75 Windsor Dr, Englewood, FL 34223
Property image
Property image
OFF MARKET

$331,400

Trulia Estimate
as of Sep 11, 2026
  • 3 Beds
  • 2 Baths
  • 1,715 sqft

75 Windsor Dr, Englewood, FL 34223

Home Highlights

Single-Family Home
1,715 sqft
$193/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 75 Windsor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

This is an annual rental, located within a deed restricted community of Englewood Isles Florida. Rent includes Pool and Lawn care at $2450 a month. Beautiful pool home 3 bedroom, 2 bath, 2 car garage, 1715 sq. ft., on a corner lot. Screened in Pool and lanai area is surrounded by 8 sliding glass doors, that let in natural light and wonderful breezes, this area is perfect for backyard BBQ's. Large bedrooms with ceiling fans in every room, kitchen includes an eat in dining or turn extended space into a family room, also this home has a large living room. The inside of the home has been newly painted. Englewood Isles is an active boating community with Marina. Home is located within 4.3 miles to beaches and golf courses. All pets are subject to owner written approval. No smoking or vaping anywhere on the property. Call to make an appointment to see this property, it wont last long! Priced at $2550.00 per month which includes pool service and lawn care.
75 Windsor Dr, Englewood, FL 34223 is a 3 bedroom, 2 bathroom, 1,715 sqft single-family home. It last sold for $147,000 on Aug 20, 2013 (5,900% above the $2,450 asking price). More recently, it was listed as a rental in June 2025 with an asking price of $2,550 per month. That rental listing was removed on July 26, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $331,400.

Home Details for 75 Windsor Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Comparable Sales for 75 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
76 WINDSOR DRIVE, Englewood, FL
0.03
Single-Family Home
$260,000
05/29/26
3
2
1,606 sqft
74 WINDSOR DRIVE, Englewood, FL
0.03
Single-Family Home
$410,000
11/10/25
3
2
1,624 sqft
6 PINE RIDGE WAY, Englewood, FL
0.06
Single-Family Home
$340,000
07/30/26
3
2
1,916 sqft
5 Bridge St, Englewood, FL
0.20
Single-Family Home
$240,101
02/23/26
3
2
1,972 sqft
9 DOVER DRIVE, Englewood, FL
0.13
Single-Family Home
$367,500
03/27/26
3
2
1,754 sqft
1921 Fairview Dr, Englewood, FL
0.20
Single-Family Home
$275,000
06/29/26
3
2.5
1,829 sqft
28 BRIDGE STREET, Englewood, FL
0.12
Single-Family Home
$365,000
10/31/25
3
2
1,991 sqft
11 BRIDGE STREET, Englewood, FL
0.17
Single-Family Home
$425,000
01/30/26
3
2
1,750 sqft
404 FIRETHORN AVENUE, Englewood, FL
0.19
Single-Family Home
$414,000
03/27/26
3
2
1,702 sqft
3 DOVER DRIVE, Englewood, FL
0.16
Single-Family Home
$450,000
04/06/26
3
2
1,820 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Englewood

Last updated Apr 2026
Average rent
$2.45K
$46MoM
Available listings
246
View rental market trends in Englewood, FL

Around this home

What Locals Say about Englewood

At least 194 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 89 % Say car is needed

  • 88 % Say parking is easy

  • 86 % Say yards are well-kept

  • 78 % Say it's quiet

  • 76 % Say there's holiday spirit

  • 72 % Say there's wildlife

  • 70 % Say people would walk alone at night

  • 69 % Say they plan to stay for at least 5 years

  • 61 % Say neighbors are friendly

  • 52 % Say it's walkable to restaurants

  • 51 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 38 % Say kids play outside

  • 38 % Say there are community events

  • 30 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • C Zb
    "Long commutes for professionals as there is only service industry or healthcare jobs in Englewood for the most part. "
    0
    Flag
  • Mikeh10006
    "No sidewalk in my area but plenty of dog parks in the area. Most restaurants in the area allow dogs. "
    1
    Flag
  • Wvasherry
    "I see people riding their bikes and walking their dogs all the time I see people just riding golf cars "
    0
    Flag
  • Wvasherry
    "Just a great place to raise your children ,a good home feeling.Good schools and a little fishing village "
    1
    Flag
  • PHOTOBOY 1948
    "Community is dog friendly IF you are responsible dog parent and pick up after your dog and do not allow it to run free or bark excessively. "
    0
    Flag
  • Farren.webb2
    "It’s a quite little beach town. Especially during the off season and their aren’t a bunch of people on vacation every where "
    0
    Flag
  • Lorrie
    "Nice, quiet neighborhood and close to all kinds of restaurants, stores, and Historic Dearborn Street-where there are lots of activities all year long. 2 beaches on the coast within a few miles. LOVE this town. It's close enough to larger cities without the high traffic and congestion!"
    9
    Flag
  • Katie S.
    "Manasota Key is a wonderful, unique place to live or visit. I own and rent a condo here and every single person who visits can't stop raving about it. It has unique restaurants, beautiful beaches, quaint shops and is within 3 miles of any chain store you could possibly want. Most of all, it's very safe and has the old Florida charm. Low hassle factor and natural beauty makes for very happy and friendly people on this stretch of paradise."
    3
    Flag
  • Michelle V.
    "Yes they would like it very much. Very dog friendly with parks and lots of places to walk. It’s a great neighborhood."
    4
    Flag
  • Trulia User
    "Not really a lot to do for the kids except the beach and even that is sometimes questionable with all the tourists but other than that it’s a nice quiet safe neighborhood "
    34
    Flag
  • Pat K.
    "Dogs are welcome. Many people walk their dogs on leashes throughout the neighborhood. Dogs ride with their owners on golf carts."
    9
    Flag
  • Grandcanhike
    "Quiet calm community, I come here once a year and love it. Inexpensive area. Older people here so if your into meeting people or partying I hope your of the right age. "
    0
    Flag
  • Amycountryman
    "Nice, quiet neighborhood with GREAT neighbors! Minutes from shopping, nightlife, restaurants and beaches. We are not in flood zone here which, being so close to Gulf of Mexico is unusual. Also there is no HOA! "
    4
    Flag
  • Mike B.
    "Small town every one knows every one . Which is good for those with kids . Everyone seems to watch out for each other and each others kids."
    11
    Flag
  • Maylush1
    "Events on Dearborn and around the community. Boat races and Christmas boat parade. Seafood festivals. The event center has great events there. Restaurants are many and very good. "
    0
    Flag
  • Shannon W.
    "A lot of entertainment on Dearborn street great for tourists always something happening especially in the winter time "
    8
    Flag
  • Amycountryman
    "East Englewood is a great place to live. Wonderful neighbors..nice, quiet neighborhood. Beautiful properties and scenery. "
    4
    Flag
  • Manasotakeybound
    "A quaint beach town that is not too busy, but offers great activities and restaurants. It is close to everything necessary to live a great life."
    0
    Flag
  • Lewis W.
    "Nice and quiet, everyone has been friendly. Homes are well taken care of. Everyone seems to take pride in there homes. Sidewalks recently put in and done very nicely! Many people walk daily, some with dogs and some without."
    0
    Flag
  • Mdbass0121
    "Lived here my entire life and have watched it grow (in good ways and bad) I will be raising my daughter here as well. we are a quaint drinking town with a fishing problem in all the best ways"
    4
    Flag
  • Manasotakeybound
    "This is a great Beach Town community where neighbors know neighbors and you can walk to restaurants, the beach and safely bike to nearly anywhere."
    0
    Flag
  • Trulia User
    "very busy during the season because it is so very close to the beaches but the community has many back routes for locals to use."
    0
    Flag
  • Amycountryman
    "very nice area to settle down in good age mix and people are very friendly, you can keep to yourself or mingle with neighbors "
    4
    Flag
  • Thomas N.
    "Englewood is a "CDP" or Census Designated Place. it is not a city, not even a town. We have no Police Dept, dont need one!"
    15
    Flag
  • Michelle V.
    "Too long. I hate River Rd and wish there was a more direct route to I-75. Otherwise it’s an okay commute."
    0
    Flag
  • Msynkegrl
    "It’s a safe neighborhood. I’ve lived here for 5 years and haven’t known of any problems with the kids that are here. It’s pretty quite really."
    1
    Flag
  • Hollyhallowell
    "I work from home so I don’t travel to an office. Though it seems it would be easy to do so in this area."
    1
    Flag
  • James G. M. D.
    "Great for dogs dog park near by all dogs on leashes and people pick up after safe and quite beautiful landscaping "
    3
    Flag
  • Trulia User
    "Almost everyone has a dog, most people are accepting as long as you pick up their excrement. My dog is accepted without a leash in our neighborhood"
    1
    Flag
  • Gijoelretired
    "Great atmosphere. I love how cozy it is here. I will be looking forward to coming back next year. This was my best spring break ever. "
    0
    Flag
  • Alicia B.
    "What makes my neighborhood most special is that all of us are like family. Everyone is friendly and nobody really avoids interacting with each other."
    5
    Flag
  • Alicia B.
    "Englewood feels like a warm and safe community. I am enjoying my time here staying with my husband's family while we searched for our own residence."
    0
    Flag
  • Hayleymurray3
    "Calm quite and everyone knows each other. Great schools for the kids and amazing restaurants. Great prices houses streets are well lit. Low crime area. "
    0
    Flag
  • Hayleymurray3
    "Easy to get through and great town. Not much traffic other then rush hour. My neighborhood is wonderful and I would recommend to anyone. "
    1
    Flag
  • Hummingstuff
    "Lots of old people. Hot. Bugs. Storms. Schools can be mediocre but that’s true for most of Florida. Great beaches when red tide isn’t occurring. Easy access to water for boating and exploring. "
    2
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jul 26, 2025
Source: Zillow Rentals
ListingRemoved
$2,450
Jul 9, 2025
Source: Zillow Rentals
PriceChange
$2,450
Price decreased by 4%
Jun 13, 2025
Source: Zillow Rentals
Listed For Rent
$2,550
Oct 25, 2014
Source: Agent Provided
ListingRemoved
$1,625
Oct 8, 2014
Source: Agent Provided
Listed For Rent
$1,625

Frequently asked questions about 75 Windsor Dr

  • What is 75 Windsor Dr estimated to be worth?
    Trulia's estimated value for 75 Windsor Dr in Englewood, FL is $331,400.
  • What is the price history for 75 Windsor Dr?
    75 Windsor Dr in Englewood, FL last sold for $147,000 in August 2013.
  • Is Englewood a buyer's or seller's market?
    Englewood is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Englewood?
    The median sale price in Englewood is $325K. That is down $6.67K from the prior month.
  • Does 75 Windsor Dr have air conditioning?
    Yes, 75 Windsor Dr in Englewood, FL has air conditioning.
  • Does 75 Windsor Dr have a pool?
    Yes, 75 Windsor Dr in Englewood, FL has a pool.

Homes for rent near 75 Windsor Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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