Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$4,150.00/month
1711 CHESTNUT AVENUE, WINTER PARK, FL - 32789
4 beds
3.0 baths
2,288 sqft
$4,150.00/month
1711 CHESTNUT AVENUE, WINTER PARK, FL - 32789
Gabriella Massaro
$4,150.00/month
4 beds
3.0 baths
2,288 sqft
1711 CHESTNUT AVENUE, WINTER PARK, FL - 32789
For Rent
Photo 1
  • Built in 1963
  • 2 garage spaces
  • Lot size: 15,847 sqft

Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park Racquet Club, and is zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. Inside, natural light pours through windows in every room, giving the home a bright, airy feel throughout. The main living areas feature classic plantation shutters, while all bedrooms are fitted with blinds, a thoughtful touch that makes every space feel finished and move-in ready. Warm engineered hardwood floors, recessed lighting, and a flowing open layout connect the living room, dining area, and family room with ease. The chef's kitchen is the heart of the home, featuring granite countertops, a large center island, rich wood cabinetry, stainless steel appliances, and a professional-grade range hood, all opening into the spacious family room with its slate tile floors, wood-burning fireplace, built-in shelving, and French doors to the backyard. The primary suite overlooks the pool and rear yard, offering a serene and private feel. Its spa-inspired en suite bath features a dual-sink vanity, a walk-in tiled shower, and a private access directly to the backyard and pool, making it ideal for those who love to start or end the day outdoors. The second bedroom enjoys its own en suite bath. A third full bath serves the remaining bedrooms, beautifully updated with designer gold fixtures, modern vanity, and stylish lighting. The split bedroom layout offers privacy and flexibility for families, guests, or a dedicated home office. Out back, your private oasis awaits with a sparkling pool, concrete deck, lush lawn, and towering mature oaks creating that quintessential Winter Park canopy. Pool and lawn maintenance are included in rent, so you can simply enjoy. The attached 2-car garage includes laundry. No pets. No exceptions.

  • Directions: Head east on Palmer Avenue. Turn left onto Phelps Avenue. Continue on Phelps Avenue, then turn right onto Chestnut Avenue. Proceed along Chestnut Avenue, and the home will be on your left.
  • County: Orange
  • Geo subdivision: CONWILL ESTATES

Nearby Schools

Lakemont Elem

Maitland Middle

Winter Park High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

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2856 KEMPER AVENUE, ORLANDO, FL - 32814
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Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6396000
Listing updated: April 3, 2026 at 7:03PM
Listing provided by: Drew Henner, PREMIER SOTHEBY'S INTL. REALTY
Last checked 3 hours ago
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