Location: Winter Park
Keyword(s): Glenridge Middle
Keyword(s) Middle School: Glenridge Middle
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2251 NAIRN DR, WINTER PARK, FL 32792
$3,20026 Days on yellowkey MLS ID: O6422217
Bed: 4 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1978 Built: 2015Community: AlomaTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year:
Middle School: Glenridge Middle
Remarks: Unfurnished – No Pets. Beautiful modern 4-bedroom, 2.5-bath home located in one of Winter Park's most established and sought-after neighborhoods. This spacious home features wood and laminate flooring throughout, a downstairs bonus room, a separate utility room, a private second-floor sun deck/terrace perfect for relaxing or entertaining, and a first-floor concrete patio. The contemporary kitchen is equipped with 42-inch European-style cabinetry, granite countertops, and stainless steel appliances. Residents also enjoy access to attractive community green spaces.Ideally situated within walking distance of Winter Park Hospital and AdventHealth Winter Park, this home is also just minutes from Cady Way Park, Ward Park, shopping, dining, and entertainment along Aloma Avenue and Lakemont Avenue. Conveniently located near Rollins College, the University of Central Florida (UCF), and Full Sail University, making it an excellent choice for healthcare professionals, faculty, and other professionals. Landscaping and lawn care are included in the rent.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Alfredo Karam (407-476-5115)
7302 SWALLOW RUN #7302, WINTER PARK, FL 32792
$1,44542 Days on yellowkey MLS ID: O6417858
REDUCED by $50 (3.3%) on 07/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 756 Built: 1985Community: Whisperwood Condo 04Condo
Elementary School: Cheney Elem
Remarks: This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY (407-897-3366)
Listing Agent: Matthew Kirsch (407-897-3366)
660 OSCEOLA AVE #101, WINTER PARK, FL 32789
$9,50023 Days on yellowkey MLS ID: O6420593
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2714 Built: 1999Community: Perle Du LacCondo
Remarks: Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of Lakes. Offering just over 2,700 square feet of thoughtfully designed living space, the home features freshly painted interiors, hardwood and travertine flooring, and elegant custom millwork throughout. The gourmet kitchen is equipped with custom cabinetry, hardwood countertops, and premium Sub Zero, Wolf, Dacor, and Bosch appliances. A versatile library with custom built ins provides the perfect space for a home office, reading room, or additional living area. The spacious primary suite is a peaceful retreat featuring picturesque lake views and a spa inspired bath with dual vanities, a soaking tub, walk in shower, private water closet, and a generous walk in closet. Two additional bedrooms, two full bathrooms, a powder room, and a dedicated laundry room are thoughtfully situated on the opposite side of the residence, offering exceptional privacy for family and guests. Just off the living room, a covered lakeside patio provides the perfect setting for morning coffee or evening sunsets overlooking Lake Virginia. From here, enjoy easy access to your private covered boat slip, making it effortless to spend the day exploring the Winter Park Chain of Lakes. Additional highlights include two assigned garage parking spaces, a private storage room, and access to Perle du Lac's exceptional amenities, including a heated pool, hot tub, beautifully landscaped grounds, and double gated security. Combining the convenience of a walkable Park Avenue lifestyle with the luxury of private lakefront boating, this residence offers one of Winter Park's most desirable living experiences.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Jennifer King (407-595-3272)
508 DUNBLANE DR, WINTER PARK, FL 32792
$2,90020 Days on yellowkey MLS ID: O6423719
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1600 Built: 1956Community: Kenilworth Shores Sec 03Single Family
Remarks: Wonderful 3 bedroom, 2 bath rental in the heart of Winter Park. Location is amazing! Central to Rollins College, UCF, Winter Park Schools, Baldwin Park, and more! Be sure to schedule a private showing.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brian Rotenberger (407-948-8478)
1000 S SEMORAN BLVD #715, WINTER PARK, FL 32792
$1,20020 Days on yellowkey MLS ID: S5153133
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 735 Built: 1969Community: Golfside Villas CondoCondo
Remarks: Enjoy comfortable living in the highly sought-after Winter Park area! Close to shopping, dining, and major roadways, this well-located rental provides exceptional value in one of Central Florida's most desirable communities. This first-floor condo is ideally located just steps from the community pool and on-site laundry facilities, offering convenience and easy access to everyday amenities. Don't miss this opportunity to make it your next home.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Leticia Morales (407-515-0318)
1947 SUMMERFIELD RD, WINTER PARK, FL 32792
$2,499103 Days on yellowkey MLS ID: O6396107
0 Days Off yellowkey (back on 7/2/2026)
REDUCED by $100 (3.8%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1422 Built: 1956Community: Kenilworth Shores Sec 07Single Family
Remarks: Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to do a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.
Listing is courtesy of: 407 PROPERTIES (407-545-2594)
Listing Agent: Steven Simpson (407-545-2594)
1814 BARKER DR, WINTER PARK, FL 32789
$10,000118 Days on yellowkey MLS ID: O6395037
0 Days Off yellowkey (back on 6/24/2026)
REDUCED by $1,000 (9.1%) on 05/13/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4200 Built: 2021Community: South Lakemont ShoresSingle Family
Elementary School: Baldwin Park Elementary
Remarks: 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 reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step outside to a private backyard oasis with a sparkling pool, outdoor kitchen area, and no rear neighbors—perfect for entertaining. The first-floor primary suite offers complete privacy with a spa-inspired bath, soaking tub, walk-in shower, and dream closet. The main level also includes a private office, full bath, dining room, laundry room, and generous living spaces. Upstairs features a large loft, rumpus room, four additional bedrooms, and two beautifully designed baths. The oversized two-car garage provides high ceilings, storage, and a flex space ideal for bikes, fitness, or workshop use. Located minutes from Park Avenue dining, shopping, and entertainment, this home delivers luxury, comfort, and an unbeatable Winter Park lifestyle. Professionally managed with exceptional service.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Tab Bish Llc (855-450-0442)
3045 AARON BURR AVE #12D, WINTER PARK, FL 32792
$1,65048 Days on yellowkey MLS ID: S5150999
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1062 Built: 1974Community: ColoniesCondo
Remarks: Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access to everything Orlando. Featuring new flooring and a clean, fresh interior, it is ideal for any lifestyle.
Listing Agent: Angel Ramirez (407-967-5368)
1317 MEDINAH CT, WINTER PARK, FL 32792
$3,650124 Days on yellowkey MLS ID: O6393971
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2015 Built: 1979Community: Greenview At Winter PinesSingle Family
Remarks: Winter Park Pines home,4 bed/2 bath ready for a new resident. On a quiet cul-de-sac, this renovated home offers a blend of modern amenities with a fantastic location. It features a brand new kitchen & bathrooms with quartz countertops, updated brushed brass fixtures, with lots of custom touches. It features engineered wood flooring in the living areas and primary bedroom, a convenient indoor laundry room, new windows and sliding doors that let in tons of natural light. Other upgrades include new doors, trim, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system, lawncare is included in the rent. This home also has a new roof, garage door, and a HVAC system. This home is also next to the scenic Cady Way trail, ideal for biking, walking, and running. Zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Call for your showing today! Sorry NO PETS.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Jackie O'Leary (407-718-0887)
2929 ANTIQUE OAKS CIR #53, WINTER PARK, FL 32792
$1,350125 Days on yellowkey MLS ID: O6393639
0 Days Off yellowkey (back on 4/2/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984Community: Parkview Village CondominiumCondo
Elementary School: Aloma Elem
Remarks: Welcome to this fully renovated residence in the heart of Winter Park, where modern upgrades meet timeless charm in one of Central Florida’s most desirable communities. Thoughtfully updated throughout, this home offers a fresh, move-in-ready living experience with stylish finishes and enhanced comfort. Ideally situated near Full Sail University and Rollins College, this property is well-suited for students, faculty, and professionals alike. Zoned for highly regarded schools including Aloma Elementary, Glenridge Middle, and Winter Park High School. Enjoy a vibrant lifestyle with easy access to nearby parks and outdoor destinations such as Kraft Azalea Garden and Mead Botanical Garden perfect for relaxing walks and enjoying nature. The renowned Park Avenue is also just a short drive away, offering boutique shopping, dining, and cultural experiences. Conveniently located with quick access to major roadways, downtown Orlando, and Orlando International Airport, this home also places you within reach of Florida’s beautiful east coast beaches, including Cocoa Beach and New Smyrna Beach ideal for weekend getaways. This fully renovated home offers the perfect combination of location, lifestyle, and modern living, making it an exceptional leasing opportunity in Winter Park. Water is included in the rent. Apply here: https://apply.link/oQ8t72Y
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Betsy Breton-Garcia, Pa (407-580-5350)
2356 COLDSTREAM DR, WINTER PARK, FL 32792
$2,825122 Days on yellowkey MLS ID: O6394600
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1619 Built: 1959Community: Brookshire HeightsSingle Family
Remarks: One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
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