5729 Crestview Dr, Lady Lake, FL 32159
Property image
Property image
OFF MARKET

5729 Crestview Dr
Lady Lake, FL 32159

  • 4 Beds
  • 3 Baths
  • 3,168 sqft (on 0.61 acres)

$588,700

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $3,836/mo*
Refinance Your Home

$588,700

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $3,836/mo*
Refinance Your Home
4 Beds
3 Baths
3,168 sqft
(on 0.61 acres)

Home Value

Trulia Estimate
$589K
Since last month
Decreased$4K (-0.6%)
Since last year
Decreased$20K (-3.2%)
Since last sale
Increased$123K (+26.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +26% in the last 10 years
MonthEstimated value
2026
August 2026$589K
July 2026$592K
June 2026$601K
May 2026$601K
April 2026$595K
March 2026$597K
February 2026$600K
January 2026$582K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
39545 HARBOR HILLS BOULEVARD, Lady Lake, FL
0.17
Single-Family Home
$570,000
06/26/26
4
2.5
2,954
39601 HARBOR HILLS BOULEVARD, Lady Lake, FL
0.17
Single-Family Home
$509,000
08/25/25
4
2
2,889
39539 HARBOR HILLS BOULEVARD, Lady Lake, FL
0.18
Single-Family Home
$450,000
11/20/25
3
2.5
2,303
6145 SPINNAKER LOOP, Lady Lake, FL
0.27
Single-Family Home
$625,000
03/26/26
4
3
3,294
39517 HILLRISE LANE, Lady Lake, FL
0.29
Single-Family Home
$500,000
04/08/26
4
3
2,532
5903 SPINNAKER LOOP, Lady Lake, FL
0.29
Single-Family Home
$651,000
03/23/26
4
2.5
2,741
5517 MEADOW HILL LOOP, Lady Lake, FL
0.28
Single-Family Home
$710,000
07/21/26
4
3
2,960
39500 HILLRISE LANE, Lady Lake, FL
0.31
Single-Family Home
$620,000
07/23/26
4
3
2,544
5349 GROVE MANOR, Lady Lake, FL
0.18
Single-Family Home
$430,000
11/14/25
4
2
2,056
5439 Meadow Hill Loop, Lady Lake, FL
0.20
Single-Family Home
$710,000
06/05/26
3
3
3,141

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5712 CRESTVIEW DRIVE, Lady Lake, FL 32159
0.14
$929,200
4
3.5
3,819
Off Market
39601 HARBOR HILLS BOULEVARD, Lady Lake, FL 32159
0.17
$503,800
4
2
2,889
Off Market
39545 HARBOR HILLS BOULEVARD, Lady Lake, FL 32159
0.17
$570,000
4
2.5
2,954
Recently Sold
39539 HARBOR HILLS BOULEVARD, Lady Lake, FL 32159
0.18
$450,000
3
2.5
2,303
Recently Sold
39527 HARBOR HILLS BOULEVARD, Lady Lake, FL 32159
0.19
$668,600
4
2.5
2,803
Off Market
5701 CRESTVIEW DRIVE, Lady Lake, FL 32159
0.20
$549,500
5
2.5
2,448
For Sale
39509 HARBOR HILLS BOULEVARD, Lady Lake, FL 32159
0.22
$548,900
4
2.5
2,874
Off Market
5418 MEADOW HILL LOOP, Lady Lake, FL 32159
0.18
$692,500
5
3.5
3,458
Off Market
5405 GROVE MANOR, Lady Lake, FL 32159
0.15
$396,500
3
2
2,335
Off Market
5441 GROVE MANOR, Lady Lake, FL 32159
0.16
$385,000
3
2
1,930
Recently Sold
5355 GROVE MANOR, Lady Lake, FL 32159
0.16
$434,000
3
2
2,195
Recently Sold
5414 MEADOW HILL LOOP, Lady Lake, FL 32159
0.20
$666,300
3
2.5
2,807
Off Market

Local Information

  • Map ViewExplore the area around 5729 Crestview Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1995
Lot Size
0.61 acres
Living Area
3,168 sqft
Price/Sqft
$186
Parking
Garage

About this House

STUNNING 4/3 HOME located on an 18 hole Gated Golf Course and nearby the shores of Lake Griffin with CHAIN OF LAKES ACCESS. The exterior offers mature landscaping, solar ground lighting, and stunning gardens located on a 0.61 acre lot with Fairways to the East and West. Views and breezes coming off Lake Griffin welcome you as you pull onto the circular driveway. Home is wheelchair accessible with wide doorways. Casual elegant design to appreciate, open foyer, living room, dining room and gallery with polished, 24x24, Travertine Marble floors. French cut Travertine flooring in the kitchen, family room, laundry, and porch. Trompe l' oeil fine art ceilings by Dale Henry and professional art lighting. The Formal living room leads you through french doors to the screened porch with wonderful views of gardens and action on the #1 Green. Triple pocket sliding glass doors lead you back inside family room with a 13' window offering fabulous views and features a Grande fireplace. The Kitchen offers GE Monogram appliances, 7ft. coffee bar with built in Borsch coffee maker, and a movable granite island with a warming drawer. Other features include a 400 bottle capacity wine cellar, 2 NEW Trane AC units 09/2017. NEW ROOF IN 2018 (GAF Timberline architectural). The Community Swimming Pool, Country Club, Golfing, Tennis Courts, Fitness Center, etc can only be used by purchasing a Social or Golfing Membership.
5729 Crestview Dr, Lady Lake, FL 32159 is a 4 bedroom, 3 bathroom, 3,168 sqft single-family home built in 1995. It last sold for $466,000 on Mar 19, 2020. It is currently off market. The Trulia Estimate is $588,700, with a rent estimate of $3,395/month.

Home Details for 5729 Crestview Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: CarpetGated Entry
Security
Security System

Exterior Features

Exterior Home Features
Roof: TileExterior: Other, Stucco, BrickFoundation Type: SlabGardenPatioPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.61 acres

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Mar 19, 2020
Source: N/A
Sold
$466,000
Sep 26, 2019
Source: Agent Provided
PriceChange
$472,900
Price decreased by 0%
Jul 13, 2019
Source: Agent Provided
Listed For Sale
$474,900
May 3, 2019
Source: Agent Provided
ListingRemoved
$474,900
Apr 3, 2019
Source: Agent Provided
PriceChange
$474,900
Price decreased by 2%

Market trends in Lady Lake

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
84
7MoM

Around this home

What Locals Say about Lady Lake

At least 92 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 78 % Say it's dog friendly

  • 77 % Say parking is easy

  • 70 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 69 % Say it's quiet

  • 64 % Say kids play outside

  • 58 % Say people would walk alone at night

  • 48 % Say neighbors are friendly

  • 45 % Say there's wildlife

  • 42 % Say they plan to stay for at least 5 years

  • 41 % Say streets are well-lit

  • 40 % Say there are sidewalks

  • 31 % Say it's walkable to restaurants

  • 27 % Say there are community events

  • 22 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Sayuri Garcia Galvan
    "Peaceful and lots of green areas. The library and playground is close. The area is quiet, sometimes during the day it can be a bit noisy but it’s not pretty often. The area feels safe and neighbors are respectful. "
    0
    Flag
  • Alafler575
    "There are Lots of people walking their dogs. A dog park is nearby also. Everyone Seems very pet friendly! "
    0
    Flag
  • Neldaortiz
    "Children’s events, sports, farmers markets, the villages, the area is clean and safe. The parks are nice also"
    0
    Flag
  • Tina Whitt
    "Safe. Low crime. Beautiful open spaces and trees and parks. Safe to walk. Friendly neighborhood . The public middle school and high school is below average "
    0
    Flag
  • Alafler575
    "Great town. Safe and great neighbors. We love it here! Lots of community events for kids and adults. Lots of Store and supermarkets. "
    0
    Flag
  • Antonia T.
    "Clean, friendly, mainly Retirees live in this area..fun to visit and look at the scenery. A lot of different “sites” to see "
    10
    Flag
  • Kenny L.
    "i live in the area for 1 year now and i had no issues here yet,the schools are pretty good and the people are also friendly and there is alot of shopping areas everything is pretty close by and the area is pretty clean"
    9
    Flag
  • In2torres
    "This community is very friendly. People always say hello children play and go to community pool. Sometimes you see children riding their bicycles. Nice "
    4
    Flag
  • Sam
    "Villages schools are great. After living here for a year, it has its pros and cons. Pros, most of the older retired people are really good to kids when your at restaurants and shopping. Cons, your around 60-70% of 50 and older. Everyone that goes to the villages schools live up to hours from you. So friends sometimes make things more inconvenient commonly."
    27
    Flag
  • Adriana D. P.
    "Nice are to live , some petty crime ( teenagers) but overall is quiet and people friendly. Near shopping areas (around 2 miles) and the Villages and The Villages Charter School (8 miles)"
    0
    Flag
  • Thom P.
    "Living in Harbor Hills is the ultimate experience because you have a truly secure, gated community (with 24 hour security personnel) in a world class Golf Course community nestled in the Florida countryside."
    0
    Flag
  • Ken W.
    "Probably the most desirable Country Club non age restricted community in Central Florida! Just minutes from the Villages and two hospitals. Great for Doctors and their families."
    0
    Flag
  • Kennethsliker
    "Charitable community with upscale homes, beautiful club house and breath taking views of Lake Griffin "
    0
    Flag
  • Joeheritage
    "Wonderfull neighborhood with very little traffic, no thru street. Very upscale well cared for homes. Close to The Villages and shopping as well as lots of restaurants."
    0
    Flag
  • Vibe19
    "Harbor Hills is a quiet gated 'all age' community with superb walker/pet friendly neighborhoods, highly manicured common areas, great neighbors, activities, un-densely populated, not too close, not too far from all the restaurant/shopping venues of The Villages."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5729 Crestview Dr

  • What is 5729 Crestview Dr estimated to be worth?
    Trulia's estimated value for 5729 Crestview Dr in Lady Lake, FL is $588,700.
  • What is the price history for 5729 Crestview Dr?
    5729 Crestview Dr in Lady Lake, FL last sold for $466,000 in March 2020.
  • Is Lady Lake a buyer's or seller's market?
    Lady Lake is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Lady Lake?
    Residents describe Lady Lake, FL as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Lady Lake, FL.
  • Does 5729 Crestview Dr have air conditioning?
    Yes, 5729 Crestview Dr in Lady Lake, FL has air conditioning.
  • Does 5729 Crestview Dr have laundry facilities?
    Yes, 5729 Crestview Dr in Lady Lake, FL has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Off Market Homes Near 5729 Crestview Dr

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