$2,900 per month
- 3 Beds
- 2 Baths
- 1,760 Sq Ft
- House for Rent
2128 Sycamore Dr, Winter Park, FL 32789
2128 Sycamore Dr, Winter Park, FL 32789
56
Winter Park, FL Houses for Rent
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$3,000 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 -
$2,390 per month
- 3 Beds
- 2 Baths
- 1,574 Sq Ft
- House for Rent
5206 Ardmore Dr, Winter Park, FL 32792
5206 Ardmore Dr, Winter Park, FL 32792Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2534.90. That covers your base rent, $2390.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
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$2,650 per month
- 3 Beds
- 2 Baths
- 1,542 Sq Ft
- House for Rent
283 N Ranger Blvd, Winter Park, FL 32792
283 N Ranger Blvd, Winter Park, FL 32792Feel at home with this spacious 3-bedroom, 2-bath home that’s designed for both comfort and fun. The open living area is bright and airy with tons of natural light, making it feel welcoming the moment you walk in. The kitchen is a standout, fully equipped with stainless steel appliances, granite countertops, and plenty of storage, so there’s room for everything. The bedrooms are generously sized,
Summer Hornburg BELMONT REALTY
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$2,650 per month
- 4 Beds
- 2 Baths
- 1,714 Sq Ft
- House for Rent
950 Hedgewood Ct, Winter Park, FL 32792
950 Hedgewood Ct, Winter Park, FL 32792Property Id: 2303285Great opportunity to rent this 4-bedroom, 2-bath single-family home located on a quiet cul-de-sac. The home features a 2-car garage and a spacious backyard ideal for outdoor entertaining. Zoned for top-rated schools and conveniently located near major roadways, shopping, dining, and everyday amenities.
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$5,500 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 32789Available for Monthly Rentals | Furnished or UnfurnishedWelcome to your luxury lake-view home in Winter Park where comfort meets style. This beautifully designed 4-bedroom / 2-bath residence features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. ( for shorter terms only 3 bedrooms, a fourth bedroom is
Cliff Glansen FLATFEE.COM
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$2,870 per month
- 4 Beds
- 3 Baths
- 1,856 Sq Ft
- House for Rent
2029 Taylor Ave, Winter Park, FL 32792
2029 Taylor Ave, Winter Park, FL 32792We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be
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$2,375 per month
- 3 Beds
- 2 Baths
- 1,238 Sq Ft
- House for Rent
1812 Pineview Cir, Winter Park, FL 32792
1812 Pineview Cir, Winter Park, FL 32792WOW!! Renovated to perfection. Recently painted inside and out and a newer kitchen featuring white shaker cabinets with quartz countertops plus new appliances make this home a great find in an amazing location. This adorable and spotless Winter Park charmer is nestled on a quiet street a stone's throw to Lakemont Elementary. Tile and laminate throughout makes this home easy breezy to maintain.
Sherrie Pillat RE/MAX ASSURED
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$2,120 per month
- 4 Beds
- 2 Baths
- 1,534 Sq Ft
- House for Rent
2045 Houndslake Dr, Winter Park, FL 32792
2045 Houndslake Dr, Winter Park, FL 32792Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently
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$1,100 per month
- 1 Bed
- 1 Bath
- 850 Sq Ft
- House for Rent
1925 S Lakemont Ave, Winter Park, FL 32792
1925 S Lakemont Ave, Winter Park, FL 32792Enjoy lakefront living in this charming waterfront Studio B apartment with beautiful views of Baldwin Lake, offering a desirable Winter Park address and the highly sought-after Baldwin Park lifestyle. Located directly across from the Lake Baldwin Trail, you’ll love being near scenic surroundings and stunning sunsets over the water. This studio includes a private bathroom and a brand new
Elena Sanchez BALDWIN PARK REALTY LLC
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$2,400 per month
- 3 Beds
- 2 Baths
- 1,896 Sq Ft
- House for Rent
5133 Oak Hill Dr, Winter Park, FL 32792
5133 Oak Hill Dr, Winter Park, FL 32792Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,
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$3,400 per month
- 4 Beds
- 3.5 Baths
- 3,215 Sq Ft
- House for Rent
8077 Pleasant Pine Cir, Winter Park, FL 32792
8077 Pleasant Pine Cir, Winter Park, FL 32792This stunning Winter Park home, AVAILABLE April 01, features 4 bedrooms and 3.5 bathrooms, plus a fenced backyard for added privacy. The open-concept living and dining area is filled with natural light and boasts hardwood floors and elegant crown molding. The kitchen, perfect for entertaining, includes a large island, stainless steel appliances, and quartz countertops. Upstairs, you’ll find a
Tatiana Diaz FLORIDA LAKES REALTY
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$4,150 per month
- 4 Beds
- 3.5 Baths
- 2,589 Sq Ft
- House for Rent
1470 Lone Feather Trail, Winter Park, FL 32792
1470 Lone Feather Trail, Winter Park, FL 32792Welcome to this inviting rental opportunity in the charming district of Winter Park, FL. Nestled in a vibrant area, this property offers a delightful experience for those looking to enjoy a serene lifestyle while still being close to modern conveniences.Key property features include spacious bedrooms and well-appointed bathrooms, all designed with comfort in mind. With ample square
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$2,250 per month
- 3 Beds
- 2 Baths
- 1,187 Sq Ft
- House for Rent
1621 Winter Green Blvd, Winter Park, FL 32792
1621 Winter Green Blvd, Winter Park, FL 32792Are you looking for a well maintained, updated single family home in Winter Park? Presenting this 3 bedroom 2 bath home in a quiet little community conveniently located to all the conveniences Winter Park has to offer. This charming home has a beautifully updated gourmet kitchen with quartz counters and a substantial amount of cabinetry and newer stainless appliances. There is new vinyl planking
Beatrice Palladino GALLERY PROPERTIES INTERNATIONAL
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$2,700 per month
- 3 Beds
- 2 Baths
- 1,643 Sq Ft
- House for Rent
2852 Scarlet Rd, Winter Park, FL 32792
2852 Scarlet Rd, Winter Park, FL 32792BEAUTIFUL HOME IN WINTER PARK!!Delight in this stunning 3-bedroom, 2-bathroom home nestled in the charming locale of Winter Park. The residence boasts a spacious family room and a dining area adorned with elegant wood-like tile flooring, setting a warm and inviting atmosphere. Marvel at the stylish light fixtures that add a touch of sophistication to every room.The heart of the
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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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$2,599 per month
- 3 Beds
- 2 Baths
- 1,736 Sq Ft
- House for Rent
191 Jergo Rd, Winter Park, FL 32792
191 Jergo Rd, Winter Park, FL 32792Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2743.90. That covers your base rent, $2599.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
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$3,650 per month
- 3 Beds
- 2 Baths
- 2,064 Sq Ft
- House for Rent
1329 Medinah Ct, Winter Park, FL 32792
1329 Medinah Ct, Winter Park, FL 32792Welcome to this fully rehabbed rental home located in the highly sought-after Winter Park Pines neighborhood. Situated right near the golf course and within a desirable school district, this home offers both comfort and convenience in a prime location. Inside, you’ll find a completely refreshed interior featuring new flooring and fresh paint throughout, creating a bright and modern living space.
Alex Scures COLONIALTOWN REALTY
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$2,115 per month
- 3 Beds
- 2 Baths
- 1,536 Sq Ft
- House for Rent
1381 Viburnum Ln, Winter Park, FL 32792
1381 Viburnum Ln, Winter Park, FL 32792Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently
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$2,799 per month
- 3 Beds
- 2 Baths
- 1,410 Sq Ft
- House for Rent
7345 Grand Ave, Winter Park, FL 32792
7345 Grand Ave, Winter Park, FL 32792Welcome to Winter Park living at its finest. This beautifully updated 3-bedroom, 2-bath pool home is perfectly positioned in one of the area’s most desirable and safe neighborhoods, zoned for top-rated schools and just minutes from all major shopping, dining, and everyday conveniences. With a truly central location, everything you need is right at your fingertips.Inside, the home offers a
Sina Albekord CORCORAN PREMIER REALTY
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$2,560 per month
- 3 Beds
- 2 Baths
- 1,475 Sq Ft
- House for Rent
2224 King Richards Ct, Winter Park, FL 32792
2224 King Richards Ct, Winter Park, FL 32792We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home
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$2,400 per month
- 3 Beds
- 2 Baths
- 1,896 Sq Ft
- House for Rent
5133 Oak Hill Dr, Winter Park, FL 32792
5133 Oak Hill Dr, Winter Park, FL 32792This pet-friendly home features modern finishes and a functional layout with ample kitchen storage, spacious living areas, and abundant natural light throughout. The private yard offers space suitable for gardening or outdoor relaxation. Conveniently located near schools, parks, dining, and local amenities. Technology-enabled maintenance services provide added convenience, and self-touring is
Daniel Reyes MAIN STREET RENEWAL LLC
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$2,400 per month
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
- House for Rent
3221 Thistle Hill Dr, Aloma, FL 32792
3221 Thistle Hill Dr, Aloma, FL 32792This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee (subject to approval).
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$2,700 per month
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
- House for Rent
2352 Smiley Ave, Winter Park, FL 32792
2352 Smiley Ave, Winter Park, FL 32792Charming Winter Park rental in a highly desirable location featuring a traditional floorplan and a gorgeous fenced yard. Enjoy separate living and dining rooms—perfect for everyday comfort and entertaining. Conveniently located just minutes from the best of Winter Park, including popular restaurants, shopping, parks, Rollins College, and nearby medical offices. Rent includes lawn maintenance and
Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC
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$2,625 per month
- 3 Beds
- 2 Baths
- 1,530 Sq Ft
- House for Rent
6877 Jackman Blvd, Winter Park, FL 32792
6877 Jackman Blvd, Winter Park, FL 32792Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
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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 January 12, 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
Vincent Scarlatos CORCORAN PREMIER REALTY
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$2,455 per month
- 3 Beds
- 2.5 Baths
- 1,397 Sq Ft
- House for Rent
3363 Hamlet Loop, Winter Park, FL 32792
3363 Hamlet Loop, Winter Park, FL 32792Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is
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$3,950 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 32789Please visit our website at www.ORLrent.com you will find photos of our homes, tenant application, pet application, sample lease and more information. If applying for any of our homes all adult applicants over the age of 18 must submit a fully completed Application online. Application fee is $95.00 for each adult. An application reservation fee must be paid in the amount of one month's rent (in
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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$2,600 per month
- 3 Beds
- 2.5 Baths
- 1,848 Sq Ft
- House for Rent
1575 Lawndale Cir, Winter Park, FL 32792
1575 Lawndale Cir, Winter Park, FL 32792**WASHER AND DRYER INCLUDED** Welcome to your dream home at 1575 Lawndale Cir, Winter Park, FL 32792! Nestled in the heart of the highly coveted Winter Park, this 2-story gem offers the perfect blend of comfort and style. Step into a world of elegance with laminate wood and ceramic tile flooring gracing every corner of this home. The spacious living areas have great natural light for a warm and
Dean Itani KELLER WILLIAMS ADVANTAGE REALTY
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$2,570 per month
- 3 Beds
- 2 Baths
- 1,653 Sq Ft
- House for Rent
1891 Aster Dr, Winter Park, FL 32792
1891 Aster Dr, Winter Park, FL 32792Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is
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$3,599 per month
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- House for Rent
1945 Gunn Rd, Winter Park, FL 32792
1945 Gunn Rd, Winter Park, FL 32792Fantastic Winter Park renovation. This 3 bedroom, 2 bathroom, plus an office home has been turned into a showplace. Great location zoned for Brookshire, Glenridge and Winter Park High School. The home features upscale fixtures, open floor plan, huge laundry room, office nook, new windows, ample dining space, new appliances and large fenced in backyard. A must see! Not furnished.
Meg Dolan FANNIE HILLMAN & ASSOCIATES
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$1,000 per month
- 1 Bed
- 1 Bath
- 408 Sq Ft
- House for Rent
5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792
5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space
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$1,600 per month
- 2 Beds
- 1.5 Baths
- 825 Sq Ft
- House for Rent
2523 Alexa Ct, Winter Park, FL 32792
2523 Alexa Ct, Winter Park, FL 32792Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard
Jaleel Smith La Rosa Realty Llc
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$2,195 per month
- 2 Beds
- 2 Baths
- 1,408 Sq Ft
- House for Rent
3007 Ash Park Point, Winter Park, FL 32792
3007 Ash Park Point, Winter Park, FL 32792Beautiful 2BR/2BA home in highly sought-after Winter Park, available immediately. This well-maintained home offers an open and inviting floor plan with abundant natural light, spacious living and dining areas, and a functional kitchen with ample storage. Both bedrooms are generously sized, each with its own full bathroom, providing comfort and privacy for residents. Property features include a
Todd Norwood BESPOKE REAL ESTATE
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$3,600 per month
- 2 Beds
- 2 Baths
- 1,393 Sq Ft
- House for Rent
220 Overlook Rd, Winter Park, FL 32789
220 Overlook Rd, Winter Park, FL 32789Charming Cape Cod–style home available for lease in the heart of Winter Park. Ideally located just one block from Lake Mizell and moments from Park Avenue and Rollins College, this residence offers an exceptional lifestyle surrounded by premier shops, dining, and local amenities.The home features a spacious and inviting floor plan with a large living room, sunroom or dining area, and two
Julie Bombardo PREMIER SOTHEBY'S INTL. REALTY
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$7,000 per month
- 4 Beds
- 5 Baths
- 3,302 Sq Ft
- House for Rent
519 Park North Ct, Winter Park, FL 32789
519 Park North Ct, Winter Park, FL 32789Discover refined single-story living at 519 Park North Court, an exceptional luxury rental in the heart of Winter Park. This beautifully appointed four-bedroom, three-and-a-half-bath residence offers an ideal blend of elegance and comfort, with a thoughtfully designed split floor plan that ensures both privacy and functionality for modern living.The home welcomes you with a formal living room
Kelly Price KELLY PRICE & COMPANY LLC
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$19,000 per month
- 5 Beds
- 5.5 Baths
- 5,164 Sq Ft
- House for Rent
1221 Richmond Rd, Winter Park, FL 32789
1221 Richmond Rd, Winter Park, FL 32789Owner/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 LLC
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$7,000 per month
- 4 Beds
- 3 Baths
- 2,310 Sq Ft
- House for Rent
1400 S Pennsylvania Ave, Winter Park, FL 32789
1400 S Pennsylvania Ave, Winter Park, FL 32789A chic and trendy residence and winter park in an incredible location. A fully remodeled, one level four bedroom home with a fence corner lot. This home has an amazing curb appeal with its wide half circle, paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living and entertaining, with designer porcelain tile, trendy light
Jack Keller JACK KELLER INC
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$2,200 per month
- 3 Beds
- 2 Baths
- 1,113 Sq Ft
- House for Rent
1931 Carrigan Ave, Winter Park, FL 32792
1931 Carrigan Ave, Winter Park, FL 32792An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not
Amanda Beckman RED DOOR INVESTMENT GRP LLC
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