, FL 32792

Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

541 Oak Reserve Ln, Winter Park, FL 32792
/16
$1,750 per month
- 2 Beds
- 1.5 Baths
- 990 Sq Ft
- Townhouse for Rent
Unlisted Address

Charming 2-bedroom, 1.5-bath townhouse located in the highly desirable Hidden Oaks community. This two-story home offers 990 sq ft of comfortable living space. The main floor features a spacious living area that flows into the dining area and kitchen, along with a convenient half bath for guests. Upstairs, you’ll find the primary bedroom with a spacious bathroom, as well as an additional

Moira Villavicencio EXP REALTY LLC

Unlisted Address
/75

$1,604 - $3,587 per month

Bainbridge Winter Park

1 - 3 Beds

1400 Morgan Stanley Ave, Winter Park, FL 32789

Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

1400 Morgan Stanley Ave, Winter Park, FL 32789
/17
$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
/28

$1,662 - $1,699 per month

Elon Winter Park

1 Bed

712 Nicolet Ave, Winter Park, FL 32789

Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

712 Nicolet Ave, Winter Park, FL 32789
/18
$1,400 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
/53

$1,700 - $4,775 per month

Juno Winter Park

Studio - 3 Beds

1305 Morgan Stanley Ave, Winter Park, FL 32789

Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

1305 Morgan Stanley Ave, Winter Park, FL 32789
/78
$11,000 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
/103

$1,769 - $6,687 per month

Paseo at Winter Park Village

1 - 3 Beds

940 W Canton Ave, Winter Park, FL 32789

Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

940 W Canton Ave, Winter Park, FL 32789
/15
$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
/39

$1,198 - $1,787 per month

Seabrook

1 - 2 Beds

3114 Terry Brook Dr, Winter Park, FL 32792

The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

3114 Terry Brook Dr, Winter Park, FL 32792
/17
$1,750 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 condo!Located on the second floor in a quiet community, perfect for families or professionals seeking comfort and convenience. 1.- Property Features2 Bedrooms1 Full BathroomSecond-floor unit (added privacy)Total area: 881 sqft 2.- Comfort & Interior FeaturesCentral Air ConditioningCentral HeatingCeiling FansHigh CeilingsOpen

Yein Ross ROSS RENTALS LLC

1695 Lee Rd Unit C206, Winter Park, FL 32789
/74

$1,574 - $5,689 per month

Vintage Winter Park Apartments

1 - 3 Beds

7490 Dwell Well Way, Winter Park, FL 32792

Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

7490 Dwell Well Way, Winter Park, FL 32792
/12
$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

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 generous space, with a private primary suite

David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
/51

$1,449 - $1,985 per month

Cranes Landing Apartments

2 - 3 Beds

3440 N Goldenrod Rd, Winter Park, FL 32792

Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

3440 N Goldenrod Rd, Winter Park, FL 32792
/17
$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
/50

$1,585 - $3,136 per month

Seven41 Winter Park

Studio - 2 Beds

741 Clay St, Winter Park, FL 32789

Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

741 Clay St, Winter Park, FL 32789
/16
$1,875 per month
- 2 Beds
- 2.5 Baths
- 959 Sq Ft
- Townhouse for Rent
295 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

295 Sandlewood Trail, Winter Park, FL 32789
/36

$883 - $2,002 per month

The Taylor at Winter Park

Studio - 3 Beds

2000 Village Ln, Winter Park, FL 32792

5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

2000 Village Ln, Winter Park, FL 32792
/34
$4,000 per month
- 4 Beds
- 3.5 Baths
- 2,196 Sq Ft
- House for Rent
1091 Wildmeadow Run, Winter Park, FL 32792

1

Maggie Walas FORTUNE INTERNATIONAL REALTY

1091 Wildmeadow Run, Winter Park, FL 32792
/50

$1,499 - $2,018 per month

Calibre Bend Apartments

1 - 2 Beds

3924 Calibre Bend Ln, Winter Park, FL 32792

Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

3924 Calibre Bend Ln, Winter Park, FL 32792
/17
$1,650 per month
- 2 Beds
- 2 Baths
- 1,018 Sq Ft
- Condo for Rent
2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792

Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for

Jacqueline Ramos JML REALTY INVESTMENTS LLC

2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
/50

$1,544 - $5,399 per month

Berkshire Winter Park

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

1874 Harmon Ave, Winter Park, FL 32789
/35
$4,500 per month
- 4 Beds
- 3 Baths
- 1,808 Sq Ft
- House for Rent
1802 Arbor Park Dr, Winter Park, FL 32789

Welcome 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

1802 Arbor Park Dr, Winter Park, FL 32789
/44

$1,343 - $3,741 per month

Liv at Winter Park Apartment Homes

Studio - 3 Beds

4755 N Goldenrod Rd, Winter Park, FL 32792

Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

4755 N Goldenrod Rd, Winter Park, FL 32792
/37
$5,900 per month
- 4 Beds
- 3 Baths
- 2,741 Sq Ft
- House for Rent
220 W Reading Way, Winter Park, FL 32789

Welcome 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

220 W Reading Way, Winter Park, FL 32789
/35

$1,299 - $2,780 per month

Summerlin at Winter Park Apartments

1 - 3 Beds

3207 Rosebud Ln, Winter Park, FL 32792

These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

3207 Rosebud Ln, Winter Park, FL 32792
/90
$13,500 per month
- 8 Beds
- 6 Baths
- 7,000 Sq Ft
- House for Rent
1860 Via Contessa, Winter Park, FL 32789

Exceptional 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

1860 Via Contessa, Winter Park, FL 32789
/39

$910 - $1,544 per month

San Jose Apartments

1 - 3 Beds

2353 Winter Woods Blvd, Winter Park, FL 32792

Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

2353 Winter Woods Blvd, Winter Park, FL 32792
/7
$1,500 per month
- 2 Beds
- 2 Baths
- 800 Sq Ft
- Condo for Rent
7326 Swallow Run Unit 7326, Winter Park, FL 32792

Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high

Jiny Lee NOBSKA REAL ESTATE LLC

7326 Swallow Run Unit 7326, Winter Park, FL 32792
/26

$1,170 - $1,975 per month

Central Place At Winter Park

1 - 3 Beds

7000 University Blvd, Winter Park, FL 32792

Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

7000 University Blvd, Winter Park, FL 32792
/14
$5,895 per month
- 4 Beds
- 3 Baths
- 2,207 Sq Ft
- House for Rent
1235 Via Estrella, Winter Park, FL 32789

Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island,

Kelly Price KELLY PRICE & COMPANY LLC

1235 Via Estrella, Winter Park, FL 32789
/16

$1,599 - $1,824 per month

The Vista at Winter Park

2 Beds

4704 Lucier Ct, Winter Park, FL 32792

*Restricted units only*App and Admin special for only $175!Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will

4704 Lucier Ct, Winter Park, FL 32792
/23
$1,750 per month
- 2 Beds
- 2 Baths
- 987 Sq Ft
- Condo for Rent
200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792

Cozy and well-maintained 2-bedroom, 2-bath condo, washer and dryer inside, located in the desirable Winter Park area. This spacious unit features an open and comfortable layout with abundant natural light, a functional kitchen, and a small patio perfect for relaxing. The community offers great amenities including a pool, tennis courts, shuffleboard, clubhouse and beautifully maintained grounds.

Nohora Gomez COLDWELL BANKER REALTY

200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
/14

$1,250 - $1,800 per month

Park Apartments

1 - 3 Beds

7528 Park Promenade Dr, Winter Park, FL 32792

WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two

7528 Park Promenade Dr, Winter Park, FL 32792
/16
$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
/11

$1,217 - $1,717 total monthly price

Solis at Winter Park

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

7502 Sun Key Blvd, Winter Park, FL 32792

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