$2,975 per month
- 3 Beds
- 2 Baths
- 1,195 Sq Ft
- House for Rent
1891 Oglesby Ave, Winter Park, FL 32789
1891 Oglesby Ave, Winter Park, FL 32789$2,975 per month
1891 Oglesby Ave, Winter Park, FL 32789
1891 Oglesby Ave, Winter Park, FL 32789$6,995 per month
2075 Jewell Ave, Winter Park, FL 32789
2075 Jewell Ave, Winter Park, FL 32789$1,650 per month
1550 Michigan Ave, Winter Park, FL 32789
Welcome 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
$7,200 per month
1016 Howell Branch Rd, Winter Park, FL 32789
Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road,where every day feels like a getaway. (Property can be leased furnished for an additional fee.) This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspiredliving space set amid lush, tropical landscaping — all within the bestof Winter Park and Maitland. *The canal
Andrew Birr PLAID PROPERTIES, LLC
$2,595 per month
1128 Park Green Place, Winter Park, FL 32789
Stylish Winter Park home available now! Split-plan, 3 bed, 2 bath layout with two car garage, fenced-in backyard with patio, and community pool with cabana. Pet-friendly (subject to deposit and approval). The master bedroom has trey ceilings and an en-suite bath with double vanity and double walk-in closets. Full-size washer and dryer, new A/C unit (2025) and fresh exterior paint (2025). Located
$2,500 per month
2846 Euston Rd, Winter Park, FL 32789
Welcome 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.
$3,300 per month
870 Carver St Unit A, Winter Park, FL 32789
Welcome 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
$4,500 per month
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
$5,900 per month
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
$13,500 per month
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
$5,895 per month
1235 Via Estrella, Winter Park, FL 32789
Rare 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
$2,500 per month
2743 Sanbina St, Winter Park, FL 32789
Welcome 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
$6,750 per month
527 Langholm Dr, Winter Park, FL 32789
Beautiful 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.
$4,000 per month
1815 Barker Dr, Winter Park, FL 32789
Furnished 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
$3,475 per month
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
$17,000 per month
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
$3,150 per month
1835 Edwin Blvd, Winter Park, FL 32789
Charming 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
$3,850 per month
1302 Michigan Ave, Winter Park, FL 32789
This 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
$19,000 per month
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
$4,495 per month
1580 Oakhurst Ave, Winter Park, FL 32789
Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are
Lisa Gould KELLER WILLIAMS WINTER PARK
$7,900 per month
300 Killarney Dr, Winter Park, FL 32789
Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney
Kelly Price KELLY PRICE & COMPANY LLC
$2,950 per month
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
$2,195 per month
1148 Park Green Place, Winter Park, FL 32789
Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments
Linda Baez DON ASHER & ASSOCIATES, INC.
$2,435 per month
1622 Arbor Park Dr, Winter Park, FL 32789
Free 1/2 month's rent move in incentive! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room with plenty of natural light
Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC
$2,650 per month
865 S Pennsylvania Ave, Winter Park, FL 32789
Historic 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