21 Windward Street, Mashpee, MA 02649
Property image
Property image
OFF MARKET

21 Windward Street
Mashpee, MA 02649

  • 2 Beds
  • 3 Baths
  • 2,342 sqft

$562,500

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $3,199/mo*
Refinance Your Home

$562,500

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $3,199/mo*
Refinance Your Home
2 Beds
3 Baths
2,342 sqft

Local Information

  • Map ViewExplore the area around 21 Windward Street.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
2000
Living Area
2,342 sqft
Price/Sqft
$240
Parking
1 Car Garage
HOA
$695/Monthly

About this House

This desirable Vineyard style end unit at Southport is a must see, offering a private and central location close to all that the community has to offer. The open kitchen features plenty of storage and overlooks the spacious dining area with a cathedral ceiling and Palladian window. Cozy up to the fireplace in the living area or read a book in the light and bright sunroom which offers both heat and air conditioning. The primary bedroom features a roomy walk in closet and a private bath. Looking for plenty of additional space for entertaining? In the fully finished lower level you will find an expansive den with an additional gas fireplace, a kitchenette with ample storage, a full bathroom, a cedar closet, two bonus rooms and a storage closet. There is so much attention to detail and many custom finishes in this home. Start living the Southport lifestyle just in time for Spring. Golf, tennis, pickleball, walking trails, indoor & outdoor pools, activities and fitness classes are just some of the amenities you will enjoy.
21 Windward Street, Mashpee, MA 02649 is a 2 bedroom, 3 bathroom, 2,342 sqft condo built in 2000. It last sold for $535,000 on Aug 17, 2023 (2% below the $545,000 asking price). It is currently off market. The Trulia Estimate is $562,500, with a rent estimate of $3,524/month.

Home Details for 21 Windward Street

Interior Features

Interior Details
Basement: Finished,FullNumber of Rooms: 4
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2342 Square Feet
Appliances & Utilities
Appliances: Gas Water Heater
Heating & Cooling
Heating: Hot WaterHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile, LaminateCommon Walls: End Unit
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Tile, Laminate

Exterior Features

Exterior Home Features
Roof: Asphalt ShingleNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Attached, Open
Pool
Pool: Community
Frontage
Responsible for Road Maintenance: Assoc MaintainedRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Private Sewer

Days on Market

Cumulative Days on Market: 136

Property Information

Year Built
Year Built: 2000Year Renovated: 2010
Property Type / Style
Property Type: ResidentialProperty Subtype: CondominiumStructure Type: OtherArchitecture: Other
Building
Building Name: SouthportConstruction Materials: ClapboardNot a New ConstructionAttached To Another StructureDoes Not Include Home Warranty
Property Information
Condition: Updated/Remodeled, ActualParcel Number: 6535297

Price & Status

Price
List Price: $545,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Mashpee
School Information
Elementary School District: MashpeeJr High / Middle School District: MashpeeHigh School District: Mashpee

Building

Building Area
Building Area: 2342 Square Feet
Community rooms
Fitness Center

Community

Community Features: Clubhouse, Putting Green, Golf, Fitness Center, Common AreaIs a Senior CommunityUnits in Building: 749

HOA

HOA Fee Includes: Professional Property Management, SewerHas an HOAHOA Fee: $695/Monthly

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash

Business

Business Information
Ownership: Condo

Miscellaneous

BasementMls Number: 22300678Showing Requirements: Appointment Required, Call Listing Agent

Additional Information

HOA Amenities: 55+ Community, Security, Trash, Maintenance Structure, Clubhouse
Last check for updates: about 4 hours ago
Listed by Carli Taylor, (774) 521-8757
Kinlin Grover Compass
Bought with: Member Non, cci.unknownoffice
Source: CCIMLS, MLS#22300678

Price History for 21 Windward Street

DatePriceEventSource
08/17/2023$535,000Sold
CCIMLS #22300678
07/16/2023$545,000PendingCCIMLS #22300678
07/10/2023$545,000PriceChange
CCIMLS #22300678
06/22/2023$565,000PriceChange
CCIMLS #22300678
03/01/2023$585,000Listed For SaleCCIMLS #22300678
02/19/2009$248,000Sold
N/A
04/28/2008$315,000ListingRemovedAgent Provided
03/22/2008$315,000Listed For SaleAgent Provided
12/18/2002$285,000Sold
N/A

Market trends in Mashpee

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$667K
$22.5KMoM
Sale-to-List Price
98.8%
0.6%MoM
Price per sq ft
$398
$6MoM
Available listings
132
21MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$3,689
Assessment$557,200
Home facts updated by county records

Comparable Sales for 21 Windward Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Longwood Road, Mashpee, MA
0.07
Condo
$545,000
06/24/26
2
2.5
1,685
19 Longwood Road, Mashpee, MA
0.11
Condo
$615,000
08/12/25
2
3
1,806
5 Kettle Lane #38, Mashpee, MA
0.21
Condo
$575,000
03/12/26
2
3
2,342
19 Longwood Rd #243, Mashpee, MA
0.12
Condo
$615,000
08/12/25
2
3
1,806
34 Bonwood Drive, Mashpee, MA
0.17
Condo
$539,000
05/04/26
2
2.5
1,685
1 Par 3 Court UNIT 1, Mashpee, MA
0.21
Condo
$675,000
05/06/26
2
3
2,338
1 Ironwood Path, Mashpee, MA
0.24
Condo
$629,000
06/30/26
2
3
2,342
8 Chippers Ln #390, Mashpee, MA
0.27
Condo
$565,000
03/02/26
2
2.5
2,527
6 Friendship Ct #90, Mashpee, MA
0.03
Condo
$535,000
11/20/25
2
2
1,338
6 Friendship Court, Mashpee, MA
0.03
Condo
$535,000
11/20/25
2
2
1,338

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 21 Windward Street.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Mashpee

At least 83 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say it's dog friendly

  • 84 % Say parking is easy

  • 80 % Say there's wildlife

  • 77 % Say yards are well-kept

  • 77 % Say it's quiet

  • 73 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 64 % Say people would walk alone at night

  • 61 % Say neighbors are friendly

  • 55 % Say kids play outside

  • 40 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 28 % Say there are sidewalks

  • 24 % Say it's walkable to grocery stores

  • 18 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Tyler Williams
    "We visit frequently and it’s always a pleasure to get away from the city. The “cape air” always has the food & drink taste better "
    0
    Flag
  • Shirleyrief
    "With easy access to Rt 28, commuters will find both bridges just 15 minutes away. Summer commutes are easy. Take a half day on Friday to arrive and a half day for a Monday morning return."
    5
    Flag
  • Tabetha L.
    "my neighborhood is quiet and has lots of families. i feel safe to let me kids go out and play without supervision cause we all watch each others kids"
    1
    Flag
  • Cordom33
    "Fireworks on the docks are a really good time. There are actually two public docks that are fun with family. "
    0
    Flag
  • Mauramurray
    "Nice neighborhood. Feels safe. Many say school system is excellent. Mashpee commons is a tremendous asset"
    6
    Flag
  • Brigitte A.
    "I am not aware of any community events. much of the year people are not here. I've lived here for 4 years and do not know any of my neighbors. no one has ever introduced themselves to me."
    0
    Flag
  • Trulia User
    "very quiet but friendly area, neighborhood. many people use their mashpee house as their summer home, but will mostly come on summer weekends. So it is very quiet."
    0
    Flag
  • Tonkahyde
    "I have lived here since 1986, my sons grew up here. Great school system but Town Hall leaves a lot to be desired.New sidewalks will improve pedestrian safety.Reasonable tax rate."
    4
    Flag
  • Rickferrari223
    "Community Center July 4 children’s baseball and races . They also have teenage dances in the summer"
    0
    Flag
  • Pmbrennan
    "This is a quiet street and we know each other. We have children playing and riding bikes in the street in the summer. The neighborhood has half year round residence and half permanent residence. "
    5
    Flag
  • Pmbrennan
    "Great street with friendly neighbors and close proximity to shopping, golf, and the beach. Also, close to Bourne and Sagamore bridges! "
    2
    Flag
  • Pmbrennan
    "I walk my dog in the morning and night. Everyone is friendly and clean up after their dogs. I see several people on my walks and there is never a problem. It is safe and enjoyable! "
    6
    Flag
  • Florence S.
    "Quiet. Great for young families. We know most people in town. Beaches are wonderful and the trails in our backyard go on for miles and miles. "
    5
    Flag
  • Blackheartz
    "It takes me minutes to get to work , stores, gas, liquor store & great restaurants, close to highway to get the Cape."
    0
    Flag
  • erinbanner
    "I've lived in this community for 3 years. The town is small enough to know and take care of each other and yet big enough to bring businesses and new opportunities for all ages. "
    2
    Flag
  • Johan B.
    "Oktoberfest, seaside lemans. barnstable fair , scallopfest. Falmouth road race. best buddies race. "
    0
    Flag
  • Atputdy1
    "Great walking areas ..... low car traffic .... friendly neighbors ..... close to willowbend golf course "
    1
    Flag
  • Jodi L. J.
    "I have lived here for over 20 years an enjoy the amount of space and community around. It is a quiet friendly neighborhood."
    3
    Flag
  • Pegala22
    "Pot lucks at the community house for those who are here year round. There is a full summer schedule of events including a 5k, earth day clean up and art events to name a few. "
    0
    Flag
  • Nancy S.
    "Beautiful area. 1 mile from Mashpee Commons, 4 miles from the beach. "
    0
    Flag
  • Ellen K.
    "I live here all year round and just love the lake, which Massachusetts' hidden treasure. If you love your privacy - yet want to have access to loads of activities - Mashpee-Wakeby Lake is the place for you!! It is Paradise on earth!!"
    0
    Flag
  • Deb B.
    "I grew up on Mashpee-Wakeby Lake in the summers and now live here full-time. It is total paradise all year long. I love the lake and waking up in the morning to it and see the trees through my skylights. I love to hear the birds singing and see the swans on the lake. It is heaven. And there is so much to do in the area - there is Mashpee Commons and South Cape Village, with their shops and restaurants, and the local library that has just been built - gorgeous - and theaters and movie houses. Plus, Mashpee is only one hour from Boston, so if you want even more excitement or want to commute for your work, you can get home to your paradise so easily."
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Air Conditioning

6 rentals with air conditioning in Mashpee, MA

Explore by feature - Washer/dryer

8 rentals with a washer/dryer in Mashpee, MA

Homes for sale near 21 Windward Street

Skip to last item
Skip to first item

Off Market Homes Near 21 Windward Street

Skip to last item
Skip to first item
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2022-04-05 08:58:10 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2022© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.